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In the mol­ecule of the title compound, C20H20Br2N4O7, one ethyl group is disordered over two positions; site-occupation factors were fixed at 0.63 and 0.37. The non-planar seven- and six-membered rings adopt chair conformations, while the two five-membered rings have envelope conformations. In the crystal structure, C—H...O and C—H...Br hydrogen bonds result in the formation of a tape-like structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054438/hk2354sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054438/hk2354Isup2.hkl
Contains datablock I

CCDC reference: 672817

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
Diethyl 5,10-dihydro-6,9-dibromo-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a, 10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top
Crystal data top
C20H20Br2N4O7F(000) = 1176
Mr = 588.22Dx = 1.745 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4974 reflections
a = 10.6430 (12) Åθ = 2.6–24.1°
b = 11.2669 (13) ŵ = 3.67 mm1
c = 18.673 (2) ÅT = 298 K
V = 2239.1 (4) Å3Block, colorless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4879 independent reflections
Radiation source: fine-focus sealed tube3828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ andω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
h = 137
Tmin = 0.406, Tmax = 0.527k = 1414
13113 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.87 e Å3
320 parametersΔρmin = 0.56 e Å3
40 restraintsAbsolute structure: Flack (1983), with 2108 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.019 (10)
Crystal data top
C20H20Br2N4O7V = 2239.1 (4) Å3
Mr = 588.22Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.6430 (12) ŵ = 3.67 mm1
b = 11.2669 (13) ÅT = 298 K
c = 18.673 (2) Å0.30 × 0.20 × 0.20 mm
Data collection top
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 = 0.527Rint = 0.033
13113 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.106Δρmax = 0.87 e Å3
S = 1.00Δρmin = 0.56 e Å3
4879 reflectionsAbsolute structure: Flack (1983), with 2108 Friedel pairs
320 parametersAbsolute structure parameter: 0.019 (10)
40 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br11.24828 (5)0.42440 (5)0.82344 (3)0.0778 (2)
Br20.83248 (6)0.04207 (5)0.93545 (3)0.07348 (19)
C11.0072 (3)0.3091 (3)0.81524 (19)0.0326 (8)
C20.9179 (4)0.2254 (3)0.83950 (17)0.0327 (8)
C30.9429 (4)0.1627 (4)0.9009 (2)0.0430 (9)
C41.1153 (4)0.3249 (3)0.8550 (2)0.0457 (9)
C51.1361 (5)0.2618 (4)0.9183 (3)0.0585 (13)
H51.20840.27540.94500.070*
C61.0509 (5)0.1809 (4)0.9407 (2)0.0580 (12)
H61.06480.13780.98240.070*
C70.7998 (3)0.2026 (3)0.7960 (2)0.0365 (8)
H7A0.82380.17060.74980.044*
H7B0.75000.14280.82030.044*
C80.9871 (3)0.3731 (3)0.7445 (2)0.0355 (8)
H8A1.05910.42400.73600.043*
H8B0.98550.31430.70660.043*
C90.6464 (3)0.3534 (3)0.83720 (18)0.0348 (8)
C100.8689 (3)0.5529 (3)0.77131 (17)0.0325 (8)
C110.5539 (4)0.5491 (4)0.8602 (2)0.0487 (10)
H11A0.48680.59480.83840.058*
H11B0.52110.51260.90340.058*
C120.6992 (5)0.6817 (3)0.8162 (2)0.0543 (11)
H12A0.76610.73610.82900.065*
H12B0.63200.72730.79450.065*
C130.7531 (3)0.3920 (3)0.72946 (16)0.0291 (7)
C140.7293 (4)0.3329 (3)0.65579 (19)0.0396 (9)
C150.8078 (10)0.2619 (9)0.5512 (4)0.069 (3)0.63
H15A0.74290.20370.56110.083*0.63
H15B0.78000.31060.51150.083*0.63
C160.9245 (11)0.2013 (11)0.5321 (7)0.106 (4)0.63
H16A0.99310.25650.53420.160*0.63
H16B0.91760.17000.48440.160*0.63
H16C0.93940.13750.56510.160*0.63
C15'0.8403 (13)0.3069 (15)0.5401 (5)0.059 (4)0.37
H15C0.83320.37810.51120.070*0.37
H15D0.77350.25310.52630.070*0.37
C16'0.9655 (12)0.2493 (13)0.5272 (8)0.055 (3)0.37
H16D1.02860.30940.52170.083*0.37
H16E0.96140.20200.48450.083*0.37
H16F0.98640.19960.56720.083*0.37
C170.6607 (3)0.4976 (3)0.74721 (17)0.0328 (7)
C180.5684 (3)0.5340 (4)0.6883 (2)0.0411 (8)
C190.5544 (5)0.5840 (6)0.5650 (2)0.0721 (15)
H19A0.53500.66820.56490.086*
H19B0.47590.54040.56630.086*
C200.6242 (5)0.5533 (5)0.4999 (2)0.0605 (12)
H20A0.64450.47030.50050.091*
H20B0.70030.59890.49780.091*
H20C0.57350.57050.45860.091*
N10.7219 (3)0.3072 (2)0.78463 (15)0.0307 (7)
N20.8741 (3)0.4448 (2)0.73897 (14)0.0312 (6)
N30.7466 (3)0.5948 (2)0.76439 (15)0.0361 (7)
N40.5948 (3)0.4576 (3)0.81106 (15)0.0368 (7)
O10.9548 (3)0.6058 (2)0.79841 (15)0.0480 (7)
O20.6257 (3)0.3098 (3)0.89449 (14)0.0496 (7)
O30.6542 (3)0.6257 (3)0.87831 (15)0.0538 (7)
O40.6307 (3)0.2891 (3)0.64205 (16)0.0628 (9)
O50.8276 (3)0.3372 (3)0.61512 (14)0.0626 (9)
O60.4591 (3)0.5415 (4)0.69709 (17)0.0794 (11)
O70.6289 (3)0.5551 (3)0.62817 (13)0.0467 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0410 (2)0.0734 (3)0.1189 (5)0.0152 (3)0.0261 (3)0.0093 (3)
Br20.0752 (3)0.0742 (3)0.0710 (3)0.0035 (3)0.0081 (3)0.0415 (3)
C10.0276 (17)0.0334 (18)0.0368 (19)0.0073 (14)0.0038 (16)0.0003 (15)
C20.0355 (19)0.0350 (18)0.0278 (18)0.0133 (16)0.0007 (15)0.0003 (14)
C30.054 (2)0.041 (2)0.034 (2)0.0088 (19)0.0053 (18)0.0040 (16)
C40.039 (2)0.042 (2)0.057 (2)0.0005 (18)0.0129 (19)0.0028 (18)
C50.049 (3)0.064 (3)0.062 (3)0.012 (2)0.027 (2)0.010 (2)
C60.067 (3)0.066 (3)0.041 (2)0.020 (3)0.015 (2)0.007 (2)
C70.0379 (19)0.0313 (17)0.040 (2)0.0056 (16)0.0014 (17)0.0063 (15)
C80.0272 (17)0.0390 (19)0.0402 (19)0.0005 (16)0.0049 (16)0.0027 (16)
C90.0302 (19)0.0404 (19)0.0339 (18)0.0081 (16)0.0006 (15)0.0048 (15)
C100.0343 (18)0.0302 (17)0.0329 (17)0.0049 (15)0.0014 (15)0.0063 (14)
C110.046 (2)0.059 (3)0.041 (2)0.012 (2)0.0123 (18)0.001 (2)
C120.062 (3)0.037 (2)0.064 (3)0.005 (2)0.010 (2)0.008 (2)
C130.0270 (16)0.0334 (16)0.0270 (17)0.0007 (16)0.0017 (14)0.0036 (13)
C140.049 (3)0.0387 (19)0.0315 (19)0.0049 (19)0.0007 (18)0.0036 (15)
C150.081 (6)0.080 (5)0.045 (4)0.003 (4)0.004 (4)0.012 (4)
C160.108 (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)
C170.0313 (18)0.0362 (17)0.0310 (16)0.0005 (16)0.0039 (16)0.0040 (13)
C180.034 (2)0.050 (2)0.039 (2)0.0094 (18)0.0005 (17)0.0057 (17)
C190.068 (3)0.106 (4)0.042 (2)0.034 (3)0.013 (2)0.017 (3)
C200.071 (3)0.064 (3)0.046 (2)0.008 (3)0.011 (2)0.005 (2)
N10.0276 (16)0.0320 (14)0.0326 (15)0.0005 (12)0.0053 (12)0.0059 (12)
N20.0278 (14)0.0289 (15)0.0369 (15)0.0004 (12)0.0041 (12)0.0036 (12)
N30.0369 (16)0.0283 (13)0.0432 (17)0.0045 (15)0.0015 (14)0.0002 (12)
N40.0337 (15)0.0392 (15)0.0376 (16)0.0040 (14)0.0086 (14)0.0014 (13)
O10.0427 (16)0.0432 (15)0.0579 (17)0.0130 (13)0.0049 (14)0.0044 (13)
O20.0588 (19)0.0536 (16)0.0366 (14)0.0038 (15)0.0131 (13)0.0123 (12)
O30.0584 (19)0.0532 (16)0.0499 (17)0.0027 (17)0.0067 (15)0.0128 (13)
O40.069 (2)0.070 (2)0.0498 (17)0.0255 (19)0.0159 (16)0.0074 (15)
O50.0555 (19)0.101 (3)0.0312 (14)0.020 (2)0.0018 (15)0.0157 (15)
O60.0393 (17)0.135 (3)0.063 (2)0.027 (2)0.0009 (16)0.022 (2)
O70.0426 (15)0.0613 (17)0.0363 (13)0.0075 (14)0.0027 (12)0.0137 (12)
Geometric parameters (Å, º) top
Br1—C41.899 (4)C13—N21.430 (5)
Br2—C31.909 (4)C13—N11.443 (4)
C1—C41.381 (5)C13—C141.549 (5)
C1—C21.413 (5)C13—C171.579 (5)
C1—C81.519 (5)C14—O41.187 (5)
C2—C31.373 (5)C14—O51.294 (5)
C2—C71.519 (5)C15—C161.462 (9)
C3—C61.384 (7)C15—O51.479 (7)
C4—C51.397 (6)C15—H15A0.9700
C5—C61.352 (7)C15—H15B0.9700
C5—H50.9300C16—H16A0.9600
C6—H60.9300C16—H16B0.9600
C7—N11.457 (4)C16—H16C0.9600
C7—H7A0.9700C15'—O51.448 (9)
C7—H7B0.9700C15'—C16'1.502 (9)
C8—N21.453 (5)C15'—H15C0.9700
C8—H8A0.9700C15'—H15D0.9700
C8—H8B0.9700C16'—H16D0.9600
C9—O21.197 (4)C16'—H16E0.9600
C9—N11.371 (5)C16'—H16F0.9600
C9—N41.386 (5)C17—N41.455 (4)
C10—O11.203 (4)C17—N31.463 (5)
C10—N21.360 (4)C17—C181.530 (5)
C10—N31.391 (5)C18—O61.178 (4)
C11—O31.414 (5)C18—O71.316 (4)
C11—N41.447 (5)C19—O71.458 (5)
C11—H11A0.9700C19—C201.467 (6)
C11—H11B0.9700C19—H19A0.9700
C12—O31.404 (5)C19—H19B0.9700
C12—N31.466 (5)C20—H20A0.9600
C12—H12A0.9700C20—H20B0.9600
C12—H12B0.9700C20—H20C0.9600
C4—C1—C2118.3 (3)O5—C14—C13111.9 (4)
C4—C1—C8121.5 (3)C16—C15—O5110.1 (9)
C2—C1—C8120.1 (3)C16—C15—H15A109.6
C3—C2—C1118.8 (4)O5—C15—H15A109.6
C3—C2—C7121.3 (4)C16—C15—H15B109.6
C1—C2—C7119.9 (3)O5—C15—H15B109.6
C2—C3—C6122.2 (4)H15A—C15—H15B108.1
C2—C3—Br2122.0 (3)O5—C15'—C16'109.8 (10)
C6—C3—Br2115.8 (3)O5—C15'—H15C109.7
C1—C4—C5121.4 (4)C16'—C15'—H15C109.7
C1—C4—Br1122.0 (3)O5—C15'—H15D109.7
C5—C4—Br1116.4 (3)C16'—C15'—H15D109.7
C6—C5—C4119.9 (4)H15C—C15'—H15D108.2
C6—C5—H5120.1C15'—C16'—H16D109.5
C4—C5—H5120.1C15'—C16'—H16E109.5
C5—C6—C3119.4 (4)H16D—C16'—H16E109.5
C5—C6—H6120.3C15'—C16'—H16F109.5
C3—C6—H6120.3H16D—C16'—H16F109.5
N1—C7—C2114.3 (3)H16E—C16'—H16F109.5
N1—C7—H7A108.7N4—C17—N3110.7 (3)
C2—C7—H7A108.7N4—C17—C18111.3 (3)
N1—C7—H7B108.7N3—C17—C18111.0 (3)
C2—C7—H7B108.7N4—C17—C13103.9 (3)
H7A—C7—H7B107.6N3—C17—C13102.8 (3)
N2—C8—C1116.2 (3)C18—C17—C13116.8 (3)
N2—C8—H8A108.2O6—C18—O7126.1 (4)
C1—C8—H8A108.2O6—C18—C17123.5 (4)
N2—C8—H8B108.2O7—C18—C17110.4 (3)
C1—C8—H8B108.2O7—C19—C20110.0 (4)
H8A—C8—H8B107.4O7—C19—H19A109.7
O2—C9—N1126.3 (3)C20—C19—H19A109.7
O2—C9—N4126.1 (4)O7—C19—H19B109.7
N1—C9—N4107.6 (3)C20—C19—H19B109.7
O1—C10—N2126.8 (3)H19A—C19—H19B108.2
O1—C10—N3125.6 (3)C19—C20—H20A109.5
N2—C10—N3107.5 (3)C19—C20—H20B109.5
O3—C11—N4111.1 (3)H20A—C20—H20B109.5
O3—C11—H11A109.4C19—C20—H20C109.5
N4—C11—H11A109.4H20A—C20—H20C109.5
O3—C11—H11B109.4H20B—C20—H20C109.5
N4—C11—H11B109.4C9—N1—C13113.3 (3)
H11A—C11—H11B108.0C9—N1—C7122.4 (3)
O3—C12—N3111.3 (3)C13—N1—C7120.6 (3)
O3—C12—H12A109.4C10—N2—C13113.0 (3)
N3—C12—H12A109.4C10—N2—C8120.0 (3)
O3—C12—H12B109.4C13—N2—C8121.5 (3)
N3—C12—H12B109.4C10—N3—C17110.5 (3)
H12A—C12—H12B108.0C10—N3—C12119.2 (3)
N2—C13—N1113.2 (3)C17—N3—C12115.4 (3)
N2—C13—C14115.9 (3)C9—N4—C11120.0 (3)
N1—C13—C14108.2 (3)C9—N4—C17111.1 (3)
N2—C13—C17102.8 (3)C11—N4—C17116.4 (3)
N1—C13—C17101.9 (3)C12—O3—C11109.5 (3)
C14—C13—C17114.1 (3)C14—O5—C15'129.4 (7)
O4—C14—O5127.1 (4)C14—O5—C15109.7 (5)
O4—C14—C13121.0 (4)C18—O7—C19117.7 (3)
C4—C1—C2—C30.6 (5)C2—C7—N1—C976.3 (4)
C8—C1—C2—C3175.3 (3)C2—C7—N1—C1380.4 (4)
C4—C1—C2—C7178.0 (3)O1—C10—N2—C13164.1 (3)
C8—C1—C2—C72.1 (5)N3—C10—N2—C1318.8 (4)
C1—C2—C3—C61.7 (6)O1—C10—N2—C89.8 (5)
C7—C2—C3—C6179.0 (4)N3—C10—N2—C8173.2 (3)
C1—C2—C3—Br2176.8 (3)N1—C13—N2—C1097.6 (3)
C7—C2—C3—Br20.5 (5)C14—C13—N2—C10136.6 (3)
C2—C1—C4—C51.1 (6)C17—C13—N2—C1011.5 (3)
C8—C1—C4—C5177.0 (4)N1—C13—N2—C856.3 (4)
C2—C1—C4—Br1174.4 (3)C14—C13—N2—C869.5 (4)
C8—C1—C4—Br11.4 (5)C17—C13—N2—C8165.4 (3)
C1—C4—C5—C61.9 (7)C1—C8—N2—C1076.9 (4)
Br1—C4—C5—C6173.9 (4)C1—C8—N2—C1375.3 (4)
C4—C5—C6—C30.9 (7)O1—C10—N3—C17164.6 (3)
C2—C3—C6—C50.9 (7)N2—C10—N3—C1718.3 (4)
Br2—C3—C6—C5177.6 (3)O1—C10—N3—C1227.3 (5)
C3—C2—C7—N1124.0 (4)N2—C10—N3—C12155.5 (3)
C1—C2—C7—N158.7 (4)N4—C17—N3—C1099.6 (3)
C4—C1—C8—N2123.9 (4)C18—C17—N3—C10136.3 (3)
C2—C1—C8—N260.4 (4)C13—C17—N3—C1010.8 (3)
N2—C13—C14—O4178.2 (3)N4—C17—N3—C1239.4 (4)
N1—C13—C14—O453.5 (5)C18—C17—N3—C1284.6 (4)
C17—C13—C14—O459.1 (5)C13—C17—N3—C12149.8 (3)
N2—C13—C14—O52.8 (4)O3—C12—N3—C1083.8 (5)
N1—C13—C14—O5125.6 (3)O3—C12—N3—C1751.5 (5)
C17—C13—C14—O5121.9 (4)O2—C9—N4—C1126.9 (6)
N2—C13—C17—N4115.6 (3)N1—C9—N4—C11155.2 (3)
N1—C13—C17—N41.8 (3)O2—C9—N4—C17167.4 (4)
C14—C13—C17—N4118.2 (3)N1—C9—N4—C1714.7 (4)
N2—C13—C17—N30.1 (3)O3—C11—N4—C986.7 (4)
N1—C13—C17—N3117.3 (3)O3—C11—N4—C1751.8 (4)
C14—C13—C17—N3126.4 (3)N3—C17—N4—C9102.1 (3)
N2—C13—C17—C18121.5 (3)C18—C17—N4—C9134.0 (3)
N1—C13—C17—C18121.1 (3)C13—C17—N4—C97.6 (4)
C14—C13—C17—C184.7 (4)N3—C17—N4—C1140.0 (4)
N4—C17—C18—O68.2 (6)C18—C17—N4—C1183.9 (4)
N3—C17—C18—O6115.5 (5)C13—C17—N4—C11149.7 (3)
C13—C17—C18—O6127.2 (5)N3—C12—O3—C1161.0 (5)
N4—C17—C18—O7171.9 (3)N4—C11—O3—C1261.0 (4)
N3—C17—C18—O764.4 (4)O4—C14—O5—C15'10.0 (11)
C13—C17—C18—O752.9 (4)C13—C14—O5—C15'171.0 (9)
O2—C9—N1—C13165.7 (4)O4—C14—O5—C158.9 (7)
N4—C9—N1—C1316.4 (4)C13—C14—O5—C15170.0 (5)
O2—C9—N1—C77.4 (6)C16'—C15'—O5—C14143.0 (10)
N4—C9—N1—C7174.7 (3)C16'—C15'—O5—C1598 (2)
N2—C13—N1—C998.5 (3)C16—C15—O5—C14142.1 (9)
C14—C13—N1—C9131.6 (3)C16—C15—O5—C15'73.5 (18)
C17—C13—N1—C911.1 (4)O6—C18—O7—C193.7 (7)
N2—C13—N1—C760.1 (4)C17—C18—O7—C19176.4 (4)
C14—C13—N1—C769.7 (4)C20—C19—O7—C18154.9 (4)
C17—C13—N1—C7169.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O50.972.412.981 (5)117
C8—H8A···Br10.972.593.198 (4)121
C7—H7B···Br20.972.583.189 (3)121
C19—H19A···O2i0.972.463.274 (6)141
C11—H11A···O4i0.972.553.343 (5)139
C8—H8B···O1ii0.972.443.178 (5)133
C7—H7B···O6iii0.972.523.302 (5)137
C6—H6···O2iv0.932.463.182 (5)134
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y1/2, z+3/2; (iii) x+1, y1/2, z+3/2; (iv) x+1/2, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC20H20Br2N4O7
Mr588.22
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)10.6430 (12), 11.2669 (13), 18.673 (2)
V3)2239.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)3.67
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick,1996)
Tmin, Tmax0.406, 0.527
No. of measured, independent and
observed [I > 2σ(I)] reflections
13113, 4879, 3828
Rint0.033
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.106, 1.00
No. of reflections4879
No. of parameters320
No. of restraints40
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.87, 0.56
Absolute structureFlack (1983), with 2108 Friedel pairs
Absolute structure parameter0.019 (10)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top
Br1—C41.899 (4)C9—O21.197 (4)
C1—C41.381 (5)C12—O31.404 (5)
C1—C81.519 (5)C18—O61.178 (4)
C8—N21.453 (5)C19—C201.467 (6)
C4—C1—C2118.3 (3)N2—C8—C1116.2 (3)
C3—C2—C7121.3 (4)O2—C9—N1126.3 (3)
C1—C4—Br1122.0 (3)N1—C9—N4107.6 (3)
C5—C4—Br1116.4 (3)O3—C12—N3111.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O50.972.412.981 (5)117.2
C8—H8A···Br10.972.593.198 (4)120.7
C7—H7B···Br20.972.583.189 (3)120.6
C19—H19A···O2i0.972.463.274 (6)141.4
C11—H11A···O4i0.972.553.343 (5)139.2
C8—H8B···O1ii0.972.443.178 (5)133.0
C7—H7B···O6iii0.972.523.302 (5)137.4
C6—H6···O2iv0.932.463.182 (5)134.4
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y1/2, z+3/2; (iii) x+1, y1/2, z+3/2; (iv) x+1/2, y+1/2, z+2.
 

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