





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616002704/zp4002sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314616002704/zp4002Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616002704/zp4002Isup3.cml |
CCDC reference: 1453514
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.094
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N2 -- H2A ... Please Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 13 Report
Alert level G PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 48 Note PLAT954_ALERT_1_G Reported (CIF) and Actual (FCF) Kmax Differ by . 1 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C22H22N2O4S | F(000) = 864 |
Mr = 410.47 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 5.6473 (2) Å | Cell parameters from 9033 reflections |
b = 26.7798 (9) Å | θ = 3.3–72.0° |
c = 13.3219 (4) Å | µ = 1.72 mm−1 |
β = 99.743 (2)° | T = 150 K |
V = 1985.66 (11) Å3 | Column, yellow |
Z = 4 | 0.20 × 0.08 × 0.05 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3830 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 3158 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.039 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.0°, θmin = 3.3° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −33→31 |
Tmin = 0.81, Tmax = 0.93 | l = −16→14 |
14981 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0443P)2 + 0.6171P] where P = (Fo2 + 2Fc2)/3 |
3830 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.31 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms were placed in calculated positions (C—H = 0.95 - 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.81665 (7) | 0.31695 (2) | 0.51587 (3) | 0.02555 (12) | |
O1 | −0.0116 (2) | 0.37752 (4) | 0.80094 (9) | 0.0313 (3) | |
O2 | 0.1931 (2) | 0.31306 (4) | 0.88190 (9) | 0.0261 (3) | |
O3 | 1.0260 (3) | 0.45058 (5) | 0.44348 (11) | 0.0373 (3) | |
O4 | 1.1080 (2) | 0.37241 (4) | 0.39666 (9) | 0.0292 (3) | |
N1 | 0.5078 (2) | 0.28245 (5) | 0.63005 (10) | 0.0247 (3) | |
N2 | 0.6910 (3) | 0.45759 (5) | 0.57515 (13) | 0.0316 (3) | |
H2A | 0.601 (4) | 0.4709 (8) | 0.6114 (17) | 0.039 (6)* | |
H2B | 0.789 (4) | 0.4766 (8) | 0.5425 (17) | 0.043 (6)* | |
C1 | 0.4979 (3) | 0.50473 (6) | 0.84071 (12) | 0.0232 (3) | |
C2 | 0.6874 (3) | 0.52120 (6) | 0.91401 (13) | 0.0257 (3) | |
H2 | 0.8334 | 0.5028 | 0.9252 | 0.031* | |
C3 | 0.6674 (3) | 0.56382 (6) | 0.97084 (13) | 0.0301 (4) | |
H3 | 0.7980 | 0.5742 | 1.0211 | 0.036* | |
C4 | 0.4573 (3) | 0.59124 (6) | 0.95430 (14) | 0.0313 (4) | |
H4 | 0.4420 | 0.6203 | 0.9937 | 0.038* | |
C5 | 0.2685 (3) | 0.57614 (7) | 0.87975 (14) | 0.0328 (4) | |
H5 | 0.1250 | 0.5953 | 0.8672 | 0.039* | |
C6 | 0.2883 (3) | 0.53313 (6) | 0.82343 (13) | 0.0290 (4) | |
H6 | 0.1580 | 0.5230 | 0.7728 | 0.035* | |
C7 | 0.5254 (3) | 0.45678 (6) | 0.79016 (12) | 0.0241 (3) | |
H7 | 0.6806 | 0.4421 | 0.8031 | 0.029* | |
C8 | 0.3566 (3) | 0.43171 (6) | 0.72829 (12) | 0.0226 (3) | |
H8 | 0.2029 | 0.4464 | 0.7081 | 0.027* | |
C9 | 0.4041 (3) | 0.38108 (6) | 0.69013 (12) | 0.0211 (3) | |
C10 | 0.5636 (3) | 0.37290 (6) | 0.62112 (12) | 0.0217 (3) | |
C11 | 0.6091 (3) | 0.32310 (6) | 0.59683 (12) | 0.0226 (3) | |
C12 | 0.3520 (3) | 0.29013 (6) | 0.69361 (12) | 0.0240 (3) | |
C13 | 0.3009 (3) | 0.33872 (6) | 0.72724 (12) | 0.0217 (3) | |
C14 | 0.2322 (3) | 0.24380 (6) | 0.72435 (14) | 0.0322 (4) | |
H14A | 0.2435 | 0.2172 | 0.6749 | 0.048* | |
H14B | 0.0627 | 0.2509 | 0.7262 | 0.048* | |
H14C | 0.3122 | 0.2331 | 0.7920 | 0.048* | |
C15 | 0.7021 (3) | 0.40730 (6) | 0.56948 (12) | 0.0228 (3) | |
C16 | 0.8451 (3) | 0.38195 (6) | 0.51149 (12) | 0.0242 (3) | |
C17 | 0.9986 (3) | 0.40561 (6) | 0.44930 (13) | 0.0255 (3) | |
C18 | 1.2648 (3) | 0.39335 (7) | 0.33177 (13) | 0.0296 (4) | |
H18A | 1.4040 | 0.4101 | 0.3735 | 0.035* | |
H18B | 1.1768 | 0.4182 | 0.2845 | 0.035* | |
C19 | 1.3474 (4) | 0.35096 (8) | 0.27367 (17) | 0.0456 (5) | |
H19A | 1.4366 | 0.3270 | 0.3213 | 0.068* | |
H19B | 1.4520 | 0.3637 | 0.2278 | 0.068* | |
H19C | 1.2077 | 0.3344 | 0.2337 | 0.068* | |
C20 | 0.1416 (3) | 0.34570 (6) | 0.80479 (12) | 0.0227 (3) | |
C21 | 0.0355 (3) | 0.31326 (7) | 0.95820 (13) | 0.0282 (4) | |
H21A | −0.0058 | 0.3481 | 0.9729 | 0.034* | |
H21B | 0.1207 | 0.2983 | 1.0221 | 0.034* | |
C22 | −0.1910 (3) | 0.28440 (7) | 0.92170 (14) | 0.0335 (4) | |
H22A | −0.2796 | 0.3003 | 0.8604 | 0.050* | |
H22B | −0.2910 | 0.2841 | 0.9751 | 0.050* | |
H22C | −0.1500 | 0.2501 | 0.9059 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0313 (2) | 0.0205 (2) | 0.0267 (2) | −0.00010 (16) | 0.01026 (16) | −0.00271 (15) |
O1 | 0.0305 (6) | 0.0294 (6) | 0.0352 (7) | 0.0074 (5) | 0.0091 (5) | 0.0038 (5) |
O2 | 0.0267 (6) | 0.0294 (6) | 0.0234 (6) | 0.0038 (5) | 0.0078 (5) | 0.0039 (5) |
O3 | 0.0499 (8) | 0.0242 (6) | 0.0433 (8) | −0.0061 (6) | 0.0234 (6) | −0.0035 (5) |
O4 | 0.0342 (6) | 0.0266 (6) | 0.0300 (7) | 0.0010 (5) | 0.0151 (5) | 0.0008 (5) |
N1 | 0.0309 (7) | 0.0197 (6) | 0.0242 (7) | −0.0020 (6) | 0.0066 (6) | −0.0013 (5) |
N2 | 0.0428 (9) | 0.0197 (7) | 0.0369 (9) | 0.0000 (7) | 0.0194 (7) | 0.0002 (6) |
C1 | 0.0262 (8) | 0.0209 (7) | 0.0232 (8) | −0.0020 (6) | 0.0062 (6) | −0.0023 (6) |
C2 | 0.0244 (8) | 0.0262 (8) | 0.0262 (9) | −0.0017 (7) | 0.0038 (6) | −0.0006 (7) |
C3 | 0.0354 (9) | 0.0279 (9) | 0.0268 (9) | −0.0078 (7) | 0.0044 (7) | −0.0052 (7) |
C4 | 0.0412 (10) | 0.0236 (8) | 0.0308 (9) | −0.0039 (7) | 0.0112 (8) | −0.0071 (7) |
C5 | 0.0341 (9) | 0.0264 (9) | 0.0385 (10) | 0.0047 (7) | 0.0079 (8) | −0.0047 (8) |
C6 | 0.0288 (9) | 0.0259 (8) | 0.0314 (9) | 0.0014 (7) | 0.0024 (7) | −0.0045 (7) |
C7 | 0.0250 (8) | 0.0221 (8) | 0.0253 (8) | 0.0034 (6) | 0.0046 (6) | −0.0025 (6) |
C8 | 0.0238 (8) | 0.0199 (8) | 0.0246 (8) | 0.0026 (6) | 0.0051 (6) | −0.0009 (6) |
C9 | 0.0215 (7) | 0.0206 (7) | 0.0201 (8) | 0.0001 (6) | 0.0003 (6) | −0.0022 (6) |
C10 | 0.0238 (8) | 0.0204 (7) | 0.0203 (8) | −0.0006 (6) | 0.0020 (6) | −0.0015 (6) |
C11 | 0.0257 (8) | 0.0217 (8) | 0.0197 (8) | −0.0011 (6) | 0.0018 (6) | −0.0025 (6) |
C12 | 0.0284 (8) | 0.0222 (8) | 0.0212 (8) | −0.0013 (6) | 0.0039 (6) | −0.0006 (6) |
C13 | 0.0226 (8) | 0.0221 (8) | 0.0196 (8) | 0.0004 (6) | 0.0015 (6) | −0.0008 (6) |
C14 | 0.0439 (10) | 0.0219 (8) | 0.0336 (10) | −0.0047 (7) | 0.0144 (8) | −0.0021 (7) |
C15 | 0.0250 (8) | 0.0209 (8) | 0.0220 (8) | −0.0012 (6) | 0.0029 (6) | −0.0010 (6) |
C16 | 0.0274 (8) | 0.0216 (8) | 0.0239 (8) | −0.0006 (6) | 0.0055 (6) | −0.0002 (6) |
C17 | 0.0282 (8) | 0.0265 (8) | 0.0226 (8) | 0.0001 (7) | 0.0061 (6) | −0.0021 (6) |
C18 | 0.0299 (9) | 0.0351 (9) | 0.0259 (9) | 0.0013 (7) | 0.0110 (7) | 0.0059 (7) |
C19 | 0.0599 (13) | 0.0407 (11) | 0.0437 (12) | 0.0131 (10) | 0.0299 (10) | 0.0083 (9) |
C20 | 0.0239 (8) | 0.0217 (7) | 0.0219 (8) | −0.0019 (6) | 0.0024 (6) | −0.0012 (6) |
C21 | 0.0339 (9) | 0.0303 (9) | 0.0228 (8) | −0.0013 (7) | 0.0114 (7) | −0.0001 (7) |
C22 | 0.0303 (9) | 0.0374 (10) | 0.0336 (10) | −0.0015 (8) | 0.0076 (7) | 0.0029 (8) |
S1—C11 | 1.7297 (17) | C8—C9 | 1.488 (2) |
S1—C16 | 1.7498 (16) | C8—H8 | 0.9500 |
O1—C20 | 1.209 (2) | C9—C13 | 1.403 (2) |
O2—C20 | 1.3428 (19) | C9—C10 | 1.409 (2) |
O2—C21 | 1.4601 (19) | C10—C11 | 1.406 (2) |
O3—C17 | 1.218 (2) | C10—C15 | 1.455 (2) |
O4—C17 | 1.346 (2) | C12—C13 | 1.421 (2) |
O4—C18 | 1.451 (2) | C12—C14 | 1.503 (2) |
N1—C12 | 1.336 (2) | C13—C20 | 1.492 (2) |
N1—C11 | 1.339 (2) | C14—H14A | 0.9800 |
N2—C15 | 1.351 (2) | C14—H14B | 0.9800 |
N2—H2A | 0.84 (2) | C14—H14C | 0.9800 |
N2—H2B | 0.92 (2) | C15—C16 | 1.386 (2) |
C1—C6 | 1.393 (2) | C16—C17 | 1.443 (2) |
C1—C2 | 1.393 (2) | C18—C19 | 1.492 (3) |
C1—C7 | 1.470 (2) | C18—H18A | 0.9900 |
C2—C3 | 1.385 (2) | C18—H18B | 0.9900 |
C2—H2 | 0.9500 | C19—H19A | 0.9800 |
C3—C4 | 1.381 (3) | C19—H19B | 0.9800 |
C3—H3 | 0.9500 | C19—H19C | 0.9800 |
C4—C5 | 1.389 (3) | C21—C22 | 1.503 (2) |
C4—H4 | 0.9500 | C21—H21A | 0.9900 |
C5—C6 | 1.389 (2) | C21—H21B | 0.9900 |
C5—H5 | 0.9500 | C22—H22A | 0.9800 |
C6—H6 | 0.9500 | C22—H22B | 0.9800 |
C7—C8 | 1.331 (2) | C22—H22C | 0.9800 |
C7—H7 | 0.9500 | ||
C11—S1—C16 | 90.11 (8) | C9—C13—C20 | 118.53 (14) |
C20—O2—C21 | 116.82 (13) | C12—C13—C20 | 120.75 (14) |
C17—O4—C18 | 115.82 (13) | C12—C14—H14A | 109.5 |
C12—N1—C11 | 116.63 (14) | C12—C14—H14B | 109.5 |
C15—N2—H2A | 119.6 (15) | H14A—C14—H14B | 109.5 |
C15—N2—H2B | 119.4 (14) | C12—C14—H14C | 109.5 |
H2A—N2—H2B | 121 (2) | H14A—C14—H14C | 109.5 |
C6—C1—C2 | 118.27 (15) | H14B—C14—H14C | 109.5 |
C6—C1—C7 | 123.63 (15) | N2—C15—C16 | 123.83 (16) |
C2—C1—C7 | 118.00 (15) | N2—C15—C10 | 124.82 (15) |
C3—C2—C1 | 121.34 (16) | C16—C15—C10 | 111.34 (14) |
C3—C2—H2 | 119.3 | C15—C16—C17 | 124.61 (15) |
C1—C2—H2 | 119.3 | C15—C16—S1 | 113.78 (12) |
C4—C3—C2 | 119.90 (16) | C17—C16—S1 | 121.57 (12) |
C4—C3—H3 | 120.1 | O3—C17—O4 | 123.05 (16) |
C2—C3—H3 | 120.1 | O3—C17—C16 | 124.46 (16) |
C3—C4—C5 | 119.62 (16) | O4—C17—C16 | 112.48 (14) |
C3—C4—H4 | 120.2 | O4—C18—C19 | 106.91 (15) |
C5—C4—H4 | 120.2 | O4—C18—H18A | 110.3 |
C4—C5—C6 | 120.36 (17) | C19—C18—H18A | 110.3 |
C4—C5—H5 | 119.8 | O4—C18—H18B | 110.3 |
C6—C5—H5 | 119.8 | C19—C18—H18B | 110.3 |
C5—C6—C1 | 120.48 (16) | H18A—C18—H18B | 108.6 |
C5—C6—H6 | 119.8 | C18—C19—H19A | 109.5 |
C1—C6—H6 | 119.8 | C18—C19—H19B | 109.5 |
C8—C7—C1 | 127.15 (15) | H19A—C19—H19B | 109.5 |
C8—C7—H7 | 116.4 | C18—C19—H19C | 109.5 |
C1—C7—H7 | 116.4 | H19A—C19—H19C | 109.5 |
C7—C8—C9 | 121.31 (14) | H19B—C19—H19C | 109.5 |
C7—C8—H8 | 119.3 | O1—C20—O2 | 123.53 (15) |
C9—C8—H8 | 119.3 | O1—C20—C13 | 124.74 (15) |
C13—C9—C10 | 116.98 (14) | O2—C20—C13 | 111.70 (13) |
C13—C9—C8 | 120.46 (14) | O2—C21—C22 | 111.01 (14) |
C10—C9—C8 | 122.44 (14) | O2—C21—H21A | 109.4 |
C11—C10—C9 | 117.36 (14) | C22—C21—H21A | 109.4 |
C11—C10—C15 | 110.97 (14) | O2—C21—H21B | 109.4 |
C9—C10—C15 | 131.64 (14) | C22—C21—H21B | 109.4 |
N1—C11—C10 | 126.14 (15) | H21A—C21—H21B | 108.0 |
N1—C11—S1 | 120.07 (12) | C21—C22—H22A | 109.5 |
C10—C11—S1 | 113.79 (12) | C21—C22—H22B | 109.5 |
N1—C12—C13 | 122.07 (15) | H22A—C22—H22B | 109.5 |
N1—C12—C14 | 114.88 (14) | C21—C22—H22C | 109.5 |
C13—C12—C14 | 123.03 (15) | H22A—C22—H22C | 109.5 |
C9—C13—C12 | 120.71 (15) | H22B—C22—H22C | 109.5 |
C6—C1—C2—C3 | 1.9 (3) | C8—C9—C13—C20 | 0.6 (2) |
C7—C1—C2—C3 | −174.57 (16) | N1—C12—C13—C9 | 3.5 (2) |
C1—C2—C3—C4 | −0.9 (3) | C14—C12—C13—C9 | −175.08 (15) |
C2—C3—C4—C5 | −0.8 (3) | N1—C12—C13—C20 | −174.94 (14) |
C3—C4—C5—C6 | 1.4 (3) | C14—C12—C13—C20 | 6.5 (2) |
C4—C5—C6—C1 | −0.2 (3) | C11—C10—C15—N2 | 177.80 (16) |
C2—C1—C6—C5 | −1.4 (3) | C9—C10—C15—N2 | −4.0 (3) |
C7—C1—C6—C5 | 174.92 (17) | C11—C10—C15—C16 | −1.02 (19) |
C6—C1—C7—C8 | −5.4 (3) | C9—C10—C15—C16 | 177.15 (16) |
C2—C1—C7—C8 | 170.89 (17) | N2—C15—C16—C17 | −0.5 (3) |
C1—C7—C8—C9 | −174.13 (16) | C10—C15—C16—C17 | 178.33 (15) |
C7—C8—C9—C13 | 107.59 (19) | N2—C15—C16—S1 | −178.27 (14) |
C7—C8—C9—C10 | −68.3 (2) | C10—C15—C16—S1 | 0.57 (18) |
C13—C9—C10—C11 | −1.1 (2) | C11—S1—C16—C15 | 0.02 (13) |
C8—C9—C10—C11 | 174.93 (14) | C11—S1—C16—C17 | −177.82 (14) |
C13—C9—C10—C15 | −179.21 (15) | C18—O4—C17—O3 | 0.4 (2) |
C8—C9—C10—C15 | −3.1 (3) | C18—O4—C17—C16 | 179.71 (13) |
C12—N1—C11—C10 | −1.2 (2) | C15—C16—C17—O3 | 2.6 (3) |
C12—N1—C11—S1 | 178.99 (12) | S1—C16—C17—O3 | −179.77 (15) |
C9—C10—C11—N1 | 2.8 (2) | C15—C16—C17—O4 | −176.65 (15) |
C15—C10—C11—N1 | −178.75 (15) | S1—C16—C17—O4 | 0.9 (2) |
C9—C10—C11—S1 | −177.40 (11) | C17—O4—C18—C19 | −174.66 (15) |
C15—C10—C11—S1 | 1.06 (17) | C21—O2—C20—O1 | 7.0 (2) |
C16—S1—C11—N1 | 179.19 (14) | C21—O2—C20—C13 | −174.78 (13) |
C16—S1—C11—C10 | −0.63 (13) | C9—C13—C20—O1 | 43.9 (2) |
C11—N1—C12—C13 | −1.9 (2) | C12—C13—C20—O1 | −137.68 (17) |
C11—N1—C12—C14 | 176.71 (14) | C9—C13—C20—O2 | −134.31 (14) |
C10—C9—C13—C12 | −1.7 (2) | C12—C13—C20—O2 | 44.1 (2) |
C8—C9—C13—C12 | −177.87 (14) | C20—O2—C21—C22 | 80.53 (18) |
C10—C9—C13—C20 | 176.70 (13) |
Cg1 and Cg2 are the centroids of the C1–C6 phenyl ring and the N1/C9–C13 pyridine ring, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O3 | 0.92 (2) | 2.15 (2) | 2.796 (2) | 127.0 (18) |
N2—H2B···O3i | 0.92 (2) | 2.20 (2) | 2.966 (2) | 140.2 (19) |
C19—H19B···Cg1i | 0.98 | 2.95 | 3.766 (2) | 141 |
C22—H22A···Cg2ii | 0.98 | 2.95 | 3.9206 (19) | 170 |
C7—H7···O1iii | 0.95 | 2.46 | 3.352 (2) | 157 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z; (iii) x+1, y, z. |