In the cation of the title compound, C
22H
34N
3O
33+·3Br
−, a 20-membered N
3O
3 donor-type macrocyclic ligand, the mean of all nine N
O distances is 5.775 (2) Å and the dihedral angle between the two benzene rings is 33.5 (2)°. N—H
Br hydrogen bonding helps to stabilize the crystal structure.
Supporting information
CCDC reference: 641509
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.004 Å
- R factor = 0.033
- wR factor = 0.089
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3,4:12,13-Dibenzo-5,8,11-trioxo-1,15,18-triazonia-3,12-cycloeicosadiene
tribromide
top
Crystal data top
C22H34N3O33+·3Br− | F(000) = 1264 |
Mr = 628.25 | Dx = 1.653 Mg m−3 |
Monoclinic, P21/c | Melting point: 513-514 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.051 (2) Å | Cell parameters from 31616 reflections |
b = 19.697 (4) Å | θ = 3.1–27.4° |
c = 12.750 (3) Å | µ = 4.82 mm−1 |
β = 90.70 (3)° | T = 153 K |
V = 2524.1 (9) Å3 | Chunk, colorless |
Z = 4 | 0.30 × 0.17 × 0.16 mm |
Data collection top
Rigaku R-AXIS SPIDER diffractometer | 5777 independent reflections |
Radiation source: Rotating Anode | 5183 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→13 |
Tmin = 0.293, Tmax = 0.462 | k = −25→25 |
39799 measured reflections | l = −16→16 |
Refinement top
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)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0451P)2 + 2.3331P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5777 reflections | Δρmax = 1.63 e Å−3 |
281 parameters | Δρmin = −1.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (3) |
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 | |
Br3 | 0.08804 (3) | 0.150432 (13) | 0.90351 (2) | 0.02925 (9) | |
Br1 | 0.67091 (3) | 0.186345 (14) | 0.73757 (2) | 0.03268 (9) | |
Br2 | 0.21646 (3) | 0.170541 (13) | 0.49400 (2) | 0.02843 (9) | |
O1 | 0.38710 (17) | 0.43892 (9) | 0.62436 (14) | 0.0239 (4) | |
O2 | 0.15256 (19) | 0.46122 (9) | 0.75571 (14) | 0.0280 (4) | |
O3 | −0.06877 (16) | 0.45383 (8) | 0.89142 (13) | 0.0225 (4) | |
N1 | 0.4365 (2) | 0.26622 (11) | 0.61357 (16) | 0.0235 (4) | |
H1A | 0.3811 | 0.2336 | 0.5855 | 0.028* | |
H1C | 0.5158 | 0.2454 | 0.6305 | 0.028* | |
N2 | 0.1395 (2) | 0.25327 (11) | 0.70492 (17) | 0.0255 (4) | |
H2A | 0.1639 | 0.2215 | 0.6558 | 0.031* | |
H2C | 0.1462 | 0.2334 | 0.7700 | 0.031* | |
N3 | −0.1102 (2) | 0.28164 (10) | 0.85940 (16) | 0.0223 (4) | |
H3A | −0.0452 | 0.2524 | 0.8833 | 0.027* | |
H3C | −0.1815 | 0.2559 | 0.8372 | 0.027* | |
C1 | 0.5201 (2) | 0.43378 (12) | 0.60572 (18) | 0.0204 (5) | |
C2 | 0.6123 (2) | 0.48527 (13) | 0.62560 (19) | 0.0231 (5) | |
H2B | 0.5833 | 0.5278 | 0.6522 | 0.028* | |
C3 | 0.7464 (3) | 0.47438 (14) | 0.60655 (19) | 0.0262 (5) | |
H3B | 0.8089 | 0.5094 | 0.6214 | 0.031* | |
C4 | 0.7898 (2) | 0.41341 (14) | 0.5664 (2) | 0.0263 (5) | |
H4A | 0.8817 | 0.4060 | 0.5540 | 0.032* | |
C5 | 0.6967 (3) | 0.36270 (13) | 0.5442 (2) | 0.0243 (5) | |
H5A | 0.7261 | 0.3209 | 0.5155 | 0.029* | |
C6 | 0.5623 (2) | 0.37183 (12) | 0.56299 (18) | 0.0210 (5) | |
C7 | 0.4628 (3) | 0.31862 (12) | 0.5299 (2) | 0.0235 (5) | |
H7A | 0.4958 | 0.2953 | 0.4665 | 0.028* | |
H7B | 0.3779 | 0.3412 | 0.5108 | 0.028* | |
C8 | 0.3760 (3) | 0.29161 (14) | 0.7126 (2) | 0.0277 (5) | |
H8A | 0.4282 | 0.3310 | 0.7383 | 0.033* | |
H8B | 0.3823 | 0.2555 | 0.7665 | 0.033* | |
C9 | 0.2333 (3) | 0.31242 (12) | 0.7002 (2) | 0.0256 (5) | |
H9A | 0.2213 | 0.3358 | 0.6321 | 0.031* | |
H9B | 0.2109 | 0.3450 | 0.7564 | 0.031* | |
C10 | −0.0014 (3) | 0.27373 (13) | 0.6850 (2) | 0.0259 (5) | |
H10A | −0.0570 | 0.2323 | 0.6804 | 0.031* | |
H10B | −0.0072 | 0.2971 | 0.6163 | 0.031* | |
C11 | −0.0582 (3) | 0.32040 (13) | 0.7688 (2) | 0.0252 (5) | |
H11A | 0.0122 | 0.3519 | 0.7936 | 0.030* | |
H11B | −0.1310 | 0.3479 | 0.7376 | 0.030* | |
C12 | −0.1534 (3) | 0.32636 (12) | 0.94900 (19) | 0.0224 (5) | |
H12A | −0.1949 | 0.2975 | 1.0031 | 0.027* | |
H12B | −0.0734 | 0.3476 | 0.9811 | 0.027* | |
C13 | −0.2500 (2) | 0.38159 (12) | 0.91820 (18) | 0.0212 (5) | |
C14 | −0.3867 (3) | 0.37096 (14) | 0.9208 (2) | 0.0267 (5) | |
H14A | −0.4193 | 0.3267 | 0.9355 | 0.032* | |
C15 | −0.4767 (3) | 0.42311 (15) | 0.9027 (2) | 0.0290 (6) | |
H15A | −0.5698 | 0.4147 | 0.9032 | 0.035* | |
C16 | −0.4283 (3) | 0.48789 (14) | 0.88377 (19) | 0.0269 (5) | |
H16A | −0.4890 | 0.5243 | 0.8735 | 0.032* | |
C17 | −0.2930 (2) | 0.50021 (13) | 0.87965 (19) | 0.0235 (5) | |
H17A | −0.2611 | 0.5447 | 0.8663 | 0.028* | |
C18 | −0.2037 (2) | 0.44693 (12) | 0.89522 (17) | 0.0197 (5) | |
C19 | −0.0132 (2) | 0.51768 (12) | 0.85900 (19) | 0.0220 (5) | |
H19A | −0.0266 | 0.5528 | 0.9134 | 0.026* | |
H19B | −0.0554 | 0.5333 | 0.7927 | 0.026* | |
C20 | 0.1327 (2) | 0.50437 (13) | 0.84382 (19) | 0.0240 (5) | |
H20A | 0.1796 | 0.5479 | 0.8329 | 0.029* | |
H20B | 0.1705 | 0.4827 | 0.9076 | 0.029* | |
C21 | 0.1865 (2) | 0.49694 (13) | 0.66220 (19) | 0.0236 (5) | |
H21A | 0.1447 | 0.5424 | 0.6629 | 0.028* | |
H21B | 0.1513 | 0.4720 | 0.6005 | 0.028* | |
C22 | 0.3349 (2) | 0.50451 (12) | 0.65295 (19) | 0.0220 (5) | |
H22A | 0.3563 | 0.5386 | 0.5986 | 0.026* | |
H22B | 0.3742 | 0.5196 | 0.7206 | 0.026* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br3 | 0.03397 (16) | 0.02065 (14) | 0.03309 (16) | 0.00244 (10) | −0.00074 (11) | 0.00123 (10) |
Br1 | 0.03250 (16) | 0.02541 (15) | 0.03992 (17) | −0.00080 (10) | −0.00837 (12) | 0.00189 (11) |
Br2 | 0.02768 (15) | 0.02353 (14) | 0.03408 (16) | −0.00057 (10) | 0.00098 (11) | −0.00788 (10) |
O1 | 0.0229 (8) | 0.0193 (8) | 0.0295 (9) | 0.0012 (7) | 0.0038 (7) | −0.0039 (7) |
O2 | 0.0401 (10) | 0.0179 (8) | 0.0262 (9) | −0.0012 (7) | 0.0115 (8) | −0.0003 (7) |
O3 | 0.0238 (8) | 0.0180 (8) | 0.0257 (9) | −0.0021 (7) | −0.0003 (7) | 0.0025 (7) |
N1 | 0.0225 (10) | 0.0202 (10) | 0.0278 (11) | −0.0016 (8) | 0.0023 (8) | −0.0025 (8) |
N2 | 0.0267 (11) | 0.0240 (10) | 0.0260 (11) | −0.0010 (9) | 0.0063 (9) | −0.0018 (9) |
N3 | 0.0264 (10) | 0.0199 (10) | 0.0206 (10) | 0.0011 (8) | 0.0007 (8) | 0.0024 (8) |
C1 | 0.0247 (11) | 0.0212 (11) | 0.0153 (10) | 0.0005 (9) | 0.0012 (9) | 0.0006 (9) |
C2 | 0.0291 (12) | 0.0222 (12) | 0.0179 (11) | −0.0013 (10) | 0.0010 (9) | −0.0002 (9) |
C3 | 0.0279 (12) | 0.0309 (13) | 0.0195 (11) | −0.0074 (10) | −0.0037 (10) | 0.0033 (10) |
C4 | 0.0212 (11) | 0.0323 (13) | 0.0253 (12) | 0.0010 (10) | −0.0005 (10) | 0.0081 (11) |
C5 | 0.0281 (12) | 0.0223 (12) | 0.0227 (12) | 0.0055 (10) | 0.0042 (10) | 0.0053 (10) |
C6 | 0.0255 (12) | 0.0193 (11) | 0.0180 (11) | −0.0001 (9) | 0.0006 (9) | 0.0018 (9) |
C7 | 0.0271 (12) | 0.0205 (12) | 0.0228 (12) | 0.0008 (10) | 0.0003 (10) | −0.0023 (9) |
C8 | 0.0290 (13) | 0.0298 (13) | 0.0243 (12) | −0.0027 (11) | 0.0019 (10) | −0.0002 (11) |
C9 | 0.0282 (13) | 0.0191 (11) | 0.0297 (13) | −0.0021 (10) | 0.0027 (10) | 0.0006 (10) |
C10 | 0.0282 (12) | 0.0272 (13) | 0.0223 (12) | −0.0011 (10) | 0.0017 (10) | −0.0025 (10) |
C11 | 0.0330 (14) | 0.0224 (12) | 0.0202 (12) | 0.0036 (10) | 0.0042 (10) | 0.0039 (10) |
C12 | 0.0289 (12) | 0.0221 (11) | 0.0161 (11) | −0.0021 (10) | 0.0005 (9) | 0.0020 (9) |
C13 | 0.0264 (12) | 0.0205 (11) | 0.0167 (11) | −0.0013 (9) | 0.0025 (9) | −0.0010 (9) |
C14 | 0.0299 (13) | 0.0274 (13) | 0.0230 (12) | −0.0067 (11) | 0.0043 (10) | −0.0036 (10) |
C15 | 0.0241 (12) | 0.0384 (15) | 0.0246 (13) | −0.0007 (11) | 0.0031 (10) | −0.0082 (11) |
C16 | 0.0290 (13) | 0.0321 (14) | 0.0197 (12) | 0.0070 (11) | −0.0001 (10) | −0.0047 (10) |
C17 | 0.0306 (13) | 0.0215 (12) | 0.0185 (11) | 0.0013 (10) | −0.0014 (9) | −0.0038 (9) |
C18 | 0.0234 (11) | 0.0220 (11) | 0.0139 (10) | −0.0005 (9) | 0.0003 (8) | −0.0023 (9) |
C19 | 0.0307 (12) | 0.0158 (11) | 0.0194 (11) | −0.0033 (9) | 0.0020 (9) | −0.0006 (9) |
C20 | 0.0291 (12) | 0.0215 (12) | 0.0214 (12) | −0.0049 (10) | 0.0033 (10) | −0.0017 (10) |
C21 | 0.0296 (12) | 0.0214 (12) | 0.0200 (11) | 0.0030 (10) | 0.0027 (10) | 0.0020 (9) |
C22 | 0.0283 (12) | 0.0183 (11) | 0.0193 (11) | 0.0035 (9) | 0.0021 (9) | −0.0015 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.365 (3) | C8—H8A | 0.9900 |
O1—C22 | 1.443 (3) | C8—H8B | 0.9900 |
O2—C20 | 1.425 (3) | C9—H9A | 0.9900 |
O2—C21 | 1.429 (3) | C9—H9B | 0.9900 |
O3—C18 | 1.364 (3) | C10—C11 | 1.526 (3) |
O3—C19 | 1.439 (3) | C10—H10A | 0.9900 |
N1—C8 | 1.495 (3) | C10—H10B | 0.9900 |
N1—C7 | 1.510 (3) | C11—H11A | 0.9900 |
N1—H1A | 0.9200 | C11—H11B | 0.9900 |
N1—H1C | 0.9200 | C12—C13 | 1.507 (3) |
N2—C10 | 1.491 (3) | C12—H12A | 0.9900 |
N2—C9 | 1.501 (3) | C12—H12B | 0.9900 |
N2—H2A | 0.9200 | C13—C14 | 1.391 (3) |
N2—H2C | 0.9200 | C13—C18 | 1.401 (3) |
N3—C11 | 1.485 (3) | C14—C15 | 1.387 (4) |
N3—C12 | 1.510 (3) | C14—H14A | 0.9500 |
N3—H3A | 0.9200 | C15—C16 | 1.388 (4) |
N3—H3C | 0.9200 | C15—H15A | 0.9500 |
C1—C2 | 1.394 (3) | C16—C17 | 1.384 (4) |
C1—C6 | 1.404 (3) | C16—H16A | 0.9500 |
C2—C3 | 1.390 (4) | C17—C18 | 1.393 (3) |
C2—H2B | 0.9500 | C17—H17A | 0.9500 |
C3—C4 | 1.379 (4) | C19—C20 | 1.505 (3) |
C3—H3B | 0.9500 | C19—H19A | 0.9900 |
C4—C5 | 1.395 (4) | C19—H19B | 0.9900 |
C4—H4A | 0.9500 | C20—H20A | 0.9900 |
C5—C6 | 1.387 (3) | C20—H20B | 0.9900 |
C5—H5A | 0.9500 | C21—C22 | 1.504 (3) |
C6—C7 | 1.505 (3) | C21—H21A | 0.9900 |
C7—H7A | 0.9900 | C21—H21B | 0.9900 |
C7—H7B | 0.9900 | C22—H22A | 0.9900 |
C8—C9 | 1.498 (4) | C22—H22B | 0.9900 |
| | | |
C1—O1—C22 | 118.08 (18) | C11—C10—H10A | 108.8 |
C20—O2—C21 | 113.65 (19) | N2—C10—H10B | 108.8 |
C18—O3—C19 | 119.13 (18) | C11—C10—H10B | 108.8 |
C8—N1—C7 | 116.4 (2) | H10A—C10—H10B | 107.7 |
C8—N1—H1A | 108.2 | N3—C11—C10 | 111.9 (2) |
C7—N1—H1A | 108.2 | N3—C11—H11A | 109.2 |
C8—N1—H1C | 108.2 | C10—C11—H11A | 109.2 |
C7—N1—H1C | 108.2 | N3—C11—H11B | 109.2 |
H1A—N1—H1C | 107.3 | C10—C11—H11B | 109.2 |
C10—N2—C9 | 112.3 (2) | H11A—C11—H11B | 107.9 |
C10—N2—H2A | 109.1 | C13—C12—N3 | 114.5 (2) |
C9—N2—H2A | 109.1 | C13—C12—H12A | 108.6 |
C10—N2—H2C | 109.1 | N3—C12—H12A | 108.6 |
C9—N2—H2C | 109.1 | C13—C12—H12B | 108.6 |
H2A—N2—H2C | 107.9 | N3—C12—H12B | 108.6 |
C11—N3—C12 | 113.31 (19) | H12A—C12—H12B | 107.6 |
C11—N3—H3A | 108.9 | C14—C13—C18 | 118.3 (2) |
C12—N3—H3A | 108.9 | C14—C13—C12 | 121.3 (2) |
C11—N3—H3C | 108.9 | C18—C13—C12 | 120.2 (2) |
C12—N3—H3C | 108.9 | C15—C14—C13 | 121.8 (2) |
H3A—N3—H3C | 107.7 | C15—C14—H14A | 119.1 |
O1—C1—C2 | 124.3 (2) | C13—C14—H14A | 119.1 |
O1—C1—C6 | 115.7 (2) | C16—C15—C14 | 118.7 (2) |
C2—C1—C6 | 120.0 (2) | C16—C15—H15A | 120.6 |
C3—C2—C1 | 120.0 (2) | C14—C15—H15A | 120.6 |
C3—C2—H2B | 120.0 | C17—C16—C15 | 121.0 (2) |
C1—C2—H2B | 120.0 | C17—C16—H16A | 119.5 |
C4—C3—C2 | 120.8 (2) | C15—C16—H16A | 119.5 |
C4—C3—H3B | 119.6 | C16—C17—C18 | 119.6 (2) |
C2—C3—H3B | 119.6 | C16—C17—H17A | 120.2 |
C3—C4—C5 | 119.0 (2) | C18—C17—H17A | 120.2 |
C3—C4—H4A | 120.5 | O3—C18—C17 | 123.9 (2) |
C5—C4—H4A | 120.5 | O3—C18—C13 | 115.6 (2) |
C6—C5—C4 | 121.6 (2) | C17—C18—C13 | 120.5 (2) |
C6—C5—H5A | 119.2 | O3—C19—C20 | 105.48 (19) |
C4—C5—H5A | 119.2 | O3—C19—H19A | 110.6 |
C5—C6—C1 | 118.6 (2) | C20—C19—H19A | 110.6 |
C5—C6—C7 | 120.4 (2) | O3—C19—H19B | 110.6 |
C1—C6—C7 | 120.8 (2) | C20—C19—H19B | 110.6 |
C6—C7—N1 | 113.5 (2) | H19A—C19—H19B | 108.8 |
C6—C7—H7A | 108.9 | O2—C20—C19 | 110.6 (2) |
N1—C7—H7A | 108.9 | O2—C20—H20A | 109.5 |
C6—C7—H7B | 108.9 | C19—C20—H20A | 109.5 |
N1—C7—H7B | 108.9 | O2—C20—H20B | 109.5 |
H7A—C7—H7B | 107.7 | C19—C20—H20B | 109.5 |
N1—C8—C9 | 113.7 (2) | H20A—C20—H20B | 108.1 |
N1—C8—H8A | 108.8 | O2—C21—C22 | 111.2 (2) |
C9—C8—H8A | 108.8 | O2—C21—H21A | 109.4 |
N1—C8—H8B | 108.8 | C22—C21—H21A | 109.4 |
C9—C8—H8B | 108.8 | O2—C21—H21B | 109.4 |
H8A—C8—H8B | 107.7 | C22—C21—H21B | 109.4 |
C8—C9—N2 | 112.6 (2) | H21A—C21—H21B | 108.0 |
C8—C9—H9A | 109.1 | O1—C22—C21 | 107.16 (19) |
N2—C9—H9A | 109.1 | O1—C22—H22A | 110.3 |
C8—C9—H9B | 109.1 | C21—C22—H22A | 110.3 |
N2—C9—H9B | 109.1 | O1—C22—H22B | 110.3 |
H9A—C9—H9B | 107.8 | C21—C22—H22B | 110.3 |
N2—C10—C11 | 114.0 (2) | H22A—C22—H22B | 108.5 |
N2—C10—H10A | 108.8 | | |
| | | |
C22—O1—C1—C2 | 8.8 (3) | C11—N3—C12—C13 | 52.8 (3) |
C22—O1—C1—C6 | −170.7 (2) | N3—C12—C13—C14 | 90.6 (3) |
O1—C1—C2—C3 | 178.2 (2) | N3—C12—C13—C18 | −95.1 (3) |
C6—C1—C2—C3 | −2.3 (4) | C18—C13—C14—C15 | −0.8 (4) |
C1—C2—C3—C4 | 1.1 (4) | C12—C13—C14—C15 | 173.6 (2) |
C2—C3—C4—C5 | 0.5 (4) | C13—C14—C15—C16 | −1.5 (4) |
C3—C4—C5—C6 | −1.0 (4) | C14—C15—C16—C17 | 2.0 (4) |
C4—C5—C6—C1 | −0.2 (4) | C15—C16—C17—C18 | −0.3 (4) |
C4—C5—C6—C7 | 174.8 (2) | C19—O3—C18—C17 | −6.7 (3) |
O1—C1—C6—C5 | −178.7 (2) | C19—O3—C18—C13 | 174.4 (2) |
C2—C1—C6—C5 | 1.8 (3) | C16—C17—C18—O3 | 179.2 (2) |
O1—C1—C6—C7 | 6.4 (3) | C16—C17—C18—C13 | −2.0 (3) |
C2—C1—C6—C7 | −173.2 (2) | C14—C13—C18—O3 | −178.6 (2) |
C5—C6—C7—N1 | 90.8 (3) | C12—C13—C18—O3 | 7.0 (3) |
C1—C6—C7—N1 | −94.3 (3) | C14—C13—C18—C17 | 2.5 (3) |
C8—N1—C7—C6 | 63.1 (3) | C12—C13—C18—C17 | −171.9 (2) |
C7—N1—C8—C9 | 71.2 (3) | C18—O3—C19—C20 | −169.61 (19) |
N1—C8—C9—N2 | 82.0 (3) | C21—O2—C20—C19 | 98.3 (2) |
C10—N2—C9—C8 | −175.9 (2) | O3—C19—C20—O2 | 68.5 (2) |
C9—N2—C10—C11 | −65.3 (3) | C20—O2—C21—C22 | 90.4 (2) |
C12—N3—C11—C10 | 173.7 (2) | C1—O1—C22—C21 | 176.5 (2) |
N2—C10—C11—N3 | −84.5 (3) | O2—C21—C22—O1 | 74.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br2 | 0.92 | 2.37 | 3.269 (2) | 167 |
N1—H1C···Br1 | 0.92 | 2.37 | 3.230 (2) | 157 |
N2—H2A···Br2 | 0.92 | 2.36 | 3.246 (2) | 161 |
N2—H2C···Br3 | 0.92 | 2.44 | 3.288 (2) | 154 |
N3—H3A···Br3 | 0.92 | 2.43 | 3.307 (2) | 160 |
N3—H3C···Br1i | 0.92 | 2.38 | 3.270 (2) | 164 |
Symmetry code: (i) x−1, y, z. |