Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618012287/fn3266sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266VIIsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618012287/fn3266VIIIsup9.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618012287/fn3266IIsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618012287/fn3266IIIsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618012287/fn3266IVsup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618012287/fn3266Vsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618012287/fn3266VIIIsup14.cml |
CCDC references: 1864481; 1864480; 1864479; 1864478; 1864477; 1864476; 1864475; 1864474
Data collection: APEX2 (Bruker, 2004) for (I), (II), (III), (IV), (V), (VI); CrysAlis PRO (Agilent, 2012) for (VII); X-AREA (Stoe & Cie, 2002) for (VIII). Cell refinement: SAINT (Bruker, 2004) for (I), (II), (III), (IV), (V), (VI); CrysAlis PRO (Agilent, 2012) for (VII); X-AREA (Stoe & Cie, 2002) for (VIII). Data reduction: SAINT (Bruker, 2004) for (I), (II), (III), (IV), (V), (VI); CrysAlis RED (Agilent, 2012) for (VII); X-RED (Stoe & Cie, 2002) for (VIII). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (II), (III), (IV), (V), (VI), (VIII); SUPERFLIP (Palatinus & Chapuis, 2007) for (VII). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C18H17N3O4S | F(000) = 776 |
Mr = 371.41 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.344 (2) Å | Cell parameters from 3259 reflections |
b = 9.6384 (9) Å | θ = 2.0–25.2° |
c = 9.443 (1) Å | µ = 0.21 mm−1 |
β = 101.060 (3)° | T = 296 K |
V = 1817.2 (3) Å3 | Block, orange |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Bruker APEXII CCD diffractometer | 3258 independent reflections |
Radiation source: fine focus sealed tube | 1971 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 25.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −24→24 |
Tmin = 0.848, Tmax = 0.980 | k = −11→10 |
20651 measured reflections | l = −11→11 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0301P)2 + 2.4078P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3258 reflections | Δρmax = 0.26 e Å−3 |
241 parameters | Δρmin = −0.28 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 | ||
C1 | 0.62363 (19) | 0.6121 (3) | 0.3110 (4) | 0.0432 (9) | |
C2 | 0.6796 (2) | 0.6754 (4) | 0.2806 (4) | 0.0529 (10) | |
H2 | 0.6762 | 0.7263 | 0.1958 | 0.063* | |
C3 | 0.7410 (2) | 0.6658 (4) | 0.3724 (4) | 0.0515 (10) | |
H3 | 0.7783 | 0.7102 | 0.3503 | 0.062* | |
C4 | 0.74613 (18) | 0.5890 (3) | 0.4979 (3) | 0.0401 (9) | |
C5 | 0.6905 (2) | 0.5242 (4) | 0.5295 (4) | 0.0525 (10) | |
H5 | 0.6943 | 0.4719 | 0.6134 | 0.063* | |
C6 | 0.6295 (2) | 0.5358 (4) | 0.4386 (4) | 0.0551 (11) | |
H6 | 0.5920 | 0.4929 | 0.4620 | 0.066* | |
N1 | 0.56308 (16) | 0.6324 (3) | 0.2120 (3) | 0.0460 (8) | |
C17 | 0.5109 (2) | 0.5603 (4) | 0.2146 (4) | 0.0501 (10) | |
H17 | 0.5134 | 0.4900 | 0.2829 | 0.060* | |
C11 | 0.44825 (19) | 0.5821 (4) | 0.1172 (4) | 0.0477 (9) | |
C12 | 0.4417 (2) | 0.6827 (4) | 0.0077 (4) | 0.0506 (10) | |
C13 | 0.3810 (2) | 0.6998 (4) | −0.0853 (5) | 0.0639 (12) | |
H13 | 0.3772 | 0.7637 | −0.1603 | 0.077* | |
C14 | 0.3264 (2) | 0.6236 (5) | −0.0680 (5) | 0.0760 (14) | |
H14 | 0.2855 | 0.6374 | −0.1299 | 0.091* | |
C15 | 0.3317 (3) | 0.5258 (5) | 0.0412 (6) | 0.0789 (14) | |
H15 | 0.2944 | 0.4751 | 0.0539 | 0.095* | |
C16 | 0.3924 (2) | 0.5046 (5) | 0.1303 (5) | 0.0668 (12) | |
H16 | 0.3961 | 0.4365 | 0.2012 | 0.080* | |
O12 | 0.49378 (15) | 0.7636 (3) | −0.0084 (3) | 0.0732 (9) | |
H12 | 0.5271 | 0.7405 | 0.0502 | 0.110* | |
S4 | 0.82316 (5) | 0.57701 (10) | 0.61683 (10) | 0.0494 (3) | |
O1 | 0.86074 (14) | 0.6983 (3) | 0.5966 (3) | 0.0657 (8) | |
O2 | 0.81221 (15) | 0.5410 (3) | 0.7568 (2) | 0.0662 (8) | |
N4 | 0.86257 (15) | 0.4427 (3) | 0.5655 (3) | 0.0411 (8) | |
H4 | 0.8547 (17) | 0.366 (4) | 0.608 (4) | 0.049* | |
O41 | 0.84031 (13) | 0.3227 (2) | 0.3499 (2) | 0.0475 (6) | |
N42 | 0.85711 (17) | 0.3240 (3) | 0.2119 (3) | 0.0522 (8) | |
C43 | 0.89615 (19) | 0.4321 (4) | 0.2091 (3) | 0.0437 (9) | |
C44 | 0.90760 (17) | 0.5044 (3) | 0.3423 (3) | 0.0378 (8) | |
C45 | 0.87241 (16) | 0.4321 (3) | 0.4238 (3) | 0.0347 (8) | |
C46 | 0.9242 (2) | 0.4639 (4) | 0.0783 (4) | 0.0716 (13) | |
H46A | 0.9719 | 0.4518 | 0.0996 | 0.107* | |
H46B | 0.9138 | 0.5581 | 0.0493 | 0.107* | |
H46C | 0.9049 | 0.4024 | 0.0015 | 0.107* | |
C47 | 0.9523 (2) | 0.6282 (4) | 0.3802 (4) | 0.0597 (11) | |
H47A | 0.9287 | 0.7107 | 0.3429 | 0.090* | |
H47B | 0.9916 | 0.6178 | 0.3388 | 0.090* | |
H47C | 0.9652 | 0.6353 | 0.4832 | 0.090* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.054 (3) | 0.036 (2) | 0.041 (2) | 0.0056 (18) | 0.0134 (19) | 0.0023 (16) |
C2 | 0.062 (3) | 0.051 (2) | 0.049 (2) | 0.005 (2) | 0.018 (2) | 0.0191 (19) |
C3 | 0.053 (3) | 0.047 (2) | 0.057 (2) | −0.0006 (19) | 0.018 (2) | 0.0134 (19) |
C4 | 0.054 (2) | 0.0303 (18) | 0.0388 (19) | −0.0002 (17) | 0.0158 (17) | −0.0039 (16) |
C5 | 0.067 (3) | 0.053 (2) | 0.037 (2) | −0.004 (2) | 0.012 (2) | 0.0098 (18) |
C6 | 0.060 (3) | 0.056 (3) | 0.051 (2) | −0.011 (2) | 0.016 (2) | 0.0090 (19) |
N1 | 0.054 (2) | 0.0428 (18) | 0.0440 (18) | 0.0036 (16) | 0.0168 (16) | −0.0002 (14) |
C17 | 0.068 (3) | 0.047 (2) | 0.037 (2) | 0.002 (2) | 0.012 (2) | 0.0001 (17) |
C11 | 0.052 (3) | 0.045 (2) | 0.047 (2) | −0.0024 (19) | 0.0108 (19) | −0.0064 (18) |
C12 | 0.053 (3) | 0.043 (2) | 0.057 (2) | 0.007 (2) | 0.014 (2) | −0.0043 (19) |
C13 | 0.067 (3) | 0.050 (3) | 0.071 (3) | 0.011 (2) | 0.005 (3) | 0.003 (2) |
C14 | 0.061 (3) | 0.071 (3) | 0.089 (4) | 0.007 (3) | −0.003 (3) | −0.018 (3) |
C15 | 0.067 (4) | 0.077 (3) | 0.092 (4) | −0.020 (3) | 0.014 (3) | −0.009 (3) |
C16 | 0.071 (3) | 0.068 (3) | 0.060 (3) | −0.014 (3) | 0.009 (2) | −0.001 (2) |
O12 | 0.066 (2) | 0.0674 (19) | 0.086 (2) | 0.0001 (17) | 0.0138 (17) | 0.0314 (17) |
S4 | 0.0697 (7) | 0.0424 (5) | 0.0352 (5) | 0.0016 (5) | 0.0077 (4) | −0.0103 (4) |
O1 | 0.080 (2) | 0.0391 (15) | 0.0739 (19) | −0.0134 (14) | 0.0050 (16) | −0.0164 (14) |
O2 | 0.090 (2) | 0.082 (2) | 0.0267 (13) | 0.0107 (17) | 0.0119 (13) | −0.0108 (13) |
N4 | 0.062 (2) | 0.0331 (17) | 0.0293 (16) | 0.0033 (15) | 0.0122 (14) | 0.0044 (12) |
O41 | 0.0687 (18) | 0.0414 (14) | 0.0358 (13) | −0.0092 (13) | 0.0183 (12) | −0.0065 (11) |
N42 | 0.081 (2) | 0.0492 (19) | 0.0310 (16) | −0.0048 (18) | 0.0225 (16) | −0.0082 (14) |
C43 | 0.056 (2) | 0.042 (2) | 0.0361 (19) | 0.0072 (19) | 0.0168 (17) | 0.0041 (16) |
C44 | 0.043 (2) | 0.0344 (19) | 0.0356 (19) | 0.0047 (16) | 0.0059 (16) | 0.0082 (15) |
C45 | 0.042 (2) | 0.0307 (18) | 0.0306 (18) | 0.0036 (16) | 0.0038 (15) | 0.0015 (15) |
C46 | 0.103 (4) | 0.068 (3) | 0.053 (2) | 0.005 (3) | 0.037 (2) | 0.007 (2) |
C47 | 0.061 (3) | 0.052 (2) | 0.062 (3) | −0.013 (2) | −0.001 (2) | 0.011 (2) |
C1—C2 | 1.371 (5) | C15—C16 | 1.369 (6) |
C1—C6 | 1.397 (5) | C15—H15 | 0.9300 |
C1—N1 | 1.410 (4) | C16—H16 | 0.9300 |
C2—C3 | 1.379 (5) | O12—H12 | 0.8200 |
C2—H2 | 0.9300 | S4—O2 | 1.425 (2) |
C3—C4 | 1.384 (5) | S4—O1 | 1.430 (3) |
C3—H3 | 0.9300 | S4—N4 | 1.644 (3) |
C4—C5 | 1.374 (5) | N4—C45 | 1.394 (4) |
C4—S4 | 1.748 (4) | N4—H4 | 0.87 (3) |
C5—C6 | 1.372 (5) | O41—C45 | 1.360 (4) |
C5—H5 | 0.9300 | O41—N42 | 1.409 (3) |
C6—H6 | 0.9300 | N42—C43 | 1.313 (4) |
N1—C17 | 1.273 (4) | C43—C44 | 1.417 (4) |
C17—C11 | 1.437 (5) | C43—C46 | 1.489 (5) |
C17—H17 | 0.9300 | C44—C45 | 1.342 (4) |
C11—C16 | 1.386 (5) | C44—C47 | 1.502 (5) |
C11—C12 | 1.405 (5) | C46—H46A | 0.9600 |
C12—O12 | 1.347 (4) | C46—H46B | 0.9600 |
C12—C13 | 1.381 (5) | C46—H46C | 0.9600 |
C13—C14 | 1.368 (6) | C47—H47A | 0.9600 |
C13—H13 | 0.9300 | C47—H47B | 0.9600 |
C14—C15 | 1.386 (6) | C47—H47C | 0.9600 |
C14—H14 | 0.9300 | ||
C2—C1—C6 | 118.6 (4) | C15—C16—C11 | 121.5 (4) |
C2—C1—N1 | 117.0 (3) | C15—C16—H16 | 119.2 |
C6—C1—N1 | 124.3 (3) | C11—C16—H16 | 119.2 |
C1—C2—C3 | 121.8 (3) | C12—O12—H12 | 109.5 |
C1—C2—H2 | 119.1 | O2—S4—O1 | 120.41 (17) |
C3—C2—H2 | 119.1 | O2—S4—N4 | 104.68 (15) |
C2—C3—C4 | 119.0 (3) | O1—S4—N4 | 107.52 (16) |
C2—C3—H3 | 120.5 | O2—S4—C4 | 109.37 (17) |
C4—C3—H3 | 120.5 | O1—S4—C4 | 107.25 (17) |
C5—C4—C3 | 119.9 (3) | N4—S4—C4 | 106.88 (15) |
C5—C4—S4 | 120.3 (3) | C45—N4—S4 | 120.6 (2) |
C3—C4—S4 | 119.8 (3) | C45—N4—H4 | 117 (2) |
C6—C5—C4 | 120.8 (3) | S4—N4—H4 | 113 (2) |
C6—C5—H5 | 119.6 | C45—O41—N42 | 106.8 (2) |
C4—C5—H5 | 119.6 | C43—N42—O41 | 106.3 (3) |
C5—C6—C1 | 119.9 (4) | N42—C43—C44 | 111.7 (3) |
C5—C6—H6 | 120.0 | N42—C43—C46 | 120.6 (3) |
C1—C6—H6 | 120.0 | C44—C43—C46 | 127.7 (3) |
C17—N1—C1 | 122.5 (3) | C45—C44—C43 | 103.8 (3) |
N1—C17—C11 | 123.2 (4) | C45—C44—C47 | 129.9 (3) |
N1—C17—H17 | 118.4 | C43—C44—C47 | 126.2 (3) |
C11—C17—H17 | 118.4 | C44—C45—O41 | 111.4 (3) |
C16—C11—C12 | 118.3 (4) | C44—C45—N4 | 134.7 (3) |
C16—C11—C17 | 120.4 (4) | O41—C45—N4 | 113.9 (3) |
C12—C11—C17 | 121.3 (4) | C43—C46—H46A | 109.5 |
O12—C12—C13 | 119.1 (4) | C43—C46—H46B | 109.5 |
O12—C12—C11 | 121.1 (4) | H46A—C46—H46B | 109.5 |
C13—C12—C11 | 119.8 (4) | C43—C46—H46C | 109.5 |
C14—C13—C12 | 120.5 (4) | H46A—C46—H46C | 109.5 |
C14—C13—H13 | 119.7 | H46B—C46—H46C | 109.5 |
C12—C13—H13 | 119.7 | C44—C47—H47A | 109.5 |
C13—C14—C15 | 120.3 (4) | C44—C47—H47B | 109.5 |
C13—C14—H14 | 119.8 | H47A—C47—H47B | 109.5 |
C15—C14—H14 | 119.8 | C44—C47—H47C | 109.5 |
C16—C15—C14 | 119.4 (4) | H47A—C47—H47C | 109.5 |
C16—C15—H15 | 120.3 | H47B—C47—H47C | 109.5 |
C14—C15—H15 | 120.3 | ||
C6—C1—C2—C3 | −0.1 (6) | C17—C11—C16—C15 | 178.3 (4) |
N1—C1—C2—C3 | 178.0 (3) | C5—C4—S4—O2 | −20.8 (3) |
C1—C2—C3—C4 | 0.6 (6) | C3—C4—S4—O2 | 158.2 (3) |
C2—C3—C4—C5 | −0.2 (5) | C5—C4—S4—O1 | −153.0 (3) |
C2—C3—C4—S4 | −179.3 (3) | C3—C4—S4—O1 | 26.1 (3) |
C3—C4—C5—C6 | −0.7 (5) | C5—C4—S4—N4 | 92.0 (3) |
S4—C4—C5—C6 | 178.4 (3) | C3—C4—S4—N4 | −89.0 (3) |
C4—C5—C6—C1 | 1.2 (6) | O2—S4—N4—C45 | 170.0 (3) |
C2—C1—C6—C5 | −0.8 (6) | O1—S4—N4—C45 | −60.8 (3) |
N1—C1—C6—C5 | −178.8 (3) | C4—S4—N4—C45 | 54.1 (3) |
C2—C1—N1—C17 | 167.3 (3) | C45—O41—N42—C43 | −1.1 (4) |
C6—C1—N1—C17 | −14.7 (5) | O41—N42—C43—C44 | 0.9 (4) |
C1—N1—C17—C11 | 178.2 (3) | O41—N42—C43—C46 | 179.2 (3) |
N1—C17—C11—C16 | −176.8 (4) | N42—C43—C44—C45 | −0.3 (4) |
N1—C17—C11—C12 | 2.6 (6) | C46—C43—C44—C45 | −178.5 (4) |
C16—C11—C12—O12 | 178.4 (4) | N42—C43—C44—C47 | 176.8 (3) |
C17—C11—C12—O12 | −1.0 (5) | C46—C43—C44—C47 | −1.4 (6) |
C16—C11—C12—C13 | −1.4 (5) | C43—C44—C45—O41 | −0.5 (4) |
C17—C11—C12—C13 | 179.2 (3) | C47—C44—C45—O41 | −177.4 (3) |
O12—C12—C13—C14 | −177.1 (4) | C43—C44—C45—N4 | 178.3 (4) |
C11—C12—C13—C14 | 2.7 (6) | C47—C44—C45—N4 | 1.4 (7) |
C12—C13—C14—C15 | −1.5 (7) | N42—O41—C45—C44 | 1.0 (4) |
C13—C14—C15—C16 | −1.1 (7) | N42—O41—C45—N4 | −178.0 (3) |
C14—C15—C16—C11 | 2.4 (7) | S4—N4—C45—C44 | 65.5 (5) |
C12—C11—C16—C15 | −1.1 (6) | S4—N4—C45—O41 | −115.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N42i | 0.87 (4) | 2.07 (4) | 2.931 (4) | 168 (3) |
O12—H12···N1 | 0.82 | 1.88 | 2.606 (4) | 147 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
C19H18BrN3O5S | F(000) = 976 |
Mr = 480.32 | Dx = 1.524 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.6043 (11) Å | Cell parameters from 6249 reflections |
b = 12.2399 (7) Å | θ = 1.5–30.3° |
c = 12.9506 (9) Å | µ = 2.10 mm−1 |
β = 103.854 (2)° | T = 296 K |
V = 2093.7 (3) Å3 | Block, orange |
Z = 4 | 0.15 × 0.15 × 0.10 mm |
Bruker APEXII CCD diffractometer | 4840 independent reflections |
Radiation source: fine focus sealed tube | 3092 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 27.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −17→17 |
Tmin = 0.673, Tmax = 0.811 | k = −15→15 |
22426 measured reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0552P)2 + 1.263P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4840 reflections | Δρmax = 0.56 e Å−3 |
270 parameters | Δρmin = −0.77 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 | ||
C1 | 0.4671 (2) | 0.2968 (2) | 0.4272 (2) | 0.0357 (6) | |
C2 | 0.4592 (2) | 0.4004 (2) | 0.3834 (2) | 0.0405 (7) | |
H2 | 0.4189 | 0.4526 | 0.4054 | 0.049* | |
C3 | 0.5106 (2) | 0.4267 (2) | 0.3076 (2) | 0.0409 (7) | |
H3 | 0.5043 | 0.4959 | 0.2772 | 0.049* | |
C4 | 0.5718 (2) | 0.3492 (2) | 0.2769 (2) | 0.0343 (6) | |
C5 | 0.5815 (2) | 0.2454 (2) | 0.3210 (2) | 0.0398 (7) | |
H5 | 0.6233 | 0.1941 | 0.3002 | 0.048* | |
C6 | 0.5285 (2) | 0.2188 (2) | 0.3963 (2) | 0.0410 (7) | |
H6 | 0.5340 | 0.1492 | 0.4261 | 0.049* | |
N1 | 0.41147 (19) | 0.27464 (18) | 0.50505 (18) | 0.0390 (6) | |
C17 | 0.3757 (2) | 0.1785 (2) | 0.5151 (2) | 0.0399 (7) | |
H17 | 0.3892 | 0.1216 | 0.4730 | 0.048* | |
C11 | 0.3155 (2) | 0.1579 (2) | 0.5902 (2) | 0.0379 (7) | |
C12 | 0.2960 (2) | 0.2422 (2) | 0.6562 (2) | 0.0341 (6) | |
C13 | 0.2305 (2) | 0.2215 (2) | 0.7237 (2) | 0.0391 (7) | |
C14 | 0.1858 (2) | 0.1214 (2) | 0.7242 (2) | 0.0436 (7) | |
H14 | 0.1418 | 0.1085 | 0.7678 | 0.052* | |
C15 | 0.2072 (3) | 0.0386 (2) | 0.6583 (3) | 0.0467 (8) | |
Br15 | 0.14289 (4) | −0.09879 (3) | 0.65963 (4) | 0.08006 (19) | |
C16 | 0.2709 (3) | 0.0545 (2) | 0.5935 (3) | 0.0474 (8) | |
H16 | 0.2850 | −0.0023 | 0.5515 | 0.057* | |
O12 | 0.33476 (17) | 0.34159 (15) | 0.65574 (17) | 0.0462 (5) | |
H12 | 0.3694 | 0.3442 | 0.6120 | 0.069* | |
O13 | 0.21597 (18) | 0.30984 (17) | 0.78226 (18) | 0.0512 (6) | |
C131 | 0.1405 (3) | 0.3022 (3) | 0.8418 (3) | 0.0627 (10) | |
H13A | 0.0771 | 0.2815 | 0.7953 | 0.094* | |
H13B | 0.1333 | 0.3718 | 0.8734 | 0.094* | |
H13C | 0.1603 | 0.2483 | 0.8966 | 0.094* | |
S4 | 0.64334 (6) | 0.38550 (6) | 0.18544 (5) | 0.0390 (2) | |
O1 | 0.58155 (19) | 0.45465 (18) | 0.10708 (16) | 0.0529 (6) | |
O2 | 0.68760 (19) | 0.28916 (16) | 0.15476 (16) | 0.0524 (6) | |
N4 | 0.7345 (2) | 0.4638 (2) | 0.2494 (2) | 0.0428 (6) | |
H4 | 0.717 (3) | 0.522 (3) | 0.260 (3) | 0.055 (11)* | |
O41 | 0.8974 (2) | 0.3981 (2) | 0.2898 (2) | 0.0783 (9) | |
N42 | 0.9723 (3) | 0.3623 (4) | 0.3778 (4) | 0.1057 (15) | |
C43 | 0.9329 (3) | 0.3685 (3) | 0.4584 (4) | 0.0758 (12) | |
C44 | 0.8324 (3) | 0.4069 (3) | 0.4312 (3) | 0.0500 (8) | |
C45 | 0.8154 (3) | 0.4230 (2) | 0.3261 (3) | 0.0443 (7) | |
C46 | 0.9924 (4) | 0.3345 (5) | 0.5680 (4) | 0.127 (2) | |
H46A | 1.0616 | 0.3215 | 0.5664 | 0.191* | |
H46B | 0.9638 | 0.2688 | 0.5889 | 0.191* | |
H46C | 0.9894 | 0.3915 | 0.6180 | 0.191* | |
C47 | 0.7629 (3) | 0.4266 (4) | 0.5036 (3) | 0.0736 (12) | |
H47A | 0.6998 | 0.4557 | 0.4632 | 0.110* | |
H47B | 0.7936 | 0.4778 | 0.5578 | 0.110* | |
H47C | 0.7508 | 0.3590 | 0.5360 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0368 (17) | 0.0374 (14) | 0.0336 (14) | −0.0034 (13) | 0.0101 (13) | −0.0004 (12) |
C2 | 0.0378 (18) | 0.0369 (15) | 0.0495 (17) | 0.0033 (13) | 0.0158 (14) | −0.0001 (13) |
C3 | 0.0461 (19) | 0.0308 (14) | 0.0463 (16) | 0.0011 (13) | 0.0123 (15) | 0.0076 (12) |
C4 | 0.0390 (17) | 0.0335 (14) | 0.0302 (14) | −0.0055 (12) | 0.0076 (13) | 0.0006 (11) |
C5 | 0.049 (2) | 0.0334 (14) | 0.0417 (15) | 0.0031 (13) | 0.0189 (15) | 0.0004 (12) |
C6 | 0.052 (2) | 0.0345 (14) | 0.0400 (15) | 0.0048 (14) | 0.0183 (15) | 0.0086 (12) |
N1 | 0.0439 (16) | 0.0374 (13) | 0.0396 (13) | −0.0017 (11) | 0.0179 (12) | 0.0007 (10) |
C17 | 0.0427 (19) | 0.0376 (15) | 0.0416 (16) | 0.0005 (14) | 0.0147 (14) | −0.0054 (13) |
C11 | 0.0370 (17) | 0.0349 (14) | 0.0437 (16) | −0.0016 (13) | 0.0134 (14) | 0.0019 (12) |
C12 | 0.0320 (17) | 0.0319 (13) | 0.0389 (15) | −0.0015 (12) | 0.0094 (13) | 0.0033 (12) |
C13 | 0.0375 (18) | 0.0389 (15) | 0.0430 (16) | 0.0017 (13) | 0.0139 (14) | 0.0037 (13) |
C14 | 0.0412 (19) | 0.0443 (17) | 0.0484 (17) | −0.0054 (14) | 0.0168 (15) | 0.0087 (14) |
C15 | 0.047 (2) | 0.0343 (15) | 0.0595 (19) | −0.0078 (14) | 0.0141 (17) | 0.0075 (14) |
Br15 | 0.0931 (4) | 0.0425 (2) | 0.1170 (4) | −0.0247 (2) | 0.0496 (3) | −0.0023 (2) |
C16 | 0.054 (2) | 0.0314 (14) | 0.0579 (19) | −0.0036 (15) | 0.0168 (17) | −0.0039 (14) |
O12 | 0.0552 (15) | 0.0354 (10) | 0.0585 (13) | −0.0097 (10) | 0.0346 (11) | −0.0059 (9) |
O13 | 0.0585 (15) | 0.0457 (12) | 0.0605 (13) | −0.0100 (11) | 0.0358 (12) | −0.0086 (10) |
C131 | 0.061 (2) | 0.080 (2) | 0.060 (2) | −0.009 (2) | 0.0386 (19) | −0.0149 (19) |
S4 | 0.0543 (5) | 0.0344 (4) | 0.0311 (3) | −0.0054 (3) | 0.0160 (3) | 0.0003 (3) |
O1 | 0.0706 (17) | 0.0508 (12) | 0.0350 (11) | −0.0066 (12) | 0.0082 (11) | 0.0108 (10) |
O2 | 0.0773 (17) | 0.0415 (11) | 0.0475 (12) | −0.0028 (11) | 0.0328 (12) | −0.0071 (9) |
N4 | 0.0513 (18) | 0.0346 (14) | 0.0461 (15) | −0.0039 (13) | 0.0187 (14) | −0.0020 (12) |
O41 | 0.0522 (17) | 0.106 (2) | 0.0832 (19) | 0.0152 (15) | 0.0285 (16) | −0.0247 (16) |
N42 | 0.056 (3) | 0.130 (4) | 0.122 (3) | 0.038 (2) | 0.005 (3) | −0.039 (3) |
C43 | 0.064 (3) | 0.063 (2) | 0.087 (3) | 0.015 (2) | −0.007 (3) | −0.013 (2) |
C44 | 0.043 (2) | 0.0467 (18) | 0.055 (2) | −0.0011 (15) | 0.0028 (16) | −0.0044 (15) |
C45 | 0.0388 (18) | 0.0403 (16) | 0.057 (2) | −0.0010 (14) | 0.0171 (16) | −0.0091 (14) |
C46 | 0.113 (5) | 0.108 (4) | 0.121 (4) | 0.038 (4) | −0.051 (4) | −0.010 (4) |
C47 | 0.072 (3) | 0.106 (3) | 0.043 (2) | −0.002 (2) | 0.013 (2) | 0.002 (2) |
C1—C2 | 1.382 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.390 (4) | O12—H12 | 0.8200 |
C1—N1 | 1.423 (3) | O13—C131 | 1.427 (4) |
C2—C3 | 1.373 (4) | C131—H13A | 0.9600 |
C2—H2 | 0.9300 | C131—H13B | 0.9600 |
C3—C4 | 1.381 (4) | C131—H13C | 0.9600 |
C3—H3 | 0.9300 | S4—O2 | 1.423 (2) |
C4—C5 | 1.386 (4) | S4—O1 | 1.430 (2) |
C4—S4 | 1.761 (3) | S4—N4 | 1.628 (3) |
C5—C6 | 1.383 (4) | N4—C45 | 1.387 (4) |
C5—H5 | 0.9300 | N4—H4 | 0.78 (4) |
C6—H6 | 0.9300 | O41—C45 | 1.345 (4) |
N1—C17 | 1.292 (4) | O41—N42 | 1.404 (5) |
C17—C11 | 1.435 (4) | N42—C43 | 1.285 (6) |
C17—H17 | 0.9300 | C43—C44 | 1.408 (5) |
C11—C12 | 1.405 (4) | C43—C46 | 1.514 (6) |
C11—C16 | 1.408 (4) | C44—C45 | 1.340 (5) |
C12—O12 | 1.326 (3) | C44—C47 | 1.502 (5) |
C12—C13 | 1.414 (4) | C46—H46A | 0.9600 |
C13—O13 | 1.362 (3) | C46—H46B | 0.9600 |
C13—C14 | 1.368 (4) | C46—H46C | 0.9600 |
C14—C15 | 1.400 (4) | C47—H47A | 0.9600 |
C14—H14 | 0.9300 | C47—H47B | 0.9600 |
C15—C16 | 1.358 (4) | C47—H47C | 0.9600 |
C15—Br15 | 1.897 (3) | ||
C2—C1—C6 | 120.3 (3) | C12—O12—H12 | 109.5 |
C2—C1—N1 | 117.6 (2) | C13—O13—C131 | 117.9 (2) |
C6—C1—N1 | 122.1 (2) | O13—C131—H13A | 109.5 |
C3—C2—C1 | 120.4 (3) | O13—C131—H13B | 109.5 |
C3—C2—H2 | 119.8 | H13A—C131—H13B | 109.5 |
C1—C2—H2 | 119.8 | O13—C131—H13C | 109.5 |
C2—C3—C4 | 119.3 (3) | H13A—C131—H13C | 109.5 |
C2—C3—H3 | 120.3 | H13B—C131—H13C | 109.5 |
C4—C3—H3 | 120.3 | O2—S4—O1 | 120.56 (13) |
C3—C4—C5 | 121.0 (3) | O2—S4—N4 | 107.97 (15) |
C3—C4—S4 | 119.2 (2) | O1—S4—N4 | 105.01 (14) |
C5—C4—S4 | 119.7 (2) | O2—S4—C4 | 108.52 (13) |
C6—C5—C4 | 119.5 (3) | O1—S4—C4 | 107.52 (14) |
C6—C5—H5 | 120.2 | N4—S4—C4 | 106.44 (13) |
C4—C5—H5 | 120.2 | C45—N4—S4 | 122.0 (2) |
C5—C6—C1 | 119.5 (3) | C45—N4—H4 | 115 (3) |
C5—C6—H6 | 120.3 | S4—N4—H4 | 114 (3) |
C1—C6—H6 | 120.3 | C45—O41—N42 | 106.8 (3) |
C17—N1—C1 | 121.5 (2) | C43—N42—O41 | 106.2 (3) |
N1—C17—C11 | 121.2 (3) | N42—C43—C44 | 112.6 (4) |
N1—C17—H17 | 119.4 | N42—C43—C46 | 120.8 (5) |
C11—C17—H17 | 119.4 | C44—C43—C46 | 126.6 (5) |
C12—C11—C16 | 119.8 (3) | C45—C44—C43 | 103.0 (3) |
C12—C11—C17 | 120.3 (2) | C45—C44—C47 | 129.0 (3) |
C16—C11—C17 | 119.9 (3) | C43—C44—C47 | 128.0 (3) |
O12—C12—C11 | 122.6 (2) | C44—C45—O41 | 111.4 (3) |
O12—C12—C13 | 118.5 (2) | C44—C45—N4 | 134.0 (3) |
C11—C12—C13 | 118.9 (2) | O41—C45—N4 | 114.5 (3) |
O13—C13—C14 | 125.8 (3) | C43—C46—H46A | 109.5 |
O13—C13—C12 | 113.5 (2) | C43—C46—H46B | 109.5 |
C14—C13—C12 | 120.7 (3) | H46A—C46—H46B | 109.5 |
C13—C14—C15 | 119.3 (3) | C43—C46—H46C | 109.5 |
C13—C14—H14 | 120.4 | H46A—C46—H46C | 109.5 |
C15—C14—H14 | 120.4 | H46B—C46—H46C | 109.5 |
C16—C15—C14 | 121.9 (3) | C44—C47—H47A | 109.5 |
C16—C15—Br15 | 119.8 (2) | C44—C47—H47B | 109.5 |
C14—C15—Br15 | 118.2 (2) | H47A—C47—H47B | 109.5 |
C15—C16—C11 | 119.4 (3) | C44—C47—H47C | 109.5 |
C15—C16—H16 | 120.3 | H47A—C47—H47C | 109.5 |
C11—C16—H16 | 120.3 | H47B—C47—H47C | 109.5 |
C6—C1—C2—C3 | 1.2 (5) | C12—C11—C16—C15 | 1.8 (5) |
N1—C1—C2—C3 | −179.7 (3) | C17—C11—C16—C15 | −174.4 (3) |
C1—C2—C3—C4 | −1.2 (5) | C14—C13—O13—C131 | −6.6 (5) |
C2—C3—C4—C5 | 0.4 (5) | C12—C13—O13—C131 | 171.5 (3) |
C2—C3—C4—S4 | −176.3 (2) | C3—C4—S4—O2 | −171.5 (2) |
C3—C4—C5—C6 | 0.5 (5) | C5—C4—S4—O2 | 11.8 (3) |
S4—C4—C5—C6 | 177.1 (2) | C3—C4—S4—O1 | −39.6 (3) |
C4—C5—C6—C1 | −0.5 (5) | C5—C4—S4—O1 | 143.7 (2) |
C2—C1—C6—C5 | −0.3 (5) | C3—C4—S4—N4 | 72.5 (3) |
N1—C1—C6—C5 | −179.4 (3) | C5—C4—S4—N4 | −104.2 (3) |
C2—C1—N1—C17 | 148.0 (3) | O2—S4—N4—C45 | −44.3 (3) |
C6—C1—N1—C17 | −32.9 (4) | O1—S4—N4—C45 | −174.1 (2) |
C1—N1—C17—C11 | −176.9 (3) | C4—S4—N4—C45 | 72.1 (3) |
N1—C17—C11—C12 | −1.3 (5) | C45—O41—N42—C43 | −0.5 (5) |
N1—C17—C11—C16 | 174.9 (3) | O41—N42—C43—C44 | 0.3 (5) |
C16—C11—C12—O12 | −179.1 (3) | O41—N42—C43—C46 | 179.2 (4) |
C17—C11—C12—O12 | −2.9 (5) | N42—C43—C44—C45 | 0.1 (5) |
C16—C11—C12—C13 | −0.8 (4) | C46—C43—C44—C45 | −178.8 (4) |
C17—C11—C12—C13 | 175.4 (3) | N42—C43—C44—C47 | −178.8 (4) |
O12—C12—C13—O13 | −0.5 (4) | C46—C43—C44—C47 | 2.4 (7) |
C11—C12—C13—O13 | −178.9 (3) | C43—C44—C45—O41 | −0.4 (4) |
O12—C12—C13—C14 | 177.7 (3) | C47—C44—C45—O41 | 178.5 (4) |
C11—C12—C13—C14 | −0.7 (4) | C43—C44—C45—N4 | −176.9 (4) |
O13—C13—C14—C15 | 179.1 (3) | C47—C44—C45—N4 | 1.9 (6) |
C12—C13—C14—C15 | 1.2 (5) | N42—O41—C45—C44 | 0.6 (4) |
C13—C14—C15—C16 | −0.1 (5) | N42—O41—C45—N4 | 177.8 (3) |
C13—C14—C15—Br15 | −179.3 (2) | S4—N4—C45—C44 | −88.8 (4) |
C14—C15—C16—C11 | −1.4 (5) | S4—N4—C45—O41 | 94.7 (3) |
Br15—C15—C16—C11 | 177.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O12i | 0.77 (4) | 2.20 (4) | 2.937 (3) | 159 (4) |
N4—H4···O13i | 0.77 (4) | 2.37 (4) | 2.904 (3) | 127 (4) |
O12—H12···N1 | 0.82 | 1.83 | 2.558 (3) | 147 |
C17—H17···O1ii | 0.93 | 2.37 | 3.285 (3) | 169 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2. |
C14H12BrNO3 | F(000) = 648 |
Mr = 322.15 | Dx = 1.662 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.297 (2) Å | Cell parameters from 3375 reflections |
b = 15.095 (3) Å | θ = 1.5–28.9° |
c = 6.4166 (13) Å | µ = 3.20 mm−1 |
β = 91.329 (6)° | T = 296 K |
V = 1287.6 (4) Å3 | Block, brown |
Z = 4 | 0.25 × 0.20 × 0.15 mm |
Bruker APEXII CCD diffractometer | 2979 independent reflections |
Radiation source: fine focus sealed tube | 1807 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 27.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −17→17 |
Tmin = 0.327, Tmax = 0.619 | k = −19→19 |
14568 measured reflections | l = −8→7 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0431P)2 + 0.5394P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
2979 reflections | Δρmax = 0.71 e Å−3 |
173 parameters | Δρmin = −0.37 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 | ||
C1 | 0.2524 (2) | 0.4272 (2) | 0.3637 (4) | 0.0341 (7) | |
C2 | 0.3399 (2) | 0.4142 (2) | 0.2541 (5) | 0.0354 (7) | |
C3 | 0.3371 (3) | 0.3646 (2) | 0.0732 (5) | 0.0446 (8) | |
H3 | 0.3955 | 0.3557 | −0.0008 | 0.054* | |
C4 | 0.2477 (3) | 0.3284 (2) | 0.0027 (5) | 0.0471 (8) | |
H4 | 0.2462 | 0.2946 | −0.1185 | 0.057* | |
C5 | 0.1609 (3) | 0.3415 (2) | 0.1093 (5) | 0.0455 (8) | |
H5 | 0.1007 | 0.3172 | 0.0596 | 0.055* | |
C6 | 0.1629 (2) | 0.3910 (2) | 0.2910 (5) | 0.0424 (8) | |
H6 | 0.1041 | 0.3998 | 0.3640 | 0.051* | |
N1 | 0.26220 (18) | 0.47903 (16) | 0.5459 (4) | 0.0366 (6) | |
H1 | 0.3226 | 0.4948 | 0.5789 | 0.044* | |
O2 | 0.42320 (15) | 0.45293 (16) | 0.3355 (3) | 0.0516 (6) | |
H2 | 0.4722 | 0.4465 | 0.2580 | 0.077* | |
C11 | 0.2154 (2) | 0.5576 (2) | 0.8504 (4) | 0.0356 (7) | |
C12 | 0.3166 (2) | 0.5806 (2) | 0.9018 (5) | 0.0363 (7) | |
O12 | 0.38985 (15) | 0.55811 (16) | 0.7852 (3) | 0.0473 (6) | |
C13 | 0.3347 (2) | 0.6292 (2) | 1.0906 (5) | 0.0362 (7) | |
C14 | 0.2567 (2) | 0.6549 (2) | 1.2122 (5) | 0.0399 (8) | |
H14 | 0.2690 | 0.6880 | 1.3323 | 0.048* | |
C15 | 0.1582 (2) | 0.6309 (2) | 1.1542 (5) | 0.0412 (8) | |
Br15 | 0.05396 (3) | 0.66606 (3) | 1.33499 (6) | 0.06282 (17) | |
C16 | 0.1355 (2) | 0.5844 (2) | 0.9809 (5) | 0.0407 (8) | |
H16 | 0.0691 | 0.5701 | 0.9467 | 0.049* | |
C17 | 0.1936 (2) | 0.5064 (2) | 0.6711 (5) | 0.0387 (7) | |
H17 | 0.1269 | 0.4916 | 0.6413 | 0.046* | |
O13 | 0.43357 (16) | 0.64571 (15) | 1.1307 (3) | 0.0452 (6) | |
C113 | 0.4586 (3) | 0.6907 (3) | 1.3208 (5) | 0.0609 (11) | |
H11A | 0.4322 | 0.6583 | 1.4360 | 0.091* | |
H11B | 0.4300 | 0.7491 | 1.3174 | 0.091* | |
H11C | 0.5304 | 0.6950 | 1.3366 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0349 (17) | 0.0357 (18) | 0.0315 (15) | −0.0037 (14) | −0.0032 (13) | 0.0012 (13) |
C2 | 0.0318 (16) | 0.0372 (17) | 0.0373 (16) | −0.0016 (14) | −0.0020 (13) | 0.0028 (14) |
C3 | 0.051 (2) | 0.0426 (19) | 0.0410 (18) | 0.0057 (17) | 0.0090 (16) | −0.0014 (15) |
C4 | 0.063 (2) | 0.0391 (19) | 0.0393 (18) | −0.0015 (17) | −0.0028 (17) | −0.0057 (15) |
C5 | 0.0426 (19) | 0.0414 (19) | 0.052 (2) | −0.0111 (16) | −0.0088 (16) | −0.0001 (17) |
C6 | 0.0369 (18) | 0.047 (2) | 0.0437 (19) | −0.0060 (15) | 0.0005 (15) | 0.0007 (16) |
N1 | 0.0302 (13) | 0.0450 (16) | 0.0347 (14) | −0.0051 (12) | 0.0017 (11) | −0.0029 (12) |
O2 | 0.0304 (12) | 0.0732 (17) | 0.0513 (14) | −0.0040 (11) | 0.0049 (11) | −0.0160 (12) |
C11 | 0.0351 (17) | 0.0379 (18) | 0.0338 (16) | 0.0019 (14) | 0.0007 (13) | 0.0016 (14) |
C12 | 0.0406 (18) | 0.0368 (18) | 0.0318 (15) | −0.0012 (15) | 0.0049 (14) | 0.0014 (14) |
O12 | 0.0335 (12) | 0.0670 (16) | 0.0417 (12) | −0.0061 (11) | 0.0082 (10) | −0.0150 (11) |
C13 | 0.0375 (18) | 0.0334 (17) | 0.0379 (17) | −0.0018 (14) | 0.0028 (14) | 0.0026 (14) |
C14 | 0.047 (2) | 0.0414 (19) | 0.0314 (16) | 0.0014 (15) | 0.0043 (14) | −0.0040 (14) |
C15 | 0.0429 (19) | 0.0424 (19) | 0.0389 (18) | 0.0072 (15) | 0.0119 (15) | 0.0010 (15) |
Br15 | 0.0519 (2) | 0.0814 (3) | 0.0560 (2) | 0.0106 (2) | 0.01965 (18) | −0.0126 (2) |
C16 | 0.0324 (17) | 0.048 (2) | 0.0421 (18) | 0.0033 (15) | 0.0036 (14) | 0.0004 (16) |
C17 | 0.0321 (17) | 0.044 (2) | 0.0402 (17) | 0.0014 (14) | 0.0029 (14) | −0.0007 (15) |
O13 | 0.0414 (13) | 0.0577 (15) | 0.0367 (13) | −0.0072 (11) | 0.0038 (10) | −0.0102 (10) |
C113 | 0.055 (2) | 0.085 (3) | 0.043 (2) | −0.015 (2) | −0.0018 (17) | −0.0154 (19) |
C1—C6 | 1.381 (4) | C11—C12 | 1.421 (4) |
C1—C2 | 1.388 (4) | C11—C16 | 1.428 (4) |
C1—N1 | 1.410 (4) | C12—O12 | 1.287 (3) |
C2—O2 | 1.347 (4) | C12—C13 | 1.431 (4) |
C2—C3 | 1.381 (4) | C13—O13 | 1.357 (3) |
C3—C4 | 1.375 (5) | C13—C14 | 1.368 (4) |
C3—H3 | 0.9300 | C14—C15 | 1.402 (4) |
C4—C5 | 1.369 (5) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.343 (4) |
C5—C6 | 1.385 (5) | C15—Br15 | 1.903 (3) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
N1—C17 | 1.297 (4) | O13—C113 | 1.428 (4) |
N1—H1 | 0.8600 | C113—H11A | 0.9600 |
O2—H2 | 0.8343 | C113—H11B | 0.9600 |
C11—C17 | 1.410 (4) | C113—H11C | 0.9600 |
C6—C1—C2 | 119.9 (3) | O12—C12—C11 | 121.7 (3) |
C6—C1—N1 | 124.2 (3) | O12—C12—C13 | 120.8 (3) |
C2—C1—N1 | 115.8 (3) | C11—C12—C13 | 117.5 (3) |
O2—C2—C3 | 124.6 (3) | O13—C13—C14 | 125.7 (3) |
O2—C2—C1 | 115.7 (3) | O13—C13—C12 | 113.4 (3) |
C3—C2—C1 | 119.7 (3) | C14—C13—C12 | 120.9 (3) |
C4—C3—C2 | 119.9 (3) | C13—C14—C15 | 119.4 (3) |
C4—C3—H3 | 120.0 | C13—C14—H14 | 120.3 |
C2—C3—H3 | 120.0 | C15—C14—H14 | 120.3 |
C5—C4—C3 | 120.7 (3) | C16—C15—C14 | 123.1 (3) |
C5—C4—H4 | 119.7 | C16—C15—Br15 | 119.8 (2) |
C3—C4—H4 | 119.7 | C14—C15—Br15 | 117.1 (2) |
C4—C5—C6 | 119.9 (3) | C15—C16—C11 | 118.5 (3) |
C4—C5—H5 | 120.0 | C15—C16—H16 | 120.7 |
C6—C5—H5 | 120.0 | C11—C16—H16 | 120.7 |
C1—C6—C5 | 119.8 (3) | N1—C17—C11 | 123.0 (3) |
C1—C6—H6 | 120.1 | N1—C17—H17 | 118.5 |
C5—C6—H6 | 120.1 | C11—C17—H17 | 118.5 |
C17—N1—C1 | 129.6 (3) | C13—O13—C113 | 117.1 (3) |
C17—N1—H1 | 115.2 | O13—C113—H11A | 109.5 |
C1—N1—H1 | 115.2 | O13—C113—H11B | 109.5 |
C2—O2—H2 | 111.4 | H11A—C113—H11B | 109.5 |
C17—C11—C12 | 120.0 (3) | O13—C113—H11C | 109.5 |
C17—C11—C16 | 119.5 (3) | H11A—C113—H11C | 109.5 |
C12—C11—C16 | 120.6 (3) | H11B—C113—H11C | 109.5 |
C6—C1—C2—O2 | 179.2 (3) | O12—C12—C13—O13 | −1.3 (4) |
N1—C1—C2—O2 | −0.2 (4) | C11—C12—C13—O13 | 177.9 (3) |
C6—C1—C2—C3 | −0.3 (5) | O12—C12—C13—C14 | 178.5 (3) |
N1—C1—C2—C3 | −179.7 (3) | C11—C12—C13—C14 | −2.3 (4) |
O2—C2—C3—C4 | −179.5 (3) | O13—C13—C14—C15 | −178.2 (3) |
C1—C2—C3—C4 | 0.0 (5) | C12—C13—C14—C15 | 2.0 (5) |
C2—C3—C4—C5 | 0.5 (5) | C13—C14—C15—C16 | −1.1 (5) |
C3—C4—C5—C6 | −0.6 (5) | C13—C14—C15—Br15 | 178.3 (2) |
C2—C1—C6—C5 | 0.2 (5) | C14—C15—C16—C11 | 0.5 (5) |
N1—C1—C6—C5 | 179.5 (3) | Br15—C15—C16—C11 | −178.8 (2) |
C4—C5—C6—C1 | 0.3 (5) | C17—C11—C16—C15 | 178.1 (3) |
C6—C1—N1—C17 | −3.9 (5) | C12—C11—C16—C15 | −0.8 (5) |
C2—C1—N1—C17 | 175.4 (3) | C1—N1—C17—C11 | 179.3 (3) |
C17—C11—C12—O12 | 2.0 (5) | C12—C11—C17—N1 | −0.6 (5) |
C16—C11—C12—O12 | −179.1 (3) | C16—C11—C17—N1 | −179.5 (3) |
C17—C11—C12—C13 | −177.2 (3) | C14—C13—O13—C113 | 2.7 (5) |
C16—C11—C12—C13 | 1.7 (4) | C12—C13—O13—C113 | −177.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 2.17 | 2.588 (3) | 109 |
N1—H1···O12 | 0.86 | 1.85 | 2.558 (3) | 139 |
O2—H2···O12i | 0.82 | 1.86 | 2.626 (3) | 151 |
C3—H3···O13i | 0.93 | 2.44 | 3.350 (4) | 166 |
C4—H4···Cg1ii | 0.93 | 2.90 | 3.731 (3) | 149 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−3/2. |
C15H14BrNO3 | Z = 2 |
Mr = 336.17 | F(000) = 340 |
Triclinic, P1 | Dx = 1.581 Mg m−3 |
a = 6.4158 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.3886 (4) Å | Cell parameters from 3426 reflections |
c = 15.2636 (7) Å | θ = 1.3–28.1° |
α = 87.081 (3)° | µ = 2.92 mm−1 |
β = 87.488 (3)° | T = 296 K |
γ = 77.948 (3)° | Block, orange |
V = 706.28 (6) Å3 | 0.30 × 0.25 × 0.20 mm |
Bruker APEXII CCD diffractometer | 3265 independent reflections |
Radiation source: fine focus sealed tube | 2240 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −8→8 |
Tmin = 0.322, Tmax = 0.558 | k = −9→9 |
16535 measured reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.072 | w = 1/[σ2(Fo2) + (0.0262P)2 + 0.2214P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3265 reflections | Δρmax = 0.37 e Å−3 |
184 parameters | Δρmin = −0.34 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 | ||
C1 | 0.7059 (3) | 0.2769 (3) | 0.22114 (15) | 0.0378 (5) | |
C2 | 0.8316 (4) | 0.2335 (3) | 0.29478 (16) | 0.0430 (6) | |
C3 | 1.0360 (4) | 0.1298 (4) | 0.2861 (2) | 0.0562 (7) | |
H3 | 1.1201 | 0.0997 | 0.3350 | 0.067* | |
C4 | 1.1154 (4) | 0.0709 (4) | 0.2047 (2) | 0.0613 (8) | |
H4 | 1.2535 | 0.0012 | 0.1994 | 0.074* | |
C5 | 0.9964 (4) | 0.1123 (4) | 0.1320 (2) | 0.0557 (7) | |
H5 | 1.0523 | 0.0720 | 0.0774 | 0.067* | |
C6 | 0.7903 (4) | 0.2157 (3) | 0.14060 (17) | 0.0483 (6) | |
H6 | 0.7076 | 0.2444 | 0.0913 | 0.058* | |
N1 | 0.4991 (3) | 0.3857 (3) | 0.23626 (12) | 0.0383 (4) | |
O2 | 0.7364 (3) | 0.2996 (3) | 0.37170 (11) | 0.0572 (5) | |
C21 | 0.8634 (5) | 0.2772 (5) | 0.44787 (17) | 0.0698 (9) | |
H21A | 0.9097 | 0.1476 | 0.4629 | 0.105* | |
H21B | 0.7802 | 0.3372 | 0.4960 | 0.105* | |
H21C | 0.9856 | 0.3316 | 0.4358 | 0.105* | |
C11 | 0.1570 (3) | 0.5531 (3) | 0.19762 (14) | 0.0349 (5) | |
C12 | 0.0995 (3) | 0.5987 (3) | 0.28483 (15) | 0.0383 (5) | |
O12 | 0.2333 (3) | 0.5482 (3) | 0.34994 (10) | 0.0543 (5) | |
H12 | 0.3443 | 0.4836 | 0.3310 | 0.081* | |
C13 | −0.1085 (4) | 0.6993 (3) | 0.30436 (15) | 0.0397 (6) | |
C14 | −0.2496 (4) | 0.7521 (3) | 0.23830 (15) | 0.0408 (6) | |
H14 | −0.3867 | 0.8181 | 0.2511 | 0.049* | |
C15 | −0.1885 (4) | 0.7075 (3) | 0.15261 (15) | 0.0391 (5) | |
Br15 | −0.38932 (4) | 0.78676 (4) | 0.06357 (2) | 0.05846 (12) | |
C16 | 0.0101 (4) | 0.6106 (3) | 0.13123 (14) | 0.0386 (5) | |
H16 | 0.0481 | 0.5827 | 0.0732 | 0.046* | |
C17 | 0.3641 (3) | 0.4427 (3) | 0.17669 (15) | 0.0392 (5) | |
H17 | 0.4003 | 0.4123 | 0.1188 | 0.047* | |
O13 | −0.1504 (3) | 0.7366 (3) | 0.39020 (11) | 0.0571 (5) | |
C113 | −0.3642 (4) | 0.8120 (5) | 0.41627 (19) | 0.0740 (9) | |
H11A | −0.4056 | 0.9354 | 0.3911 | 0.111* | |
H11B | −0.3762 | 0.8153 | 0.4791 | 0.111* | |
H11C | −0.4558 | 0.7364 | 0.3962 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0342 (12) | 0.0336 (13) | 0.0459 (14) | −0.0069 (10) | 0.0021 (11) | −0.0065 (11) |
C2 | 0.0375 (13) | 0.0395 (14) | 0.0508 (15) | −0.0055 (11) | 0.0004 (11) | −0.0037 (12) |
C3 | 0.0420 (15) | 0.0516 (17) | 0.0711 (19) | 0.0007 (13) | −0.0099 (14) | −0.0015 (14) |
C4 | 0.0365 (14) | 0.0458 (17) | 0.097 (2) | 0.0020 (12) | 0.0068 (16) | −0.0110 (16) |
C5 | 0.0505 (16) | 0.0447 (16) | 0.0718 (19) | −0.0088 (13) | 0.0171 (15) | −0.0216 (14) |
C6 | 0.0468 (15) | 0.0464 (16) | 0.0517 (16) | −0.0082 (12) | 0.0027 (12) | −0.0119 (12) |
N1 | 0.0309 (10) | 0.0418 (12) | 0.0416 (11) | −0.0045 (8) | −0.0011 (9) | −0.0060 (9) |
O2 | 0.0471 (10) | 0.0755 (13) | 0.0432 (10) | 0.0023 (9) | −0.0091 (8) | −0.0034 (9) |
C21 | 0.0687 (19) | 0.091 (2) | 0.0463 (16) | −0.0094 (17) | −0.0180 (14) | 0.0079 (15) |
C11 | 0.0345 (12) | 0.0351 (13) | 0.0357 (12) | −0.0081 (10) | −0.0007 (10) | −0.0035 (10) |
C12 | 0.0335 (12) | 0.0438 (14) | 0.0379 (13) | −0.0073 (10) | −0.0042 (10) | −0.0046 (11) |
O12 | 0.0375 (9) | 0.0823 (14) | 0.0377 (9) | 0.0036 (9) | −0.0064 (7) | −0.0141 (9) |
C13 | 0.0370 (13) | 0.0456 (15) | 0.0366 (13) | −0.0079 (11) | 0.0015 (10) | −0.0084 (11) |
C14 | 0.0331 (12) | 0.0388 (14) | 0.0484 (15) | −0.0015 (10) | −0.0016 (11) | −0.0049 (11) |
C15 | 0.0381 (13) | 0.0404 (14) | 0.0382 (13) | −0.0070 (11) | −0.0064 (10) | 0.0036 (11) |
Br15 | 0.04838 (17) | 0.0752 (2) | 0.04735 (17) | −0.00178 (13) | −0.01454 (12) | 0.00530 (13) |
C16 | 0.0428 (14) | 0.0414 (14) | 0.0317 (12) | −0.0089 (11) | −0.0005 (10) | −0.0028 (10) |
C17 | 0.0410 (13) | 0.0400 (14) | 0.0367 (13) | −0.0078 (11) | 0.0021 (11) | −0.0069 (11) |
O13 | 0.0431 (10) | 0.0845 (14) | 0.0388 (10) | 0.0011 (9) | 0.0021 (8) | −0.0184 (9) |
C113 | 0.0469 (17) | 0.112 (3) | 0.0578 (18) | −0.0015 (17) | 0.0124 (14) | −0.0313 (18) |
C1—C6 | 1.380 (3) | C11—C12 | 1.404 (3) |
C1—C2 | 1.397 (3) | C11—C17 | 1.439 (3) |
C1—N1 | 1.416 (3) | C12—O12 | 1.329 (3) |
C2—O2 | 1.364 (3) | C12—C13 | 1.413 (3) |
C2—C3 | 1.379 (3) | O12—H12 | 0.8200 |
C3—C4 | 1.378 (4) | C13—O13 | 1.356 (3) |
C3—H3 | 0.9300 | C13—C14 | 1.372 (3) |
C4—C5 | 1.361 (4) | C14—C15 | 1.385 (3) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—C6 | 1.386 (3) | C15—C16 | 1.360 (3) |
C5—H5 | 0.9300 | C15—Br15 | 1.899 (2) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
N1—C17 | 1.277 (3) | C17—H17 | 0.9300 |
O2—C21 | 1.432 (3) | O13—C113 | 1.416 (3) |
C21—H21A | 0.9600 | C113—H11A | 0.9600 |
C21—H21B | 0.9600 | C113—H11B | 0.9600 |
C21—H21C | 0.9600 | C113—H11C | 0.9600 |
C11—C16 | 1.403 (3) | ||
C6—C1—C2 | 119.0 (2) | C12—C11—C17 | 120.0 (2) |
C6—C1—N1 | 125.3 (2) | O12—C12—C11 | 122.2 (2) |
C2—C1—N1 | 115.7 (2) | O12—C12—C13 | 118.8 (2) |
O2—C2—C3 | 124.9 (2) | C11—C12—C13 | 119.0 (2) |
O2—C2—C1 | 115.3 (2) | C12—O12—H12 | 109.5 |
C3—C2—C1 | 119.8 (2) | O13—C13—C14 | 125.2 (2) |
C4—C3—C2 | 119.7 (3) | O13—C13—C12 | 114.98 (19) |
C4—C3—H3 | 120.1 | C14—C13—C12 | 119.8 (2) |
C2—C3—H3 | 120.1 | C13—C14—C15 | 120.2 (2) |
C5—C4—C3 | 121.6 (2) | C13—C14—H14 | 119.9 |
C5—C4—H4 | 119.2 | C15—C14—H14 | 119.9 |
C3—C4—H4 | 119.2 | C16—C15—C14 | 121.7 (2) |
C4—C5—C6 | 118.8 (3) | C16—C15—Br15 | 119.87 (17) |
C4—C5—H5 | 120.6 | C14—C15—Br15 | 118.38 (17) |
C6—C5—H5 | 120.6 | C15—C16—C11 | 119.3 (2) |
C1—C6—C5 | 121.1 (2) | C15—C16—H16 | 120.4 |
C1—C6—H6 | 119.4 | C11—C16—H16 | 120.4 |
C5—C6—H6 | 119.4 | N1—C17—C11 | 121.1 (2) |
C17—N1—C1 | 124.6 (2) | N1—C17—H17 | 119.4 |
C2—O2—C21 | 118.1 (2) | C11—C17—H17 | 119.4 |
O2—C21—H21A | 109.5 | C13—O13—C113 | 117.68 (19) |
O2—C21—H21B | 109.5 | O13—C113—H11A | 109.5 |
H21A—C21—H21B | 109.5 | O13—C113—H11B | 109.5 |
O2—C21—H21C | 109.5 | H11A—C113—H11B | 109.5 |
H21A—C21—H21C | 109.5 | O13—C113—H11C | 109.5 |
H21B—C21—H21C | 109.5 | H11A—C113—H11C | 109.5 |
C16—C11—C12 | 120.0 (2) | H11B—C113—H11C | 109.5 |
C16—C11—C17 | 119.9 (2) | ||
C6—C1—C2—O2 | 179.8 (2) | C17—C11—C12—C13 | −176.8 (2) |
N1—C1—C2—O2 | 1.0 (3) | O12—C12—C13—O13 | 0.7 (3) |
C6—C1—C2—C3 | −0.5 (4) | C11—C12—C13—O13 | 179.8 (2) |
N1—C1—C2—C3 | −179.3 (2) | O12—C12—C13—C14 | −179.7 (2) |
O2—C2—C3—C4 | −179.9 (2) | C11—C12—C13—C14 | −0.6 (3) |
C1—C2—C3—C4 | 0.5 (4) | O13—C13—C14—C15 | 179.4 (2) |
C2—C3—C4—C5 | −0.1 (4) | C12—C13—C14—C15 | −0.2 (4) |
C3—C4—C5—C6 | −0.3 (4) | C13—C14—C15—C16 | 0.3 (4) |
C2—C1—C6—C5 | 0.1 (4) | C13—C14—C15—Br15 | −179.26 (17) |
N1—C1—C6—C5 | 178.8 (2) | C14—C15—C16—C11 | 0.4 (3) |
C4—C5—C6—C1 | 0.2 (4) | Br15—C15—C16—C11 | 179.91 (16) |
C6—C1—N1—C17 | −0.6 (4) | C12—C11—C16—C15 | −1.1 (3) |
C2—C1—N1—C17 | 178.1 (2) | C17—C11—C16—C15 | 177.0 (2) |
C3—C2—O2—C21 | 6.9 (4) | C1—N1—C17—C11 | −179.9 (2) |
C1—C2—O2—C21 | −173.5 (2) | C16—C11—C17—N1 | −178.6 (2) |
C16—C11—C12—O12 | −179.7 (2) | C12—C11—C17—N1 | −0.5 (3) |
C17—C11—C12—O12 | 2.2 (3) | C14—C13—O13—C113 | 9.7 (4) |
C16—C11—C12—C13 | 1.3 (3) | C12—C13—O13—C113 | −170.7 (2) |
C15H15NO3 | Dx = 1.276 Mg m−3 |
Mr = 257.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2601 reflections |
a = 23.689 (2) Å | θ = 1.7–25.9° |
b = 7.6951 (7) Å | µ = 0.09 mm−1 |
c = 7.3488 (7) Å | T = 296 K |
V = 1339.6 (2) Å3 | Block, orange |
Z = 4 | 0.24 × 0.18 × 0.10 mm |
F(000) = 544 |
Bruker APEXII CCD diffractometer | 2600 independent reflections |
Radiation source: fine focus sealed tube | 1975 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.9°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −25→29 |
Tmin = 0.859, Tmax = 0.991 | k = −9→9 |
16375 measured reflections | l = −9→9 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0332P)2 + 0.1885P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.11 e Å−3 |
2600 reflections | Δρmin = −0.14 e Å−3 |
175 parameters | Absolute structure: Flack x determined using 772 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.1 (5) |
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 | ||
C1 | 0.08903 (10) | 0.8870 (4) | 0.8423 (4) | 0.0426 (6) | |
C2 | 0.05117 (11) | 0.8302 (3) | 0.9757 (4) | 0.0440 (6) | |
C3 | 0.03195 (12) | 0.9445 (4) | 1.1060 (4) | 0.0536 (8) | |
H3 | 0.0065 | 0.9072 | 1.1940 | 0.064* | |
C4 | 0.05065 (13) | 1.1152 (4) | 1.1057 (5) | 0.0604 (8) | |
H4 | 0.0381 | 1.1916 | 1.1949 | 0.072* | |
C5 | 0.08757 (13) | 1.1722 (4) | 0.9747 (5) | 0.0601 (8) | |
H5 | 0.0996 | 1.2872 | 0.9744 | 0.072* | |
C6 | 0.10676 (12) | 1.0587 (4) | 0.8435 (4) | 0.0520 (7) | |
H6 | 0.1318 | 1.0977 | 0.7550 | 0.062* | |
N1 | 0.10993 (10) | 0.7621 (3) | 0.7191 (3) | 0.0476 (6) | |
O2 | 0.03493 (8) | 0.6604 (2) | 0.9623 (3) | 0.0565 (5) | |
C21 | −0.00134 (18) | 0.5945 (4) | 1.0988 (5) | 0.0867 (12) | |
H21A | 0.0163 | 0.6069 | 1.2156 | 0.130* | |
H21B | −0.0088 | 0.4738 | 1.0758 | 0.130* | |
H21C | −0.0362 | 0.6581 | 1.0975 | 0.130* | |
C11 | 0.14629 (11) | 0.6758 (4) | 0.4306 (4) | 0.0455 (7) | |
C12 | 0.15948 (11) | 0.5091 (4) | 0.4888 (4) | 0.0446 (7) | |
O12 | 0.14804 (9) | 0.4517 (3) | 0.6586 (3) | 0.0572 (6) | |
H12 | 0.1349 | 0.5315 | 0.7193 | 0.086* | |
C13 | 0.18589 (11) | 0.3938 (4) | 0.3682 (4) | 0.0488 (7) | |
C14 | 0.19927 (13) | 0.4473 (5) | 0.1956 (4) | 0.0601 (8) | |
H14 | 0.2174 | 0.3711 | 0.1166 | 0.072* | |
C15 | 0.18608 (14) | 0.6141 (5) | 0.1373 (4) | 0.0675 (9) | |
H15 | 0.1953 | 0.6489 | 0.0198 | 0.081* | |
C16 | 0.15970 (14) | 0.7267 (4) | 0.2517 (4) | 0.0589 (9) | |
H16 | 0.1505 | 0.8377 | 0.2117 | 0.071* | |
C17 | 0.12071 (12) | 0.8011 (4) | 0.5539 (4) | 0.0494 (7) | |
H17 | 0.1120 | 0.9118 | 0.5115 | 0.059* | |
O13 | 0.19690 (9) | 0.2318 (3) | 0.4367 (3) | 0.0650 (6) | |
C113 | 0.23182 (15) | 0.1230 (4) | 0.3301 (6) | 0.0888 (12) | |
H11A | 0.2135 | 0.0985 | 0.2165 | 0.133* | |
H11B | 0.2386 | 0.0163 | 0.3941 | 0.133* | |
H11C | 0.2671 | 0.1805 | 0.3073 | 0.133* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0371 (15) | 0.0494 (16) | 0.0413 (14) | 0.0062 (13) | −0.0021 (14) | 0.0032 (14) |
C2 | 0.0405 (14) | 0.0425 (15) | 0.0489 (16) | 0.0024 (12) | 0.0037 (14) | 0.0049 (15) |
C3 | 0.0544 (18) | 0.0513 (18) | 0.0552 (19) | 0.0063 (14) | 0.0128 (15) | 0.0003 (17) |
C4 | 0.067 (2) | 0.0498 (18) | 0.064 (2) | 0.0061 (16) | 0.0085 (18) | −0.0072 (17) |
C5 | 0.0624 (19) | 0.0469 (17) | 0.071 (2) | −0.0071 (15) | −0.0017 (19) | −0.0025 (19) |
C6 | 0.0426 (16) | 0.0571 (19) | 0.0564 (18) | −0.0058 (14) | 0.0026 (15) | 0.0043 (17) |
N1 | 0.0408 (14) | 0.0587 (15) | 0.0433 (14) | 0.0015 (11) | 0.0041 (11) | −0.0008 (12) |
O2 | 0.0641 (13) | 0.0466 (11) | 0.0588 (12) | −0.0035 (10) | 0.0163 (12) | −0.0005 (11) |
C21 | 0.111 (3) | 0.062 (2) | 0.086 (3) | −0.020 (2) | 0.047 (3) | 0.000 (2) |
C11 | 0.0388 (15) | 0.0598 (18) | 0.0379 (15) | −0.0012 (13) | −0.0005 (13) | 0.0023 (15) |
C12 | 0.0333 (14) | 0.0589 (18) | 0.0415 (15) | −0.0056 (12) | 0.0013 (12) | −0.0016 (15) |
O12 | 0.0651 (14) | 0.0602 (12) | 0.0463 (12) | 0.0025 (11) | 0.0135 (10) | 0.0059 (10) |
C13 | 0.0421 (15) | 0.0571 (18) | 0.0473 (17) | −0.0041 (14) | −0.0009 (14) | −0.0083 (15) |
C14 | 0.0545 (19) | 0.077 (2) | 0.0490 (19) | −0.0030 (17) | 0.0061 (15) | −0.0160 (17) |
C15 | 0.071 (2) | 0.091 (3) | 0.0405 (17) | −0.0070 (19) | 0.0064 (16) | −0.0023 (19) |
C16 | 0.061 (2) | 0.071 (2) | 0.0448 (19) | −0.0006 (17) | −0.0027 (16) | 0.0073 (17) |
C17 | 0.0443 (17) | 0.0546 (18) | 0.0493 (18) | 0.0048 (14) | −0.0042 (14) | 0.0044 (14) |
O13 | 0.0678 (14) | 0.0600 (13) | 0.0671 (14) | 0.0044 (10) | 0.0093 (12) | −0.0085 (12) |
C113 | 0.094 (3) | 0.074 (2) | 0.098 (3) | 0.011 (2) | 0.010 (3) | −0.028 (2) |
C1—C6 | 1.387 (4) | C11—C16 | 1.408 (4) |
C1—C2 | 1.399 (4) | C11—C17 | 1.455 (4) |
C1—N1 | 1.410 (4) | C12—O12 | 1.351 (3) |
C2—O2 | 1.366 (3) | C12—C13 | 1.401 (4) |
C2—C3 | 1.377 (4) | O12—H12 | 0.8200 |
C3—C4 | 1.386 (4) | C13—O13 | 1.370 (3) |
C3—H3 | 0.9300 | C13—C14 | 1.371 (4) |
C4—C5 | 1.373 (4) | C14—C15 | 1.389 (4) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—C6 | 1.378 (4) | C15—C16 | 1.359 (4) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
N1—C17 | 1.276 (3) | C17—H17 | 0.9300 |
O2—C21 | 1.415 (4) | O13—C113 | 1.414 (4) |
C21—H21A | 0.9600 | C113—H11A | 0.9600 |
C21—H21B | 0.9600 | C113—H11B | 0.9600 |
C21—H21C | 0.9600 | C113—H11C | 0.9600 |
C11—C12 | 1.388 (4) | ||
C6—C1—C2 | 119.1 (3) | C16—C11—C17 | 119.4 (3) |
C6—C1—N1 | 123.2 (3) | O12—C12—C11 | 122.8 (2) |
C2—C1—N1 | 117.6 (2) | O12—C12—C13 | 117.8 (3) |
O2—C2—C3 | 124.6 (2) | C11—C12—C13 | 119.4 (3) |
O2—C2—C1 | 115.4 (2) | C12—O12—H12 | 109.5 |
C3—C2—C1 | 120.0 (3) | O13—C13—C14 | 124.7 (3) |
C2—C3—C4 | 119.9 (3) | O13—C13—C12 | 115.4 (3) |
C2—C3—H3 | 120.1 | C14—C13—C12 | 119.9 (3) |
C4—C3—H3 | 120.1 | C13—C14—C15 | 120.7 (3) |
C5—C4—C3 | 120.5 (3) | C13—C14—H14 | 119.6 |
C5—C4—H4 | 119.8 | C15—C14—H14 | 119.6 |
C3—C4—H4 | 119.8 | C16—C15—C14 | 120.1 (3) |
C4—C5—C6 | 119.9 (3) | C16—C15—H15 | 120.0 |
C4—C5—H5 | 120.0 | C14—C15—H15 | 120.0 |
C6—C5—H5 | 120.0 | C15—C16—C11 | 120.3 (3) |
C5—C6—C1 | 120.6 (3) | C15—C16—H16 | 119.8 |
C5—C6—H6 | 119.7 | C11—C16—H16 | 119.8 |
C1—C6—H6 | 119.7 | N1—C17—C11 | 121.3 (3) |
C17—N1—C1 | 121.4 (3) | N1—C17—H17 | 119.3 |
C2—O2—C21 | 117.6 (2) | C11—C17—H17 | 119.3 |
O2—C21—H21A | 109.5 | C13—O13—C113 | 116.5 (3) |
O2—C21—H21B | 109.5 | O13—C113—H11A | 109.5 |
H21A—C21—H21B | 109.5 | O13—C113—H11B | 109.5 |
O2—C21—H21C | 109.5 | H11A—C113—H11B | 109.5 |
H21A—C21—H21C | 109.5 | O13—C113—H11C | 109.5 |
H21B—C21—H21C | 109.5 | H11A—C113—H11C | 109.5 |
C12—C11—C16 | 119.6 (3) | H11B—C113—H11C | 109.5 |
C12—C11—C17 | 120.9 (3) | ||
C6—C1—C2—O2 | 178.6 (2) | C16—C11—C12—C13 | −0.1 (4) |
N1—C1—C2—O2 | −5.2 (3) | C17—C11—C12—C13 | −177.8 (3) |
C6—C1—C2—C3 | 0.0 (4) | O12—C12—C13—O13 | 0.6 (4) |
N1—C1—C2—C3 | 176.3 (2) | C11—C12—C13—O13 | −179.5 (2) |
O2—C2—C3—C4 | −179.1 (3) | O12—C12—C13—C14 | −178.8 (3) |
C1—C2—C3—C4 | −0.7 (4) | C11—C12—C13—C14 | 1.1 (4) |
C2—C3—C4—C5 | 1.0 (5) | O13—C13—C14—C15 | 179.5 (3) |
C3—C4—C5—C6 | −0.7 (5) | C12—C13—C14—C15 | −1.1 (4) |
C4—C5—C6—C1 | 0.1 (5) | C13—C14—C15—C16 | 0.1 (5) |
C2—C1—C6—C5 | 0.3 (4) | C14—C15—C16—C11 | 0.9 (5) |
N1—C1—C6—C5 | −175.7 (3) | C12—C11—C16—C15 | −0.9 (4) |
C6—C1—N1—C17 | −37.9 (4) | C17—C11—C16—C15 | 176.8 (3) |
C2—C1—N1—C17 | 146.0 (3) | C1—N1—C17—C11 | 175.2 (2) |
C3—C2—O2—C21 | −4.3 (4) | C12—C11—C17—N1 | 0.4 (4) |
C1—C2—O2—C21 | 177.2 (3) | C16—C11—C17—N1 | −177.3 (3) |
C16—C11—C12—O12 | 179.8 (3) | C14—C13—O13—C113 | 9.8 (4) |
C17—C11—C12—O12 | 2.1 (4) | C12—C13—O13—C113 | −169.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···N1 | 0.82 | 1.87 | 2.592 (3) | 146 |
C3—H3···Cg1i | 0.93 | 2.83 | 3.646 (3) | 148 |
C16—H16···Cg1ii | 0.93 | 2.88 | 3.630 (3) | 138 |
Symmetry codes: (i) −x, −y+2, z+1/2; (ii) x, y, z−1. |
C22H18FNO2S | F(000) = 792 |
Mr = 379.43 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5004 (8) Å | Cell parameters from 4428 reflections |
b = 14.2911 (11) Å | θ = 2.1–28.0° |
c = 13.6497 (9) Å | µ = 0.20 mm−1 |
β = 97.524 (2)° | T = 296 K |
V = 1837.3 (2) Å3 | Block, yellow |
Z = 4 | 0.15 × 0.14 × 0.11 mm |
Bruker APEXII CCD diffractometer | 4250 independent reflections |
Radiation source: fine focus sealed tube | 2556 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 27.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −12→12 |
Tmin = 0.921, Tmax = 0.978 | k = −18→18 |
31822 measured reflections | l = −17→17 |
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0469P)2 + 0.4922P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4250 reflections | Δρmax = 0.18 e Å−3 |
258 parameters | Δρmin = −0.26 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 | Occ. (<1) | |
S1 | 0.56580 (6) | 0.11525 (4) | 0.69220 (4) | 0.04948 (18) | |
C2 | 0.6399 (2) | 0.19223 (14) | 0.61476 (14) | 0.0389 (5) | |
C3 | 0.7107 (2) | 0.14473 (14) | 0.54891 (13) | 0.0383 (5) | |
C3A | 0.7046 (2) | 0.04557 (14) | 0.56027 (14) | 0.0404 (5) | 0.705 (4) |
C4 | 0.7730 (16) | −0.0256 (2) | 0.5007 (8) | 0.0525 (6) | 0.705 (4) |
H4A | 0.8640 | −0.0022 | 0.4865 | 0.063* | 0.705 (4) |
H4B | 0.7134 | −0.0361 | 0.4384 | 0.063* | 0.705 (4) |
C5 | 0.7945 (4) | −0.1174 (2) | 0.5571 (3) | 0.0604 (10) | 0.705 (4) |
H5A | 0.8234 | −0.1654 | 0.5137 | 0.073* | 0.705 (4) |
H5B | 0.8697 | −0.1099 | 0.6119 | 0.073* | 0.705 (4) |
C6 | 0.6592 (4) | −0.1478 (2) | 0.5961 (3) | 0.0645 (12) | 0.705 (4) |
H6A | 0.5860 | −0.1578 | 0.5406 | 0.077* | 0.705 (4) |
H6B | 0.6764 | −0.2072 | 0.6300 | 0.077* | 0.705 (4) |
C7 | 0.6049 (9) | −0.0788 (2) | 0.6661 (5) | 0.0505 (16) | 0.705 (4) |
H7A | 0.5038 | −0.0879 | 0.6663 | 0.061* | 0.705 (4) |
H7B | 0.6518 | −0.0896 | 0.7326 | 0.061* | 0.705 (4) |
C7A | 0.6322 (2) | 0.01980 (14) | 0.63571 (14) | 0.0434 (5) | 0.705 (4) |
C23A | 0.7046 (2) | 0.04557 (14) | 0.56027 (14) | 0.0404 (5) | 0.295 (4) |
C24 | 0.772 (4) | −0.0272 (4) | 0.502 (2) | 0.0525 (6) | 0.295 (4) |
H24A | 0.8746 | −0.0251 | 0.5199 | 0.063* | 0.295 (4) |
H24B | 0.7521 | −0.0125 | 0.4320 | 0.063* | 0.295 (4) |
C25 | 0.7197 (11) | −0.1255 (4) | 0.5195 (6) | 0.0604 (10) | 0.295 (4) |
H25A | 0.6239 | −0.1329 | 0.4858 | 0.073* | 0.295 (4) |
H25B | 0.7800 | −0.1708 | 0.4923 | 0.073* | 0.295 (4) |
C26 | 0.7207 (11) | −0.1440 (5) | 0.6290 (6) | 0.0645 (12) | 0.295 (4) |
H26A | 0.6868 | −0.2071 | 0.6375 | 0.077* | 0.295 (4) |
H26B | 0.8179 | −0.1406 | 0.6612 | 0.077* | 0.295 (4) |
C27 | 0.631 (3) | −0.0766 (5) | 0.6796 (13) | 0.0505 (16) | 0.295 (4) |
H27A | 0.5342 | −0.0995 | 0.6734 | 0.061* | 0.295 (4) |
H27B | 0.6671 | −0.0735 | 0.7494 | 0.061* | 0.295 (4) |
C27A | 0.6322 (2) | 0.01980 (14) | 0.63571 (14) | 0.0434 (5) | 0.295 (4) |
N1 | 0.62359 (17) | 0.28869 (11) | 0.61552 (11) | 0.0403 (4) | |
C17 | 0.5359 (2) | 0.32940 (15) | 0.66555 (14) | 0.0429 (5) | |
H17 | 0.4811 | 0.2928 | 0.7023 | 0.051* | |
C11 | 0.5192 (2) | 0.42981 (14) | 0.66705 (14) | 0.0393 (5) | |
C12 | 0.6008 (2) | 0.48950 (15) | 0.61540 (14) | 0.0422 (5) | |
C13 | 0.5780 (2) | 0.58533 (16) | 0.61636 (16) | 0.0527 (6) | |
H13 | 0.6321 | 0.6247 | 0.5819 | 0.063* | |
C14 | 0.4762 (2) | 0.62265 (16) | 0.66784 (16) | 0.0527 (6) | |
H14 | 0.4603 | 0.6869 | 0.6679 | 0.063* | |
C15 | 0.3985 (2) | 0.56345 (17) | 0.71917 (15) | 0.0487 (6) | |
F15 | 0.29897 (15) | 0.60168 (10) | 0.77035 (10) | 0.0706 (4) | |
C16 | 0.4178 (2) | 0.46901 (15) | 0.72061 (14) | 0.0453 (5) | |
H16 | 0.3643 | 0.4309 | 0.7568 | 0.054* | |
O12 | 0.70270 (16) | 0.45725 (10) | 0.56372 (12) | 0.0558 (4) | |
H12 | 0.7034 | 0.3999 | 0.5651 | 0.084* | |
C37 | 0.7832 (2) | 0.19103 (14) | 0.47101 (14) | 0.0391 (5) | |
O37 | 0.75072 (16) | 0.16958 (11) | 0.38463 (10) | 0.0574 (4) | |
C31 | 0.8958 (2) | 0.26031 (13) | 0.50165 (13) | 0.0362 (4) | |
C32 | 0.9657 (2) | 0.26220 (16) | 0.59733 (14) | 0.0457 (5) | |
H32 | 0.9381 | 0.2216 | 0.6445 | 0.055* | |
C33 | 1.0760 (2) | 0.32384 (17) | 0.62318 (16) | 0.0554 (6) | |
H33 | 1.1239 | 0.3236 | 0.6871 | 0.067* | |
C34 | 1.1153 (2) | 0.38579 (17) | 0.55424 (16) | 0.0574 (6) | |
H34 | 1.1888 | 0.4280 | 0.5718 | 0.069* | |
C35 | 1.0452 (2) | 0.38492 (16) | 0.45926 (16) | 0.0542 (6) | |
H35 | 1.0711 | 0.4271 | 0.4129 | 0.065* | |
C36 | 0.9374 (2) | 0.32224 (15) | 0.43251 (14) | 0.0449 (5) | |
H36 | 0.8920 | 0.3213 | 0.3679 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0570 (4) | 0.0474 (3) | 0.0483 (3) | −0.0084 (3) | 0.0229 (3) | 0.0002 (3) |
C2 | 0.0380 (11) | 0.0401 (12) | 0.0397 (10) | −0.0061 (9) | 0.0088 (9) | −0.0001 (9) |
C3 | 0.0353 (11) | 0.0422 (12) | 0.0383 (10) | −0.0055 (9) | 0.0078 (9) | −0.0002 (9) |
C3A | 0.0389 (11) | 0.0419 (12) | 0.0402 (11) | −0.0039 (9) | 0.0047 (9) | −0.0021 (9) |
C4 | 0.0541 (14) | 0.0469 (14) | 0.0580 (14) | 0.0013 (11) | 0.0128 (11) | −0.0051 (12) |
C5 | 0.059 (3) | 0.0471 (18) | 0.074 (3) | 0.0081 (19) | 0.0052 (19) | −0.0031 (17) |
C6 | 0.073 (3) | 0.0391 (16) | 0.080 (3) | −0.0122 (19) | 0.005 (2) | −0.0029 (18) |
C7 | 0.049 (4) | 0.0455 (14) | 0.054 (2) | −0.0141 (13) | −0.002 (3) | 0.0075 (12) |
C7A | 0.0423 (12) | 0.0430 (12) | 0.0450 (11) | −0.0075 (10) | 0.0054 (9) | −0.0003 (10) |
C23A | 0.0389 (11) | 0.0419 (12) | 0.0402 (11) | −0.0039 (9) | 0.0047 (9) | −0.0021 (9) |
C24 | 0.0541 (14) | 0.0469 (14) | 0.0580 (14) | 0.0013 (11) | 0.0128 (11) | −0.0051 (12) |
C25 | 0.059 (3) | 0.0471 (18) | 0.074 (3) | 0.0081 (19) | 0.0052 (19) | −0.0031 (17) |
C26 | 0.073 (3) | 0.0391 (16) | 0.080 (3) | −0.0122 (19) | 0.005 (2) | −0.0029 (18) |
C27 | 0.049 (4) | 0.0455 (14) | 0.054 (2) | −0.0141 (13) | −0.002 (3) | 0.0075 (12) |
C27A | 0.0423 (12) | 0.0430 (12) | 0.0450 (11) | −0.0075 (10) | 0.0054 (9) | −0.0003 (10) |
N1 | 0.0407 (10) | 0.0383 (10) | 0.0429 (9) | −0.0034 (8) | 0.0095 (8) | −0.0024 (8) |
C17 | 0.0423 (12) | 0.0451 (13) | 0.0429 (11) | −0.0064 (10) | 0.0116 (9) | 0.0011 (9) |
C11 | 0.0366 (11) | 0.0419 (12) | 0.0393 (11) | −0.0010 (9) | 0.0047 (9) | −0.0034 (9) |
C12 | 0.0400 (12) | 0.0452 (13) | 0.0423 (11) | −0.0048 (10) | 0.0090 (9) | −0.0038 (9) |
C13 | 0.0594 (15) | 0.0429 (13) | 0.0574 (14) | −0.0076 (11) | 0.0142 (11) | −0.0012 (11) |
C14 | 0.0649 (15) | 0.0409 (13) | 0.0520 (13) | 0.0055 (11) | 0.0063 (11) | −0.0048 (11) |
C15 | 0.0480 (13) | 0.0572 (15) | 0.0415 (12) | 0.0104 (11) | 0.0081 (10) | −0.0057 (11) |
F15 | 0.0758 (10) | 0.0716 (10) | 0.0700 (9) | 0.0245 (8) | 0.0305 (8) | −0.0028 (7) |
C16 | 0.0448 (12) | 0.0506 (14) | 0.0418 (11) | −0.0021 (10) | 0.0104 (9) | 0.0003 (10) |
O12 | 0.0577 (10) | 0.0436 (9) | 0.0726 (10) | −0.0071 (8) | 0.0330 (8) | −0.0034 (8) |
C37 | 0.0400 (11) | 0.0412 (12) | 0.0373 (11) | −0.0007 (9) | 0.0092 (9) | −0.0008 (9) |
O37 | 0.0703 (11) | 0.0638 (11) | 0.0389 (8) | −0.0181 (8) | 0.0104 (8) | −0.0059 (7) |
C31 | 0.0348 (10) | 0.0395 (11) | 0.0360 (10) | −0.0007 (9) | 0.0110 (8) | 0.0011 (9) |
C32 | 0.0413 (12) | 0.0581 (14) | 0.0387 (11) | −0.0066 (10) | 0.0086 (9) | 0.0068 (10) |
C33 | 0.0474 (13) | 0.0770 (18) | 0.0414 (12) | −0.0128 (12) | 0.0042 (10) | −0.0044 (11) |
C34 | 0.0513 (14) | 0.0677 (16) | 0.0541 (14) | −0.0199 (12) | 0.0102 (11) | −0.0077 (12) |
C35 | 0.0574 (14) | 0.0570 (15) | 0.0511 (13) | −0.0158 (12) | 0.0173 (11) | 0.0081 (11) |
C36 | 0.0460 (13) | 0.0530 (14) | 0.0368 (11) | −0.0051 (10) | 0.0093 (9) | 0.0036 (10) |
S1—C7A | 1.726 (2) | C27—H27B | 0.9700 |
S1—C2 | 1.7374 (19) | N1—C17 | 1.283 (2) |
C2—C3 | 1.371 (3) | C17—C11 | 1.444 (3) |
C2—N1 | 1.387 (2) | C17—H17 | 0.9300 |
C3—C3A | 1.427 (3) | C11—C16 | 1.400 (3) |
C3—C37 | 1.495 (3) | C11—C12 | 1.403 (3) |
C3A—C7A | 1.362 (3) | C12—O12 | 1.351 (2) |
C3A—C4 | 1.502 (3) | C12—C13 | 1.387 (3) |
C4—C5 | 1.520 (7) | C13—C14 | 1.375 (3) |
C4—H4A | 0.9700 | C13—H13 | 0.9300 |
C4—H4B | 0.9700 | C14—C15 | 1.374 (3) |
C5—C6 | 1.518 (4) | C14—H14 | 0.9300 |
C5—H5A | 0.9700 | C15—F15 | 1.361 (2) |
C5—H5B | 0.9700 | C15—C16 | 1.362 (3) |
C6—C7 | 1.510 (4) | C16—H16 | 0.9300 |
C6—H6A | 0.9700 | O12—H12 | 0.8200 |
C6—H6B | 0.9700 | C37—O37 | 1.218 (2) |
C7—C7A | 1.501 (3) | C37—C31 | 1.478 (3) |
C7—H7A | 0.9700 | C31—C32 | 1.386 (3) |
C7—H7B | 0.9700 | C31—C36 | 1.388 (3) |
C24—C25 | 1.522 (8) | C32—C33 | 1.379 (3) |
C24—H24A | 0.9700 | C32—H32 | 0.9300 |
C24—H24B | 0.9700 | C33—C34 | 1.379 (3) |
C25—C26 | 1.516 (5) | C33—H33 | 0.9300 |
C25—H25A | 0.9700 | C34—C35 | 1.378 (3) |
C25—H25B | 0.9700 | C34—H34 | 0.9300 |
C26—C27 | 1.511 (5) | C35—C36 | 1.374 (3) |
C26—H26A | 0.9700 | C35—H35 | 0.9300 |
C26—H26B | 0.9700 | C36—H36 | 0.9300 |
C27—H27A | 0.9700 | ||
C7A—S1—C2 | 91.59 (10) | C25—C26—H26B | 108.7 |
C3—C2—N1 | 124.19 (18) | H26A—C26—H26B | 107.6 |
C3—C2—S1 | 110.98 (15) | C26—C27—H27A | 109.3 |
N1—C2—S1 | 124.74 (15) | C26—C27—H27B | 109.3 |
C2—C3—C3A | 112.97 (17) | H27A—C27—H27B | 108.0 |
C2—C3—C37 | 123.94 (18) | C17—N1—C2 | 122.38 (17) |
C3A—C3—C37 | 123.07 (17) | N1—C17—C11 | 122.56 (18) |
C7A—C3A—C3 | 112.46 (18) | N1—C17—H17 | 118.7 |
C7A—C3A—C4 | 121.5 (2) | C11—C17—H17 | 118.7 |
C3—C3A—C4 | 126.0 (2) | C16—C11—C12 | 118.83 (19) |
C3A—C4—C5 | 110.5 (4) | C16—C11—C17 | 119.30 (18) |
C3A—C4—H4A | 109.6 | C12—C11—C17 | 121.86 (18) |
C5—C4—H4A | 109.6 | O12—C12—C13 | 117.73 (18) |
C3A—C4—H4B | 109.6 | O12—C12—C11 | 122.39 (19) |
C5—C4—H4B | 109.6 | C13—C12—C11 | 119.89 (19) |
H4A—C4—H4B | 108.1 | C14—C13—C12 | 120.6 (2) |
C6—C5—C4 | 111.2 (6) | C14—C13—H13 | 119.7 |
C6—C5—H5A | 109.4 | C12—C13—H13 | 119.7 |
C4—C5—H5A | 109.4 | C15—C14—C13 | 118.9 (2) |
C6—C5—H5B | 109.4 | C15—C14—H14 | 120.6 |
C4—C5—H5B | 109.4 | C13—C14—H14 | 120.6 |
H5A—C5—H5B | 108.0 | F15—C15—C16 | 119.5 (2) |
C7—C6—C5 | 114.2 (4) | F15—C15—C14 | 118.1 (2) |
C7—C6—H6A | 108.7 | C16—C15—C14 | 122.5 (2) |
C5—C6—H6A | 108.7 | C15—C16—C11 | 119.3 (2) |
C7—C6—H6B | 108.7 | C15—C16—H16 | 120.3 |
C5—C6—H6B | 108.7 | C11—C16—H16 | 120.3 |
H6A—C6—H6B | 107.6 | C12—O12—H12 | 109.5 |
C7A—C7—C6 | 110.7 (2) | O37—C37—C31 | 121.64 (17) |
C7A—C7—H7A | 109.5 | O37—C37—C3 | 119.70 (18) |
C6—C7—H7A | 109.5 | C31—C37—C3 | 118.64 (16) |
C7A—C7—H7B | 109.5 | C32—C31—C36 | 118.96 (18) |
C6—C7—H7B | 109.5 | C32—C31—C37 | 121.32 (17) |
H7A—C7—H7B | 108.1 | C36—C31—C37 | 119.65 (17) |
C3A—C7A—C7 | 125.8 (2) | C33—C32—C31 | 120.53 (19) |
C3A—C7A—S1 | 111.98 (16) | C33—C32—H32 | 119.7 |
C7—C7A—S1 | 122.14 (18) | C31—C32—H32 | 119.7 |
C25—C24—H24A | 109.1 | C34—C33—C32 | 120.0 (2) |
C25—C24—H24B | 109.1 | C34—C33—H33 | 120.0 |
H24A—C24—H24B | 107.8 | C32—C33—H33 | 120.0 |
C26—C25—C24 | 110.9 (9) | C35—C34—C33 | 119.7 (2) |
C26—C25—H25A | 109.5 | C35—C34—H34 | 120.1 |
C24—C25—H25A | 109.5 | C33—C34—H34 | 120.1 |
C26—C25—H25B | 109.5 | C36—C35—C34 | 120.5 (2) |
C24—C25—H25B | 109.5 | C36—C35—H35 | 119.7 |
H25A—C25—H25B | 108.1 | C34—C35—H35 | 119.7 |
C27—C26—C25 | 114.1 (7) | C35—C36—C31 | 120.23 (19) |
C27—C26—H26A | 108.7 | C35—C36—H36 | 119.9 |
C25—C26—H26A | 108.7 | C31—C36—H36 | 119.9 |
C27—C26—H26B | 108.7 | ||
C7A—S1—C2—C3 | 0.46 (16) | C16—C11—C12—O12 | 178.61 (19) |
C7A—S1—C2—N1 | 177.20 (18) | C17—C11—C12—O12 | −2.1 (3) |
N1—C2—C3—C3A | −176.38 (18) | C16—C11—C12—C13 | −1.4 (3) |
S1—C2—C3—C3A | 0.4 (2) | C17—C11—C12—C13 | 177.94 (19) |
N1—C2—C3—C37 | 1.8 (3) | O12—C12—C13—C14 | −179.8 (2) |
S1—C2—C3—C37 | 178.58 (15) | C11—C12—C13—C14 | 0.2 (3) |
C2—C3—C3A—C7A | −1.3 (3) | C12—C13—C14—C15 | 0.7 (3) |
C37—C3—C3A—C7A | −179.54 (18) | C13—C14—C15—F15 | 179.48 (19) |
C2—C3—C3A—C4 | −179.0 (8) | C13—C14—C15—C16 | −0.4 (3) |
C37—C3—C3A—C4 | 2.7 (9) | F15—C15—C16—C11 | 179.33 (17) |
C7A—C3A—C4—C5 | −19.9 (14) | C14—C15—C16—C11 | −0.8 (3) |
C3—C3A—C4—C5 | 157.6 (5) | C12—C11—C16—C15 | 1.7 (3) |
C3A—C4—C5—C6 | 49.4 (12) | C17—C11—C16—C15 | −177.66 (19) |
C4—C5—C6—C7 | −59.9 (8) | C2—C3—C37—O37 | −123.6 (2) |
C5—C6—C7—C7A | 35.4 (7) | C3A—C3—C37—O37 | 54.4 (3) |
C3—C3A—C7A—C7 | 179.1 (5) | C2—C3—C37—C31 | 58.0 (3) |
C4—C3A—C7A—C7 | −3.0 (9) | C3A—C3—C37—C31 | −124.0 (2) |
C3—C3A—C7A—S1 | 1.6 (2) | O37—C37—C31—C32 | −157.9 (2) |
C4—C3A—C7A—S1 | 179.5 (8) | C3—C37—C31—C32 | 20.5 (3) |
C6—C7—C7A—C3A | −4.5 (8) | O37—C37—C31—C36 | 19.2 (3) |
C6—C7—C7A—S1 | 172.8 (3) | C3—C37—C31—C36 | −162.43 (18) |
C2—S1—C7A—C3A | −1.22 (16) | C36—C31—C32—C33 | −0.8 (3) |
C2—S1—C7A—C7 | −178.8 (4) | C37—C31—C32—C33 | 176.3 (2) |
C24—C25—C26—C27 | 58.5 (15) | C31—C32—C33—C34 | 1.6 (3) |
C3—C2—N1—C17 | 166.97 (19) | C32—C33—C34—C35 | −0.9 (4) |
S1—C2—N1—C17 | −9.3 (3) | C33—C34—C35—C36 | −0.6 (4) |
C2—N1—C17—C11 | 179.60 (18) | C34—C35—C36—C31 | 1.4 (3) |
N1—C17—C11—C16 | 177.76 (19) | C32—C31—C36—C35 | −0.7 (3) |
N1—C17—C11—C12 | −1.6 (3) | C37—C31—C36—C35 | −177.83 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···N1 | 0.82 | 1.93 | 2.647 (2) | 146 |
C16—H16···O37i | 0.93 | 2.60 | 3.519 (3) | 170 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
C22H19NO2S | F(000) = 760 |
Mr = 361.44 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.26395 (15) Å | Cell parameters from 5377 reflections |
b = 14.2886 (2) Å | θ = 4.5–71.3° |
c = 13.6476 (2) Å | µ = 1.73 mm−1 |
β = 96.7581 (15)° | T = 173 K |
V = 1793.97 (5) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.14 × 0.08 mm |
Agilent Eos Gemini diffractometer | 3115 reflections with I > 2σ(I) |
Radiation source: Enhance (Cu) X-ray Source | Rint = 0.053 |
ω scans | θmax = 71.5°, θmin = 4.5° |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | h = −11→10 |
Tmin = 0.529, Tmax = 0.871 | k = −17→17 |
11619 measured reflections | l = −16→14 |
3464 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.2663P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.120 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.33 e Å−3 |
3464 reflections | Δρmin = −0.23 e Å−3 |
250 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
12 restraints | Extinction coefficient: 0.0025 (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) | |
S1 | 0.55852 (4) | 0.11521 (3) | 0.69559 (3) | 0.02965 (15) | |
C2 | 0.63345 (15) | 0.19433 (10) | 0.61848 (11) | 0.0254 (3) | |
C3 | 0.70610 (15) | 0.14810 (10) | 0.55080 (11) | 0.0251 (3) | |
C3A | 0.70094 (15) | 0.04847 (10) | 0.56033 (11) | 0.0258 (3) | 0.851 (3) |
C4 | 0.7727 (7) | −0.02081 (13) | 0.4986 (4) | 0.0312 (4) | 0.851 (3) |
H4A | 0.8668 | 0.0046 | 0.4832 | 0.037* | 0.851 (3) |
H4B | 0.7102 | −0.0314 | 0.4356 | 0.037* | 0.851 (3) |
C5 | 0.7976 (2) | −0.11332 (13) | 0.55391 (16) | 0.0363 (5) | 0.851 (3) |
H5A | 0.8288 | −0.1615 | 0.5086 | 0.044* | 0.851 (3) |
H5B | 0.8766 | −0.1054 | 0.6088 | 0.044* | 0.851 (3) |
C6 | 0.6602 (3) | −0.14642 (13) | 0.59497 (19) | 0.0395 (5) | 0.851 (3) |
H6A | 0.5823 | −0.1553 | 0.5396 | 0.047* | 0.851 (3) |
H6B | 0.6795 | −0.2078 | 0.6275 | 0.047* | 0.851 (3) |
C7 | 0.6075 (5) | −0.07816 (14) | 0.6689 (3) | 0.0329 (8) | 0.851 (3) |
H7A | 0.5035 | −0.0897 | 0.6745 | 0.039* | 0.851 (3) |
H7B | 0.6629 | −0.0882 | 0.7346 | 0.039* | 0.851 (3) |
C7A | 0.62763 (16) | 0.02109 (10) | 0.63626 (11) | 0.0276 (3) | 0.851 (3) |
C23A | 0.70094 (15) | 0.04847 (10) | 0.56033 (11) | 0.0258 (3) | 0.149 (3) |
C24 | 0.768 (4) | −0.0232 (5) | 0.498 (2) | 0.0312 (4) | 0.149 (3) |
H24A | 0.8754 | −0.0207 | 0.5137 | 0.037* | 0.149 (3) |
H24B | 0.7437 | −0.0075 | 0.4278 | 0.037* | 0.149 (3) |
C25 | 0.7162 (14) | −0.1225 (5) | 0.5165 (7) | 0.0363 (5) | 0.149 (3) |
H25A | 0.6157 | −0.1304 | 0.4837 | 0.044* | 0.149 (3) |
H25B | 0.7791 | −0.1679 | 0.4868 | 0.044* | 0.149 (3) |
C26 | 0.7193 (15) | −0.1433 (6) | 0.6260 (7) | 0.0395 (5) | 0.149 (3) |
H26A | 0.8208 | −0.1392 | 0.6578 | 0.047* | 0.149 (3) |
H26B | 0.6851 | −0.2081 | 0.6343 | 0.047* | 0.149 (3) |
C27 | 0.625 (4) | −0.0763 (6) | 0.6780 (18) | 0.0329 (8) | 0.149 (3) |
H27A | 0.5237 | −0.0996 | 0.6708 | 0.039* | 0.149 (3) |
H27B | 0.6606 | −0.0746 | 0.7493 | 0.039* | 0.149 (3) |
C27A | 0.62763 (16) | 0.02109 (10) | 0.63626 (11) | 0.0276 (3) | 0.149 (3) |
N1 | 0.61670 (13) | 0.29061 (9) | 0.62116 (9) | 0.0263 (3) | |
C17 | 0.52975 (16) | 0.33089 (11) | 0.67516 (11) | 0.0275 (3) | |
H17 | 0.4753 | 0.2934 | 0.7151 | 0.033* | |
C11 | 0.51262 (15) | 0.43149 (11) | 0.67676 (11) | 0.0264 (3) | |
C12 | 0.59258 (16) | 0.49131 (11) | 0.62112 (11) | 0.0284 (3) | |
C13 | 0.56826 (19) | 0.58760 (12) | 0.62206 (13) | 0.0359 (4) | |
H13 | 0.6216 | 0.6279 | 0.5843 | 0.043* | |
C14 | 0.46701 (19) | 0.62449 (11) | 0.67769 (13) | 0.0367 (4) | |
H14 | 0.4501 | 0.6901 | 0.6771 | 0.044* | |
C15 | 0.38928 (18) | 0.56681 (12) | 0.73469 (12) | 0.0360 (4) | |
H15 | 0.3209 | 0.5930 | 0.7736 | 0.043* | |
C16 | 0.41197 (17) | 0.47130 (11) | 0.73444 (12) | 0.0311 (3) | |
H16 | 0.3591 | 0.4320 | 0.7736 | 0.037* | |
O12 | 0.69347 (13) | 0.45874 (8) | 0.56601 (9) | 0.0367 (3) | |
H12 | 0.6982 | 0.4002 | 0.5708 | 0.055* | |
C37 | 0.77923 (15) | 0.19624 (10) | 0.47298 (11) | 0.0246 (3) | |
O37 | 0.74685 (12) | 0.17582 (8) | 0.38636 (8) | 0.0338 (3) | |
C31 | 0.89546 (15) | 0.26512 (10) | 0.50409 (11) | 0.0248 (3) | |
C32 | 0.96622 (16) | 0.26563 (11) | 0.59988 (11) | 0.0294 (3) | |
H32 | 0.9356 | 0.2243 | 0.6479 | 0.035* | |
C33 | 1.08136 (17) | 0.32642 (13) | 0.62539 (12) | 0.0348 (4) | |
H33 | 1.1308 | 0.3258 | 0.6904 | 0.042* | |
C34 | 1.12419 (18) | 0.38811 (12) | 0.55594 (13) | 0.0373 (4) | |
H34 | 1.2026 | 0.4300 | 0.5735 | 0.045* | |
C35 | 1.05239 (19) | 0.38872 (12) | 0.46057 (13) | 0.0366 (4) | |
H35 | 1.0811 | 0.4316 | 0.4133 | 0.044* | |
C36 | 0.93955 (17) | 0.32723 (12) | 0.43432 (11) | 0.0307 (3) | |
H36 | 0.8918 | 0.3271 | 0.3688 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0350 (2) | 0.0249 (2) | 0.0313 (2) | −0.00451 (13) | 0.01304 (16) | −0.00084 (13) |
C2 | 0.0258 (7) | 0.0232 (7) | 0.0275 (7) | −0.0037 (5) | 0.0053 (5) | 0.0001 (5) |
C3 | 0.0226 (7) | 0.0240 (7) | 0.0286 (7) | −0.0023 (5) | 0.0027 (5) | −0.0013 (5) |
C3A | 0.0232 (7) | 0.0230 (7) | 0.0307 (7) | −0.0017 (5) | 0.0017 (5) | −0.0017 (6) |
C4 | 0.0311 (9) | 0.0264 (8) | 0.0366 (8) | 0.0017 (6) | 0.0065 (7) | −0.0043 (6) |
C5 | 0.0358 (11) | 0.0272 (10) | 0.0447 (12) | 0.0074 (8) | 0.0003 (8) | −0.0042 (8) |
C6 | 0.0437 (13) | 0.0222 (8) | 0.0516 (14) | −0.0040 (8) | 0.0019 (10) | −0.0019 (8) |
C7 | 0.0344 (17) | 0.0248 (8) | 0.0390 (12) | −0.0067 (7) | 0.0025 (13) | 0.0036 (7) |
C7A | 0.0277 (7) | 0.0216 (7) | 0.0334 (8) | −0.0019 (5) | 0.0036 (6) | −0.0019 (6) |
C23A | 0.0232 (7) | 0.0230 (7) | 0.0307 (7) | −0.0017 (5) | 0.0017 (5) | −0.0017 (6) |
C24 | 0.0311 (9) | 0.0264 (8) | 0.0366 (8) | 0.0017 (6) | 0.0065 (7) | −0.0043 (6) |
C25 | 0.0358 (11) | 0.0272 (10) | 0.0447 (12) | 0.0074 (8) | 0.0003 (8) | −0.0042 (8) |
C26 | 0.0437 (13) | 0.0222 (8) | 0.0516 (14) | −0.0040 (8) | 0.0019 (10) | −0.0019 (8) |
C27 | 0.0344 (17) | 0.0248 (8) | 0.0390 (12) | −0.0067 (7) | 0.0025 (13) | 0.0036 (7) |
C27A | 0.0277 (7) | 0.0216 (7) | 0.0334 (8) | −0.0019 (5) | 0.0036 (6) | −0.0019 (6) |
N1 | 0.0271 (6) | 0.0222 (6) | 0.0303 (6) | −0.0026 (5) | 0.0057 (5) | −0.0011 (5) |
C17 | 0.0269 (7) | 0.0253 (7) | 0.0309 (7) | −0.0031 (6) | 0.0064 (6) | −0.0007 (6) |
C11 | 0.0246 (7) | 0.0248 (7) | 0.0293 (7) | −0.0011 (6) | 0.0010 (5) | −0.0034 (6) |
C12 | 0.0284 (7) | 0.0259 (7) | 0.0306 (7) | −0.0031 (6) | 0.0026 (6) | −0.0033 (6) |
C13 | 0.0437 (9) | 0.0258 (8) | 0.0384 (9) | −0.0043 (7) | 0.0049 (7) | 0.0007 (6) |
C14 | 0.0439 (9) | 0.0244 (8) | 0.0402 (9) | 0.0046 (6) | −0.0017 (7) | −0.0047 (6) |
C15 | 0.0353 (8) | 0.0345 (8) | 0.0382 (8) | 0.0079 (7) | 0.0039 (7) | −0.0075 (7) |
C16 | 0.0301 (7) | 0.0312 (8) | 0.0324 (8) | −0.0008 (6) | 0.0051 (6) | −0.0031 (6) |
O12 | 0.0411 (6) | 0.0260 (6) | 0.0468 (7) | −0.0045 (5) | 0.0205 (5) | −0.0018 (5) |
C37 | 0.0238 (7) | 0.0239 (7) | 0.0266 (7) | 0.0024 (5) | 0.0047 (5) | 0.0005 (5) |
O37 | 0.0393 (6) | 0.0361 (6) | 0.0264 (6) | −0.0064 (5) | 0.0048 (4) | −0.0033 (4) |
C31 | 0.0235 (6) | 0.0252 (7) | 0.0265 (7) | 0.0006 (5) | 0.0069 (5) | −0.0001 (5) |
C32 | 0.0284 (7) | 0.0348 (8) | 0.0256 (7) | −0.0014 (6) | 0.0062 (6) | 0.0027 (6) |
C33 | 0.0299 (8) | 0.0468 (10) | 0.0273 (8) | −0.0047 (7) | 0.0019 (6) | −0.0027 (7) |
C34 | 0.0321 (8) | 0.0432 (10) | 0.0372 (9) | −0.0129 (7) | 0.0066 (7) | −0.0057 (7) |
C35 | 0.0393 (9) | 0.0397 (9) | 0.0320 (8) | −0.0113 (7) | 0.0093 (7) | 0.0042 (6) |
C36 | 0.0325 (8) | 0.0358 (8) | 0.0239 (7) | −0.0047 (6) | 0.0041 (6) | 0.0036 (6) |
S1—C7A | 1.7310 (15) | C27—H27B | 0.9900 |
S1—C2 | 1.7433 (14) | N1—C17 | 1.290 (2) |
C2—C3 | 1.374 (2) | C17—C11 | 1.447 (2) |
C2—N1 | 1.3853 (19) | C17—H17 | 0.9500 |
C3—C3A | 1.431 (2) | C11—C16 | 1.409 (2) |
C3—C37 | 1.493 (2) | C11—C12 | 1.410 (2) |
C3A—C7A | 1.361 (2) | C12—O12 | 1.3496 (19) |
C3A—C4 | 1.505 (2) | C12—C13 | 1.395 (2) |
C4—C5 | 1.527 (4) | C13—C14 | 1.379 (2) |
C4—H4A | 0.9900 | C13—H13 | 0.9500 |
C4—H4B | 0.9900 | C14—C15 | 1.391 (3) |
C5—C6 | 1.525 (3) | C14—H14 | 0.9500 |
C5—H5A | 0.9900 | C15—C16 | 1.381 (2) |
C5—H5B | 0.9900 | C15—H15 | 0.9500 |
C6—C7 | 1.524 (3) | C16—H16 | 0.9500 |
C6—H6A | 0.9900 | O12—H12 | 0.8400 |
C6—H6B | 0.9900 | C37—O37 | 1.2203 (18) |
C7—C7A | 1.504 (2) | C37—C31 | 1.484 (2) |
C7—H7A | 0.9900 | C31—C32 | 1.392 (2) |
C7—H7B | 0.9900 | C31—C36 | 1.397 (2) |
C24—C25 | 1.528 (7) | C32—C33 | 1.388 (2) |
C24—H24A | 0.9900 | C32—H32 | 0.9500 |
C24—H24B | 0.9900 | C33—C34 | 1.386 (2) |
C25—C26 | 1.521 (5) | C33—H33 | 0.9500 |
C25—H25A | 0.9900 | C34—C35 | 1.390 (2) |
C25—H25B | 0.9900 | C34—H34 | 0.9500 |
C26—C27 | 1.525 (6) | C35—C36 | 1.380 (2) |
C26—H26A | 0.9900 | C35—H35 | 0.9500 |
C26—H26B | 0.9900 | C36—H36 | 0.9500 |
C27—H27A | 0.9900 | ||
C7A—S1—C2 | 91.49 (7) | C27—C26—H26B | 109.0 |
C3—C2—N1 | 124.07 (13) | H26A—C26—H26B | 107.8 |
C3—C2—S1 | 110.81 (11) | C26—C27—H27A | 109.3 |
N1—C2—S1 | 125.04 (11) | C26—C27—H27B | 109.3 |
C2—C3—C3A | 113.13 (13) | H27A—C27—H27B | 108.0 |
C2—C3—C37 | 123.76 (13) | C17—N1—C2 | 122.53 (13) |
C3A—C3—C37 | 123.08 (13) | N1—C17—C11 | 121.95 (13) |
C7A—C3A—C3 | 112.34 (13) | N1—C17—H17 | 119.0 |
C7A—C3A—C4 | 122.01 (14) | C11—C17—H17 | 119.0 |
C3—C3A—C4 | 125.59 (14) | C16—C11—C12 | 118.70 (14) |
C3A—C4—C5 | 110.1 (2) | C16—C11—C17 | 119.38 (14) |
C3A—C4—H4A | 109.6 | C12—C11—C17 | 121.92 (13) |
C5—C4—H4A | 109.6 | O12—C12—C13 | 117.94 (14) |
C3A—C4—H4B | 109.6 | O12—C12—C11 | 122.23 (14) |
C5—C4—H4B | 109.6 | C13—C12—C11 | 119.83 (14) |
H4A—C4—H4B | 108.2 | C14—C13—C12 | 120.22 (16) |
C6—C5—C4 | 111.5 (3) | C14—C13—H13 | 119.9 |
C6—C5—H5A | 109.3 | C12—C13—H13 | 119.9 |
C4—C5—H5A | 109.3 | C13—C14—C15 | 120.79 (15) |
C6—C5—H5B | 109.3 | C13—C14—H14 | 119.6 |
C4—C5—H5B | 109.3 | C15—C14—H14 | 119.6 |
H5A—C5—H5B | 108.0 | C16—C15—C14 | 119.68 (15) |
C7—C6—C5 | 113.0 (2) | C16—C15—H15 | 120.2 |
C7—C6—H6A | 109.0 | C14—C15—H15 | 120.2 |
C5—C6—H6A | 109.0 | C15—C16—C11 | 120.75 (15) |
C7—C6—H6B | 109.0 | C15—C16—H16 | 119.6 |
C5—C6—H6B | 109.0 | C11—C16—H16 | 119.6 |
H6A—C6—H6B | 107.8 | C12—O12—H12 | 109.5 |
C7A—C7—C6 | 110.32 (16) | O37—C37—C31 | 121.55 (13) |
C7A—C7—H7A | 109.6 | O37—C37—C3 | 119.91 (13) |
C6—C7—H7A | 109.6 | C31—C37—C3 | 118.48 (12) |
C7A—C7—H7B | 109.6 | C32—C31—C36 | 119.58 (14) |
C6—C7—H7B | 109.6 | C32—C31—C37 | 121.20 (13) |
H7A—C7—H7B | 108.1 | C36—C31—C37 | 119.13 (13) |
C3A—C7A—C7 | 125.88 (15) | C33—C32—C31 | 120.13 (14) |
C3A—C7A—S1 | 112.20 (11) | C33—C32—H32 | 119.9 |
C7—C7A—S1 | 121.92 (13) | C31—C32—H32 | 119.9 |
C25—C24—H24A | 109.1 | C34—C33—C32 | 120.00 (15) |
C25—C24—H24B | 109.1 | C34—C33—H33 | 120.0 |
H24A—C24—H24B | 107.9 | C32—C33—H33 | 120.0 |
C26—C25—C24 | 111.7 (9) | C33—C34—C35 | 120.02 (15) |
C26—C25—H25A | 109.3 | C33—C34—H34 | 120.0 |
C24—C25—H25A | 109.3 | C35—C34—H34 | 120.0 |
C26—C25—H25B | 109.3 | C36—C35—C34 | 120.22 (15) |
C24—C25—H25B | 109.3 | C36—C35—H35 | 119.9 |
H25A—C25—H25B | 107.9 | C34—C35—H35 | 119.9 |
C25—C26—C27 | 112.9 (8) | C35—C36—C31 | 120.04 (14) |
C25—C26—H26A | 109.0 | C35—C36—H36 | 120.0 |
C27—C26—H26A | 109.0 | C31—C36—H36 | 120.0 |
C25—C26—H26B | 109.0 | ||
C7A—S1—C2—C3 | 0.53 (11) | N1—C17—C11—C12 | −1.5 (2) |
C7A—S1—C2—N1 | 177.55 (13) | C16—C11—C12—O12 | 178.33 (14) |
N1—C2—C3—C3A | −176.67 (13) | C17—C11—C12—O12 | −2.5 (2) |
S1—C2—C3—C3A | 0.39 (15) | C16—C11—C12—C13 | −1.6 (2) |
N1—C2—C3—C37 | 1.5 (2) | C17—C11—C12—C13 | 177.53 (14) |
S1—C2—C3—C37 | 178.55 (11) | O12—C12—C13—C14 | −179.58 (15) |
C2—C3—C3A—C7A | −1.43 (17) | C11—C12—C13—C14 | 0.4 (2) |
C37—C3—C3A—C7A | −179.61 (13) | C12—C13—C14—C15 | 1.0 (3) |
C2—C3—C3A—C4 | −178.6 (4) | C13—C14—C15—C16 | −1.0 (3) |
C37—C3—C3A—C4 | 3.2 (4) | C14—C15—C16—C11 | −0.3 (2) |
C7A—C3A—C4—C5 | −20.2 (6) | C12—C11—C16—C15 | 1.6 (2) |
C3—C3A—C4—C5 | 156.8 (2) | C17—C11—C16—C15 | −177.61 (14) |
C3A—C4—C5—C6 | 49.3 (5) | C2—C3—C37—O37 | −124.18 (16) |
C4—C5—C6—C7 | −61.3 (4) | C3A—C3—C37—O37 | 53.80 (19) |
C5—C6—C7—C7A | 38.6 (4) | C2—C3—C37—C31 | 58.68 (19) |
C3—C3A—C7A—C7 | −177.4 (3) | C3A—C3—C37—C31 | −123.34 (15) |
C4—C3A—C7A—C7 | −0.1 (5) | O37—C37—C31—C32 | −157.83 (14) |
C3—C3A—C7A—S1 | 1.82 (16) | C3—C37—C31—C32 | 19.3 (2) |
C4—C3A—C7A—S1 | 179.1 (4) | O37—C37—C31—C36 | 18.8 (2) |
C6—C7—C7A—C3A | −9.0 (5) | C3—C37—C31—C36 | −164.15 (13) |
C6—C7—C7A—S1 | 171.9 (2) | C36—C31—C32—C33 | −1.0 (2) |
C2—S1—C7A—C3A | −1.36 (12) | C37—C31—C32—C33 | 175.53 (14) |
C2—S1—C7A—C7 | 177.9 (3) | C31—C32—C33—C34 | 1.3 (3) |
C24—C25—C26—C27 | 58.9 (17) | C32—C33—C34—C35 | −0.4 (3) |
C3—C2—N1—C17 | 169.02 (14) | C33—C34—C35—C36 | −0.8 (3) |
S1—C2—N1—C17 | −7.6 (2) | C34—C35—C36—C31 | 1.1 (3) |
C2—N1—C17—C11 | −179.59 (13) | C32—C31—C36—C35 | −0.1 (2) |
N1—C17—C11—C16 | 177.66 (14) | C37—C31—C36—C35 | −176.79 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···N1 | 0.84 | 1.90 | 2.6400 (17) | 146 |
C16—H16···O37i | 0.95 | 2.49 | 3.4357 (19) | 174 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
C13H11NO2 | Z = 4 |
Mr = 213.23 | F(000) = 448 |
Triclinic, P1 | Dx = 1.369 Mg m−3 |
a = 9.0479 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1564 (8) Å | Cell parameters from 4751 reflections |
c = 12.3659 (10) Å | θ = 1.8–27.5° |
α = 69.677 (6)° | µ = 0.09 mm−1 |
β = 89.940 (6)° | T = 293 K |
γ = 77.004 (6)° | Block, yellow |
V = 1034.62 (15) Å3 | 0.48 × 0.38 × 0.22 mm |
Stoe IPDS II CCD diffractometer | 4751 independent reflections |
Radiation source: fine focus sealed tube | 3487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω and 2θ scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (X-RED; Stoe & Cie, 2002) | h = −11→11 |
Tmin = 0.912, Tmax = 0.980 | k = −13→13 |
13249 measured reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.0679P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4751 reflections | Δρmax = 0.18 e Å−3 |
291 parameters | Δρmin = −0.15 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 | ||
C1 | 0.92308 (14) | 0.34762 (14) | 0.06265 (10) | 0.0399 (3) | |
C2 | 1.01087 (15) | 0.31376 (14) | 0.16580 (10) | 0.0412 (3) | |
C3 | 1.14018 (15) | 0.20072 (15) | 0.19535 (12) | 0.0474 (3) | |
H3 | 1.1987 | 0.1765 | 0.2643 | 0.057* | |
C4 | 1.18218 (17) | 0.12439 (17) | 0.12316 (13) | 0.0555 (4) | |
H4 | 1.2691 | 0.0489 | 0.1435 | 0.067* | |
C5 | 1.09625 (18) | 0.15913 (19) | 0.02095 (14) | 0.0634 (4) | |
H5 | 1.1257 | 0.1076 | −0.0278 | 0.076* | |
C6 | 0.96670 (17) | 0.27004 (17) | −0.00922 (12) | 0.0540 (4) | |
H6 | 0.9085 | 0.2928 | −0.0780 | 0.065* | |
N1 | 0.79121 (12) | 0.46273 (11) | 0.03740 (9) | 0.0402 (2) | |
H1 | 0.7652 | 0.4951 | 0.0921 | 0.048* | |
O2 | 0.96512 (12) | 0.39546 (12) | 0.23130 (9) | 0.0589 (3) | |
H2 | 1.0320 | 0.3769 | 0.2827 | 0.088* | |
C11 | 0.57558 (14) | 0.63938 (13) | −0.07642 (10) | 0.0400 (3) | |
C12 | 0.53017 (15) | 0.69214 (14) | 0.01471 (11) | 0.0440 (3) | |
O12 | 0.60181 (11) | 0.63258 (11) | 0.11722 (8) | 0.0526 (2) | |
C13 | 0.40299 (19) | 0.81114 (17) | −0.01265 (14) | 0.0613 (4) | |
H13 | 0.3711 | 0.8505 | 0.0434 | 0.074* | |
C14 | 0.3257 (2) | 0.86974 (18) | −0.11988 (14) | 0.0636 (4) | |
H14 | 0.2427 | 0.9485 | −0.1351 | 0.076* | |
C15 | 0.36759 (17) | 0.81482 (16) | −0.20666 (12) | 0.0538 (3) | |
H15 | 0.3118 | 0.8546 | −0.2784 | 0.065* | |
C16 | 0.49144 (16) | 0.70209 (15) | −0.18540 (11) | 0.0469 (3) | |
H16 | 0.5211 | 0.6658 | −0.2436 | 0.056* | |
C17 | 0.70537 (14) | 0.52471 (14) | −0.05897 (10) | 0.0409 (3) | |
H17 | 0.7306 | 0.4920 | −0.1197 | 0.049* | |
C21 | 0.34279 (14) | 0.64514 (14) | 0.44373 (10) | 0.0392 (3) | |
C22 | 0.41444 (14) | 0.67838 (14) | 0.34054 (10) | 0.0411 (3) | |
C23 | 0.48403 (16) | 0.79342 (15) | 0.31012 (12) | 0.0483 (3) | |
H23 | 0.5315 | 0.8173 | 0.2416 | 0.058* | |
C24 | 0.48302 (19) | 0.87163 (18) | 0.38061 (14) | 0.0598 (4) | |
H24 | 0.5295 | 0.9488 | 0.3593 | 0.072* | |
C25 | 0.4139 (2) | 0.8376 (2) | 0.48294 (15) | 0.0688 (5) | |
H25 | 0.4149 | 0.8908 | 0.5307 | 0.083* | |
C26 | 0.34351 (18) | 0.72453 (17) | 0.51422 (12) | 0.0554 (4) | |
H26 | 0.2964 | 0.7017 | 0.5830 | 0.066* | |
N21 | 0.27014 (11) | 0.52960 (11) | 0.46926 (8) | 0.0392 (2) | |
H21 | 0.2624 | 0.4960 | 0.4151 | 0.047* | |
O22 | 0.41281 (13) | 0.59542 (11) | 0.27619 (9) | 0.0586 (3) | |
H22 | 0.4723 | 0.6127 | 0.2260 | 0.088* | |
C31 | 0.14221 (14) | 0.35391 (14) | 0.58288 (10) | 0.0395 (3) | |
C32 | 0.12577 (15) | 0.29890 (14) | 0.49314 (11) | 0.0433 (3) | |
O32 | 0.16995 (12) | 0.35677 (11) | 0.39094 (8) | 0.0525 (2) | |
C33 | 0.05751 (19) | 0.18025 (17) | 0.52079 (14) | 0.0585 (4) | |
H33 | 0.0473 | 0.1393 | 0.4655 | 0.070* | |
C34 | 0.00618 (19) | 0.12459 (17) | 0.62719 (14) | 0.0596 (4) | |
H34 | −0.0384 | 0.0466 | 0.6425 | 0.072* | |
C35 | 0.01871 (17) | 0.18111 (16) | 0.71306 (12) | 0.0531 (3) | |
H35 | −0.0189 | 0.1428 | 0.7843 | 0.064* | |
C36 | 0.08676 (16) | 0.29333 (15) | 0.69180 (11) | 0.0465 (3) | |
H36 | 0.0969 | 0.3306 | 0.7495 | 0.056* | |
C37 | 0.21374 (14) | 0.46853 (14) | 0.56551 (10) | 0.0409 (3) | |
H37 | 0.2210 | 0.5021 | 0.6259 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0399 (6) | 0.0475 (7) | 0.0364 (6) | −0.0135 (5) | 0.0087 (5) | −0.0180 (5) |
C2 | 0.0464 (7) | 0.0470 (7) | 0.0361 (6) | −0.0174 (5) | 0.0080 (5) | −0.0182 (5) |
C3 | 0.0477 (8) | 0.0515 (8) | 0.0417 (7) | −0.0131 (6) | 0.0007 (6) | −0.0141 (6) |
C4 | 0.0503 (8) | 0.0558 (9) | 0.0563 (8) | −0.0019 (6) | 0.0056 (6) | −0.0219 (7) |
C5 | 0.0651 (10) | 0.0730 (10) | 0.0559 (9) | 0.0025 (8) | 0.0054 (7) | −0.0395 (8) |
C6 | 0.0536 (8) | 0.0684 (9) | 0.0438 (7) | −0.0042 (7) | 0.0010 (6) | −0.0311 (7) |
N1 | 0.0432 (6) | 0.0490 (6) | 0.0346 (5) | −0.0123 (5) | 0.0086 (4) | −0.0214 (5) |
O2 | 0.0667 (7) | 0.0685 (7) | 0.0471 (5) | −0.0031 (5) | −0.0068 (5) | −0.0356 (5) |
C11 | 0.0426 (7) | 0.0431 (7) | 0.0372 (6) | −0.0154 (5) | 0.0103 (5) | −0.0147 (5) |
C12 | 0.0493 (7) | 0.0472 (7) | 0.0392 (6) | −0.0146 (6) | 0.0119 (5) | −0.0180 (6) |
O12 | 0.0583 (6) | 0.0632 (6) | 0.0380 (5) | −0.0079 (5) | 0.0093 (4) | −0.0243 (4) |
C13 | 0.0701 (10) | 0.0594 (9) | 0.0530 (8) | −0.0009 (7) | 0.0126 (7) | −0.0276 (7) |
C14 | 0.0662 (10) | 0.0531 (9) | 0.0587 (9) | 0.0042 (7) | 0.0072 (7) | −0.0158 (7) |
C15 | 0.0575 (9) | 0.0523 (8) | 0.0420 (7) | −0.0086 (6) | 0.0025 (6) | −0.0081 (6) |
C16 | 0.0521 (8) | 0.0508 (8) | 0.0379 (6) | −0.0144 (6) | 0.0083 (5) | −0.0148 (6) |
C17 | 0.0449 (7) | 0.0492 (7) | 0.0349 (6) | −0.0156 (5) | 0.0098 (5) | −0.0198 (5) |
C21 | 0.0375 (6) | 0.0476 (7) | 0.0348 (6) | −0.0104 (5) | 0.0021 (5) | −0.0173 (5) |
C22 | 0.0399 (7) | 0.0464 (7) | 0.0358 (6) | −0.0058 (5) | 0.0024 (5) | −0.0159 (5) |
C23 | 0.0481 (8) | 0.0527 (8) | 0.0416 (7) | −0.0143 (6) | 0.0071 (6) | −0.0126 (6) |
C24 | 0.0713 (10) | 0.0608 (9) | 0.0561 (8) | −0.0333 (8) | 0.0070 (7) | −0.0207 (7) |
C25 | 0.0978 (13) | 0.0792 (11) | 0.0567 (9) | −0.0480 (10) | 0.0172 (9) | −0.0408 (9) |
C26 | 0.0688 (9) | 0.0704 (10) | 0.0435 (7) | −0.0324 (8) | 0.0150 (6) | −0.0310 (7) |
N21 | 0.0415 (6) | 0.0480 (6) | 0.0334 (5) | −0.0122 (4) | 0.0040 (4) | −0.0201 (4) |
O22 | 0.0799 (7) | 0.0630 (6) | 0.0486 (6) | −0.0277 (5) | 0.0273 (5) | −0.0325 (5) |
C31 | 0.0379 (6) | 0.0441 (7) | 0.0351 (6) | −0.0069 (5) | −0.0003 (5) | −0.0141 (5) |
C32 | 0.0443 (7) | 0.0481 (7) | 0.0383 (6) | −0.0085 (5) | −0.0008 (5) | −0.0179 (6) |
O32 | 0.0656 (6) | 0.0643 (6) | 0.0381 (5) | −0.0234 (5) | 0.0069 (4) | −0.0262 (4) |
C33 | 0.0747 (10) | 0.0577 (9) | 0.0548 (8) | −0.0244 (7) | 0.0037 (7) | −0.0290 (7) |
C34 | 0.0698 (10) | 0.0506 (9) | 0.0591 (9) | −0.0251 (7) | 0.0026 (7) | −0.0138 (7) |
C35 | 0.0580 (9) | 0.0531 (8) | 0.0426 (7) | −0.0161 (7) | 0.0050 (6) | −0.0086 (6) |
C36 | 0.0509 (8) | 0.0517 (8) | 0.0364 (6) | −0.0121 (6) | 0.0025 (5) | −0.0150 (6) |
C37 | 0.0419 (7) | 0.0505 (7) | 0.0333 (6) | −0.0095 (5) | 0.0023 (5) | −0.0194 (5) |
C1—C6 | 1.3828 (18) | C21—C26 | 1.3786 (18) |
C1—C2 | 1.3967 (17) | C21—C22 | 1.4001 (17) |
C1—N1 | 1.4169 (17) | C21—N21 | 1.4135 (16) |
C2—O2 | 1.3518 (15) | C22—O22 | 1.3471 (15) |
C2—C3 | 1.3878 (19) | C22—C23 | 1.3886 (19) |
C3—C4 | 1.375 (2) | C23—C24 | 1.367 (2) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.377 (2) | C24—C25 | 1.380 (2) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C6 | 1.377 (2) | C25—C26 | 1.376 (2) |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
N1—C17 | 1.2963 (17) | N21—C37 | 1.3000 (16) |
N1—H1 | 0.8600 | N21—H21 | 0.8600 |
O2—H2 | 0.8200 | O22—H22 | 0.8200 |
C11—C16 | 1.4104 (18) | C31—C37 | 1.4089 (18) |
C11—C17 | 1.4117 (18) | C31—C36 | 1.4163 (17) |
C11—C12 | 1.4302 (17) | C31—C32 | 1.4263 (17) |
C12—O12 | 1.2983 (16) | C32—O32 | 1.3004 (15) |
C12—C13 | 1.411 (2) | C32—C33 | 1.414 (2) |
C13—C14 | 1.367 (2) | C33—C34 | 1.366 (2) |
C13—H13 | 0.9300 | C33—H33 | 0.9300 |
C14—C15 | 1.388 (2) | C34—C35 | 1.387 (2) |
C14—H14 | 0.9300 | C34—H34 | 0.9300 |
C15—C16 | 1.360 (2) | C35—C36 | 1.362 (2) |
C15—H15 | 0.9300 | C35—H35 | 0.9300 |
C16—H16 | 0.9300 | C36—H36 | 0.9300 |
C17—H17 | 0.9300 | C37—H37 | 0.9300 |
C6—C1—C2 | 119.93 (12) | C26—C21—C22 | 120.25 (12) |
C6—C1—N1 | 123.23 (12) | C26—C21—N21 | 123.08 (11) |
C2—C1—N1 | 116.84 (11) | C22—C21—N21 | 116.66 (11) |
O2—C2—C3 | 123.39 (12) | O22—C22—C23 | 123.44 (11) |
O2—C2—C1 | 117.45 (12) | O22—C22—C21 | 117.71 (11) |
C3—C2—C1 | 119.15 (12) | C23—C22—C21 | 118.84 (12) |
C4—C3—C2 | 120.32 (13) | C24—C23—C22 | 120.21 (13) |
C4—C3—H3 | 119.8 | C24—C23—H23 | 119.9 |
C2—C3—H3 | 119.8 | C22—C23—H23 | 119.9 |
C3—C4—C5 | 120.35 (14) | C23—C24—C25 | 120.83 (13) |
C3—C4—H4 | 119.8 | C23—C24—H24 | 119.6 |
C5—C4—H4 | 119.8 | C25—C24—H24 | 119.6 |
C4—C5—C6 | 120.13 (14) | C26—C25—C24 | 119.82 (14) |
C4—C5—H5 | 119.9 | C26—C25—H25 | 120.1 |
C6—C5—H5 | 119.9 | C24—C25—H25 | 120.1 |
C5—C6—C1 | 120.11 (13) | C25—C26—C21 | 120.04 (13) |
C5—C6—H6 | 119.9 | C25—C26—H26 | 120.0 |
C1—C6—H6 | 119.9 | C21—C26—H26 | 120.0 |
C17—N1—C1 | 127.23 (11) | C37—N21—C21 | 127.21 (11) |
C17—N1—H1 | 116.4 | C37—N21—H21 | 116.4 |
C1—N1—H1 | 116.4 | C21—N21—H21 | 116.4 |
C2—O2—H2 | 109.5 | C22—O22—H22 | 109.5 |
C16—C11—C17 | 119.09 (11) | C37—C31—C36 | 118.75 (11) |
C16—C11—C12 | 120.28 (12) | C37—C31—C32 | 121.04 (11) |
C17—C11—C12 | 120.63 (12) | C36—C31—C32 | 120.21 (12) |
O12—C12—C13 | 122.04 (12) | O32—C32—C33 | 122.12 (12) |
O12—C12—C11 | 121.54 (12) | O32—C32—C31 | 121.29 (11) |
C13—C12—C11 | 116.41 (13) | C33—C32—C31 | 116.58 (12) |
C14—C13—C12 | 121.38 (14) | C34—C33—C32 | 121.30 (14) |
C14—C13—H13 | 119.3 | C34—C33—H33 | 119.3 |
C12—C13—H13 | 119.3 | C32—C33—H33 | 119.3 |
C13—C14—C15 | 121.79 (15) | C33—C34—C35 | 121.83 (14) |
C13—C14—H14 | 119.1 | C33—C34—H34 | 119.1 |
C15—C14—H14 | 119.1 | C35—C34—H34 | 119.1 |
C16—C15—C14 | 119.09 (14) | C36—C35—C34 | 119.23 (13) |
C16—C15—H15 | 120.5 | C36—C35—H35 | 120.4 |
C14—C15—H15 | 120.5 | C34—C35—H35 | 120.4 |
C15—C16—C11 | 121.00 (13) | C35—C36—C31 | 120.81 (13) |
C15—C16—H16 | 119.5 | C35—C36—H36 | 119.6 |
C11—C16—H16 | 119.5 | C31—C36—H36 | 119.6 |
N1—C17—C11 | 123.32 (12) | N21—C37—C31 | 123.22 (12) |
N1—C17—H17 | 118.3 | N21—C37—H37 | 118.4 |
C11—C17—H17 | 118.3 | C31—C37—H37 | 118.4 |
C6—C1—C2—O2 | 178.34 (12) | C26—C21—C22—O22 | 178.70 (13) |
N1—C1—C2—O2 | −1.58 (17) | N21—C21—C22—O22 | −2.11 (18) |
C6—C1—C2—C3 | −0.88 (19) | C26—C21—C22—C23 | −0.8 (2) |
N1—C1—C2—C3 | 179.20 (11) | N21—C21—C22—C23 | 178.35 (12) |
O2—C2—C3—C4 | −178.34 (13) | O22—C22—C23—C24 | −179.05 (14) |
C1—C2—C3—C4 | 0.83 (19) | C21—C22—C23—C24 | 0.5 (2) |
C2—C3—C4—C5 | −0.1 (2) | C22—C23—C24—C25 | 0.3 (2) |
C3—C4—C5—C6 | −0.5 (3) | C23—C24—C25—C26 | −0.7 (3) |
C4—C5—C6—C1 | 0.5 (3) | C24—C25—C26—C21 | 0.3 (3) |
C2—C1—C6—C5 | 0.2 (2) | C22—C21—C26—C25 | 0.4 (2) |
N1—C1—C6—C5 | −179.85 (14) | N21—C21—C26—C25 | −178.70 (15) |
C6—C1—N1—C17 | −9.8 (2) | C26—C21—N21—C37 | −10.1 (2) |
C2—C1—N1—C17 | 170.08 (12) | C22—C21—N21—C37 | 170.70 (12) |
C16—C11—C12—O12 | 177.13 (12) | C37—C31—C32—O32 | −3.1 (2) |
C17—C11—C12—O12 | −3.24 (19) | C36—C31—C32—O32 | 177.05 (13) |
C16—C11—C12—C13 | −2.34 (18) | C37—C31—C32—C33 | 177.69 (13) |
C17—C11—C12—C13 | 177.28 (13) | C36—C31—C32—C33 | −2.14 (19) |
O12—C12—C13—C14 | −177.83 (15) | O32—C32—C33—C34 | −177.31 (15) |
C11—C12—C13—C14 | 1.6 (2) | C31—C32—C33—C34 | 1.9 (2) |
C12—C13—C14—C15 | 0.4 (3) | C32—C33—C34—C35 | −0.2 (3) |
C13—C14—C15—C16 | −1.8 (2) | C33—C34—C35—C36 | −1.3 (2) |
C14—C15—C16—C11 | 1.0 (2) | C34—C35—C36—C31 | 1.0 (2) |
C17—C11—C16—C15 | −178.57 (13) | C37—C31—C36—C35 | −179.09 (13) |
C12—C11—C16—C15 | 1.06 (19) | C32—C31—C36—C35 | 0.7 (2) |
C1—N1—C17—C11 | −179.94 (11) | C21—N21—C37—C31 | 179.61 (12) |
C16—C11—C17—N1 | 178.50 (12) | C36—C31—C37—N21 | 178.97 (12) |
C12—C11—C17—N1 | −1.13 (19) | C32—C31—C37—N21 | −0.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 2.29 | 2.6605 (15) | 106 |
N1—H1···O12 | 0.86 | 1.90 | 2.5955 (16) | 137 |
N21—H21···O22 | 0.86 | 2.29 | 2.6620 (15) | 106 |
N21—H21···O32 | 0.86 | 1.90 | 2.5960 (16) | 137 |
O22—H22···O12 | 0.82 | 1.77 | 2.5882 (15) | 174 |
O2—H2···O32i | 0.82 | 1.76 | 2.5744 (15) | 174 |
Symmetry code: (i) x+1, y, z. |
Parameter | (I) | (II) | (III) | (IV) | (V) | (VI) | (VII) | (VIII), molecule 1 | (VIII), molecule 2 |
C11—C12 | 1.405 (5) | 1.405 (4) | 1.421 (4) | 1.404 (3) | 1.388 (4) | 1.403 (3) | 1.410 (2) | 1.4302 (17) | 1.4263 (17) |
C12—C13 | 1.381 (5) | 1.414 (4) | 1.431 (4) | 1.413 (3) | 1.401 (4) | 1.387 (3) | 1.395 (2) | 1.411 (2) | 1.414 (2) |
C13—C14 | 1.368 (6) | 1.368 (4) | 1.368 (4) | 1.372 (3) | 1.371 (4) | 1.375 (3) | 1.379 (2) | 1.367 (2) | 1.366 (2) |
C14—C15 | 1.386 (6) | 1.400 (4) | 1.402 (4) | 1.385 (3) | 1.389 (4) | 1.374 (3) | 1.391 (3) | 1.388 (2) | 1.387 (2) |
C15—C16 | 1.369 (6) | 1.358 (4) | 1.343 (4) | 1.360 (3) | 1.359 (4) | 1.362 (3) | 1.381 (2) | 1.360 (2) | 1.362 (2) |
C16—C11 | 1.386 (5) | 1.408 (4) | 1.428 (4) | 1.403 (3) | 1.408 (4) | 1.400 (3) | 1.409 (2) | 1.4104 (18) | 1.4163 (17) |
C11—C17 | 1.437 (5) | 1.437 (5) | 1.410 (4) | 1.439 (3) | 1.455 (4) | 1.444 (3) | 1.447 (2) | 1.4117 (18) | 1.4089 (18) |
C17—N1 | 1.273 (4) | 1.292 (4) | 1.297 (4) | 1.277 (3) | 1.276 (3) | 1.283 (2) | 1.290 (2) | 1.2963 (17) | 1.3000 (16) |
C12—O12 | 1.347 (4) | 1.326 (3) | 1.287 (3) | 1.379 (3) | 1.351 (3) | 1.351 (2) | 1.3496 (19) | 1.2983 (16) | 1.3004 (15) |
For molecule 2 in compound (VIII), the atom numbering corresponds to that shown in Fig. 8(b). |
Q | θ | φ | |
(VI), major | 0.474 (6) | 53.1 (7) | 133.6 (9) |
(VI), minor | 0.476 (13) | 121.8 (19) | 316 (2) |
(VII), major | 0.478 (3) | 50.3 (4) | 137.9 (5) |
(VII), minor | 0.477 (14) | 121 (2) | 320 (3) |
For the major-disorder components, the ring-puckering angles are calculated for the atom sequence C3A–C4–C5–C6–C7–C7A. For the minor-disorder components, the ring-puckering angles are calculated for the atom sequence C23A–C24–C25–C26–C27–C27A. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | N4—H4···N42i | 0.87 (4) | 2.07 (4) | 2.931 (4) | 168 (3) |
O12—H12···N1 | 0.82 | 1.88 | 2.606 (4) | 147 | |
(II) | N4—H4···O12ii | 0.77 (4) | 2.20 (4) | 2.937 (3) | 159 (4) |
N4—H4···O12ii | 0.77 (4) | 2.37 (4) | 2.904 (3) | 127 (4) | |
O12—H12···N1 | 0.82 | 1.83 | 2.558 (3) | 147 | |
C17—H17···O1iii | 0.93 | 2.37 | 3.285 (3) | 169 | |
(III) | N1—H1···O2 | 0.86 | 2.17 | 2.588 (3) | 109 |
N1—H1···O12 | 0.86 | 1.85 | 2.558 (3) | 139 | |
O2—H2···O12ii | 0.82 | 1.86 | 2.626 (3) | 151 | |
C3—H3···O13ii | 0.93 | 2.44 | 3.350 (4) | 166 | |
C4—H4···Cg1iv | 0.93 | 2.90 | 3.731 (3) | 149 | |
(IV) | O12—H12···N1 | 0.82 | 1.81 | 2.543 (3) | 147 |
(V) | O12—H12···N1 | 0.82 | 1.87 | 2.592 (3) | 146 |
C3—H3···Cg1v | 0.93 | 2.83 | 3.646 (3) | 148 | |
C16—H16···Cg1vi | 0.93 | 2.88 | 3.630 (3) | 139 | |
(VI) | O12—H12···N1 | 0.82 | 1.93 | 2.647 (2) | 146 |
C16—H16···O37vii | 0.93 | 2.60 | 3.519 (3) | 170 | |
(VII) | O12—H12···N1 | 0.84 | 1.90 | 2.6400 (17) | 146 |
C16—H16···O37vii | 0.95 | 2.49 | 3.4357 (19) | 174 | |
(VIII) | N1—H1···O2 | 0.86 | 2.29 | 2.6605 (15) | 106 |
N1—H1···O12 | 0.86 | 1.90 | 2.5955 (16) | 137 | |
N21—H21···O22 | 0.86 | 2.29 | 2.6620 (15) | 106 | |
N21—H21···O32 | 0.86 | 1.90 | 2.5960 (16) | 137 | |
O22—H22···O12 | 0.82 | 1.77 | 2.5882 (16) | 174 | |
O2—H2···O32viii | 0.82 | 1.76 | 2.5744 (15) | 174 |
Symmetry codes:
(i) x, -y+1/2, z+1/2;
(ii) -x+1, -y+1, -z+1;
(iii) -x+1, y+1/2, -z+1/2;
(iv) x, -y+1/2, z-1/2;
(v) -x, -y+2, z+1/2;
(vi) x, y, z-1;
(vii) x-1/2, -y+1/2, z+1/2;
(viii) x+1, y, z. Cg1 represents the centroid of the C1–C6 ring. |
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