

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008829/cu3152sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESMeOHsup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESEtOHsup3.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESCAFsup4.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESUREFormIIsup5.hkl |
![]() | Rietveld powder data file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESsup6.rtv |
![]() | Rietveld powder data file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESNAMsup7.rtv |
![]() | Rietveld powder data file (CIF format) https://doi.org/10.1107/S2053229619008829/cu3152LESUREFormIsup8.rtv |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619008829/cu3152sup9.pdf |
CCDC references: 1888112; 1888108; 1888111; 1888110; 1888109; 1888107; 1888106
Data collection: DataCollector (PANalytical, 2010) for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Cell refinement: MRIA (Zlokazov & Chernyshev, 1992) for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Data reduction: DataCollector for LESForm2, LESNAM, LESUREFormI; CrystalClear-SM Expert 2.0 (Rigaku, 2009) for LESEtOH; CrysAlis PRO (Rigaku OD, 2015) for LESUREFormII. Program(s) used to solve structure: simulated annealing (Zhukov et al., 2001) for LESForm2, LESNAM, LESUREFormI; SHELXT (Sheldrick, 2015a) for LESEtOH. Program(s) used to refine structure: MRIA for LESForm2, LESNAM, LESUREFormI; SHELXL97 (Sheldrick, 2008a) for LESMeOH; SHELXL2016 (Sheldrick, 2015b) for LESEtOH; SHELXL2014 (Sheldrick, 2015b) for LESCAF; olex2.refine (Bourhis et al., 2015) for LESUREFormII. Molecular graphics: Mercury (Macrae et al., 2008) for LESForm2, LESNAM, LESUREFormI; OLEX2 (Dolomanov et al., 2009) for LESEtOH; OLEX2 (Dolomanov et al., 2009) for LESUREFormII. Software used to prepare material for publication: MRIA and SHELXL97 (Sheldrick, 2008a) for LESForm2, LESNAM, LESUREFormI; OLEX2 (Dolomanov et al., 2009) for LESEtOH; OLEX2 (Dolomanov et al., 2009) for LESUREFormII.
C17H14BrN3O2S | F(000) = 1632 |
Mr = 404.28 | Dx = 1.525 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ac 2ab | T = 298 K |
a = 22.1247 (17) Å | Particle morphology: needle |
b = 8.7081 (8) Å | colorless |
c = 18.2738 (15) Å | flat_sheet, 15 × 1 mm |
V = 3520.7 (5) Å3 | Specimen preparation: Prepared at 298 K and 101 kPa |
Z = 8 |
EMPYREAN (PANanalytical) diffractometer | Data collection mode: reflection |
Radiation source: line-focus sealed tube | Scan method: continuous |
Curved Germanium (111) monochromator | 2θmin = 5.004°, 2θmax = 80.008°, 2θstep = 0.017° |
Specimen mounting: thin layer on the non-diffracting silicon plate |
Refinement on Inet | 132 parameters |
Least-squares matrix: full with fixed elements per cycle | 78 restraints |
Rp = 0.032 | 0 constraints |
Rwp = 0.042 | H-atom parameters not refined |
Rexp = 0.022 | Weighting scheme based on measured s.u.'s |
RBragg = 0.065 | (Δ/σ)max = 0.004 |
4413 data points | Background function: Chebyshev polynomial up to the 5th order |
Excluded region(s): none | Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [010], texture parameter r = 1.09(1). |
Profile function: split-type pseudo-Voigt (Toraya, 1986) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.25630 (6) | 0.62021 (15) | 0.80770 (8) | 0.0641 (7)* | |
S1 | 0.47830 (14) | 0.4168 (3) | 0.91070 (18) | 0.0570 (15)* | |
O1 | 0.4941 (3) | 0.6432 (7) | 0.7807 (3) | 0.061 (3)* | |
O2 | 0.5854 (3) | 0.5645 (8) | 0.7597 (4) | 0.058 (3)* | |
H2 | 0.5867 | 0.6424 | 0.7345 | 0.087* | |
N1 | 0.3724 (3) | 0.5451 (8) | 0.8737 (5) | 0.060 (4)* | |
N2 | 0.3379 (4) | 0.3943 (9) | 0.7863 (4) | 0.062 (4)* | |
N3 | 0.3915 (4) | 0.3324 (9) | 0.8117 (4) | 0.059 (4)* | |
C1 | 0.3753 (4) | 0.6723 (11) | 0.9268 (6) | 0.062 (5)* | |
C2 | 0.3495 (5) | 0.6511 (10) | 0.9973 (6) | 0.070 (5)* | |
C3 | 0.3505 (5) | 0.7805 (12) | 1.0451 (5) | 0.066 (5)* | |
C4 | 0.3738 (4) | 0.9229 (11) | 1.0206 (6) | 0.061 (5)* | |
C5 | 0.4001 (4) | 0.9329 (12) | 0.9533 (6) | 0.064 (5)* | |
H5 | 0.4191 | 1.0238 | 0.9398 | 0.077* | |
C6 | 0.3993 (4) | 0.8072 (12) | 0.9028 (6) | 0.060 (5)* | |
H6 | 0.4145 | 0.8173 | 0.8556 | 0.072* | |
C7 | 0.3229 (5) | 0.5120 (13) | 1.0201 (6) | 0.063 (5)* | |
H7 | 0.3232 | 0.4288 | 0.9881 | 0.076* | |
C8 | 0.2967 (5) | 0.4947 (13) | 1.0872 (6) | 0.068 (5)* | |
H8 | 0.2790 | 0.4027 | 1.1016 | 0.082* | |
C9 | 0.2981 (5) | 0.6264 (11) | 1.1342 (8) | 0.072 (5)* | |
H9 | 0.2814 | 0.6188 | 1.1808 | 0.086* | |
C10 | 0.3225 (4) | 0.7588 (14) | 1.1137 (7) | 0.070 (5)* | |
H10 | 0.3211 | 0.8412 | 1.1461 | 0.084* | |
C11 | 0.3788 (5) | 1.0585 (12) | 1.0703 (6) | 0.060 (5)* | |
H11 | 0.3413 | 1.1020 | 1.0899 | 0.072* | |
C12 | 0.4313 (4) | 1.1643 (11) | 1.0604 (6) | 0.070 (5)* | |
H12A | 0.4577 | 1.1462 | 1.0189 | 0.084* | |
H12B | 0.4254 | 1.2716 | 1.0726 | 0.084* | |
C13 | 0.4336 (4) | 1.0553 (10) | 1.1202 (6) | 0.072 (5)* | |
H13A | 0.4289 | 1.0947 | 1.1695 | 0.086* | |
H13B | 0.4611 | 0.9691 | 1.1157 | 0.086* | |
C14 | 0.3271 (5) | 0.5148 (13) | 0.8249 (6) | 0.064 (5)* | |
C15 | 0.4120 (4) | 0.4269 (11) | 0.8627 (7) | 0.067 (5)* | |
C16 | 0.5328 (5) | 0.4103 (11) | 0.8358 (6) | 0.074 (5)* | |
H16A | 0.5728 | 0.3935 | 0.8560 | 0.089* | |
H16B | 0.5233 | 0.3237 | 0.8045 | 0.089* | |
C17 | 0.5338 (5) | 0.5543 (12) | 0.7900 (6) | 0.069 (5)* |
Br1—C14 | 1.842 (10) | C5—H5 | 0.9303 |
S1—C15 | 1.711 (11) | C6—H6 | 0.9299 |
S1—C16 | 1.825 (12) | C7—C8 | 1.366 (15) |
O1—C17 | 1.183 (12) | C7—H7 | 0.9296 |
O2—C17 | 1.272 (12) | C8—C9 | 1.433 (16) |
O2—H2 | 0.8202 | C8—H8 | 0.9300 |
N1—C15 | 1.368 (12) | C9—C10 | 1.327 (16) |
N1—C14 | 1.367 (13) | C9—H9 | 0.9298 |
N1—C1 | 1.474 (13) | C10—H10 | 0.9299 |
N2—C14 | 1.287 (14) | C11—C12 | 1.493 (14) |
N2—N3 | 1.383 (11) | C11—C13 | 1.517 (15) |
N3—C15 | 1.324 (13) | C11—H11 | 0.9803 |
C1—C6 | 1.362 (14) | C12—C13 | 1.448 (15) |
C1—C2 | 1.421 (15) | C12—H12A | 0.9701 |
C2—C7 | 1.410 (14) | C12—H12B | 0.9702 |
C2—C3 | 1.425 (14) | C13—H13A | 0.9701 |
C3—C10 | 1.412 (15) | C13—H13B | 0.9697 |
C3—C4 | 1.416 (14) | C16—C17 | 1.507 (14) |
C4—C5 | 1.363 (15) | C16—H16A | 0.9702 |
C4—C11 | 1.494 (14) | C16—H16B | 0.9702 |
C5—C6 | 1.432 (15) | ||
C15—S1—C16 | 100.6 (5) | C9—C10—H10 | 118.5 |
C17—O2—H2 | 109.5 | C3—C10—H10 | 118.5 |
C15—N1—C14 | 103.2 (8) | C12—C11—C4 | 118.1 (9) |
C15—N1—C1 | 129.4 (8) | C12—C11—C13 | 57.5 (7) |
C14—N1—C1 | 127.3 (8) | C4—C11—C13 | 114.2 (8) |
C14—N2—N3 | 107.1 (8) | C12—C11—H11 | 117.7 |
C15—N3—N2 | 106.7 (8) | C4—C11—H11 | 117.6 |
C6—C1—C2 | 124.1 (9) | C13—C11—H11 | 117.7 |
C6—C1—N1 | 116.9 (9) | C13—C12—C11 | 62.1 (7) |
C2—C1—N1 | 118.8 (8) | C13—C12—H12A | 117.6 |
C7—C2—C1 | 123.1 (9) | C11—C12—H12A | 117.6 |
C7—C2—C3 | 120.3 (10) | C13—C12—H12B | 117.6 |
C1—C2—C3 | 116.5 (9) | C11—C12—H12B | 117.6 |
C10—C3—C4 | 123.9 (10) | H12A—C12—H12B | 114.6 |
C10—C3—C2 | 115.6 (10) | C12—C13—C11 | 60.4 (7) |
C4—C3—C2 | 120.3 (9) | C12—C13—H13A | 117.7 |
C5—C4—C3 | 119.8 (9) | C11—C13—H13A | 117.7 |
C5—C4—C11 | 117.8 (9) | C12—C13—H13B | 117.7 |
C3—C4—C11 | 121.8 (9) | C11—C13—H13B | 117.7 |
C4—C5—C6 | 121.8 (9) | H13A—C13—H13B | 114.9 |
C4—C5—H5 | 119.1 | N2—C14—N1 | 112.3 (9) |
C6—C5—H5 | 119.1 | N2—C14—Br1 | 118.1 (8) |
C1—C6—C5 | 117.2 (10) | N1—C14—Br1 | 129.7 (8) |
C1—C6—H6 | 121.4 | N3—C15—N1 | 110.6 (9) |
C5—C6—H6 | 121.4 | N3—C15—S1 | 128.6 (8) |
C8—C7—C2 | 122.5 (10) | N1—C15—S1 | 120.9 (8) |
C8—C7—H7 | 118.7 | C17—C16—S1 | 113.6 (7) |
C2—C7—H7 | 118.8 | C17—C16—H16A | 108.9 |
C7—C8—C9 | 116.2 (10) | S1—C16—H16A | 108.9 |
C7—C8—H8 | 121.9 | C17—C16—H16B | 108.9 |
C9—C8—H8 | 121.9 | S1—C16—H16B | 108.9 |
C10—C9—C8 | 122.3 (12) | H16A—C16—H16B | 107.7 |
C10—C9—H9 | 118.9 | O1—C17—O2 | 123.9 (10) |
C8—C9—H9 | 118.8 | O1—C17—C16 | 127.8 (10) |
C9—C10—C3 | 123.1 (11) | O2—C17—C16 | 108.2 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N3i | 0.82 | 1.92 | 2.721 (10) | 166 |
C16—H16B···O1ii | 0.97 | 2.25 | 3.209 (12) | 172 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
C17H14BrN3O2S·CH4O | Z = 2 |
Mr = 436.33 | F(000) = 444 |
Triclinic, P1 | Dx = 1.535 Mg m−3 |
a = 9.0092 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2165 (10) Å | Cell parameters from 8298 reflections |
c = 11.6947 (13) Å | θ = 3.1–27.5° |
α = 80.899 (6)° | µ = 2.31 mm−1 |
β = 79.931 (6)° | T = 298 K |
γ = 88.024 (6)° | Block, colorless |
V = 944.03 (18) Å3 | 0.24 × 0.20 × 0.20 mm |
XtaLABmini diffractometer | 4311 independent reflections |
Radiation source: fine-focus sealed tube | 3038 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | h = −11→11 |
Tmin = 0.593, Tmax = 1.000 | k = −11→11 |
10109 measured reflections | l = −15→15 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0465P)2 + 0.9973P] where P = (Fo2 + 2Fc2)/3 |
4311 reflections | (Δ/σ)max = 0.063 |
296 parameters | Δρmax = 0.94 e Å−3 |
0 restraints | Δρmin = −0.86 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C50 | 0.6036 (5) | 0.4240 (5) | 0.1837 (5) | 0.0761 (14) | |
H50A | 0.6282 | 0.3496 | 0.2449 | 0.114* | |
H50B | 0.5182 | 0.3932 | 0.1548 | 0.114* | |
H50C | 0.5797 | 0.5142 | 0.2144 | 0.114* | |
O10 | 0.7258 (3) | 0.4455 (3) | 0.0926 (3) | 0.0561 (7) | |
H1O | 1.089 (6) | 0.550 (6) | −0.132 (5) | 0.086 (18)* | |
H2 | 0.513 (4) | −0.009 (4) | −0.247 (3) | 0.036 (9)* | |
H3 | 0.531 (4) | −0.126 (4) | −0.404 (3) | 0.035 (9)* | |
H6 | 1.022 (4) | −0.258 (4) | −0.502 (3) | 0.042 (10)* | |
H7 | 1.239 (5) | −0.222 (5) | −0.440 (4) | 0.065 (12)* | |
H8 | 1.218 (5) | −0.099 (5) | −0.284 (4) | 0.066 (14)* | |
H9 | 1.004 (4) | −0.007 (4) | −0.190 (3) | 0.046 (10)* | |
H10O | 0.730 (6) | 0.380 (6) | 0.048 (5) | 0.096 (18)* | |
H11 | 0.832 (4) | −0.238 (4) | −0.593 (3) | 0.050 (11)* | |
H12A | 0.628 (5) | −0.259 (5) | −0.676 (4) | 0.075 (14)* | |
H12B | 0.526 (6) | −0.234 (6) | −0.563 (5) | 0.091 (18)* | |
H13A | 0.626 (5) | −0.428 (5) | −0.454 (4) | 0.076 (15)* | |
H13B | 0.739 (6) | −0.476 (7) | −0.572 (5) | 0.112 (19)* | |
H15A | 0.741 (4) | 0.501 (4) | −0.153 (3) | 0.038 (9)* | |
H15B | 0.806 (5) | 0.541 (5) | −0.274 (4) | 0.069 (14)* | |
C1 | 0.7317 (4) | −0.0283 (3) | −0.2432 (3) | 0.0336 (7) | |
C2 | 0.6032 (4) | −0.0459 (4) | −0.2846 (3) | 0.0406 (8) | |
C3 | 0.6103 (4) | −0.1160 (4) | −0.3834 (3) | 0.0420 (8) | |
C4 | 0.7411 (4) | −0.1703 (3) | −0.4382 (3) | 0.0349 (7) | |
C5 | 0.8772 (4) | −0.1532 (3) | −0.3939 (3) | 0.0328 (7) | |
C6 | 1.0180 (4) | −0.2066 (4) | −0.4455 (3) | 0.0442 (8) | |
C7 | 1.1459 (5) | −0.1867 (5) | −0.4028 (4) | 0.0539 (10) | |
C8 | 1.1411 (5) | −0.1131 (5) | −0.3068 (4) | 0.0540 (10) | |
C9 | 1.0083 (4) | −0.0597 (4) | −0.2545 (3) | 0.0420 (8) | |
C10 | 0.8732 (3) | −0.0790 (3) | −0.2962 (3) | 0.0315 (6) | |
C11 | 0.7465 (5) | −0.2486 (4) | −0.5411 (3) | 0.0442 (8) | |
C12 | 0.6126 (7) | −0.2750 (6) | −0.5926 (5) | 0.0686 (13) | |
C13 | 0.6816 (7) | −0.3982 (5) | −0.5269 (5) | 0.0692 (13) | |
C14 | 0.7160 (4) | −0.0164 (4) | −0.0261 (3) | 0.0450 (8) | |
C15 | 0.7298 (4) | 0.1915 (4) | −0.1413 (3) | 0.0377 (7) | |
C16 | 0.8088 (5) | 0.4727 (4) | −0.2207 (4) | 0.0488 (9) | |
C17 | 0.9691 (4) | 0.4561 (4) | −0.1991 (3) | 0.0487 (9) | |
N1 | 0.7245 (3) | 0.0443 (3) | −0.1420 (2) | 0.0347 (6) | |
N2 | 0.7153 (4) | 0.0826 (4) | 0.0401 (3) | 0.0540 (8) | |
N3 | 0.7241 (4) | 0.2187 (3) | −0.0341 (3) | 0.0497 (8) | |
O1 | 0.9965 (4) | 0.5531 (3) | −0.1372 (3) | 0.0678 (9) | |
O2 | 1.0564 (4) | 0.3668 (5) | −0.2325 (4) | 0.0966 (13) | |
S1 | 0.74005 (12) | 0.31669 (10) | −0.27007 (8) | 0.0485 (2) | |
Br1 | 0.70985 (6) | −0.21732 (5) | 0.02152 (4) | 0.06994 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C50 | 0.065 (3) | 0.069 (3) | 0.089 (4) | −0.006 (2) | 0.014 (3) | −0.027 (3) |
O10 | 0.0597 (18) | 0.0557 (17) | 0.0564 (17) | −0.0125 (13) | −0.0029 (13) | −0.0245 (13) |
C1 | 0.0428 (19) | 0.0292 (15) | 0.0290 (15) | −0.0032 (13) | −0.0043 (13) | −0.0069 (12) |
C2 | 0.0373 (19) | 0.048 (2) | 0.0388 (18) | 0.0004 (15) | −0.0055 (15) | −0.0144 (15) |
C3 | 0.037 (2) | 0.053 (2) | 0.0410 (19) | −0.0098 (16) | −0.0138 (16) | −0.0133 (15) |
C4 | 0.0431 (19) | 0.0337 (16) | 0.0286 (15) | −0.0081 (14) | −0.0051 (13) | −0.0063 (12) |
C5 | 0.0405 (18) | 0.0257 (15) | 0.0313 (16) | −0.0045 (13) | −0.0022 (13) | −0.0047 (11) |
C6 | 0.049 (2) | 0.0377 (19) | 0.045 (2) | −0.0014 (16) | 0.0010 (16) | −0.0137 (15) |
C7 | 0.038 (2) | 0.058 (2) | 0.063 (3) | 0.0051 (18) | −0.0003 (18) | −0.0108 (19) |
C8 | 0.039 (2) | 0.060 (3) | 0.066 (3) | −0.0036 (18) | −0.017 (2) | −0.011 (2) |
C9 | 0.041 (2) | 0.0422 (19) | 0.045 (2) | −0.0029 (15) | −0.0130 (16) | −0.0097 (15) |
C10 | 0.0351 (17) | 0.0279 (15) | 0.0314 (15) | −0.0054 (12) | −0.0056 (13) | −0.0031 (12) |
C11 | 0.054 (2) | 0.044 (2) | 0.0372 (19) | −0.0083 (16) | −0.0032 (17) | −0.0168 (15) |
C12 | 0.084 (4) | 0.083 (3) | 0.054 (3) | 0.009 (3) | −0.034 (3) | −0.035 (3) |
C13 | 0.113 (4) | 0.047 (2) | 0.055 (3) | −0.022 (3) | −0.024 (3) | −0.014 (2) |
C14 | 0.055 (2) | 0.049 (2) | 0.0305 (17) | 0.0001 (17) | −0.0072 (15) | −0.0065 (15) |
C15 | 0.0438 (19) | 0.0342 (17) | 0.0386 (18) | 0.0014 (14) | −0.0103 (14) | −0.0126 (13) |
C16 | 0.055 (2) | 0.0332 (19) | 0.060 (3) | −0.0022 (17) | −0.014 (2) | −0.0061 (18) |
C17 | 0.050 (2) | 0.047 (2) | 0.048 (2) | −0.0031 (17) | −0.0012 (17) | −0.0123 (16) |
N1 | 0.0444 (16) | 0.0328 (14) | 0.0287 (13) | −0.0022 (11) | −0.0082 (11) | −0.0078 (10) |
N2 | 0.076 (2) | 0.0551 (19) | 0.0343 (16) | −0.0005 (16) | −0.0103 (15) | −0.0167 (14) |
N3 | 0.069 (2) | 0.0429 (17) | 0.0426 (17) | −0.0002 (15) | −0.0134 (15) | −0.0185 (13) |
O1 | 0.0542 (19) | 0.067 (2) | 0.092 (2) | −0.0058 (15) | −0.0163 (17) | −0.0378 (17) |
O2 | 0.067 (2) | 0.127 (3) | 0.120 (3) | 0.032 (2) | −0.030 (2) | −0.082 (3) |
S1 | 0.0670 (6) | 0.0374 (5) | 0.0449 (5) | −0.0030 (4) | −0.0204 (4) | −0.0058 (4) |
Br1 | 0.1107 (4) | 0.0471 (3) | 0.0479 (3) | −0.0046 (2) | −0.0114 (2) | 0.00364 (17) |
C50—O10 | 1.388 (5) | C11—C12 | 1.483 (6) |
C1—C2 | 1.355 (5) | C11—C13 | 1.490 (5) |
C1—C10 | 1.414 (4) | C12—C13 | 1.452 (7) |
C1—N1 | 1.440 (4) | C14—N2 | 1.286 (4) |
C2—C3 | 1.401 (5) | C14—N1 | 1.372 (4) |
C3—C4 | 1.359 (5) | C14—Br1 | 1.848 (4) |
C4—C5 | 1.434 (4) | C15—N3 | 1.309 (4) |
C4—C11 | 1.491 (4) | C15—N1 | 1.360 (4) |
C5—C6 | 1.414 (5) | C15—S1 | 1.737 (3) |
C5—C10 | 1.417 (4) | C16—C17 | 1.507 (6) |
C6—C7 | 1.362 (5) | C16—S1 | 1.798 (4) |
C7—C8 | 1.394 (6) | C17—O2 | 1.182 (5) |
C8—C9 | 1.359 (6) | C17—O1 | 1.291 (4) |
C9—C10 | 1.415 (5) | N2—N3 | 1.404 (4) |
C2—C1—C10 | 122.1 (3) | C13—C11—C4 | 121.1 (4) |
C2—C1—N1 | 119.1 (3) | C13—C12—C11 | 61.0 (3) |
C10—C1—N1 | 118.8 (3) | C12—C13—C11 | 60.5 (3) |
C1—C2—C3 | 119.1 (3) | N2—C14—N1 | 111.7 (3) |
C4—C3—C2 | 122.5 (3) | N2—C14—Br1 | 126.5 (3) |
C3—C4—C5 | 118.6 (3) | N1—C14—Br1 | 121.8 (2) |
C3—C4—C11 | 122.0 (3) | N3—C15—N1 | 110.6 (3) |
C5—C4—C11 | 119.4 (3) | N3—C15—S1 | 128.1 (3) |
C6—C5—C10 | 118.0 (3) | N1—C15—S1 | 121.4 (2) |
C6—C5—C4 | 122.2 (3) | C17—C16—S1 | 114.1 (3) |
C10—C5—C4 | 119.8 (3) | O2—C17—O1 | 124.9 (4) |
C7—C6—C5 | 120.9 (3) | O2—C17—C16 | 125.3 (4) |
C6—C7—C8 | 120.8 (4) | O1—C17—C16 | 109.8 (3) |
C9—C8—C7 | 120.3 (4) | C15—N1—C14 | 104.1 (3) |
C8—C9—C10 | 120.5 (3) | C15—N1—C1 | 126.9 (3) |
C1—C10—C9 | 122.6 (3) | C14—N1—C1 | 128.9 (3) |
C1—C10—C5 | 117.9 (3) | C14—N2—N3 | 106.5 (3) |
C9—C10—C5 | 119.5 (3) | C15—N3—N2 | 107.1 (3) |
C12—C11—C13 | 58.5 (3) | C15—S1—C16 | 98.94 (18) |
C12—C11—C4 | 124.0 (4) |
C17H14BrN3O2S·C2H6O | F(000) = 920 |
Mr = 450.35 | Dx = 1.515 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.292 (6) Å | Cell parameters from 5384 reflections |
b = 7.366 (3) Å | θ = 2.6–33.7° |
c = 20.193 (9) Å | µ = 2.21 mm−1 |
β = 92.857 (6)° | T = 298 K |
V = 1974.6 (15) Å3 | Unknown, colorless |
Z = 4 | 0.30 × 0.20 × 0.16 mm |
Bruker P4 diffractometer | 7427 independent reflections |
Graphite monochromator | 5089 reflections with I > 2σ(I) |
Detector resolution: 13.6612 pixels mm-1 | Rint = 0.090 |
ω scans | θmax = 33.9°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | h = −20→20 |
Tmin = 0.705, Tmax = 1.000 | k = −11→11 |
27732 measured reflections | l = −31→31 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.2431P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
7427 reflections | Δρmax = 0.47 e Å−3 |
253 parameters | Δρmin = −1.08 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C18 | 0.3314 (3) | −0.0865 (7) | 0.02307 (19) | 0.0603 (11) | |
H18A | 0.272983 | −0.067955 | −0.006899 | 0.072* | |
H18B | 0.374089 | −0.177230 | 0.003854 | 0.072* | |
C19 | 0.3882 (4) | 0.0879 (8) | 0.0323 (3) | 0.0717 (13) | |
H19A | 0.414475 | 0.124160 | −0.009131 | 0.107* | |
H19B | 0.442787 | 0.071145 | 0.064645 | 0.107* | |
H19C | 0.343748 | 0.180363 | 0.047240 | 0.107* | |
O3 | 0.3003 (2) | −0.1474 (4) | 0.08556 (13) | 0.0522 (7) | |
C3 | −0.0229 (2) | 0.3128 (4) | −0.10467 (15) | 0.0339 (6) | |
C5 | 0.1662 (2) | 0.3143 (4) | −0.08782 (15) | 0.0341 (6) | |
C4 | 0.0328 (2) | 0.2524 (4) | −0.00459 (16) | 0.0341 (6) | |
C8 | 0.3655 (2) | 0.3465 (5) | −0.12646 (18) | 0.0415 (7) | |
C10 | 0.2084 (2) | 0.1669 (4) | −0.12271 (15) | 0.0347 (6) | |
C11 | 0.1553 (3) | 0.0054 (5) | −0.13743 (17) | 0.0431 (7) | |
H11 | 0.090727 | −0.009759 | −0.122554 | 0.052* | |
C6 | 0.2195 (3) | 0.4679 (5) | −0.07391 (19) | 0.0455 (8) | |
H6 | 0.189930 | 0.563663 | −0.051981 | 0.055* | |
C9 | 0.3080 (2) | 0.1874 (4) | −0.14386 (16) | 0.0369 (6) | |
C7 | 0.3197 (3) | 0.4816 (5) | −0.0928 (2) | 0.0487 (8) | |
H7 | 0.355980 | 0.586321 | −0.082071 | 0.058* | |
C2 | −0.1561 (3) | 0.3426 (7) | −0.20609 (19) | 0.0559 (10) | |
H2A | −0.172110 | 0.216044 | −0.198498 | 0.067* | |
H2B | −0.194083 | 0.415013 | −0.175956 | 0.067* | |
C15 | 0.4739 (3) | 0.3584 (6) | −0.1430 (2) | 0.0526 (9) | |
H15 | 0.513584 | 0.251510 | −0.129247 | 0.063* | |
C14 | 0.3499 (3) | 0.0441 (5) | −0.18076 (18) | 0.0496 (8) | |
H14 | 0.415133 | 0.054526 | −0.194891 | 0.060* | |
C1 | −0.1888 (3) | 0.3912 (6) | −0.27584 (18) | 0.0513 (9) | |
C13 | 0.2953 (3) | −0.1084 (6) | −0.1956 (2) | 0.0579 (10) | |
H13 | 0.323020 | −0.199635 | −0.220815 | 0.069* | |
C12 | 0.1975 (3) | −0.1293 (5) | −0.1733 (2) | 0.0553 (9) | |
H12 | 0.161472 | −0.235097 | −0.182992 | 0.066* | |
C17 | 0.5072 (4) | 0.4438 (9) | −0.2042 (3) | 0.0862 (17) | |
H17A | 0.561193 | 0.385489 | −0.226812 | 0.103* | |
H17B | 0.456508 | 0.502162 | −0.233142 | 0.103* | |
C16 | 0.5318 (4) | 0.5272 (9) | −0.1410 (4) | 0.100 (2) | |
H16A | 0.496717 | 0.638137 | −0.130386 | 0.120* | |
H16B | 0.601340 | 0.521533 | −0.124061 | 0.120* | |
N3 | 0.0645 (2) | 0.2975 (3) | −0.06619 (13) | 0.0340 (5) | |
N1 | −0.0650 (2) | 0.2395 (4) | −0.00459 (14) | 0.0393 (6) | |
N2 | −0.1014 (2) | 0.2777 (4) | −0.06951 (13) | 0.0393 (6) | |
O1 | −0.1297 (2) | 0.5079 (4) | −0.30334 (13) | 0.0549 (7) | |
O2 | −0.2634 (3) | 0.3316 (7) | −0.30162 (18) | 0.1058 (17) | |
S0AA | −0.02337 (6) | 0.37733 (14) | −0.18711 (4) | 0.0467 (2) | |
Br1 | 0.11792 (3) | 0.21793 (5) | 0.06975 (2) | 0.04423 (13) | |
H1 | −0.166 (4) | 0.546 (8) | −0.338 (3) | 0.094 (18)* | |
H3 | 0.251 (4) | −0.181 (7) | 0.086 (2) | 0.055 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C18 | 0.054 (2) | 0.087 (3) | 0.0402 (19) | −0.010 (2) | 0.0061 (16) | −0.0119 (19) |
C19 | 0.062 (3) | 0.083 (3) | 0.070 (3) | −0.010 (2) | 0.005 (2) | 0.007 (2) |
O3 | 0.0393 (14) | 0.076 (2) | 0.0409 (14) | −0.0065 (13) | 0.0017 (11) | −0.0067 (12) |
C3 | 0.0318 (14) | 0.0391 (17) | 0.0308 (14) | 0.0038 (11) | 0.0021 (11) | 0.0008 (11) |
C5 | 0.0293 (13) | 0.0422 (17) | 0.0312 (14) | 0.0024 (11) | 0.0055 (11) | −0.0012 (11) |
C4 | 0.0367 (15) | 0.0358 (16) | 0.0303 (14) | 0.0037 (11) | 0.0062 (11) | −0.0011 (10) |
C8 | 0.0347 (16) | 0.0408 (17) | 0.0494 (19) | 0.0015 (12) | 0.0072 (13) | 0.0039 (14) |
C10 | 0.0348 (15) | 0.0390 (16) | 0.0304 (14) | 0.0047 (11) | 0.0034 (11) | 0.0007 (11) |
C11 | 0.0443 (18) | 0.0409 (18) | 0.0445 (18) | −0.0018 (13) | 0.0048 (14) | −0.0032 (13) |
C6 | 0.0414 (17) | 0.0384 (17) | 0.057 (2) | 0.0005 (13) | 0.0111 (15) | −0.0107 (14) |
C9 | 0.0360 (15) | 0.0382 (17) | 0.0367 (15) | 0.0060 (11) | 0.0041 (12) | 0.0027 (12) |
C7 | 0.0406 (18) | 0.0426 (19) | 0.064 (2) | −0.0054 (13) | 0.0102 (16) | −0.0070 (16) |
C2 | 0.0365 (18) | 0.092 (3) | 0.0391 (18) | −0.0113 (18) | −0.0009 (14) | 0.0156 (18) |
C15 | 0.0346 (17) | 0.055 (2) | 0.069 (3) | 0.0038 (14) | 0.0146 (16) | 0.0071 (18) |
C14 | 0.049 (2) | 0.052 (2) | 0.048 (2) | 0.0128 (16) | 0.0162 (16) | −0.0036 (16) |
C1 | 0.0389 (18) | 0.077 (3) | 0.0373 (17) | −0.0081 (16) | −0.0013 (14) | 0.0103 (16) |
C13 | 0.064 (3) | 0.049 (2) | 0.061 (2) | 0.0141 (18) | 0.0073 (19) | −0.0174 (17) |
C12 | 0.061 (2) | 0.045 (2) | 0.060 (2) | 0.0020 (16) | 0.0023 (19) | −0.0142 (17) |
C17 | 0.058 (3) | 0.109 (5) | 0.094 (4) | −0.006 (3) | 0.024 (3) | 0.029 (3) |
C16 | 0.047 (3) | 0.097 (4) | 0.158 (6) | −0.029 (3) | 0.035 (3) | −0.049 (4) |
N3 | 0.0324 (12) | 0.0406 (15) | 0.0293 (12) | 0.0023 (10) | 0.0043 (9) | 0.0000 (10) |
N1 | 0.0379 (14) | 0.0492 (16) | 0.0312 (13) | 0.0019 (11) | 0.0076 (11) | 0.0018 (10) |
N2 | 0.0300 (13) | 0.0531 (16) | 0.0349 (14) | 0.0026 (10) | 0.0047 (10) | 0.0056 (11) |
O1 | 0.0473 (15) | 0.077 (2) | 0.0392 (14) | −0.0084 (12) | −0.0052 (11) | 0.0173 (12) |
O2 | 0.070 (2) | 0.184 (4) | 0.061 (2) | −0.064 (3) | −0.0287 (18) | 0.041 (2) |
S0AA | 0.0358 (4) | 0.0725 (6) | 0.0321 (4) | −0.0019 (4) | 0.0029 (3) | 0.0102 (4) |
Br1 | 0.0451 (2) | 0.0533 (2) | 0.03372 (18) | 0.00474 (14) | −0.00408 (13) | −0.00126 (13) |
C18—C19 | 1.497 (7) | C10—C9 | 1.420 (4) |
C18—O3 | 1.420 (5) | C11—C12 | 1.366 (5) |
C3—N3 | 1.370 (4) | C6—C7 | 1.408 (5) |
C3—N2 | 1.316 (4) | C9—C14 | 1.421 (5) |
C3—S0AA | 1.731 (3) | C2—C1 | 1.497 (5) |
C5—C10 | 1.424 (4) | C2—S0AA | 1.805 (4) |
C5—C6 | 1.357 (5) | C15—C17 | 1.475 (6) |
C5—N3 | 1.445 (4) | C15—C16 | 1.462 (6) |
C4—N3 | 1.374 (4) | C14—C13 | 1.363 (6) |
C4—N1 | 1.303 (4) | C1—O1 | 1.307 (4) |
C4—Br1 | 1.852 (3) | C1—O2 | 1.181 (5) |
C8—C9 | 1.433 (5) | C13—C12 | 1.405 (6) |
C8—C7 | 1.365 (5) | C17—C16 | 1.440 (8) |
C8—C15 | 1.498 (5) | N1—N2 | 1.403 (4) |
C10—C11 | 1.407 (5) | ||
O3—C18—C19 | 109.1 (3) | C14—C9—C8 | 121.2 (3) |
N3—C3—S0AA | 122.0 (2) | C8—C7—C6 | 122.3 (3) |
N2—C3—N3 | 110.5 (3) | C1—C2—S0AA | 113.6 (3) |
N2—C3—S0AA | 127.4 (2) | C17—C15—C8 | 123.0 (4) |
C10—C5—N3 | 118.8 (3) | C16—C15—C8 | 123.7 (4) |
C6—C5—C10 | 121.6 (3) | C16—C15—C17 | 58.7 (4) |
C6—C5—N3 | 119.7 (3) | C13—C14—C9 | 120.7 (3) |
N3—C4—Br1 | 124.4 (2) | O1—C1—C2 | 113.9 (3) |
N1—C4—N3 | 111.6 (3) | O2—C1—C2 | 121.6 (4) |
N1—C4—Br1 | 124.0 (2) | O2—C1—O1 | 124.5 (4) |
C9—C8—C15 | 120.0 (3) | C14—C13—C12 | 120.7 (3) |
C7—C8—C9 | 118.2 (3) | C11—C12—C13 | 120.1 (4) |
C7—C8—C15 | 121.7 (3) | C16—C17—C15 | 60.2 (4) |
C11—C10—C5 | 122.9 (3) | C17—C16—C15 | 61.1 (3) |
C11—C10—C9 | 119.4 (3) | C3—N3—C5 | 126.9 (3) |
C9—C10—C5 | 117.6 (3) | C3—N3—C4 | 104.1 (2) |
C12—C11—C10 | 120.8 (3) | C4—N3—C5 | 128.9 (3) |
C5—C6—C7 | 119.7 (3) | C4—N1—N2 | 106.4 (3) |
C10—C9—C8 | 120.5 (3) | C3—N2—N1 | 107.3 (3) |
C10—C9—C14 | 118.3 (3) | C3—S0AA—C2 | 97.01 (16) |
C17H14BrN3O2S·C8H10N4O2 | F(000) = 1224 |
Mr = 598.48 | Dx = 1.548 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1245 (8) Å | Cell parameters from 9049 reflections |
b = 6.6975 (3) Å | θ = 2.3–25.0° |
c = 25.8260 (13) Å | µ = 1.73 mm−1 |
β = 101.045 (2)° | T = 100 K |
V = 2567.6 (2) Å3 | Needle, colorless |
Z = 4 | 0.36 × 0.16 × 0.12 mm |
Bruker APEXII CCD diffractometer | 3978 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.055 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | θmax = 25.1°, θmin = 2.3° |
Tmin = 0.725, Tmax = 0.813 | h = −18→18 |
50811 measured reflections | k = −7→7 |
4550 independent reflections | l = −30→30 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.028P)2 + 1.9564P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.064 | (Δ/σ)max = 0.002 |
S = 1.05 | Δρmax = 0.32 e Å−3 |
4550 reflections | Δρmin = −0.37 e Å−3 |
380 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
24 restraints | Extinction coefficient: 0.0026 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | −0.08457 (2) | 0.50120 (3) | 0.42784 (2) | 0.02481 (8) | |
S1 | 0.15757 (3) | 0.07735 (7) | 0.33567 (2) | 0.01130 (11) | |
O2 | 0.11198 (9) | 0.3122 (2) | 0.23544 (6) | 0.0181 (3) | |
O1 | 0.00443 (9) | 0.0971 (2) | 0.19952 (5) | 0.0191 (3) | |
O4 | 0.32277 (9) | 0.0085 (2) | 0.28471 (6) | 0.0210 (3) | |
N1 | 0.05026 (10) | 0.2933 (2) | 0.38752 (5) | 0.0101 (3) | |
N2 | −0.08880 (10) | 0.2061 (2) | 0.35014 (6) | 0.0145 (3) | |
N3 | −0.02705 (10) | 0.0970 (2) | 0.32720 (6) | 0.0126 (3) | |
N5 | 0.47547 (11) | 0.0177 (2) | 0.30379 (6) | 0.0134 (3) | |
N4 | 0.39632 (10) | 0.0141 (2) | 0.21525 (6) | 0.0148 (3) | |
C17 | 0.07199 (12) | 0.1368 (3) | 0.23120 (7) | 0.0119 (4) | |
C2 | 0.17140 (12) | 0.3015 (3) | 0.46632 (7) | 0.0109 (4) | |
C15 | 0.05423 (12) | 0.1528 (3) | 0.34962 (7) | 0.0099 (4) | |
C6 | 0.15341 (13) | 0.5718 (3) | 0.40230 (7) | 0.0150 (4) | |
H6 | 0.1215 | 0.6316 | 0.3709 | 0.018* | |
C1 | 0.12592 (12) | 0.3938 (3) | 0.41912 (7) | 0.0108 (4) | |
C5 | 0.22950 (13) | 0.6663 (3) | 0.43190 (7) | 0.0169 (4) | |
H5 | 0.2475 | 0.7918 | 0.4203 | 0.020* | |
C16 | 0.11882 (12) | −0.0173 (3) | 0.26965 (7) | 0.0108 (4) | |
H16A | 0.1711 | −0.0707 | 0.2562 | 0.013* | |
H16B | 0.0768 | −0.1294 | 0.2712 | 0.013* | |
C7 | 0.14070 (13) | 0.1205 (3) | 0.48548 (7) | 0.0154 (4) | |
H7 | 0.0889 | 0.0560 | 0.4661 | 0.018* | |
C10 | 0.29445 (13) | 0.3041 (3) | 0.54251 (7) | 0.0148 (4) | |
H10 | 0.3476 | 0.3628 | 0.5621 | 0.018* | |
C4 | 0.27881 (12) | 0.5839 (3) | 0.47703 (7) | 0.0140 (4) | |
C14 | −0.04003 (12) | 0.3191 (3) | 0.38544 (7) | 0.0131 (4) | |
C8 | 0.18514 (14) | 0.0385 (3) | 0.53165 (8) | 0.0194 (4) | |
H8 | 0.1635 | −0.0814 | 0.5444 | 0.023* | |
C18 | 0.39426 (13) | 0.0133 (3) | 0.26912 (7) | 0.0139 (4) | |
C3 | 0.24972 (12) | 0.3980 (3) | 0.49547 (7) | 0.0111 (4) | |
C9 | 0.26253 (14) | 0.1309 (3) | 0.56018 (7) | 0.0195 (4) | |
H9 | 0.2932 | 0.0725 | 0.5921 | 0.023* | |
C12 | 0.39116 (13) | 0.8855 (3) | 0.49048 (8) | 0.0212 (4) | |
H12A | 0.3531 | 0.9527 | 0.4600 | 0.025* | |
H12B | 0.4201 | 0.9763 | 0.5190 | 0.025* | |
C24 | 0.47776 (14) | 0.0179 (3) | 0.36096 (7) | 0.0199 (4) | |
H24A | 0.4162 | 0.0264 | 0.3675 | 0.030* | |
H24B | 0.5126 | 0.1330 | 0.3770 | 0.030* | |
H24C | 0.5060 | −0.1055 | 0.3764 | 0.030* | |
C11 | 0.36156 (14) | 0.6845 (3) | 0.50608 (8) | 0.0216 (5) | |
H11 | 0.3765 | 0.6554 | 0.5448 | 0.026* | |
C13 | 0.44229 (15) | 0.7072 (3) | 0.47971 (11) | 0.0351 (6) | |
H13A | 0.5028 | 0.6865 | 0.5016 | 0.042* | |
H13B | 0.4358 | 0.6629 | 0.4426 | 0.042* | |
O5 | 0.46964 (17) | 0.0151 (9) | 0.14481 (10) | 0.0199 (6) | 0.857 (2) |
C19 | 0.47475 (13) | 0.0159 (3) | 0.19330 (8) | 0.0143 (3) | 0.857 (2) |
C20 | 0.55463 (12) | 0.0172 (3) | 0.23196 (7) | 0.0131 (4) | 0.857 (2) |
C21 | 0.55541 (13) | 0.0186 (3) | 0.28544 (8) | 0.0143 (3) | 0.857 (2) |
N7 | 0.6382 (3) | 0.0231 (11) | 0.3154 (2) | 0.0181 (9) | 0.857 (2) |
C22 | 0.69100 (16) | 0.0208 (3) | 0.27914 (9) | 0.0200 (5) | 0.857 (2) |
H22 | 0.7549 | 0.0212 | 0.2881 | 0.024* | 0.857 (2) |
N6 | 0.64561 (13) | 0.0181 (3) | 0.22900 (8) | 0.0169 (5) | 0.857 (2) |
C25 | 0.68535 (17) | 0.0205 (4) | 0.18157 (10) | 0.0236 (6) | 0.857 (2) |
H25A | 0.6784 | 0.1537 | 0.1656 | 0.035* | 0.857 (2) |
H25B | 0.6547 | −0.0779 | 0.1563 | 0.035* | 0.857 (2) |
H25C | 0.7495 | −0.0127 | 0.1911 | 0.035* | 0.857 (2) |
O5A | 0.6289 (18) | 0.005 (7) | 0.3178 (12) | 0.0199 (6) | 0.143 (2) |
C19A | 0.55541 (13) | 0.0186 (3) | 0.28544 (8) | 0.0143 (3) | 0.143 (2) |
C20A | 0.55463 (12) | 0.0172 (3) | 0.23196 (7) | 0.0131 (4) | 0.143 (2) |
C21A | 0.47475 (13) | 0.0159 (3) | 0.19330 (8) | 0.0143 (3) | 0.143 (2) |
N7A | 0.4844 (14) | 0.026 (8) | 0.1435 (7) | 0.0181 (9) | 0.143 (2) |
C22A | 0.5732 (8) | 0.010 (2) | 0.1500 (5) | 0.0200 (5) | 0.143 (2) |
H22A | 0.6032 | −0.0017 | 0.1210 | 0.024* | 0.143 (2) |
N6A | 0.6184 (7) | 0.0095 (18) | 0.2006 (4) | 0.0169 (5) | 0.143 (2) |
C25A | 0.7161 (8) | 0.005 (2) | 0.2186 (6) | 0.0236 (6) | 0.143 (2) |
H25D | 0.7458 | 0.0242 | 0.1884 | 0.035* | 0.143 (2) |
H25E | 0.7338 | −0.1246 | 0.2351 | 0.035* | 0.143 (2) |
H25F | 0.7341 | 0.1116 | 0.2444 | 0.035* | 0.143 (2) |
H1 | 0.0849 (18) | 0.398 (4) | 0.2154 (10) | 0.039 (7)* | |
C23 | 0.30883 (15) | 0.0128 (4) | 0.17853 (9) | 0.0241 (5) | |
H23A | 0.320 (4) | 0.013 (9) | 0.1432 (9) | 0.036* | 0.52 (3) |
H23B | 0.277 (3) | −0.110 (5) | 0.181 (2) | 0.036* | 0.52 (3) |
H23C | 0.270 (3) | 0.110 (6) | 0.1900 (19) | 0.036* | 0.52 (3) |
H23D | 0.314 (4) | −0.086 (7) | 0.1522 (18) | 0.036* | 0.48 (3) |
H23E | 0.262 (3) | −0.041 (9) | 0.195 (2) | 0.036* | 0.48 (3) |
H23F | 0.301 (4) | 0.137 (5) | 0.159 (2) | 0.036* | 0.48 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01944 (12) | 0.03109 (14) | 0.02490 (13) | 0.00250 (9) | 0.00677 (8) | −0.01601 (9) |
S1 | 0.0087 (2) | 0.0139 (2) | 0.0102 (2) | 0.00115 (17) | −0.00080 (17) | −0.00037 (17) |
O2 | 0.0136 (7) | 0.0149 (7) | 0.0227 (7) | −0.0018 (6) | −0.0042 (6) | 0.0093 (6) |
O1 | 0.0178 (7) | 0.0190 (7) | 0.0166 (7) | 0.0023 (6) | −0.0063 (6) | −0.0033 (6) |
O4 | 0.0119 (7) | 0.0274 (8) | 0.0249 (8) | −0.0009 (6) | 0.0064 (6) | −0.0004 (6) |
N1 | 0.0109 (8) | 0.0108 (8) | 0.0079 (7) | −0.0010 (6) | 0.0001 (6) | −0.0011 (6) |
N2 | 0.0123 (8) | 0.0162 (8) | 0.0155 (8) | 0.0004 (6) | 0.0038 (6) | −0.0041 (6) |
N3 | 0.0098 (8) | 0.0148 (8) | 0.0135 (8) | 0.0000 (6) | 0.0027 (6) | −0.0038 (6) |
N5 | 0.0129 (8) | 0.0154 (8) | 0.0120 (8) | 0.0005 (6) | 0.0024 (6) | 0.0017 (6) |
N4 | 0.0120 (8) | 0.0168 (8) | 0.0143 (8) | 0.0000 (6) | −0.0007 (6) | 0.0017 (6) |
C17 | 0.0108 (9) | 0.0162 (10) | 0.0096 (9) | 0.0023 (7) | 0.0043 (7) | −0.0018 (7) |
C2 | 0.0116 (9) | 0.0123 (9) | 0.0089 (8) | 0.0014 (7) | 0.0024 (7) | −0.0021 (7) |
C15 | 0.0122 (9) | 0.0091 (9) | 0.0081 (8) | −0.0001 (7) | 0.0013 (7) | 0.0008 (7) |
C6 | 0.0183 (10) | 0.0156 (9) | 0.0093 (9) | −0.0014 (8) | −0.0017 (7) | 0.0017 (7) |
C1 | 0.0108 (9) | 0.0125 (10) | 0.0084 (8) | −0.0004 (7) | −0.0002 (7) | −0.0040 (7) |
C5 | 0.0202 (10) | 0.0148 (10) | 0.0145 (10) | −0.0066 (8) | 0.0008 (8) | 0.0014 (7) |
C16 | 0.0109 (9) | 0.0111 (9) | 0.0100 (9) | 0.0001 (7) | 0.0008 (7) | −0.0032 (7) |
C7 | 0.0178 (10) | 0.0145 (10) | 0.0136 (9) | −0.0019 (8) | 0.0021 (8) | −0.0014 (7) |
C10 | 0.0132 (10) | 0.0203 (10) | 0.0100 (9) | 0.0030 (8) | −0.0005 (7) | −0.0026 (7) |
C4 | 0.0132 (9) | 0.0178 (10) | 0.0111 (9) | −0.0020 (8) | 0.0023 (7) | −0.0040 (7) |
C14 | 0.0132 (10) | 0.0158 (10) | 0.0106 (9) | −0.0001 (7) | 0.0033 (7) | −0.0030 (7) |
C8 | 0.0277 (11) | 0.0146 (10) | 0.0162 (10) | −0.0004 (8) | 0.0049 (8) | 0.0046 (8) |
C18 | 0.0139 (10) | 0.0098 (9) | 0.0178 (10) | 0.0008 (7) | 0.0026 (8) | 0.0010 (7) |
C3 | 0.0096 (9) | 0.0153 (10) | 0.0087 (8) | 0.0019 (7) | 0.0024 (7) | −0.0039 (7) |
C9 | 0.0235 (11) | 0.0218 (11) | 0.0116 (9) | 0.0080 (9) | −0.0003 (8) | 0.0042 (8) |
C12 | 0.0162 (10) | 0.0182 (11) | 0.0275 (11) | −0.0050 (8) | 0.0002 (8) | −0.0049 (9) |
C24 | 0.0210 (11) | 0.0261 (11) | 0.0128 (10) | −0.0009 (8) | 0.0034 (8) | 0.0009 (8) |
C11 | 0.0207 (11) | 0.0249 (11) | 0.0163 (10) | −0.0089 (9) | −0.0041 (8) | 0.0023 (8) |
C13 | 0.0175 (11) | 0.0222 (12) | 0.0667 (17) | −0.0034 (9) | 0.0106 (11) | −0.0068 (11) |
O5 | 0.0227 (14) | 0.0254 (14) | 0.0121 (8) | −0.0019 (16) | 0.0049 (8) | 0.0008 (7) |
C19 | 0.0148 (7) | 0.0089 (7) | 0.0184 (7) | 0.0003 (5) | 0.0015 (6) | 0.0017 (5) |
C20 | 0.0128 (9) | 0.0103 (9) | 0.0169 (10) | 0.0012 (7) | 0.0043 (7) | 0.0010 (7) |
C21 | 0.0148 (7) | 0.0089 (7) | 0.0184 (7) | 0.0003 (5) | 0.0015 (6) | 0.0017 (5) |
N7 | 0.0111 (15) | 0.018 (2) | 0.0223 (14) | −0.0006 (12) | −0.0043 (13) | 0.0055 (10) |
C22 | 0.0117 (11) | 0.0226 (13) | 0.0256 (13) | 0.0027 (9) | 0.0028 (10) | 0.0068 (10) |
N6 | 0.0143 (11) | 0.0170 (10) | 0.0204 (12) | 0.0035 (8) | 0.0062 (9) | 0.0034 (9) |
C25 | 0.0229 (14) | 0.0251 (13) | 0.0269 (14) | 0.0031 (10) | 0.0151 (11) | 0.0017 (11) |
O5A | 0.0227 (14) | 0.0254 (14) | 0.0121 (8) | −0.0019 (16) | 0.0049 (8) | 0.0008 (7) |
C19A | 0.0148 (7) | 0.0089 (7) | 0.0184 (7) | 0.0003 (5) | 0.0015 (6) | 0.0017 (5) |
C20A | 0.0128 (9) | 0.0103 (9) | 0.0169 (10) | 0.0012 (7) | 0.0043 (7) | 0.0010 (7) |
C21A | 0.0148 (7) | 0.0089 (7) | 0.0184 (7) | 0.0003 (5) | 0.0015 (6) | 0.0017 (5) |
N7A | 0.0111 (15) | 0.018 (2) | 0.0223 (14) | −0.0006 (12) | −0.0043 (13) | 0.0055 (10) |
C22A | 0.0117 (11) | 0.0226 (13) | 0.0256 (13) | 0.0027 (9) | 0.0028 (10) | 0.0068 (10) |
N6A | 0.0143 (11) | 0.0170 (10) | 0.0204 (12) | 0.0035 (8) | 0.0062 (9) | 0.0034 (9) |
C25A | 0.0229 (14) | 0.0251 (13) | 0.0269 (14) | 0.0031 (10) | 0.0151 (11) | 0.0017 (11) |
C23 | 0.0156 (11) | 0.0314 (13) | 0.0217 (11) | −0.0026 (9) | −0.0054 (9) | 0.0030 (9) |
Br1—C14 | 1.8502 (18) | C12—C13 | 1.478 (3) |
S1—C15 | 1.7447 (18) | C12—C11 | 1.498 (3) |
S1—C16 | 1.8080 (17) | C12—H12A | 0.9900 |
O2—C17 | 1.316 (2) | C12—H12B | 0.9900 |
O2—H1 | 0.83 (3) | C24—H24A | 0.9800 |
O1—C17 | 1.210 (2) | C24—H24B | 0.9800 |
O4—C18 | 1.224 (2) | C24—H24C | 0.9800 |
N1—C15 | 1.367 (2) | C11—C13 | 1.515 (3) |
N1—C14 | 1.367 (2) | C11—H11 | 1.0000 |
N1—C1 | 1.439 (2) | C13—H13A | 0.9900 |
N2—C14 | 1.300 (2) | C13—H13B | 0.9900 |
N2—N3 | 1.403 (2) | O5—C19 | 1.240 (3) |
N3—C15 | 1.309 (2) | C19—C20 | 1.412 (3) |
N5—C18 | 1.375 (3) | C20—C21 | 1.379 (3) |
N5—C19A | 1.380 (2) | C20—N6 | 1.393 (3) |
N5—C21 | 1.380 (2) | C21—N7 | 1.340 (4) |
N5—C24 | 1.470 (2) | N7—C22 | 1.342 (8) |
N4—C18 | 1.398 (2) | C22—N6 | 1.345 (3) |
N4—C21A | 1.409 (2) | C22—H22 | 0.9500 |
N4—C19 | 1.409 (2) | N6—C25 | 1.464 (3) |
N4—C23 | 1.473 (3) | C25—H25A | 0.9800 |
C17—C16 | 1.511 (2) | C25—H25B | 0.9800 |
C2—C7 | 1.421 (3) | C25—H25C | 0.9800 |
C2—C1 | 1.421 (2) | O5A—C19A | 1.259 (18) |
C2—C3 | 1.430 (3) | C19A—C20A | 1.379 (3) |
C6—C1 | 1.361 (3) | C20A—N6A | 1.374 (10) |
C6—C5 | 1.404 (3) | C20A—C21A | 1.412 (3) |
C6—H6 | 0.9500 | C21A—N7A | 1.325 (18) |
C5—C4 | 1.373 (3) | C21A—C22A | 2.027 (11) |
C5—H5 | 0.9500 | N7A—C22A | 1.326 (19) |
C16—H16A | 0.9900 | C22A—N6A | 1.354 (14) |
C16—H16B | 0.9900 | C22A—H22A | 0.9500 |
C7—C8 | 1.367 (3) | N6A—C25A | 1.461 (13) |
C7—H7 | 0.9500 | C25A—H25D | 0.9800 |
C10—C9 | 1.368 (3) | C25A—H25E | 0.9800 |
C10—C3 | 1.419 (3) | C25A—H25F | 0.9800 |
C10—H10 | 0.9500 | C23—H23A | 0.960 (10) |
C4—C3 | 1.432 (3) | C23—H23B | 0.962 (10) |
C4—C11 | 1.491 (3) | C23—H23C | 0.961 (10) |
C8—C9 | 1.402 (3) | C23—H23D | 0.962 (10) |
C8—H8 | 0.9500 | C23—H23E | 0.960 (10) |
C9—H9 | 0.9500 | C23—H23F | 0.962 (10) |
C15—S1—C16 | 98.92 (8) | C4—C11—H11 | 114.9 |
C17—O2—H1 | 113.8 (19) | C12—C11—H11 | 114.9 |
C15—N1—C14 | 103.85 (14) | C13—C11—H11 | 114.9 |
C15—N1—C1 | 126.07 (15) | C12—C13—C11 | 60.06 (14) |
C14—N1—C1 | 129.99 (15) | C12—C13—H13A | 117.8 |
C14—N2—N3 | 105.38 (14) | C11—C13—H13A | 117.8 |
C15—N3—N2 | 107.98 (14) | C12—C13—H13B | 117.8 |
C18—N5—C19A | 120.57 (16) | C11—C13—H13B | 117.8 |
C18—N5—C21 | 120.57 (16) | H13A—C13—H13B | 114.9 |
C18—N5—C24 | 120.02 (16) | O5—C19—N4 | 120.8 (2) |
C19A—N5—C24 | 119.41 (16) | O5—C19—C20 | 126.4 (2) |
C21—N5—C24 | 119.41 (16) | N4—C19—C20 | 112.82 (16) |
C18—N4—C21A | 125.54 (16) | C21—C20—N6 | 103.64 (17) |
C18—N4—C19 | 125.54 (16) | C21—C20—C19 | 123.38 (17) |
C18—N4—C23 | 116.89 (16) | N6—C20—C19 | 132.98 (18) |
C21A—N4—C23 | 117.56 (16) | N7—C21—C20 | 114.0 (3) |
C19—N4—C23 | 117.56 (16) | N7—C21—N5 | 125.8 (3) |
O1—C17—O2 | 124.56 (17) | C20—C21—N5 | 120.24 (17) |
O1—C17—C16 | 121.56 (17) | C21—N7—C22 | 102.2 (4) |
O2—C17—C16 | 113.88 (15) | N7—C22—N6 | 114.2 (2) |
C7—C2—C1 | 122.22 (17) | N7—C22—H22 | 122.9 |
C7—C2—C3 | 119.68 (16) | N6—C22—H22 | 122.9 |
C1—C2—C3 | 118.09 (16) | C22—N6—C20 | 105.95 (18) |
N3—C15—N1 | 110.31 (15) | C22—N6—C25 | 126.2 (2) |
N3—C15—S1 | 128.91 (14) | C20—N6—C25 | 127.9 (2) |
N1—C15—S1 | 120.75 (13) | N6—C25—H25A | 109.5 |
C1—C6—C5 | 119.32 (17) | N6—C25—H25B | 109.5 |
C1—C6—H6 | 120.3 | H25A—C25—H25B | 109.5 |
C5—C6—H6 | 120.3 | N6—C25—H25C | 109.5 |
C6—C1—C2 | 121.84 (16) | H25A—C25—H25C | 109.5 |
C6—C1—N1 | 119.16 (16) | H25B—C25—H25C | 109.5 |
C2—C1—N1 | 118.97 (16) | O5A—C19A—C20A | 120.1 (18) |
C4—C5—C6 | 122.41 (18) | O5A—C19A—N5 | 119.4 (17) |
C4—C5—H5 | 118.8 | C20A—C19A—N5 | 120.24 (17) |
C6—C5—H5 | 118.8 | N6A—C20A—C19A | 135.9 (5) |
C17—C16—S1 | 114.00 (12) | N6A—C20A—C21A | 100.7 (5) |
C17—C16—H16A | 108.8 | C19A—C20A—C21A | 123.38 (17) |
S1—C16—H16A | 108.8 | N7A—C21A—N4 | 130.5 (9) |
C17—C16—H16B | 108.8 | N7A—C21A—C20A | 116.6 (9) |
S1—C16—H16B | 108.8 | N4—C21A—C20A | 112.82 (16) |
H16A—C16—H16B | 107.6 | N7A—C21A—C22A | 40.2 (9) |
C8—C7—C2 | 120.52 (18) | N4—C21A—C22A | 170.3 (4) |
C8—C7—H7 | 119.7 | C20A—C21A—C22A | 76.7 (3) |
C2—C7—H7 | 119.7 | C21A—N7A—C22A | 99.7 (13) |
C9—C10—C3 | 121.36 (18) | N7A—C22A—N6A | 115.8 (12) |
C9—C10—H10 | 119.3 | N7A—C22A—C21A | 40.1 (8) |
C3—C10—H10 | 119.3 | N6A—C22A—C21A | 75.9 (6) |
C5—C4—C3 | 118.69 (17) | N7A—C22A—H22A | 122.1 |
C5—C4—C11 | 120.83 (18) | N6A—C22A—H22A | 122.1 |
C3—C4—C11 | 120.47 (16) | C21A—C22A—H22A | 161.6 |
N2—C14—N1 | 112.46 (15) | C22A—N6A—C20A | 106.6 (8) |
N2—C14—Br1 | 125.24 (14) | C22A—N6A—C25A | 126.9 (11) |
N1—C14—Br1 | 122.29 (13) | C20A—N6A—C25A | 126.5 (10) |
C7—C8—C9 | 120.18 (18) | N6A—C25A—H25D | 109.5 |
C7—C8—H8 | 119.9 | N6A—C25A—H25E | 109.5 |
C9—C8—H8 | 119.9 | H25D—C25A—H25E | 109.5 |
O4—C18—N5 | 121.44 (17) | N6A—C25A—H25F | 109.5 |
O4—C18—N4 | 121.12 (17) | H25D—C25A—H25F | 109.5 |
N5—C18—N4 | 117.44 (16) | H25E—C25A—H25F | 109.5 |
C10—C3—C2 | 117.46 (17) | N4—C23—H23A | 108 (3) |
C10—C3—C4 | 122.92 (17) | N4—C23—H23B | 111 (3) |
C2—C3—C4 | 119.60 (16) | H23A—C23—H23B | 104 (4) |
C10—C9—C8 | 120.76 (18) | N4—C23—H23C | 109 (3) |
C10—C9—H9 | 119.6 | H23A—C23—H23C | 122 (4) |
C8—C9—H9 | 119.6 | H23B—C23—H23C | 102 (4) |
C13—C12—C11 | 61.21 (14) | N4—C23—H23D | 106 (3) |
C13—C12—H12A | 117.6 | H23A—C23—H23D | 43 (4) |
C11—C12—H12A | 117.6 | H23B—C23—H23D | 65 (4) |
C13—C12—H12B | 117.6 | H23C—C23—H23D | 145 (4) |
C11—C12—H12B | 117.6 | N4—C23—H23E | 112 (4) |
H12A—C12—H12B | 114.8 | H23A—C23—H23E | 134 (5) |
N5—C24—H24A | 109.5 | H23B—C23—H23E | 40 (4) |
N5—C24—H24B | 109.5 | H23C—C23—H23E | 65 (4) |
H24A—C24—H24B | 109.5 | H23D—C23—H23E | 103 (5) |
N5—C24—H24C | 109.5 | N4—C23—H23F | 109 (3) |
H24A—C24—H24C | 109.5 | H23A—C23—H23F | 63 (4) |
H24B—C24—H24C | 109.5 | H23B—C23—H23F | 139 (5) |
C4—C11—C12 | 122.40 (18) | H23C—C23—H23F | 63 (4) |
C4—C11—C13 | 119.35 (18) | H23D—C23—H23F | 105 (5) |
C12—C11—C13 | 58.72 (14) | H23E—C23—H23F | 121 (5) |
C14—N2—N3—C15 | −0.72 (19) | C3—C4—C11—C12 | −175.73 (17) |
N2—N3—C15—N1 | 1.0 (2) | C5—C4—C11—C13 | −64.7 (3) |
N2—N3—C15—S1 | −177.09 (13) | C3—C4—C11—C13 | 114.7 (2) |
C14—N1—C15—N3 | −0.86 (19) | C13—C12—C11—C4 | −107.1 (2) |
C1—N1—C15—N3 | −177.82 (16) | C4—C11—C13—C12 | 112.2 (2) |
C14—N1—C15—S1 | 177.41 (13) | C18—N4—C19—O5 | 179.5 (4) |
C1—N1—C15—S1 | 0.4 (2) | C23—N4—C19—O5 | −0.5 (4) |
C16—S1—C15—N3 | 20.07 (19) | C18—N4—C19—C20 | −0.1 (2) |
C16—S1—C15—N1 | −157.84 (14) | C23—N4—C19—C20 | 179.96 (16) |
C5—C6—C1—C2 | 0.8 (3) | O5—C19—C20—C21 | 179.9 (4) |
C5—C6—C1—N1 | −177.35 (17) | N4—C19—C20—C21 | −0.6 (2) |
C7—C2—C1—C6 | 176.97 (17) | O5—C19—C20—N6 | 0.1 (5) |
C3—C2—C1—C6 | −1.9 (3) | N4—C19—C20—N6 | 179.59 (19) |
C7—C2—C1—N1 | −4.8 (3) | N6—C20—C21—N7 | 0.9 (4) |
C3—C2—C1—N1 | 176.25 (15) | C19—C20—C21—N7 | −178.9 (4) |
C15—N1—C1—C6 | 92.4 (2) | N6—C20—C21—N5 | −179.84 (16) |
C14—N1—C1—C6 | −83.8 (2) | C19—C20—C21—N5 | 0.3 (3) |
C15—N1—C1—C2 | −85.9 (2) | C18—N5—C21—N7 | 179.8 (4) |
C14—N1—C1—C2 | 98.0 (2) | C24—N5—C21—N7 | −1.3 (5) |
C1—C6—C5—C4 | 1.3 (3) | C18—N5—C21—C20 | 0.7 (3) |
O1—C17—C16—S1 | −138.28 (15) | C24—N5—C21—C20 | 179.62 (16) |
O2—C17—C16—S1 | 42.42 (19) | C20—C21—N7—C22 | −1.1 (6) |
C15—S1—C16—C17 | 60.03 (14) | N5—C21—N7—C22 | 179.7 (2) |
C1—C2—C7—C8 | −178.56 (18) | C21—N7—C22—N6 | 0.9 (6) |
C3—C2—C7—C8 | 0.3 (3) | N7—C22—N6—C20 | −0.4 (4) |
C6—C5—C4—C3 | −2.1 (3) | N7—C22—N6—C25 | 178.3 (4) |
C6—C5—C4—C11 | 177.29 (18) | C21—C20—N6—C22 | −0.3 (2) |
N3—N2—C14—N1 | 0.2 (2) | C19—C20—N6—C22 | 179.5 (2) |
N3—N2—C14—Br1 | 178.72 (13) | C21—C20—N6—C25 | −178.9 (2) |
C15—N1—C14—N2 | 0.4 (2) | C19—C20—N6—C25 | 0.9 (4) |
C1—N1—C14—N2 | 177.18 (17) | C18—N5—C19A—O5A | −174 (2) |
C15—N1—C14—Br1 | −178.20 (13) | C24—N5—C19A—O5A | 5 (2) |
C1—N1—C14—Br1 | −1.4 (3) | C18—N5—C19A—C20A | 0.7 (3) |
C2—C7—C8—C9 | −1.0 (3) | C24—N5—C19A—C20A | 179.62 (16) |
C19A—N5—C18—O4 | 178.50 (17) | O5A—C19A—C20A—N6A | −2 (2) |
C21—N5—C18—O4 | 178.50 (17) | N5—C19A—C20A—N6A | −176.8 (8) |
C24—N5—C18—O4 | −0.4 (3) | O5A—C19A—C20A—C21A | 175 (2) |
C19A—N5—C18—N4 | −1.3 (2) | N5—C19A—C20A—C21A | 0.3 (3) |
C21—N5—C18—N4 | −1.3 (2) | C18—N4—C21A—N7A | −176 (3) |
C24—N5—C18—N4 | 179.78 (16) | C23—N4—C21A—N7A | 4 (3) |
C21A—N4—C18—O4 | −178.81 (17) | C18—N4—C21A—C20A | −0.1 (2) |
C19—N4—C18—O4 | −178.81 (17) | C23—N4—C21A—C20A | 179.96 (16) |
C23—N4—C18—O4 | 1.2 (3) | N6A—C20A—C21A—N7A | −6 (3) |
C21A—N4—C18—N5 | 1.0 (3) | C19A—C20A—C21A—N7A | 176 (3) |
C19—N4—C18—N5 | 1.0 (3) | N6A—C20A—C21A—N4 | 177.3 (5) |
C23—N4—C18—N5 | −179.01 (16) | C19A—C20A—C21A—N4 | −0.6 (2) |
C9—C10—C3—C2 | −1.8 (3) | N6A—C20A—C21A—C22A | −0.9 (7) |
C9—C10—C3—C4 | 177.12 (17) | C19A—C20A—C21A—C22A | −178.9 (4) |
C7—C2—C3—C10 | 1.1 (2) | N4—C21A—N7A—C22A | −176.5 (10) |
C1—C2—C3—C10 | 180.00 (16) | C20A—C21A—N7A—C22A | 7 (4) |
C7—C2—C3—C4 | −177.91 (16) | C21A—N7A—C22A—N6A | −6 (4) |
C1—C2—C3—C4 | 1.0 (2) | N7A—C22A—N6A—C20A | 3 (3) |
C5—C4—C3—C10 | −177.98 (17) | C21A—C22A—N6A—C20A | −1.0 (7) |
C11—C4—C3—C10 | 2.6 (3) | N7A—C22A—N6A—C25A | −176 (3) |
C5—C4—C3—C2 | 0.9 (3) | C21A—C22A—N6A—C25A | 179.7 (14) |
C11—C4—C3—C2 | −178.49 (17) | C19A—C20A—N6A—C22A | 179.0 (7) |
C3—C10—C9—C8 | 1.2 (3) | C21A—C20A—N6A—C22A | 1.4 (10) |
C7—C8—C9—C10 | 0.3 (3) | C19A—C20A—N6A—C25A | −1.8 (17) |
C5—C4—C11—C12 | 4.9 (3) | C21A—C20A—N6A—C25A | −179.3 (12) |
C17H14BrN3O2S·C6H6N2O | Z = 4 |
Mr = 526.41 | F(000) = 1072 |
Monoclinic, P21/c | Dx = 1.542 Mg m−3 |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.5418 Å |
a = 14.0851 (14) Å | T = 298 K |
b = 6.9721 (7) Å | Particle morphology: needle |
c = 23.1952 (19) Å | colorless |
β = 95.476 (15)° | flat_sheet, 15 × 1 mm |
V = 2267.4 (4) Å3 | Specimen preparation: Prepared at 298 K and 101 kPa |
EMPYREAN (PANanalytical) diffractometer | Data collection mode: reflection |
Radiation source: line-focus sealed tube | Scan method: continuous |
Curved Germanium (111) monochromator | 2θmin = 5.003°, 2θmax = 80.007°, 2θstep = 0.017° |
Specimen mounting: thin layer on the non-diffracting silicon plate |
Refinement on Inet | 167 parameters |
Least-squares matrix: full with fixed elements per cycle | 99 restraints |
Rp = 0.036 | 0 constraints |
Rwp = 0.051 | H-atom parameters not refined |
Rexp = 0.021 | Weighting scheme based on measured s.u.'s |
RBragg = 0.073 | (Δ/σ)max = 0.004 |
4413 data points | Background function: Chebyshev polynomial up to the 5th order |
Excluded region(s): none | Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [100], texture parameter r = 0.84(1). |
Profile function: split-type pseudo-Voigt (Toraya, 1986) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.37370 (10) | 0.1272 (4) | −0.03870 (9) | 0.0610 (11)* | |
S1 | 0.2391 (3) | 0.2821 (7) | 0.1718 (2) | 0.055 (3)* | |
O1 | 0.1483 (5) | 0.3472 (14) | 0.2726 (4) | 0.058 (5)* | |
O2 | 0.0012 (6) | 0.3451 (16) | 0.2357 (4) | 0.053 (5)* | |
H2 | −0.0074 | 0.3682 | 0.2695 | 0.079* | |
N1 | 0.3270 (6) | 0.2150 (16) | 0.0755 (5) | 0.061 (7)* | |
N2 | 0.2049 (7) | 0.1883 (17) | 0.0084 (5) | 0.064 (7)* | |
N3 | 0.1702 (7) | 0.2236 (17) | 0.0616 (6) | 0.059 (6)* | |
C1 | 0.4264 (8) | 0.226 (2) | 0.1017 (6) | 0.063 (9)* | |
C2 | 0.4661 (8) | 0.070 (2) | 0.1353 (6) | 0.060 (7)* | |
C3 | 0.5624 (7) | 0.088 (2) | 0.1590 (6) | 0.059 (7)* | |
C4 | 0.6159 (8) | 0.260 (2) | 0.1491 (6) | 0.065 (8)* | |
C5 | 0.5737 (7) | 0.399 (3) | 0.1159 (6) | 0.067 (8)* | |
H5 | 0.6086 | 0.5084 | 0.1085 | 0.080* | |
C6 | 0.4761 (9) | 0.385 (2) | 0.0914 (6) | 0.072 (8)* | |
H6 | 0.4480 | 0.4838 | 0.0689 | 0.086* | |
C7 | 0.4143 (7) | −0.096 (3) | 0.1470 (6) | 0.066 (8)* | |
H7 | 0.3507 | −0.1065 | 0.1325 | 0.079* | |
C8 | 0.4566 (9) | −0.242 (2) | 0.1796 (6) | 0.071 (9)* | |
H8 | 0.4225 | −0.3531 | 0.1857 | 0.085* | |
C9 | 0.5503 (9) | −0.224 (2) | 0.2036 (6) | 0.063 (9)* | |
H9 | 0.5776 | −0.3214 | 0.2272 | 0.076* | |
C10 | 0.6032 (7) | −0.065 (2) | 0.1930 (5) | 0.062 (8)* | |
H10 | 0.6666 | −0.0574 | 0.2083 | 0.074* | |
C11 | 0.7161 (9) | 0.272 (2) | 0.1729 (6) | 0.066 (9)* | |
H11 | 0.7521 | 0.1546 | 0.1670 | 0.079* | |
C12 | 0.7491 (9) | 0.372 (2) | 0.2265 (6) | 0.072 (8)* | |
H12A | 0.7025 | 0.4436 | 0.2460 | 0.086* | |
H12B | 0.7995 | 0.3130 | 0.2519 | 0.086* | |
C13 | 0.7728 (9) | 0.442 (3) | 0.1710 (6) | 0.075 (8)* | |
H13A | 0.7413 | 0.5582 | 0.1560 | 0.090* | |
H13B | 0.8382 | 0.4278 | 0.1619 | 0.090* | |
C14 | 0.2962 (9) | 0.185 (2) | 0.0182 (6) | 0.065 (8)* | |
C15 | 0.2449 (10) | 0.237 (2) | 0.0997 (7) | 0.069 (9)* | |
C16 | 0.1090 (8) | 0.291 (2) | 0.1709 (6) | 0.076 (9)* | |
H16A | 0.0826 | 0.3907 | 0.1451 | 0.091* | |
H16B | 0.0809 | 0.1689 | 0.1584 | 0.091* | |
C17 | 0.0909 (8) | 0.332 (2) | 0.2309 (6) | 0.071 (8)* | |
O3 | −0.0614 (6) | 0.2835 (13) | 0.3322 (4) | 0.055 (5)* | |
N4 | 0.0712 (6) | 0.3115 (17) | 0.3925 (5) | 0.058 (7)* | |
H4A | 0.1052 | 0.3314 | 0.3642 | 0.070* | |
H4B | 0.0976 | 0.3104 | 0.4275 | 0.070* | |
N5 | −0.2345 (8) | 0.2092 (16) | 0.4621 (5) | 0.062 (7)* | |
C18 | −0.0245 (10) | 0.282 (2) | 0.3819 (6) | 0.067 (8)* | |
C19 | −0.0829 (8) | 0.258 (2) | 0.4301 (7) | 0.061 (9)* | |
C20 | −0.1820 (9) | 0.234 (2) | 0.4199 (7) | 0.065 (8)* | |
H20 | −0.2105 | 0.2348 | 0.3820 | 0.078* | |
C21 | −0.1972 (9) | 0.199 (2) | 0.5166 (6) | 0.071 (9)* | |
H21 | −0.2365 | 0.1752 | 0.5458 | 0.085* | |
C22 | −0.0998 (8) | 0.225 (2) | 0.5307 (7) | 0.074 (9)* | |
H22 | −0.0746 | 0.2247 | 0.5693 | 0.089* | |
C23 | −0.0406 (10) | 0.2501 (19) | 0.4871 (7) | 0.070 (9)* | |
H23 | 0.0251 | 0.2616 | 0.4954 | 0.084* |
Br1—C14 | 1.836 (14) | C9—H9 | 0.9299 |
S1—C15 | 1.712 (16) | C10—H10 | 0.9300 |
S1—C16 | 1.832 (12) | C11—C13 | 1.43 (2) |
O1—C17 | 1.205 (15) | C11—C12 | 1.46 (2) |
O2—C17 | 1.282 (14) | C11—H11 | 0.9797 |
O2—H2 | 0.8200 | C12—C13 | 1.44 (2) |
N1—C15 | 1.341 (18) | C12—H12A | 0.9703 |
N1—C14 | 1.374 (18) | C12—H12B | 0.9700 |
N1—C1 | 1.474 (15) | C13—H13A | 0.9701 |
N2—C14 | 1.285 (15) | C13—H13B | 0.9701 |
N2—N3 | 1.392 (17) | C16—C17 | 1.47 (2) |
N3—C15 | 1.311 (17) | C16—H16A | 0.9702 |
C1—C6 | 1.34 (2) | C16—H16B | 0.9701 |
C1—C2 | 1.42 (2) | O3—C18 | 1.219 (17) |
C2—C7 | 1.41 (2) | N4—C18 | 1.363 (17) |
C2—C3 | 1.419 (16) | N4—H4A | 0.8601 |
C3—C10 | 1.41 (2) | N4—H4B | 0.8600 |
C3—C4 | 1.44 (2) | N5—C20 | 1.29 (2) |
C4—C5 | 1.34 (2) | N5—C21 | 1.324 (18) |
C4—C11 | 1.468 (17) | C18—C19 | 1.46 (2) |
C5—C6 | 1.440 (16) | C19—C23 | 1.40 (2) |
C5—H5 | 0.9301 | C19—C20 | 1.404 (17) |
C6—H6 | 0.9302 | C20—H20 | 0.9301 |
C7—C8 | 1.37 (2) | C21—C22 | 1.391 (17) |
C7—H7 | 0.9300 | C21—H21 | 0.9299 |
C8—C9 | 1.388 (18) | C22—C23 | 1.38 (2) |
C8—H8 | 0.9298 | C22—H22 | 0.9300 |
C9—C10 | 1.37 (2) | C23—H23 | 0.9299 |
C15—S1—C16 | 97.8 (7) | C13—C12—H12B | 117.9 |
C17—O2—H2 | 109.5 | C11—C12—H12B | 117.9 |
C15—N1—C14 | 102.5 (10) | H12A—C12—H12B | 115.0 |
C15—N1—C1 | 130.1 (12) | C11—C13—C12 | 61.1 (10) |
C14—N1—C1 | 127.3 (11) | C11—C13—H13A | 117.7 |
C14—N2—N3 | 106.1 (11) | C12—C13—H13A | 117.7 |
C15—N3—N2 | 106.4 (11) | C11—C13—H13B | 117.7 |
C6—C1—C2 | 123.0 (11) | C12—C13—H13B | 117.7 |
C6—C1—N1 | 117.5 (12) | H13A—C13—H13B | 114.7 |
C2—C1—N1 | 119.5 (12) | N2—C14—N1 | 112.8 (12) |
C7—C2—C3 | 119.4 (13) | N2—C14—Br1 | 122.0 (11) |
C7—C2—C1 | 123.4 (11) | N1—C14—Br1 | 125.0 (9) |
C3—C2—C1 | 117.1 (14) | N3—C15—N1 | 112.2 (13) |
C10—C3—C2 | 118.2 (13) | N3—C15—S1 | 124.2 (12) |
C10—C3—C4 | 121.5 (10) | N1—C15—S1 | 123.6 (10) |
C2—C3—C4 | 120.3 (13) | C17—C16—S1 | 105.1 (8) |
C5—C4—C3 | 118.8 (11) | C17—C16—H16A | 110.7 |
C5—C4—C11 | 122.0 (12) | S1—C16—H16A | 110.7 |
C3—C4—C11 | 119.1 (12) | C17—C16—H16B | 110.7 |
C4—C5—C6 | 122.0 (14) | S1—C16—H16B | 110.7 |
C4—C5—H5 | 119.0 | H16A—C16—H16B | 108.8 |
C6—C5—H5 | 119.0 | O1—C17—O2 | 121.0 (13) |
C1—C6—C5 | 118.8 (14) | O1—C17—C16 | 127.9 (11) |
C1—C6—H6 | 120.6 | O2—C17—C16 | 111.0 (11) |
C5—C6—H6 | 120.6 | C18—N4—H4A | 120.0 |
C8—C7—C2 | 120.7 (11) | C18—N4—H4B | 120.0 |
C8—C7—H7 | 119.6 | H4A—N4—H4B | 120.0 |
C2—C7—H7 | 119.6 | C20—N5—C21 | 121.7 (12) |
C7—C8—C9 | 120.1 (13) | O3—C18—N4 | 119.6 (13) |
C7—C8—H8 | 119.9 | O3—C18—C19 | 120.4 (12) |
C9—C8—H8 | 119.9 | N4—C18—C19 | 120.0 (12) |
C10—C9—C8 | 120.8 (13) | C23—C19—C20 | 118.8 (14) |
C10—C9—H9 | 119.6 | C23—C19—C18 | 120.6 (12) |
C8—C9—H9 | 119.6 | C20—C19—C18 | 120.6 (13) |
C9—C10—C3 | 120.7 (10) | N5—C20—C19 | 121.3 (14) |
C9—C10—H10 | 119.6 | N5—C20—H20 | 119.3 |
C3—C10—H10 | 119.6 | C19—C20—H20 | 119.3 |
C13—C11—C12 | 59.8 (10) | N5—C21—C22 | 120.7 (13) |
C13—C11—C4 | 123.7 (13) | N5—C21—H21 | 119.6 |
C12—C11—C4 | 124.3 (12) | C22—C21—H21 | 119.6 |
C13—C11—H11 | 113.0 | C23—C22—C21 | 119.6 (14) |
C12—C11—H11 | 113.0 | C23—C22—H22 | 120.2 |
C4—C11—H11 | 113.0 | C21—C22—H22 | 120.2 |
C13—C12—C11 | 59.1 (10) | C22—C23—C19 | 117.7 (12) |
C13—C12—H12A | 117.9 | C22—C23—H23 | 121.1 |
C11—C12—H12A | 117.9 | C19—C23—H23 | 121.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.82 | 1.80 | 2.520 (13) | 145 |
N4—H4A···O1 | 0.86 | 2.27 | 3.091 (14) | 160 |
N4—H4B···N2i | 0.86 | 2.29 | 3.132 (16) | 165 |
C12—H12B···O3ii | 0.97 | 2.58 | 3.502 (16) | 159 |
C23—H23···N2i | 0.93 | 2.55 | 3.473 (17) | 174 |
C23—H23···N3i | 0.93 | 2.44 | 3.295 (18) | 153 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x+1, y, z. |
C17H14BrN3O2S·CH4N2O | V = 980.16 (17) Å3 |
Mr = 464.34 | Z = 2 |
Triclinic, P1 | F(000) = 472 |
Hall symbol: -P 1 | Dx = 1.573 Mg m−3 |
a = 10.8067 (12) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 12.1242 (12) Å | T = 298 K |
c = 7.5869 (7) Å | Particle morphology: needle |
α = 97.387 (17)° | colorless |
β = 92.495 (13)° | flat_sheet, 15 × 1 mm |
γ = 95.230 (15)° | Specimen preparation: Prepared at 298 K and 101 kPa |
EMPYREAN (PANanalytical) diffractometer | Data collection mode: reflection |
Radiation source: line-focus sealed tube | Scan method: continuous |
Curved Germanium (111) monochromator | 2θmin = 4.996°, 2θmax = 80.000°, 2θstep = 0.017° |
Specimen mounting: thin layer on the non-diffracting silicon plate |
Refinement on Inet | 148 parameters |
Least-squares matrix: full with fixed elements per cycle | 85 restraints |
Rp = 0.024 | 0 constraints |
Rwp = 0.033 | H-atom parameters not refined |
Rexp = 0.022 | Weighting scheme based on measured s.u.'s |
RBragg = 0.049 | (Δ/σ)max = 0.002 |
4413 data points | Background function: Chebyshev polynomial up to the 5th order |
Excluded region(s): none | Preferred orientation correction: March-Dollase texture correction (Dollase, 1986). Direction of preferred orientation [010], texture parameter r = 1.05(1). |
Profile function: split-type pseudo-Voigt (Toraya, 1986) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.30960 (18) | −0.02870 (16) | 0.2836 (3) | 0.0490 (11)* | |
S1 | 0.7021 (4) | 0.2846 (4) | 0.1731 (7) | 0.052 (2)* | |
O1 | 1.0111 (8) | 0.1568 (8) | 0.3158 (13) | 0.047 (5)* | |
O2 | 0.8684 (8) | 0.2410 (7) | 0.4532 (12) | 0.044 (5)* | |
H2 | 0.9048 | 0.2216 | 0.5395 | 0.066* | |
N1 | 0.4940 (10) | 0.1456 (9) | 0.2287 (16) | 0.055 (6)* | |
N2 | 0.5665 (10) | −0.0185 (9) | 0.2113 (15) | 0.050 (6)* | |
N3 | 0.6674 (10) | 0.0629 (9) | 0.1877 (15) | 0.054 (6)* | |
C1 | 0.4147 (13) | 0.2383 (12) | 0.253 (2) | 0.062 (8)* | |
C2 | 0.4128 (13) | 0.3011 (12) | 0.423 (2) | 0.064 (8)* | |
C3 | 0.3422 (12) | 0.3945 (11) | 0.438 (2) | 0.063 (8)* | |
C4 | 0.2752 (13) | 0.4198 (11) | 0.284 (2) | 0.058 (8)* | |
C5 | 0.2832 (13) | 0.3560 (13) | 0.124 (2) | 0.064 (8)* | |
H5 | 0.2385 | 0.3728 | 0.0245 | 0.077* | |
C6 | 0.3576 (13) | 0.2646 (12) | 0.103 (2) | 0.057 (8)* | |
H6 | 0.3667 | 0.2247 | −0.0082 | 0.068* | |
C7 | 0.4755 (13) | 0.2760 (12) | 0.577 (2) | 0.061 (8)* | |
H7 | 0.5232 | 0.2156 | 0.5681 | 0.073* | |
C8 | 0.4687 (13) | 0.3368 (13) | 0.738 (2) | 0.064 (8)* | |
H8 | 0.5099 | 0.3173 | 0.8382 | 0.077* | |
C9 | 0.3995 (13) | 0.4291 (12) | 0.754 (2) | 0.061 (8)* | |
H9 | 0.3975 | 0.4733 | 0.8634 | 0.073* | |
C10 | 0.3349 (12) | 0.4539 (11) | 0.608 (2) | 0.067 (9)* | |
H10 | 0.2842 | 0.5121 | 0.6222 | 0.081* | |
C11 | 0.2030 (13) | 0.5170 (12) | 0.297 (2) | 0.059 (8)* | |
H11 | 0.2414 | 0.5824 | 0.3761 | 0.071* | |
C12 | 0.1262 (13) | 0.5434 (12) | 0.145 (2) | 0.065 (8)* | |
H12A | 0.1223 | 0.6215 | 0.1316 | 0.078* | |
H12B | 0.1237 | 0.4934 | 0.0339 | 0.078* | |
C13 | 0.0657 (14) | 0.5015 (12) | 0.295 (2) | 0.068 (8)* | |
H13A | 0.0259 | 0.4256 | 0.2768 | 0.082* | |
H13B | 0.0245 | 0.5537 | 0.3745 | 0.082* | |
C14 | 0.4687 (14) | 0.0355 (12) | 0.238 (2) | 0.056 (8)* | |
C15 | 0.6188 (13) | 0.1569 (13) | 0.196 (2) | 0.063 (8)* | |
C16 | 0.8559 (14) | 0.2417 (12) | 0.156 (2) | 0.064 (8)* | |
H16A | 0.8521 | 0.1799 | 0.0606 | 0.077* | |
H16B | 0.9080 | 0.3030 | 0.1188 | 0.077* | |
C17 | 0.9212 (13) | 0.2070 (12) | 0.312 (2) | 0.057 (8)* | |
O3 | 0.9751 (8) | 0.1785 (8) | 0.7321 (13) | 0.055 (5)* | |
N4 | 1.1348 (10) | 0.0911 (8) | 0.6355 (16) | 0.054 (7)* | |
H4A | 1.1171 | 0.1036 | 0.5287 | 0.065* | |
H4B | 1.1976 | 0.0553 | 0.6573 | 0.065* | |
N5 | 1.0938 (10) | 0.1120 (9) | 0.9363 (16) | 0.053 (6)* | |
H5A | 1.0506 | 0.1376 | 1.0221 | 0.064* | |
H5B | 1.1566 | 0.0760 | 0.9577 | 0.064* | |
C18 | 1.0634 (13) | 0.1280 (12) | 0.770 (2) | 0.059 (8)* |
Br1—C14 | 1.886 (15) | C7—H7 | 0.9303 |
S1—C15 | 1.751 (16) | C8—C9 | 1.40 (2) |
S1—C16 | 1.791 (16) | C8—H8 | 0.9303 |
O1—C17 | 1.193 (18) | C9—C10 | 1.36 (2) |
O2—C17 | 1.274 (17) | C9—H9 | 0.9301 |
O2—H2 | 0.8200 | C10—H10 | 0.9298 |
N1—C14 | 1.350 (19) | C11—C12 | 1.48 (2) |
N1—C15 | 1.380 (18) | C11—C13 | 1.48 (2) |
N1—C1 | 1.472 (19) | C11—H11 | 0.9801 |
N2—C14 | 1.303 (19) | C12—C13 | 1.46 (2) |
N2—N3 | 1.436 (15) | C12—H12A | 0.9703 |
N3—C15 | 1.29 (2) | C12—H12B | 0.9701 |
C1—C6 | 1.36 (2) | C13—H13A | 0.9698 |
C1—C2 | 1.41 (2) | C13—H13B | 0.9704 |
C2—C7 | 1.41 (2) | C16—C17 | 1.48 (2) |
C2—C3 | 1.42 (2) | C16—H16A | 0.9699 |
C3—C10 | 1.41 (2) | C16—H16B | 0.9699 |
C3—C4 | 1.43 (2) | O3—C18 | 1.223 (18) |
C4—C5 | 1.36 (2) | N4—C18 | 1.360 (18) |
C4—C11 | 1.47 (2) | N4—H4A | 0.8599 |
C5—C6 | 1.42 (2) | N4—H4B | 0.8603 |
C5—H5 | 0.9301 | N5—C18 | 1.33 (2) |
C6—H6 | 0.9301 | N5—H5A | 0.8601 |
C7—C8 | 1.35 (2) | N5—H5B | 0.8599 |
C15—S1—C16 | 100.1 (7) | C4—C11—H11 | 114.6 |
C17—O2—H2 | 109.5 | C12—C11—H11 | 114.6 |
C14—N1—C15 | 104.1 (12) | C13—C11—H11 | 114.6 |
C14—N1—C1 | 131.0 (12) | C13—C12—C11 | 60.4 (11) |
C15—N1—C1 | 124.9 (12) | C13—C12—H12A | 117.7 |
C14—N2—N3 | 106.8 (11) | C11—C12—H12A | 117.8 |
C15—N3—N2 | 105.2 (11) | C13—C12—H12B | 117.7 |
C6—C1—C2 | 124.1 (14) | C11—C12—H12B | 117.7 |
C6—C1—N1 | 116.2 (13) | H12A—C12—H12B | 114.8 |
C2—C1—N1 | 119.3 (13) | C12—C13—C11 | 60.3 (11) |
C7—C2—C1 | 124.1 (14) | C12—C13—H13A | 117.8 |
C7—C2—C3 | 118.3 (13) | C11—C13—H13A | 117.8 |
C1—C2—C3 | 117.6 (14) | C12—C13—H13B | 117.7 |
C10—C3—C2 | 117.8 (14) | C11—C13—H13B | 117.8 |
C10—C3—C4 | 122.9 (13) | H13A—C13—H13B | 114.8 |
C2—C3—C4 | 119.2 (13) | N2—C14—N1 | 111.6 (13) |
C5—C4—C3 | 119.7 (13) | N2—C14—Br1 | 125.5 (11) |
C5—C4—C11 | 120.4 (14) | N1—C14—Br1 | 122.9 (11) |
C3—C4—C11 | 119.9 (13) | N3—C15—N1 | 112.2 (13) |
C4—C5—C6 | 122.3 (15) | N3—C15—S1 | 124.1 (11) |
C4—C5—H5 | 118.8 | N1—C15—S1 | 123.7 (12) |
C6—C5—H5 | 118.9 | C17—C16—S1 | 120.1 (11) |
C1—C6—C5 | 116.9 (14) | C17—C16—H16A | 107.3 |
C1—C6—H6 | 121.5 | S1—C16—H16A | 107.3 |
C5—C6—H6 | 121.6 | C17—C16—H16B | 107.3 |
C8—C7—C2 | 122.2 (14) | S1—C16—H16B | 107.3 |
C8—C7—H7 | 118.9 | H16A—C16—H16B | 106.9 |
C2—C7—H7 | 118.9 | O1—C17—O2 | 122.0 (14) |
C7—C8—C9 | 119.7 (14) | O1—C17—C16 | 128.3 (14) |
C7—C8—H8 | 120.2 | O2—C17—C16 | 109.7 (13) |
C9—C8—H8 | 120.1 | C18—N4—H4A | 120.0 |
C10—C9—C8 | 119.6 (13) | C18—N4—H4B | 120.0 |
C10—C9—H9 | 120.2 | H4A—N4—H4B | 120.0 |
C8—C9—H9 | 120.2 | C18—N5—H5A | 120.0 |
C9—C10—C3 | 122.2 (13) | C18—N5—H5B | 120.0 |
C9—C10—H10 | 118.9 | H5A—N5—H5B | 120.0 |
C3—C10—H10 | 118.9 | O3—C18—N5 | 122.7 (13) |
C4—C11—C12 | 122.3 (13) | O3—C18—N4 | 117.5 (13) |
C4—C11—C13 | 120.2 (12) | N5—C18—N4 | 119.8 (13) |
C12—C11—C13 | 59.3 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.82 | 1.78 | 2.596 (13) | 177 |
N4—H4A···O1 | 0.86 | 2.14 | 2.952 (15) | 157 |
N4—H4B···N3i | 0.86 | 2.50 | 3.313 (15) | 159 |
N5—H5A···O1ii | 0.86 | 2.27 | 3.049 (15) | 150 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y, z+1. |
C17H14BrN3O2S·CH4N2O | F(000) = 1887.4843 |
Mr = 464.35 | Dx = 1.571 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9993 (5) Å | Cell parameters from 4931 reflections |
b = 15.2290 (5) Å | θ = 3.7–23.5° |
c = 24.0797 (10) Å | µ = 2.23 mm−1 |
β = 103.193 (4)° | T = 150 K |
V = 3927.1 (3) Å3 | Needle, colourless |
Z = 8 | 0.30 × 0.12 × 0.10 mm |
Xcalibur, Eos, Nova diffractometer | 8975 independent reflections |
Radiation source: micro-focus sealed X-ray tube, Mova (Mo) X-ray Source | 5645 reflections with I ≥ 2u(I) |
Mirror monochromator | Rint = 0.093 |
Detector resolution: 8.0419 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
ω scans | h = −14→14 |
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −19→19 |
Tmin = 0.715, Tmax = 1.000 | l = −31→30 |
33889 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 62 constraints |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0312P)2 + 2.5686P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
8975 reflections | Δρmax = 2.18 e Å−3 |
509 parameters | Δρmin = −1.29 e Å−3 |
x | y | z | Uiso*/Ueq | ||
C1 | −0.1045 (5) | 0.1033 (3) | 0.5001 (2) | 0.0274 (12) | |
C2 | 0.0310 (5) | 0.1885 (3) | 0.5537 (2) | 0.0276 (12) | |
C3 | 0.2048 (5) | 0.2431 (3) | 0.6468 (2) | 0.0338 (13) | |
H3a | 0.1318 (5) | 0.2404 (3) | 0.6630 (2) | 0.0405 (15)* | |
H3b | 0.2562 (5) | 0.2917 (3) | 0.6646 (2) | 0.0405 (15)* | |
C4 | 0.2779 (5) | 0.1585 (3) | 0.6599 (2) | 0.0283 (12) | |
C5 | 0.0297 (4) | 0.1942 (3) | 0.44944 (19) | 0.0227 (11) | |
C6 | 0.0898 (5) | 0.1378 (3) | 0.4208 (2) | 0.0298 (12) | |
H6 | 0.1029 (5) | 0.0799 (3) | 0.4329 (2) | 0.0358 (15)* | |
C7 | 0.1320 (5) | 0.1668 (3) | 0.3734 (2) | 0.0307 (12) | |
H7 | 0.1694 (5) | 0.1270 (3) | 0.3532 (2) | 0.0369 (14)* | |
C8 | 0.1194 (5) | 0.2529 (3) | 0.3561 (2) | 0.0278 (12) | |
C9 | 0.0563 (4) | 0.3129 (3) | 0.3853 (2) | 0.0239 (11) | |
C10 | 0.0077 (4) | 0.2831 (3) | 0.43232 (18) | 0.0202 (10) | |
C11 | −0.0574 (4) | 0.3429 (3) | 0.4598 (2) | 0.0239 (11) | |
H11 | −0.0917 (4) | 0.3235 (3) | 0.4896 (2) | 0.0287 (13)* | |
C12 | −0.0706 (5) | 0.4292 (3) | 0.4432 (2) | 0.0293 (12) | |
H12 | −0.1134 (5) | 0.4679 (3) | 0.4618 (2) | 0.0352 (14)* | |
C13 | −0.0202 (5) | 0.4593 (3) | 0.3985 (2) | 0.0307 (12) | |
H13 | −0.0278 (5) | 0.5182 (3) | 0.3880 (2) | 0.0369 (15)* | |
C14 | 0.0405 (5) | 0.4024 (3) | 0.3699 (2) | 0.0307 (12) | |
H14 | 0.0720 (5) | 0.4232 (3) | 0.3397 (2) | 0.0368 (15)* | |
C15 | 0.1741 (5) | 0.2854 (3) | 0.3085 (2) | 0.0360 (13) | |
H15 | 0.1148 (5) | 0.3100 (3) | 0.2755 (2) | 0.0432 (16)* | |
C16 | 0.2860 (5) | 0.2410 (3) | 0.2962 (2) | 0.0401 (14) | |
H16a | 0.3195 (5) | 0.1906 (3) | 0.3193 (2) | 0.0482 (17)* | |
H16b | 0.2926 (5) | 0.2378 (3) | 0.2567 (2) | 0.0482 (17)* | |
C17 | 0.2991 (6) | 0.3289 (4) | 0.3241 (3) | 0.0544 (17) | |
H17a | 0.3135 (6) | 0.3791 (4) | 0.3016 (3) | 0.065 (2)* | |
H17b | 0.3404 (6) | 0.3319 (4) | 0.3642 (3) | 0.065 (2)* | |
C21 | 0.4302 (5) | 0.3990 (3) | 0.54182 (19) | 0.0236 (11) | |
C22 | 0.6134 (5) | 0.3569 (3) | 0.58664 (19) | 0.0251 (11) | |
C23 | 0.8035 (5) | 0.2990 (3) | 0.67225 (19) | 0.0280 (12) | |
H23a | 0.8531 (5) | 0.2465 (3) | 0.68289 (19) | 0.0336 (14)* | |
H23b | 0.7290 (5) | 0.2939 (3) | 0.68713 (19) | 0.0336 (14)* | |
C24 | 0.8779 (5) | 0.3785 (3) | 0.69850 (19) | 0.0243 (11) | |
C25 | 0.5555 (4) | 0.3168 (3) | 0.48275 (18) | 0.0197 (10) | |
C26 | 0.6144 (5) | 0.3585 (3) | 0.4467 (2) | 0.0273 (11) | |
H26 | 0.6428 (5) | 0.4158 (3) | 0.4542 (2) | 0.0327 (14)* | |
C27 | 0.6321 (5) | 0.3144 (3) | 0.39807 (19) | 0.0260 (11) | |
H27 | 0.6736 (5) | 0.3433 (3) | 0.37381 (19) | 0.0312 (13)* | |
C28 | 0.5907 (4) | 0.2303 (3) | 0.38480 (18) | 0.0203 (10) | |
C29 | 0.5256 (4) | 0.1865 (3) | 0.42229 (18) | 0.0195 (10) | |
C30 | 0.5081 (4) | 0.2298 (3) | 0.47223 (18) | 0.0184 (10) | |
C31 | 0.4453 (5) | 0.1869 (3) | 0.50923 (19) | 0.0275 (11) | |
H31 | 0.4361 (5) | 0.2151 (3) | 0.54229 (19) | 0.0330 (14)* | |
C32 | 0.3978 (5) | 0.1047 (3) | 0.4973 (2) | 0.0375 (14) | |
H32 | 0.3559 (5) | 0.0771 (3) | 0.5219 (2) | 0.0450 (16)* | |
C33 | 0.4125 (5) | 0.0619 (3) | 0.4476 (2) | 0.0349 (13) | |
H33 | 0.3787 (5) | 0.0062 (3) | 0.4393 (2) | 0.0419 (16)* | |
C34 | 0.4752 (5) | 0.1005 (3) | 0.41153 (19) | 0.0273 (12) | |
H34 | 0.4853 (5) | 0.0703 (3) | 0.37934 (19) | 0.0328 (14)* | |
C35 | 0.6106 (5) | 0.1871 (3) | 0.33281 (19) | 0.0294 (12) | |
H35 | 0.5807 (5) | 0.1264 (3) | 0.32770 (19) | 0.0352 (14)* | |
C36 | 0.7263 (5) | 0.2052 (4) | 0.3112 (2) | 0.0389 (14) | |
H36a | 0.7846 (5) | 0.2486 (4) | 0.3314 (2) | 0.0467 (16)* | |
H36b | 0.7644 (5) | 0.1564 (4) | 0.2957 (2) | 0.0467 (16)* | |
C37 | 0.6026 (5) | 0.2368 (3) | 0.2784 (2) | 0.0358 (13) | |
H37a | 0.5658 (5) | 0.2072 (3) | 0.2429 (2) | 0.0430 (16)* | |
H37b | 0.5860 (5) | 0.2993 (3) | 0.2786 (2) | 0.0430 (16)* | |
C40 | 0.5287 (4) | 0.4946 (3) | 0.25027 (19) | 0.0199 (10) | |
N1 | −0.1192 (4) | 0.0935 (3) | 0.55236 (18) | 0.0340 (11) | |
N2 | −0.0296 (4) | 0.1491 (3) | 0.58705 (17) | 0.0337 (11) | |
N3 | −0.0131 (4) | 0.1637 (2) | 0.49808 (16) | 0.0247 (9) | |
N4 | 0.5597 (4) | 0.3923 (2) | 0.62437 (17) | 0.0282 (10) | |
N5 | 0.4392 (4) | 0.4191 (2) | 0.59548 (17) | 0.0274 (9) | |
N6 | 0.5367 (4) | 0.3603 (2) | 0.53353 (15) | 0.0225 (9) | |
N11 | 0.6314 (4) | 0.5156 (3) | 0.29063 (17) | 0.0323 (10) | |
H11a | 0.6826 (14) | 0.545 (2) | 0.2755 (3) | 0.0388 (12)* | |
H11b | 0.6089 (5) | 0.548 (2) | 0.3160 (8) | 0.0388 (12)* | |
N12 | 0.4175 (4) | 0.5096 (2) | 0.26117 (16) | 0.0252 (9) | |
H12a | 0.4122 (4) | 0.5322 (2) | 0.29330 (16) | 0.0303 (11)* | |
H12b | 0.3507 (4) | 0.4968 (2) | 0.23611 (16) | 0.0303 (11)* | |
O1 | 0.2329 (3) | 0.0913 (2) | 0.67171 (16) | 0.0400 (10) | |
O2 | 0.3967 (3) | 0.1674 (2) | 0.65853 (16) | 0.0375 (9) | |
H2 | 0.4322 (13) | 0.1199 (8) | 0.665 (2) | 0.0562 (14)* | |
O3 | 0.9978 (3) | 0.3701 (2) | 0.70006 (15) | 0.0315 (8) | |
H3 | 1.0365 (6) | 0.410 (2) | 0.7189 (19) | 0.0473 (13)* | |
O4 | 0.8308 (3) | 0.4412 (2) | 0.71645 (14) | 0.0302 (8) | |
O5 | 0.5392 (3) | 0.46065 (19) | 0.20385 (12) | 0.0231 (7) | |
S2 | 0.75922 (12) | 0.30727 (9) | 0.59523 (5) | 0.0317 (3) | |
Br2 | 0.29317 (5) | 0.41848 (3) | 0.48198 (2) | 0.02899 (14) | |
Br1 | −0.18605 (5) | 0.04226 (3) | 0.43618 (2) | 0.03785 (16) | |
C41 | 0.1220 (5) | −0.0328 (3) | 0.29262 (19) | 0.0217 (10) | |
N13 | 0.2225 (4) | −0.0661 (2) | 0.32990 (17) | 0.0298 (10) | |
H13a | 0.2016 (10) | −0.079 (2) | 0.3614 (5) | 0.0358 (12)* | |
H13b | 0.246 (2) | −0.1132 (13) | 0.3157 (6) | 0.0358 (12)* | |
N14 | 0.0095 (4) | −0.0435 (3) | 0.30283 (17) | 0.0320 (10) | |
H14a | 0.0011 (4) | −0.0712 (3) | 0.33285 (17) | 0.0384 (12)* | |
H14b | −0.0550 (4) | −0.0226 (3) | 0.27944 (17) | 0.0384 (12)* | |
O6 | 0.1381 (3) | 0.0078 (2) | 0.24932 (13) | 0.0260 (8) | |
S1 | 0.15579 (13) | 0.26295 (8) | 0.57135 (5) | 0.0351 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.022 (3) | 0.027 (3) | 0.033 (3) | 0.003 (2) | 0.007 (2) | 0.017 (2) |
C2 | 0.030 (3) | 0.028 (3) | 0.024 (3) | 0.009 (2) | 0.005 (2) | 0.013 (2) |
C3 | 0.033 (3) | 0.041 (3) | 0.028 (3) | 0.003 (2) | 0.006 (3) | 0.001 (2) |
C4 | 0.021 (3) | 0.041 (3) | 0.021 (3) | 0.005 (2) | 0.000 (2) | 0.006 (2) |
C5 | 0.021 (3) | 0.023 (2) | 0.025 (3) | −0.008 (2) | 0.005 (2) | 0.004 (2) |
C6 | 0.038 (3) | 0.014 (2) | 0.042 (3) | 0.000 (2) | 0.018 (3) | 0.005 (2) |
C7 | 0.035 (3) | 0.026 (3) | 0.038 (3) | 0.001 (2) | 0.022 (3) | 0.002 (2) |
C8 | 0.036 (3) | 0.027 (3) | 0.024 (3) | −0.004 (2) | 0.013 (2) | 0.000 (2) |
C9 | 0.023 (3) | 0.023 (2) | 0.027 (3) | −0.005 (2) | 0.009 (2) | 0.005 (2) |
C10 | 0.016 (2) | 0.022 (2) | 0.021 (2) | 0.0008 (18) | 0.000 (2) | 0.0051 (19) |
C11 | 0.018 (3) | 0.028 (3) | 0.026 (3) | −0.004 (2) | 0.005 (2) | 0.007 (2) |
C12 | 0.027 (3) | 0.032 (3) | 0.029 (3) | 0.002 (2) | 0.007 (2) | −0.002 (2) |
C13 | 0.032 (3) | 0.020 (2) | 0.039 (3) | 0.002 (2) | 0.007 (3) | 0.010 (2) |
C14 | 0.035 (3) | 0.027 (3) | 0.032 (3) | −0.001 (2) | 0.013 (3) | 0.007 (2) |
C15 | 0.039 (3) | 0.042 (3) | 0.032 (3) | 0.008 (3) | 0.018 (3) | 0.009 (2) |
C16 | 0.044 (4) | 0.052 (4) | 0.030 (3) | 0.009 (3) | 0.022 (3) | 0.010 (3) |
C17 | 0.063 (5) | 0.043 (4) | 0.064 (4) | −0.002 (3) | 0.031 (4) | 0.011 (3) |
C21 | 0.025 (3) | 0.027 (3) | 0.021 (3) | 0.000 (2) | 0.010 (2) | −0.001 (2) |
C22 | 0.030 (3) | 0.028 (3) | 0.019 (2) | −0.002 (2) | 0.008 (2) | −0.004 (2) |
C23 | 0.028 (3) | 0.028 (3) | 0.029 (3) | −0.002 (2) | 0.008 (2) | 0.001 (2) |
C24 | 0.026 (3) | 0.031 (3) | 0.015 (2) | 0.002 (2) | 0.003 (2) | 0.005 (2) |
C25 | 0.018 (2) | 0.022 (2) | 0.019 (2) | −0.0013 (19) | 0.004 (2) | −0.0052 (19) |
C26 | 0.030 (3) | 0.020 (2) | 0.033 (3) | −0.005 (2) | 0.011 (3) | −0.007 (2) |
C27 | 0.032 (3) | 0.031 (3) | 0.019 (2) | −0.008 (2) | 0.012 (2) | 0.000 (2) |
C28 | 0.018 (3) | 0.026 (2) | 0.017 (2) | −0.0003 (19) | 0.004 (2) | −0.0036 (19) |
C29 | 0.020 (3) | 0.021 (2) | 0.017 (2) | 0.0013 (19) | 0.003 (2) | −0.0042 (18) |
C30 | 0.017 (2) | 0.018 (2) | 0.019 (2) | 0.0002 (18) | 0.002 (2) | −0.0036 (18) |
C31 | 0.033 (3) | 0.030 (3) | 0.021 (3) | −0.002 (2) | 0.010 (2) | −0.002 (2) |
C32 | 0.045 (4) | 0.032 (3) | 0.038 (3) | −0.011 (3) | 0.016 (3) | 0.006 (2) |
C33 | 0.043 (4) | 0.018 (3) | 0.043 (3) | −0.006 (2) | 0.008 (3) | −0.004 (2) |
C34 | 0.038 (3) | 0.024 (3) | 0.022 (3) | −0.002 (2) | 0.011 (2) | −0.003 (2) |
C35 | 0.037 (3) | 0.035 (3) | 0.018 (2) | 0.000 (2) | 0.009 (2) | −0.010 (2) |
C36 | 0.038 (3) | 0.056 (4) | 0.026 (3) | −0.001 (3) | 0.015 (3) | −0.016 (3) |
C37 | 0.048 (4) | 0.040 (3) | 0.019 (3) | 0.004 (3) | 0.007 (3) | −0.005 (2) |
C40 | 0.024 (3) | 0.018 (2) | 0.020 (2) | −0.0006 (19) | 0.010 (2) | 0.0015 (19) |
N1 | 0.027 (3) | 0.039 (3) | 0.040 (3) | 0.009 (2) | 0.016 (2) | 0.023 (2) |
N2 | 0.036 (3) | 0.036 (2) | 0.032 (2) | 0.009 (2) | 0.015 (2) | 0.008 (2) |
N3 | 0.026 (2) | 0.025 (2) | 0.024 (2) | 0.0021 (17) | 0.006 (2) | 0.0090 (17) |
N4 | 0.024 (2) | 0.034 (2) | 0.027 (2) | 0.0009 (18) | 0.007 (2) | −0.0079 (18) |
N5 | 0.027 (2) | 0.028 (2) | 0.028 (2) | 0.0012 (18) | 0.009 (2) | −0.0054 (18) |
N6 | 0.025 (2) | 0.023 (2) | 0.019 (2) | 0.0012 (17) | 0.0044 (19) | −0.0044 (16) |
N11 | 0.025 (3) | 0.046 (3) | 0.028 (2) | −0.007 (2) | 0.010 (2) | −0.011 (2) |
N12 | 0.024 (2) | 0.031 (2) | 0.023 (2) | −0.0013 (18) | 0.010 (2) | −0.0038 (17) |
O1 | 0.023 (2) | 0.038 (2) | 0.059 (3) | −0.0024 (16) | 0.010 (2) | 0.0193 (18) |
O2 | 0.028 (2) | 0.035 (2) | 0.049 (2) | 0.0020 (16) | 0.009 (2) | 0.0096 (18) |
O3 | 0.024 (2) | 0.034 (2) | 0.035 (2) | −0.0020 (15) | 0.0061 (18) | −0.0117 (16) |
O4 | 0.0211 (19) | 0.0300 (19) | 0.042 (2) | 0.0006 (14) | 0.0133 (17) | −0.0096 (16) |
O5 | 0.0235 (19) | 0.0261 (17) | 0.0216 (17) | −0.0045 (14) | 0.0092 (16) | −0.0061 (14) |
S2 | 0.0255 (7) | 0.0453 (8) | 0.0239 (7) | 0.0053 (6) | 0.0048 (6) | −0.0096 (6) |
Br2 | 0.0251 (3) | 0.0304 (3) | 0.0302 (3) | 0.0016 (2) | 0.0036 (2) | −0.0084 (2) |
Br1 | 0.0327 (3) | 0.0335 (3) | 0.0433 (3) | −0.0112 (2) | 0.0003 (3) | 0.0119 (2) |
C41 | 0.023 (3) | 0.021 (2) | 0.021 (2) | −0.007 (2) | 0.003 (2) | 0.0021 (19) |
N13 | 0.035 (3) | 0.030 (2) | 0.025 (2) | 0.0035 (19) | 0.008 (2) | 0.0053 (18) |
N14 | 0.022 (2) | 0.049 (3) | 0.025 (2) | −0.003 (2) | 0.005 (2) | 0.0139 (19) |
O6 | 0.0199 (19) | 0.0347 (18) | 0.0262 (18) | 0.0009 (14) | 0.0113 (16) | 0.0075 (15) |
S1 | 0.0376 (9) | 0.0371 (7) | 0.0278 (7) | −0.0048 (6) | 0.0016 (7) | 0.0075 (6) |
C1—N1 | 1.314 (6) | C22—N6 | 1.363 (5) |
C1—N3 | 1.371 (6) | C22—S2 | 1.742 (5) |
C1—Br1 | 1.845 (5) | C23—C24 | 1.516 (6) |
C2—N2 | 1.302 (6) | C23—S2 | 1.811 (5) |
C2—N3 | 1.369 (6) | C24—O3 | 1.317 (6) |
C2—S1 | 1.756 (5) | C24—O4 | 1.211 (5) |
C3—C4 | 1.514 (6) | C25—C26 | 1.354 (6) |
C3—S1 | 1.798 (5) | C25—C30 | 1.426 (6) |
C4—O1 | 1.199 (6) | C25—N6 | 1.446 (5) |
C4—O2 | 1.322 (6) | C26—C27 | 1.402 (6) |
C5—C6 | 1.363 (6) | C27—C28 | 1.373 (6) |
C5—C10 | 1.420 (6) | C28—C29 | 1.437 (6) |
C5—N3 | 1.436 (6) | C28—C35 | 1.474 (6) |
C6—C7 | 1.398 (6) | C29—C30 | 1.422 (6) |
C7—C8 | 1.372 (6) | C29—C34 | 1.422 (6) |
C8—C9 | 1.426 (6) | C30—C31 | 1.406 (6) |
C8—C15 | 1.497 (7) | C31—C32 | 1.362 (6) |
C9—C10 | 1.431 (6) | C32—C33 | 1.402 (7) |
C9—C14 | 1.414 (6) | C33—C34 | 1.361 (7) |
C10—C11 | 1.413 (6) | C35—C36 | 1.505 (7) |
C11—C12 | 1.372 (6) | C35—C37 | 1.498 (6) |
C12—C13 | 1.397 (7) | C36—C37 | 1.488 (7) |
C13—C14 | 1.370 (7) | C40—N11 | 1.349 (6) |
C15—C16 | 1.493 (7) | C40—N12 | 1.329 (6) |
C15—C17 | 1.495 (8) | C40—O5 | 1.261 (5) |
C16—C17 | 1.491 (7) | N1—N2 | 1.418 (6) |
C21—N5 | 1.310 (5) | N4—N5 | 1.409 (5) |
C21—N6 | 1.366 (6) | C41—N13 | 1.353 (6) |
C21—Br2 | 1.856 (5) | C41—N14 | 1.325 (6) |
C22—N4 | 1.308 (6) | C41—O6 | 1.259 (5) |
N3—C1—N1 | 111.1 (4) | O4—C24—O3 | 125.0 (4) |
Br1—C1—N1 | 126.8 (4) | C30—C25—C26 | 122.1 (4) |
Br1—C1—N3 | 122.0 (4) | N6—C25—C26 | 120.6 (4) |
N3—C2—N2 | 111.0 (4) | N6—C25—C30 | 117.3 (4) |
S1—C2—N2 | 129.1 (4) | C27—C26—C25 | 119.3 (4) |
S1—C2—N3 | 119.9 (4) | C28—C27—C26 | 122.7 (4) |
S1—C3—C4 | 112.1 (3) | C29—C28—C27 | 118.2 (4) |
O1—C4—C3 | 123.2 (5) | C35—C28—C27 | 120.5 (4) |
O2—C4—C3 | 112.9 (4) | C35—C28—C29 | 121.2 (4) |
O2—C4—O1 | 123.9 (5) | C30—C29—C28 | 119.9 (4) |
C10—C5—C6 | 121.6 (4) | C34—C29—C28 | 122.8 (4) |
N3—C5—C6 | 119.7 (4) | C34—C29—C30 | 117.3 (4) |
N3—C5—C10 | 118.7 (4) | C29—C30—C25 | 117.8 (4) |
C7—C6—C5 | 120.2 (4) | C31—C30—C25 | 122.1 (4) |
C8—C7—C6 | 121.4 (5) | C31—C30—C29 | 120.1 (4) |
C9—C8—C7 | 119.2 (4) | C32—C31—C30 | 120.8 (4) |
C15—C8—C7 | 121.3 (4) | C33—C32—C31 | 119.6 (5) |
C15—C8—C9 | 119.5 (4) | C34—C33—C32 | 121.2 (4) |
C10—C9—C8 | 120.0 (4) | C33—C34—C29 | 121.0 (4) |
C14—C9—C8 | 122.2 (4) | C36—C35—C28 | 120.8 (4) |
C14—C9—C10 | 117.9 (4) | C37—C35—C28 | 121.8 (4) |
C9—C10—C5 | 117.5 (4) | C37—C35—C36 | 59.4 (3) |
C11—C10—C5 | 123.3 (4) | C37—C36—C35 | 60.0 (3) |
C11—C10—C9 | 119.2 (4) | C36—C37—C35 | 60.5 (3) |
C12—C11—C10 | 120.7 (4) | N12—C40—N11 | 118.3 (4) |
C13—C12—C11 | 120.4 (5) | O5—C40—N11 | 120.3 (4) |
C14—C13—C12 | 120.3 (4) | O5—C40—N12 | 121.4 (4) |
C13—C14—C9 | 121.5 (5) | N2—N1—C1 | 106.0 (4) |
C16—C15—C8 | 119.8 (4) | N1—N2—C2 | 107.3 (4) |
C17—C15—C8 | 117.5 (5) | C2—N3—C1 | 104.5 (4) |
C17—C15—C16 | 59.9 (4) | C5—N3—C1 | 128.7 (4) |
C17—C16—C15 | 60.1 (4) | C5—N3—C2 | 126.8 (4) |
C16—C17—C15 | 60.0 (4) | N5—N4—C22 | 107.4 (4) |
N6—C21—N5 | 111.8 (4) | N4—N5—C21 | 105.7 (4) |
Br2—C21—N5 | 126.4 (4) | C22—N6—C21 | 104.3 (4) |
Br2—C21—N6 | 121.8 (3) | C25—N6—C21 | 127.8 (4) |
N6—C22—N4 | 110.8 (4) | C25—N6—C22 | 126.7 (4) |
S2—C22—N4 | 130.3 (4) | C23—S2—C22 | 100.2 (2) |
S2—C22—N6 | 119.0 (3) | N14—C41—N13 | 119.2 (4) |
S2—C23—C24 | 111.4 (3) | O6—C41—N13 | 119.0 (4) |
O3—C24—C23 | 112.1 (4) | O6—C41—N14 | 121.8 (4) |
O4—C24—C23 | 122.9 (5) | C3—S1—C2 | 100.0 (2) |
pKa API/coformer | ΔpKa = pKa(base) - pKa(acid) | Expected binary system | |
Lesinurad | 3.2 | – | – |
Caffeine | 0.6 | -2.6 | Cocrystal |
Nicotinamide | 3.35 | 0.15 | Cocrystal |
Urea | 0.1 | -0.31 | Cocrystal |
Allopurinol | 10.2 | 7.0 | Salt |
Febuxostat | 3.3 | 0.1 | Cocrystal |
LES (Form 2) | LES–MeOH (1:1) | LES–EtOH (1:1) | LES–CAF (1:1) | LES–NAM (1:1) | LES–URE (1:1) Form I | LES–URE (2:2) Form II | |
CCDC No. | 1888106 | 1888107 | 1888109 | 1888110 | 1888111 | 1888108 | 1888112 |
Chemical formula | C17H14BrN3O2S | C17H14BrN3O2S.CH4O | C17H14BrN3O2S.C2H6O | C17H14BrN3O2S.C8H10N4O2 | C17H14BrN3O2S.C6H6N2O | C17H14BrN3O2S.CH4N2O | 2C17H14BrN3O2S.2CH4N2O |
Mr | 404.28 | 436.33 | 450.35 | 598.48 | 526.41 | 464.34 | 464.35 |
Crystal system, space group | Orthorhombic, Pbca | Triclinic, P1 | Monoclinic, P21/n | Monoclinic, P21/c | Monoclinic, P21/c | Triclinic, P1 | Monoclinic, P21/c |
T (K) | 298 (2) | 298 (2) | 298 (2) | 100 (2) | 298 (2) | 298 (2) | 150 (2) |
a (Å) | 22.1247 (17) | 9.0092 (10) | 13.292 (6) | 15.1245 (8) | 14.0851 (14) | 10.8067 (12) | 10.9993 (5) |
b (Å) | 8.7081 (8) | 9.2165 (10) | 7.366 (3) | 6.6975 (3) | 6.9721 (7) | 12.1242 (12) | 15.2290 (5) |
c (Å) | 18.2738 (15) | 11.6947 (13) | 20.193 (9) | 25.8260 (13) | 23.1952 (19) | 7.5869 (7) | 24.0797 (10) |
α, β, γ (°) | 90, 90, 90 | 80.899 (6), 79.931 (6), 88.024 (6) | 90, 92.857 (6), 90 | 90, 101.045 (2), 90 | 90, 95.476 (15), 90 | 97.387 (17), 92.495 (13), 95.230 (15) | 90, 103.193 (4), 90 |
V (Å3) | 3520.7 (5) | 944.03 (18) | 1974.6 (15) | 2567.6 (2) | 2267.4 (4) | 980.16 (17) | 3927.1 (3) |
Z | 8 | 2 | 4 | 4 | 4 | 2 | 8 |
ρcalc (Mg m-3) | 1.525 | 1.535 | 1.515 | 1.548 | 1.542 | 1.573 | 1.571 |
µ (mm-1) | 4.416 | 2.311 | 2.212 | 1.729 | 3.639 | 4.117 | 2.230 |
Radiation | Cu Kα | Mo Kα | Mo Kα | Mo Kα | Cu Kα | Cu Kα | Mo Kα |
Specimen shape, size (mm) | Flat sheet, 15 × 1 | 0.24 × 0.20 × 0.20 | 0.30 × 0.20 × 0.16 | 0.36 × 0.16 × 0.12 | Flat sheet, 15 × 1 | Flat sheet, 15 × 1 | 0.30 × 0.12 × 0.10 |
Data collection | |||||||
No. of measured, independent and observed reflections | – | 10109, 4311, 3038 | 7427, 5089, 3396 | 50811, 4550, 3978 | – | – | 33889, 8975, 5645 |
θ values (°) | 2θmin = 5.004, 2θmax = 80.008, 2θstep = 0.017 | θmax = 27.5, θmin = 3.1 | θmax = 33.7, θmin = 2.6 | θmax = 25.1, θmin = 2.3 | 2θmin = 5.003, 2θmax = 80.007, 2θstep = 0.017 | 2θmin = 4.996, 2θmax = 80.000, 2θstep = 0.017 | θmax = 23.5, θmin = 3.7 |
Refinement | |||||||
R factors, WR2, goodness of fit | Rp = 0.0319, Rwp = 0.0418, Rexp = 0.0217, χ2 = 1.925 | 0.0519, 0.1279, 1.043 | 0.0684, 0.1926, 1.202 | 0.0256, 0.0639, 1.045 | Rp = 0.0360, Rwp = 0.0506, Rexp = 0.0213, χ2 =2.381 | Rp = 0.0244, Rwp = 0.0330, Rexp = 0.0217, χ2 = 1.518 | 0.0645, 0.1317, 1.049 |
Method of structure determination | PXRD | SCXRD | SCXRD | SCXRD | PXRD | PXRD | SCXRD |
Homo and heterosynthons | Mode of interaction | BEs (in kcal mol-1) | |
BSSE | BSSE+D3 | ||
Lesinurad dimer I | Br···π and acid–triazole | 17.4 | 21.9 |
Lesinurad dimer II | Acid–acid dimer | 20.6 | 21.1 |
Lesinurad dimer III | Acid–triazole and C—H···O | 12.8 | 14.0 |
Lesinurad dimer IV | C—H···π stacking | 8.0 | 13.2 |
Caffeine dimer | π–π stacking | 11.7 | 15.7 |
Lesinurad–caffeine I | Acid–imidazole and C—H···O | 15.3 | 16.2 |
Lesinurad–caffeine II | Acid–carbonyl | 13.1 | 14.3 |
Lesinurad–caffeine III | S···O and C—H···π | 5.6 | 9.8 |
Lesinurad–nicotinamide I | Acid–amide | 19.5 | 20.0 |
Lesinurad–nicotinamide II | Acid–pyridine | 13.1 | 13.8 |
Lesinurad–urea I | Acid–amide | 20.9 | 21.1 |
Lesinurad–urea II | N—H···O and N—H···N | 17.1 | 18.5 |
Urea dimer | Amide–amide dimer | 15.6 | 16.0 |
Lesinurad–allopurinol | N—H···O and O—H···N | 32.5 | 33.3 |
Lesinurad–febuxostat | Acid–acid dimer | 21.2 | 21.7 |
O—H stretch | N—H stretch | C═O stretch | C═O (coformer) | N—H (coformer) | |
LES | 3422 | – | 1723 | – | – |
LES–MeOH (1:1) | Broad | – | 1732 | – | – |
LES–EtOH (1:1) | 3646 | – | 1719 | – | – |
LES–CAF (1:1) | 3418 (Broad) | – | 1702, 1660 | 1702, 1663 | – |
LES–NAM (1:1) | – | 3355, 3267, 3172 | 1718, 1666 | 1698, 1680 | 3366, 3160 |
LES–URE (1:1, Form I) | 3460 | 3328, 3215 | 1698 | 1683 | 3447, 3347, 3262 |
LES–ALO (1:1) | – | – | 1718, 1699 | 1700 | 3400 |
LES–FEB (1:1) | – | 3185 (broad) | 1699 | 1675 | – |
Endotherm Peak (°C) | Melting peak of coformer (°C) | Enthalpy of fusion (ΔH) (J g-1) | |
LES | 175.6 | – | -58.6 |
LES–MeOH (1:1) | 94.7, 148.9 (broad) | – | -93.5, 1.4 |
LES–EtOH (1:1) | 77.1, 149.5 (broad) | – | -95.6, 1.0 |
LES–CAF (1:1) | 147.9 | 227–228 | -89.1 |
LES–NAM (1:1) | 179.8 | 128–129 | -117.5 |
LES–URE (1:1, Form I) | 160.0 | 133–135 | -149.1 |
LES–URE (1:1, Form II) | 135.3 | -102.2 | |
LES–ALO (1:1) | 176.3 | >350 | -30.7 |
LES–FEB (1:1) | 166.1 | 238–239 | -88.4 |
Absorption coefficient (mg ml-1)-1 | Solubility (mg l-1) at 4 h), λmax = 291 nm | Solubility (mg l-1) at 24 h, λmax = 291 nm | Solid phase after 24 h | |
LES (Form 2) | 56.5 | 14.2 | 20.5 | LES (Form 2) |
LES–CAF (1:1) | 48.6 | 282.6 (×19.9) | 250.1 (×12.2) | LES (Form 2) |
LES–NAM (1:1) | 45.9 | 161.4 (×11.4) | 145.5 (×7.1) | LES (Form 2) + LES–NAM |
LES–URE (Form I, 1:1) | 49.7 | 604.9 (×42.6) | 514.6 (×25.1) | LES (Form 2) |
LES–ALO (1:1) | 54.8 | 169.0 (×11.9) | 143.5 (×7.0) | LES (Form 2) + ALO |