Download citation
Download citation
link to html
In the title mol­ecule, C22H22N2O4S, the bicyclic core is slightly folded [1.9 (1)°], while pairwise inter­molecular N—H...O hydrogen bonding forms dimers across centers of symmetry. The dihedral angle between the phenyl ring an the six-membered ring of the bicyclic core is 75.50 (4)°. The mol­ecular conformation is stabilized by an intra­molecular N—H...O hydrogen bond with graph-set motif S(6) and by a weak C—H...O contact, forming an S(7) motif. In the crystal, π–π inter­actions [centroid-to-centroid distance = 3.7484 (10) Å] between phenyl rings and two weak C—H...π inter­actions are also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616002704/zp4002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616002704/zp4002Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616002704/zp4002Isup3.cml
Supplementary material

CCDC reference: 1453514

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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).

Diethyl 3-amino-6-methyl-4-[(E)-2-phenylethenyl]thieno[2,3-b]pyridine-2,5-dicarboxylate top
Crystal data top
C22H22N2O4SF(000) = 864
Mr = 410.47Dx = 1.373 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 5.6473 (2) ÅCell parameters from 9033 reflections
b = 26.7798 (9) Åθ = 3.3–72.0°
c = 13.3219 (4) ŵ = 1.72 mm1
β = 99.743 (2)°T = 150 K
V = 1985.66 (11) Å3Column, yellow
Z = 40.20 × 0.08 × 0.05 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
3830 independent reflections
Radiation source: INCOATEC IµS micro–focus source3158 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.039
Detector resolution: 10.4167 pixels mm-1θmax = 72.0°, θmin = 3.3°
ω scansh = 66
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
k = 3331
Tmin = 0.81, Tmax = 0.93l = 1614
14981 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.094H 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 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.31 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.81665 (7)0.31695 (2)0.51587 (3)0.02555 (12)
O10.0116 (2)0.37752 (4)0.80094 (9)0.0313 (3)
O20.1931 (2)0.31306 (4)0.88190 (9)0.0261 (3)
O31.0260 (3)0.45058 (5)0.44348 (11)0.0373 (3)
O41.1080 (2)0.37241 (4)0.39666 (9)0.0292 (3)
N10.5078 (2)0.28245 (5)0.63005 (10)0.0247 (3)
N20.6910 (3)0.45759 (5)0.57515 (13)0.0316 (3)
H2A0.601 (4)0.4709 (8)0.6114 (17)0.039 (6)*
H2B0.789 (4)0.4766 (8)0.5425 (17)0.043 (6)*
C10.4979 (3)0.50473 (6)0.84071 (12)0.0232 (3)
C20.6874 (3)0.52120 (6)0.91401 (13)0.0257 (3)
H20.83340.50280.92520.031*
C30.6674 (3)0.56382 (6)0.97084 (13)0.0301 (4)
H30.79800.57421.02110.036*
C40.4573 (3)0.59124 (6)0.95430 (14)0.0313 (4)
H40.44200.62030.99370.038*
C50.2685 (3)0.57614 (7)0.87975 (14)0.0328 (4)
H50.12500.59530.86720.039*
C60.2883 (3)0.53313 (6)0.82343 (13)0.0290 (4)
H60.15800.52300.77280.035*
C70.5254 (3)0.45678 (6)0.79016 (12)0.0241 (3)
H70.68060.44210.80310.029*
C80.3566 (3)0.43171 (6)0.72829 (12)0.0226 (3)
H80.20290.44640.70810.027*
C90.4041 (3)0.38108 (6)0.69013 (12)0.0211 (3)
C100.5636 (3)0.37290 (6)0.62112 (12)0.0217 (3)
C110.6091 (3)0.32310 (6)0.59683 (12)0.0226 (3)
C120.3520 (3)0.29013 (6)0.69361 (12)0.0240 (3)
C130.3009 (3)0.33872 (6)0.72724 (12)0.0217 (3)
C140.2322 (3)0.24380 (6)0.72435 (14)0.0322 (4)
H14A0.24350.21720.67490.048*
H14B0.06270.25090.72620.048*
H14C0.31220.23310.79200.048*
C150.7021 (3)0.40730 (6)0.56948 (12)0.0228 (3)
C160.8451 (3)0.38195 (6)0.51149 (12)0.0242 (3)
C170.9986 (3)0.40561 (6)0.44930 (13)0.0255 (3)
C181.2648 (3)0.39335 (7)0.33177 (13)0.0296 (4)
H18A1.40400.41010.37350.035*
H18B1.17680.41820.28450.035*
C191.3474 (4)0.35096 (8)0.27367 (17)0.0456 (5)
H19A1.43660.32700.32130.068*
H19B1.45200.36370.22780.068*
H19C1.20770.33440.23370.068*
C200.1416 (3)0.34570 (6)0.80479 (12)0.0227 (3)
C210.0355 (3)0.31326 (7)0.95820 (13)0.0282 (4)
H21A0.00580.34810.97290.034*
H21B0.12070.29831.02210.034*
C220.1910 (3)0.28440 (7)0.92170 (14)0.0335 (4)
H22A0.27960.30030.86040.050*
H22B0.29100.28410.97510.050*
H22C0.15000.25010.90590.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0313 (2)0.0205 (2)0.0267 (2)0.00010 (16)0.01026 (16)0.00271 (15)
O10.0305 (6)0.0294 (6)0.0352 (7)0.0074 (5)0.0091 (5)0.0038 (5)
O20.0267 (6)0.0294 (6)0.0234 (6)0.0038 (5)0.0078 (5)0.0039 (5)
O30.0499 (8)0.0242 (6)0.0433 (8)0.0061 (6)0.0234 (6)0.0035 (5)
O40.0342 (6)0.0266 (6)0.0300 (7)0.0010 (5)0.0151 (5)0.0008 (5)
N10.0309 (7)0.0197 (6)0.0242 (7)0.0020 (6)0.0066 (6)0.0013 (5)
N20.0428 (9)0.0197 (7)0.0369 (9)0.0000 (7)0.0194 (7)0.0002 (6)
C10.0262 (8)0.0209 (7)0.0232 (8)0.0020 (6)0.0062 (6)0.0023 (6)
C20.0244 (8)0.0262 (8)0.0262 (9)0.0017 (7)0.0038 (6)0.0006 (7)
C30.0354 (9)0.0279 (9)0.0268 (9)0.0078 (7)0.0044 (7)0.0052 (7)
C40.0412 (10)0.0236 (8)0.0308 (9)0.0039 (7)0.0112 (8)0.0071 (7)
C50.0341 (9)0.0264 (9)0.0385 (10)0.0047 (7)0.0079 (8)0.0047 (8)
C60.0288 (9)0.0259 (8)0.0314 (9)0.0014 (7)0.0024 (7)0.0045 (7)
C70.0250 (8)0.0221 (8)0.0253 (8)0.0034 (6)0.0046 (6)0.0025 (6)
C80.0238 (8)0.0199 (8)0.0246 (8)0.0026 (6)0.0051 (6)0.0009 (6)
C90.0215 (7)0.0206 (7)0.0201 (8)0.0001 (6)0.0003 (6)0.0022 (6)
C100.0238 (8)0.0204 (7)0.0203 (8)0.0006 (6)0.0020 (6)0.0015 (6)
C110.0257 (8)0.0217 (8)0.0197 (8)0.0011 (6)0.0018 (6)0.0025 (6)
C120.0284 (8)0.0222 (8)0.0212 (8)0.0013 (6)0.0039 (6)0.0006 (6)
C130.0226 (8)0.0221 (8)0.0196 (8)0.0004 (6)0.0015 (6)0.0008 (6)
C140.0439 (10)0.0219 (8)0.0336 (10)0.0047 (7)0.0144 (8)0.0021 (7)
C150.0250 (8)0.0209 (8)0.0220 (8)0.0012 (6)0.0029 (6)0.0010 (6)
C160.0274 (8)0.0216 (8)0.0239 (8)0.0006 (6)0.0055 (6)0.0002 (6)
C170.0282 (8)0.0265 (8)0.0226 (8)0.0001 (7)0.0061 (6)0.0021 (6)
C180.0299 (9)0.0351 (9)0.0259 (9)0.0013 (7)0.0110 (7)0.0059 (7)
C190.0599 (13)0.0407 (11)0.0437 (12)0.0131 (10)0.0299 (10)0.0083 (9)
C200.0239 (8)0.0217 (7)0.0219 (8)0.0019 (6)0.0024 (6)0.0012 (6)
C210.0339 (9)0.0303 (9)0.0228 (8)0.0013 (7)0.0114 (7)0.0001 (7)
C220.0303 (9)0.0374 (10)0.0336 (10)0.0015 (8)0.0076 (7)0.0029 (8)
Geometric parameters (Å, º) top
S1—C111.7297 (17)C8—C91.488 (2)
S1—C161.7498 (16)C8—H80.9500
O1—C201.209 (2)C9—C131.403 (2)
O2—C201.3428 (19)C9—C101.409 (2)
O2—C211.4601 (19)C10—C111.406 (2)
O3—C171.218 (2)C10—C151.455 (2)
O4—C171.346 (2)C12—C131.421 (2)
O4—C181.451 (2)C12—C141.503 (2)
N1—C121.336 (2)C13—C201.492 (2)
N1—C111.339 (2)C14—H14A0.9800
N2—C151.351 (2)C14—H14B0.9800
N2—H2A0.84 (2)C14—H14C0.9800
N2—H2B0.92 (2)C15—C161.386 (2)
C1—C61.393 (2)C16—C171.443 (2)
C1—C21.393 (2)C18—C191.492 (3)
C1—C71.470 (2)C18—H18A0.9900
C2—C31.385 (2)C18—H18B0.9900
C2—H20.9500C19—H19A0.9800
C3—C41.381 (3)C19—H19B0.9800
C3—H30.9500C19—H19C0.9800
C4—C51.389 (3)C21—C221.503 (2)
C4—H40.9500C21—H21A0.9900
C5—C61.389 (2)C21—H21B0.9900
C5—H50.9500C22—H22A0.9800
C6—H60.9500C22—H22B0.9800
C7—C81.331 (2)C22—H22C0.9800
C7—H70.9500
C11—S1—C1690.11 (8)C9—C13—C20118.53 (14)
C20—O2—C21116.82 (13)C12—C13—C20120.75 (14)
C17—O4—C18115.82 (13)C12—C14—H14A109.5
C12—N1—C11116.63 (14)C12—C14—H14B109.5
C15—N2—H2A119.6 (15)H14A—C14—H14B109.5
C15—N2—H2B119.4 (14)C12—C14—H14C109.5
H2A—N2—H2B121 (2)H14A—C14—H14C109.5
C6—C1—C2118.27 (15)H14B—C14—H14C109.5
C6—C1—C7123.63 (15)N2—C15—C16123.83 (16)
C2—C1—C7118.00 (15)N2—C15—C10124.82 (15)
C3—C2—C1121.34 (16)C16—C15—C10111.34 (14)
C3—C2—H2119.3C15—C16—C17124.61 (15)
C1—C2—H2119.3C15—C16—S1113.78 (12)
C4—C3—C2119.90 (16)C17—C16—S1121.57 (12)
C4—C3—H3120.1O3—C17—O4123.05 (16)
C2—C3—H3120.1O3—C17—C16124.46 (16)
C3—C4—C5119.62 (16)O4—C17—C16112.48 (14)
C3—C4—H4120.2O4—C18—C19106.91 (15)
C5—C4—H4120.2O4—C18—H18A110.3
C4—C5—C6120.36 (17)C19—C18—H18A110.3
C4—C5—H5119.8O4—C18—H18B110.3
C6—C5—H5119.8C19—C18—H18B110.3
C5—C6—C1120.48 (16)H18A—C18—H18B108.6
C5—C6—H6119.8C18—C19—H19A109.5
C1—C6—H6119.8C18—C19—H19B109.5
C8—C7—C1127.15 (15)H19A—C19—H19B109.5
C8—C7—H7116.4C18—C19—H19C109.5
C1—C7—H7116.4H19A—C19—H19C109.5
C7—C8—C9121.31 (14)H19B—C19—H19C109.5
C7—C8—H8119.3O1—C20—O2123.53 (15)
C9—C8—H8119.3O1—C20—C13124.74 (15)
C13—C9—C10116.98 (14)O2—C20—C13111.70 (13)
C13—C9—C8120.46 (14)O2—C21—C22111.01 (14)
C10—C9—C8122.44 (14)O2—C21—H21A109.4
C11—C10—C9117.36 (14)C22—C21—H21A109.4
C11—C10—C15110.97 (14)O2—C21—H21B109.4
C9—C10—C15131.64 (14)C22—C21—H21B109.4
N1—C11—C10126.14 (15)H21A—C21—H21B108.0
N1—C11—S1120.07 (12)C21—C22—H22A109.5
C10—C11—S1113.79 (12)C21—C22—H22B109.5
N1—C12—C13122.07 (15)H22A—C22—H22B109.5
N1—C12—C14114.88 (14)C21—C22—H22C109.5
C13—C12—C14123.03 (15)H22A—C22—H22C109.5
C9—C13—C12120.71 (15)H22B—C22—H22C109.5
C6—C1—C2—C31.9 (3)C8—C9—C13—C200.6 (2)
C7—C1—C2—C3174.57 (16)N1—C12—C13—C93.5 (2)
C1—C2—C3—C40.9 (3)C14—C12—C13—C9175.08 (15)
C2—C3—C4—C50.8 (3)N1—C12—C13—C20174.94 (14)
C3—C4—C5—C61.4 (3)C14—C12—C13—C206.5 (2)
C4—C5—C6—C10.2 (3)C11—C10—C15—N2177.80 (16)
C2—C1—C6—C51.4 (3)C9—C10—C15—N24.0 (3)
C7—C1—C6—C5174.92 (17)C11—C10—C15—C161.02 (19)
C6—C1—C7—C85.4 (3)C9—C10—C15—C16177.15 (16)
C2—C1—C7—C8170.89 (17)N2—C15—C16—C170.5 (3)
C1—C7—C8—C9174.13 (16)C10—C15—C16—C17178.33 (15)
C7—C8—C9—C13107.59 (19)N2—C15—C16—S1178.27 (14)
C7—C8—C9—C1068.3 (2)C10—C15—C16—S10.57 (18)
C13—C9—C10—C111.1 (2)C11—S1—C16—C150.02 (13)
C8—C9—C10—C11174.93 (14)C11—S1—C16—C17177.82 (14)
C13—C9—C10—C15179.21 (15)C18—O4—C17—O30.4 (2)
C8—C9—C10—C153.1 (3)C18—O4—C17—C16179.71 (13)
C12—N1—C11—C101.2 (2)C15—C16—C17—O32.6 (3)
C12—N1—C11—S1178.99 (12)S1—C16—C17—O3179.77 (15)
C9—C10—C11—N12.8 (2)C15—C16—C17—O4176.65 (15)
C15—C10—C11—N1178.75 (15)S1—C16—C17—O40.9 (2)
C9—C10—C11—S1177.40 (11)C17—O4—C18—C19174.66 (15)
C15—C10—C11—S11.06 (17)C21—O2—C20—O17.0 (2)
C16—S1—C11—N1179.19 (14)C21—O2—C20—C13174.78 (13)
C16—S1—C11—C100.63 (13)C9—C13—C20—O143.9 (2)
C11—N1—C12—C131.9 (2)C12—C13—C20—O1137.68 (17)
C11—N1—C12—C14176.71 (14)C9—C13—C20—O2134.31 (14)
C10—C9—C13—C121.7 (2)C12—C13—C20—O244.1 (2)
C8—C9—C13—C12177.87 (14)C20—O2—C21—C2280.53 (18)
C10—C9—C13—C20176.70 (13)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 phenyl ring and the N1/C9–C13 pyridine ring, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2B···O30.92 (2)2.15 (2)2.796 (2)127.0 (18)
N2—H2B···O3i0.92 (2)2.20 (2)2.966 (2)140.2 (19)
C19—H19B···Cg1i0.982.953.766 (2)141
C22—H22A···Cg2ii0.982.953.9206 (19)170
C7—H7···O1iii0.952.463.352 (2)157
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z; (iii) x+1, y, z.
 

Follow IUCrData
Sign up for e-alerts
Follow IUCrData on Twitter
Follow us on facebook
Sign up for RSS feeds