Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019556/nc2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019556/nc2016Isup2.hkl |
CCDC reference: 610854
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.037
- wR factor = 0.098
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.07 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.86 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 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 1.069 Tmax scaled 0.850 Tmin scaled 0.717
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C20H14BrN3O3·0.5C7H8 | Z = 2 |
Mr = 470.32 | F(000) = 478 |
Triclinic, P1 | Dx = 1.516 Mg m−3 |
Hall symbol: -P 1 | Melting point: 488 K |
a = 8.2708 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7547 (3) Å | Cell parameters from 15871 reflections |
c = 12.3929 (3) Å | θ = 2.0–27.5° |
α = 88.1844 (17)° | µ = 2.03 mm−1 |
β = 85.3535 (16)° | T = 160 K |
γ = 69.6152 (13)° | Tablet, orange |
V = 1029.91 (5) Å3 | 0.20 × 0.13 × 0.08 mm |
Nonius KappaCCD area-detector diffractometer | 4718 independent reflections |
Radiation source: Nonius FR590 sealed tube generator | 3707 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.047 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 2.0° |
φ and ω scans with κ offsets | h = −10→10 |
Absorption correction: multi-scan (Blessing, 1995) | k = −13→13 |
Tmin = 0.671, Tmax = 0.795 | l = −16→16 |
23736 measured reflections |
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)] = 0.037 | Hydrogen site location: geom & difmap |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.053P)2 + 0.3064P] where P = (Fo2 + 2Fc2)/3 |
4718 reflections | (Δ/σ)max = 0.001 |
304 parameters | Δρmax = 0.39 e Å−3 |
42 restraints | Δρmin = −0.54 e Å−3 |
Experimental. Solvent used: toluene Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.516 (1) Frames collected: 361 Seconds exposure per frame: 24 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 33.0 |
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) | |
Br | 0.44009 (4) | 0.04891 (3) | 0.766823 (18) | 0.05472 (12) | |
O1 | 1.3161 (2) | 0.42359 (16) | −0.20657 (14) | 0.0430 (4) | |
H1 | 1.284 (4) | 0.418 (3) | −0.151 (3) | 0.065 (10)* | |
O2 | 1.4231 (2) | 0.55577 (18) | −0.30282 (13) | 0.0528 (4) | |
O3 | 0.9806 (2) | 0.01190 (14) | 0.16860 (13) | 0.0379 (3) | |
H3 | 0.935 (4) | 0.018 (3) | 0.235 (3) | 0.064 (9)* | |
N1 | 1.2353 (2) | 0.46922 (16) | −0.00150 (13) | 0.0301 (4) | |
N2 | 1.1797 (2) | 0.44947 (16) | 0.09301 (13) | 0.0307 (4) | |
N3 | 0.8637 (2) | 0.10556 (17) | 0.35734 (14) | 0.0321 (4) | |
C1 | 1.3672 (3) | 0.5279 (2) | −0.21609 (18) | 0.0377 (5) | |
C2 | 1.3519 (3) | 0.6092 (2) | −0.11623 (17) | 0.0323 (4) | |
C3 | 1.2868 (2) | 0.58301 (19) | −0.01285 (16) | 0.0299 (4) | |
C4 | 1.2786 (3) | 0.6647 (2) | 0.07402 (18) | 0.0351 (5) | |
H4 | 1.2337 | 0.6470 | 0.1435 | 0.042* | |
C5 | 1.3351 (3) | 0.7707 (2) | 0.0599 (2) | 0.0393 (5) | |
H5 | 1.3295 | 0.8259 | 0.1194 | 0.047* | |
C6 | 1.4002 (3) | 0.7969 (2) | −0.0416 (2) | 0.0409 (5) | |
H6 | 1.4399 | 0.8697 | −0.0513 | 0.049* | |
C7 | 1.4076 (3) | 0.7175 (2) | −0.12851 (19) | 0.0385 (5) | |
H7 | 1.4512 | 0.7370 | −0.1978 | 0.046* | |
C8 | 1.1351 (2) | 0.33465 (19) | 0.10655 (16) | 0.0292 (4) | |
C9 | 1.0639 (3) | 0.3183 (2) | 0.20855 (16) | 0.0302 (4) | |
H9 | 1.0518 | 0.3815 | 0.2633 | 0.036* | |
C10 | 1.0092 (2) | 0.21081 (19) | 0.23262 (15) | 0.0289 (4) | |
C11 | 1.0312 (3) | 0.11612 (19) | 0.15073 (16) | 0.0308 (4) | |
C12 | 1.1057 (3) | 0.1325 (2) | 0.04804 (17) | 0.0336 (4) | |
H12 | 1.1212 | 0.0686 | −0.0067 | 0.040* | |
C13 | 1.1561 (3) | 0.2394 (2) | 0.02591 (16) | 0.0319 (4) | |
H13 | 1.2056 | 0.2496 | −0.0442 | 0.038* | |
C14 | 0.9216 (3) | 0.2012 (2) | 0.33750 (16) | 0.0320 (4) | |
H14 | 0.9071 | 0.2657 | 0.3915 | 0.038* | |
C15 | 0.7677 (3) | 0.0982 (2) | 0.45573 (16) | 0.0326 (4) | |
C16 | 0.6688 (3) | 0.2086 (2) | 0.51642 (18) | 0.0394 (5) | |
H16 | 0.6655 | 0.2944 | 0.4933 | 0.047* | |
C17 | 0.5748 (3) | 0.1940 (2) | 0.61074 (18) | 0.0424 (5) | |
H17 | 0.5088 | 0.2691 | 0.6534 | 0.051* | |
C18 | 0.5788 (3) | 0.0681 (2) | 0.64176 (16) | 0.0376 (5) | |
C19 | 0.6741 (3) | −0.0424 (2) | 0.58207 (18) | 0.0379 (5) | |
H19 | 0.6750 | −0.1279 | 0.6045 | 0.046* | |
C20 | 0.7687 (3) | −0.0268 (2) | 0.48883 (17) | 0.0356 (5) | |
H20 | 0.8352 | −0.1024 | 0.4468 | 0.043* | |
C21 | −0.0859 (13) | 0.3670 (8) | 0.6524 (6) | 0.090 (2) | 0.50 |
H21A | −0.1945 | 0.4248 | 0.6888 | 0.135* | 0.50 |
H21B | 0.0030 | 0.3373 | 0.7046 | 0.135* | 0.50 |
H21C | −0.1036 | 0.2898 | 0.6227 | 0.135* | 0.50 |
C22 | −0.0283 (7) | 0.4422 (5) | 0.5623 (3) | 0.0560 (14) | 0.50 |
C23 | −0.1486 (5) | 0.5402 (5) | 0.5054 (4) | 0.059 (2) | 0.50 |
H23 | −0.2687 | 0.5610 | 0.5240 | 0.070* | 0.50 |
C24 | −0.0929 (10) | 0.6079 (4) | 0.4215 (4) | 0.076 (2) | 0.50 |
H24 | −0.1751 | 0.6749 | 0.3826 | 0.091* | 0.50 |
C25 | 0.0829 (11) | 0.5775 (6) | 0.3943 (3) | 0.080 (2) | 0.50 |
H25 | 0.1210 | 0.6238 | 0.3369 | 0.096* | 0.50 |
C26 | 0.2032 (7) | 0.4795 (7) | 0.4511 (4) | 0.075 (2) | 0.50 |
H26 | 0.3233 | 0.4587 | 0.4326 | 0.090* | 0.50 |
C27 | 0.1475 (6) | 0.4118 (5) | 0.5351 (4) | 0.0517 (18) | 0.50 |
H27 | 0.2297 | 0.3448 | 0.5739 | 0.062* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.0791 (2) | 0.0700 (2) | 0.03262 (14) | −0.05045 (16) | 0.00867 (11) | −0.00286 (11) |
O1 | 0.0588 (11) | 0.0394 (9) | 0.0303 (8) | −0.0175 (8) | 0.0041 (8) | −0.0060 (7) |
O2 | 0.0641 (11) | 0.0561 (10) | 0.0358 (9) | −0.0208 (9) | 0.0101 (8) | 0.0005 (8) |
O3 | 0.0499 (9) | 0.0324 (8) | 0.0354 (8) | −0.0209 (7) | 0.0077 (7) | −0.0081 (6) |
N1 | 0.0308 (8) | 0.0283 (8) | 0.0313 (9) | −0.0103 (7) | −0.0026 (7) | −0.0007 (7) |
N2 | 0.0323 (9) | 0.0301 (8) | 0.0305 (8) | −0.0115 (7) | −0.0015 (7) | −0.0027 (7) |
N3 | 0.0363 (9) | 0.0321 (9) | 0.0290 (8) | −0.0135 (8) | −0.0012 (7) | −0.0011 (7) |
C1 | 0.0363 (11) | 0.0354 (11) | 0.0364 (11) | −0.0067 (9) | −0.0008 (9) | 0.0019 (9) |
C2 | 0.0271 (10) | 0.0309 (10) | 0.0350 (11) | −0.0054 (8) | −0.0024 (8) | 0.0013 (8) |
C3 | 0.0272 (10) | 0.0264 (9) | 0.0349 (10) | −0.0077 (8) | −0.0023 (8) | −0.0005 (8) |
C4 | 0.0367 (11) | 0.0326 (11) | 0.0359 (11) | −0.0120 (9) | −0.0025 (9) | −0.0028 (9) |
C5 | 0.0396 (12) | 0.0300 (11) | 0.0492 (13) | −0.0113 (9) | −0.0089 (10) | −0.0049 (9) |
C6 | 0.0352 (11) | 0.0318 (11) | 0.0580 (14) | −0.0140 (10) | −0.0073 (10) | 0.0039 (10) |
C7 | 0.0323 (11) | 0.0364 (11) | 0.0455 (12) | −0.0112 (9) | −0.0023 (9) | 0.0083 (10) |
C8 | 0.0301 (10) | 0.0275 (10) | 0.0304 (10) | −0.0099 (8) | −0.0030 (8) | −0.0037 (8) |
C9 | 0.0328 (10) | 0.0298 (10) | 0.0281 (9) | −0.0105 (8) | −0.0025 (8) | −0.0063 (8) |
C10 | 0.0299 (10) | 0.0292 (10) | 0.0274 (9) | −0.0098 (8) | −0.0018 (8) | −0.0045 (8) |
C11 | 0.0305 (10) | 0.0269 (10) | 0.0347 (10) | −0.0097 (8) | −0.0004 (8) | −0.0036 (8) |
C12 | 0.0382 (11) | 0.0304 (10) | 0.0319 (10) | −0.0118 (9) | 0.0029 (8) | −0.0098 (8) |
C13 | 0.0341 (10) | 0.0305 (10) | 0.0289 (10) | −0.0092 (9) | 0.0024 (8) | −0.0042 (8) |
C14 | 0.0366 (11) | 0.0327 (10) | 0.0272 (10) | −0.0121 (9) | −0.0038 (8) | −0.0033 (8) |
C15 | 0.0369 (11) | 0.0353 (11) | 0.0280 (10) | −0.0154 (9) | −0.0030 (8) | 0.0007 (8) |
C16 | 0.0520 (13) | 0.0334 (11) | 0.0358 (11) | −0.0203 (10) | 0.0043 (10) | −0.0003 (9) |
C17 | 0.0549 (14) | 0.0403 (12) | 0.0353 (11) | −0.0224 (11) | 0.0077 (10) | −0.0071 (9) |
C18 | 0.0485 (12) | 0.0490 (13) | 0.0257 (10) | −0.0300 (11) | −0.0041 (9) | 0.0028 (9) |
C19 | 0.0460 (12) | 0.0363 (11) | 0.0374 (11) | −0.0210 (10) | −0.0085 (10) | 0.0070 (9) |
C20 | 0.0399 (11) | 0.0326 (11) | 0.0363 (11) | −0.0145 (9) | −0.0047 (9) | −0.0006 (9) |
C21 | 0.133 (6) | 0.082 (5) | 0.071 (5) | −0.064 (4) | 0.029 (4) | −0.026 (4) |
C22 | 0.072 (4) | 0.058 (3) | 0.049 (3) | −0.038 (3) | 0.015 (3) | −0.026 (3) |
C23 | 0.060 (4) | 0.047 (4) | 0.069 (5) | −0.016 (3) | −0.010 (3) | −0.022 (4) |
C24 | 0.110 (6) | 0.057 (4) | 0.070 (5) | −0.036 (4) | −0.029 (4) | −0.009 (4) |
C25 | 0.145 (6) | 0.073 (4) | 0.048 (4) | −0.070 (4) | 0.004 (4) | −0.022 (3) |
C26 | 0.091 (5) | 0.082 (4) | 0.067 (4) | −0.055 (4) | 0.032 (3) | −0.035 (3) |
C27 | 0.057 (3) | 0.056 (4) | 0.047 (4) | −0.024 (3) | −0.006 (3) | −0.007 (3) |
Br—C18 | 1.902 (2) | C12—C13 | 1.366 (3) |
O1—C1 | 1.329 (3) | C12—H12 | 0.9500 |
O1—H1 | 0.73 (3) | C13—H13 | 0.9500 |
O2—C1 | 1.206 (3) | C14—H14 | 0.9500 |
O3—C11 | 1.333 (2) | C15—C16 | 1.387 (3) |
O3—H3 | 0.87 (3) | C15—C20 | 1.391 (3) |
N1—N2 | 1.262 (2) | C16—C17 | 1.386 (3) |
N1—C3 | 1.429 (3) | C16—H16 | 0.9500 |
N2—C8 | 1.408 (3) | C17—C18 | 1.387 (3) |
N3—C14 | 1.286 (3) | C17—H17 | 0.9500 |
N3—C15 | 1.416 (3) | C18—C19 | 1.374 (3) |
C1—C2 | 1.509 (3) | C19—C20 | 1.381 (3) |
C2—C7 | 1.394 (3) | C19—H19 | 0.9500 |
C2—C3 | 1.408 (3) | C20—H20 | 0.9500 |
C3—C4 | 1.393 (3) | C21—C22 | 1.501 (8) |
C4—C5 | 1.377 (3) | C21—H21A | 0.9800 |
C4—H4 | 0.9500 | C21—H21B | 0.9800 |
C5—C6 | 1.387 (3) | C21—H21C | 0.9800 |
C5—H5 | 0.9500 | C22—C23 | 1.3900 |
C6—C7 | 1.380 (3) | C22—C27 | 1.3900 |
C6—H6 | 0.9500 | C23—C24 | 1.3900 |
C7—H7 | 0.9500 | C23—H23 | 0.9500 |
C8—C9 | 1.383 (3) | C24—C25 | 1.3900 |
C8—C13 | 1.411 (3) | C24—H24 | 0.9500 |
C9—C10 | 1.396 (3) | C25—C26 | 1.3900 |
C9—H9 | 0.9500 | C25—H25 | 0.9500 |
C10—C11 | 1.417 (3) | C26—C27 | 1.3900 |
C10—C14 | 1.455 (3) | C26—H26 | 0.9500 |
C11—C12 | 1.402 (3) | C27—H27 | 0.9500 |
C1—O1—H1 | 110 (3) | N3—C14—H14 | 119.9 |
C11—O3—H3 | 107 (2) | C10—C14—H14 | 119.9 |
N2—N1—C3 | 114.77 (16) | C16—C15—C20 | 119.55 (19) |
N1—N2—C8 | 115.49 (16) | C16—C15—N3 | 123.41 (18) |
C14—N3—C15 | 121.65 (18) | C20—C15—N3 | 116.98 (19) |
O2—C1—O1 | 120.1 (2) | C17—C16—C15 | 120.2 (2) |
O2—C1—C2 | 121.8 (2) | C17—C16—H16 | 119.9 |
O1—C1—C2 | 118.12 (18) | C15—C16—H16 | 119.9 |
C7—C2—C3 | 118.3 (2) | C16—C17—C18 | 118.9 (2) |
C7—C2—C1 | 116.84 (19) | C16—C17—H17 | 120.6 |
C3—C2—C1 | 124.82 (18) | C18—C17—H17 | 120.6 |
C4—C3—C2 | 120.05 (18) | C19—C18—C17 | 121.8 (2) |
C4—C3—N1 | 122.57 (18) | C19—C18—Br | 119.18 (16) |
C2—C3—N1 | 117.36 (18) | C17—C18—Br | 118.92 (17) |
C5—C4—C3 | 120.5 (2) | C18—C19—C20 | 118.79 (19) |
C5—C4—H4 | 119.8 | C18—C19—H19 | 120.6 |
C3—C4—H4 | 119.8 | C20—C19—H19 | 120.6 |
C4—C5—C6 | 119.9 (2) | C19—C20—C15 | 120.7 (2) |
C4—C5—H5 | 120.1 | C19—C20—H20 | 119.6 |
C6—C5—H5 | 120.1 | C15—C20—H20 | 119.6 |
C7—C6—C5 | 120.3 (2) | C22—C21—H21A | 109.5 |
C7—C6—H6 | 119.9 | C22—C21—H21B | 109.5 |
C5—C6—H6 | 119.9 | H21A—C21—H21B | 109.5 |
C6—C7—C2 | 121.0 (2) | C22—C21—H21C | 109.5 |
C6—C7—H7 | 119.5 | H21A—C21—H21C | 109.5 |
C2—C7—H7 | 119.5 | H21B—C21—H21C | 109.5 |
C9—C8—N2 | 115.10 (17) | C23—C22—C27 | 120.0 |
C9—C8—C13 | 119.31 (18) | C23—C22—C21 | 120.8 (6) |
N2—C8—C13 | 125.58 (18) | C27—C22—C21 | 119.2 (6) |
C8—C9—C10 | 121.28 (18) | C24—C23—C22 | 120.0 |
C8—C9—H9 | 119.4 | C24—C23—H23 | 120.0 |
C10—C9—H9 | 119.4 | C22—C23—H23 | 120.0 |
C9—C10—C11 | 118.66 (18) | C23—C24—C25 | 120.0 |
C9—C10—C14 | 120.44 (18) | C23—C24—H24 | 120.0 |
C11—C10—C14 | 120.78 (18) | C25—C24—H24 | 120.0 |
O3—C11—C12 | 118.90 (18) | C24—C25—C26 | 120.0 |
O3—C11—C10 | 121.44 (18) | C24—C25—H25 | 120.0 |
C12—C11—C10 | 119.66 (18) | C26—C25—H25 | 120.0 |
C13—C12—C11 | 120.66 (18) | C27—C26—C25 | 120.0 |
C13—C12—H12 | 119.7 | C27—C26—H26 | 120.0 |
C11—C12—H12 | 119.7 | C25—C26—H26 | 120.0 |
C12—C13—C8 | 120.41 (19) | C26—C27—C22 | 120.0 |
C12—C13—H13 | 119.8 | C26—C27—H27 | 120.0 |
C8—C13—H13 | 119.8 | C22—C27—H27 | 120.0 |
N3—C14—C10 | 120.22 (18) | ||
C3—N1—N2—C8 | −177.49 (15) | O3—C11—C12—C13 | 178.73 (18) |
O2—C1—C2—C7 | −0.8 (3) | C10—C11—C12—C13 | −0.5 (3) |
O1—C1—C2—C7 | 179.60 (19) | C11—C12—C13—C8 | 0.5 (3) |
O2—C1—C2—C3 | 179.5 (2) | C9—C8—C13—C12 | 0.4 (3) |
O1—C1—C2—C3 | −0.1 (3) | N2—C8—C13—C12 | −179.05 (19) |
C7—C2—C3—C4 | 0.2 (3) | C15—N3—C14—C10 | −175.66 (17) |
C1—C2—C3—C4 | 179.93 (19) | C9—C10—C14—N3 | 176.46 (18) |
C7—C2—C3—N1 | −178.19 (17) | C11—C10—C14—N3 | 0.4 (3) |
C1—C2—C3—N1 | 1.5 (3) | C14—N3—C15—C16 | 27.4 (3) |
N2—N1—C3—C4 | 0.9 (3) | C14—N3—C15—C20 | −155.52 (19) |
N2—N1—C3—C2 | 179.22 (17) | C20—C15—C16—C17 | 1.5 (3) |
C2—C3—C4—C5 | −0.5 (3) | N3—C15—C16—C17 | 178.5 (2) |
N1—C3—C4—C5 | 177.81 (18) | C15—C16—C17—C18 | −1.3 (4) |
C3—C4—C5—C6 | 0.2 (3) | C16—C17—C18—C19 | 0.5 (4) |
C4—C5—C6—C7 | 0.4 (3) | C16—C17—C18—Br | −176.64 (17) |
C5—C6—C7—C2 | −0.7 (3) | C17—C18—C19—C20 | 0.2 (3) |
C3—C2—C7—C6 | 0.4 (3) | Br—C18—C19—C20 | 177.29 (16) |
C1—C2—C7—C6 | −179.37 (19) | C18—C19—C20—C15 | 0.0 (3) |
N1—N2—C8—C9 | −175.97 (17) | C16—C15—C20—C19 | −0.8 (3) |
N1—N2—C8—C13 | 3.5 (3) | N3—C15—C20—C19 | −177.98 (18) |
N2—C8—C9—C10 | 178.24 (17) | C27—C22—C23—C24 | 0.0 |
C13—C8—C9—C10 | −1.3 (3) | C21—C22—C23—C24 | −179.3 (5) |
C8—C9—C10—C11 | 1.2 (3) | C22—C23—C24—C25 | 0.0 |
C8—C9—C10—C14 | −174.88 (18) | C23—C24—C25—C26 | 0.0 |
C9—C10—C11—O3 | −179.55 (18) | C24—C25—C26—C27 | 0.0 |
C14—C10—C11—O3 | −3.4 (3) | C25—C26—C27—C22 | 0.0 |
C9—C10—C11—C12 | −0.4 (3) | C23—C22—C27—C26 | 0.0 |
C14—C10—C11—C12 | 175.75 (18) | C21—C22—C27—C26 | 179.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.73 (3) | 1.92 (3) | 2.593 (2) | 154 (4) |
O3—H3···N3 | 0.87 (3) | 1.76 (3) | 2.554 (2) | 151 (3) |
C6—H6···Bri | 0.95 | 2.92 | 3.630 (2) | 133 |
C12—H12···O3ii | 0.95 | 2.53 | 3.388 (3) | 151 |
C17—H17···O1iii | 0.95 | 2.49 | 3.419 (3) | 166 |
C26—H26···O2iv | 0.95 | 2.50 | 3.374 (6) | 153 |
Symmetry codes: (i) x+1, y+1, z−1; (ii) −x+2, −y, −z; (iii) x−1, y, z+1; (iv) −x+2, −y+1, −z. |
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