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In the title compound, C24H22ClN3OS, variations in C—N bond lengths and angles around the N atoms indicate delocalization of the N-atom lone pair. The benzothio­phene moiety is essentially planar. The dimethyl­amino­phenyl and o-chloro­benzene rings form dihedral angles of 41.9 (1) and 26.2 (2)°, respectively, with the benzothio­phene plane. The molecular structure is stabilized by N—H...Cl, N—H...N, C—H...N, C—H...S and C—H...O hydrogen bonds. Mol­ecules pack as layers parallel to (101).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031988/ci6479sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031988/ci6479Isup2.hkl
Contains datablock I

CCDC reference: 262449

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.069
  • wR factor = 0.158
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found




Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C6
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

N-(2-Chlorophenyl)-2-((1E)-[4-(dimethylamino)phenyl]methyleneamino)-4,7- dihydro-1-benzothiophene-3-carboxamide top
Crystal data top
C24H22ClN3OSF(000) = 912
Mr = 435.97Dx = 1.326 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 541 reflections
a = 9.9850 (8) Åθ = 2.0–27.2°
b = 13.6440 (11) ŵ = 0.29 mm1
c = 16.3425 (14) ÅT = 296 K
β = 101.292 (1)°Block, red
V = 2183.3 (3) Å30.23 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4061 independent reflections
Radiation source: fine-focus sealed tube3506 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1012
Tmin = 0.939, Tmax = 0.966k = 1416
16005 measured reflectionsl = 1919
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.24 w = 1/[σ2(Fo2) + (0.0546P)2 + 1.4409P]
where P = (Fo2 + 2Fc2)/3
4061 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.33 e Å3
12 restraintsΔρmin = 0.17 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.96870 (10)0.43413 (8)0.37566 (6)0.0740 (3)
S10.74091 (11)0.11292 (7)0.11049 (6)0.0623 (3)
O10.6047 (2)0.45903 (16)0.11918 (13)0.0566 (6)
N10.8178 (3)0.21847 (18)0.25454 (15)0.0456 (6)
N20.7254 (3)0.40825 (18)0.24350 (15)0.0465 (6)
H20.76940.35940.26920.056*
N31.1523 (3)0.1019 (2)0.62001 (17)0.0574 (7)
C10.9169 (3)0.1598 (2)0.28166 (19)0.0477 (7)
H10.95070.12210.24280.057*
C20.7506 (3)0.2176 (2)0.17209 (18)0.0440 (7)
C30.6763 (3)0.2935 (2)0.12889 (17)0.0383 (6)
C40.5201 (4)0.3279 (3)0.01807 (18)0.0546 (8)
H4A0.44880.35600.00720.066*
H4B0.57310.38150.03450.066*
C50.4559 (7)0.2716 (4)0.0940 (3)0.124 (2)
H50.38680.30170.13220.149*
C60.4918 (7)0.1813 (5)0.1102 (3)0.138 (3)
H60.45670.15630.16290.165*
C70.5815 (5)0.1183 (3)0.0522 (2)0.0759 (12)
H7A0.65670.09680.07740.091*
H7B0.53140.06070.04060.091*
C80.6370 (3)0.1711 (3)0.02815 (19)0.0532 (8)
C90.6118 (3)0.2656 (2)0.04561 (17)0.0418 (7)
C100.6640 (3)0.3936 (2)0.16192 (17)0.0384 (6)
C110.7239 (3)0.4949 (2)0.28933 (17)0.0421 (7)
C120.8319 (4)0.5151 (2)0.35471 (19)0.0513 (8)
C130.8324 (5)0.5966 (3)0.4050 (2)0.0680 (11)
H130.90600.60880.44840.082*
C140.7225 (5)0.6594 (3)0.3901 (3)0.0744 (12)
H140.72110.71420.42370.089*
C150.6153 (4)0.6413 (3)0.3257 (2)0.0659 (10)
H150.54160.68430.31570.079*
C160.6152 (4)0.5604 (2)0.2758 (2)0.0541 (8)
H160.54150.54930.23230.065*
C170.9788 (3)0.1486 (2)0.36774 (19)0.0456 (7)
C181.0980 (3)0.0929 (2)0.3919 (2)0.0484 (8)
H181.13910.06540.35100.058*
C191.1558 (3)0.0779 (2)0.4740 (2)0.0484 (8)
H191.23540.04100.48750.058*
C201.0972 (3)0.1170 (2)0.53809 (19)0.0448 (7)
C210.9772 (3)0.1732 (2)0.5141 (2)0.0508 (8)
H210.93570.20060.55490.061*
C220.9214 (3)0.1879 (2)0.4321 (2)0.0499 (8)
H220.84240.22540.41840.060*
C231.2778 (4)0.0471 (3)0.6453 (2)0.0737 (11)
H23A1.26690.01730.62130.111*
H23B1.29900.04200.70500.111*
H23C1.35080.08030.62630.111*
C241.0897 (4)0.1407 (4)0.6856 (2)0.0795 (12)
H24A1.08810.21100.68260.119*
H24B1.14130.12050.73880.119*
H24C0.99790.11650.67900.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0684 (6)0.0819 (7)0.0618 (6)0.0002 (5)0.0112 (5)0.0063 (5)
S10.0789 (7)0.0478 (5)0.0554 (5)0.0160 (5)0.0019 (4)0.0095 (4)
O10.0716 (16)0.0446 (13)0.0471 (12)0.0093 (12)0.0041 (11)0.0004 (10)
N10.0505 (15)0.0440 (15)0.0406 (13)0.0048 (12)0.0047 (11)0.0015 (11)
N20.0594 (16)0.0388 (14)0.0381 (13)0.0039 (12)0.0019 (11)0.0018 (11)
N30.0487 (16)0.072 (2)0.0496 (16)0.0078 (15)0.0055 (13)0.0080 (14)
C10.0518 (19)0.0455 (18)0.0469 (17)0.0050 (15)0.0125 (14)0.0001 (14)
C20.0475 (17)0.0435 (17)0.0415 (16)0.0010 (14)0.0104 (13)0.0010 (13)
C30.0376 (15)0.0414 (16)0.0368 (14)0.0017 (13)0.0100 (12)0.0010 (12)
C40.066 (2)0.059 (2)0.0373 (16)0.0026 (17)0.0047 (15)0.0012 (15)
C50.185 (5)0.086 (3)0.067 (3)0.034 (3)0.057 (3)0.020 (2)
C60.166 (5)0.119 (4)0.091 (3)0.053 (4)0.066 (3)0.057 (3)
C70.102 (3)0.070 (3)0.052 (2)0.008 (2)0.005 (2)0.0222 (19)
C80.060 (2)0.055 (2)0.0437 (17)0.0039 (16)0.0081 (15)0.0095 (15)
C90.0434 (17)0.0477 (18)0.0355 (15)0.0010 (14)0.0105 (12)0.0031 (13)
C100.0359 (15)0.0413 (16)0.0388 (15)0.0034 (13)0.0090 (12)0.0016 (13)
C110.0542 (18)0.0388 (16)0.0351 (14)0.0090 (14)0.0134 (13)0.0008 (12)
C120.062 (2)0.0499 (19)0.0413 (16)0.0115 (16)0.0094 (14)0.0018 (14)
C130.090 (3)0.063 (2)0.049 (2)0.025 (2)0.0104 (19)0.0125 (17)
C140.106 (3)0.054 (2)0.069 (2)0.013 (2)0.030 (2)0.022 (2)
C150.077 (3)0.051 (2)0.074 (2)0.0024 (19)0.025 (2)0.0110 (18)
C160.060 (2)0.0498 (19)0.0534 (19)0.0016 (17)0.0121 (16)0.0077 (15)
C170.0450 (17)0.0415 (17)0.0496 (17)0.0051 (14)0.0079 (14)0.0026 (14)
C180.0456 (18)0.0493 (19)0.0516 (18)0.0092 (15)0.0132 (14)0.0011 (14)
C190.0380 (16)0.0506 (19)0.0549 (18)0.0091 (14)0.0051 (14)0.0047 (15)
C200.0398 (16)0.0469 (18)0.0471 (17)0.0035 (14)0.0071 (13)0.0050 (14)
C210.0482 (19)0.057 (2)0.0499 (18)0.0094 (16)0.0160 (14)0.0009 (15)
C220.0435 (18)0.0501 (19)0.0553 (18)0.0144 (15)0.0080 (14)0.0077 (15)
C230.057 (2)0.097 (3)0.062 (2)0.011 (2)0.0001 (18)0.017 (2)
C240.072 (3)0.120 (4)0.047 (2)0.013 (3)0.0137 (18)0.011 (2)
Geometric parameters (Å, º) top
Cl1—C121.738 (4)C8—C91.355 (4)
S1—C81.724 (3)C11—C121.389 (4)
S1—C21.740 (3)C11—C161.390 (5)
O1—C101.214 (3)C12—C131.383 (5)
N1—C11.283 (4)C13—C141.376 (6)
N1—C21.383 (4)C13—H130.93
N2—C101.369 (4)C14—C151.369 (6)
N2—C111.401 (4)C14—H140.93
N2—H20.86C15—C161.372 (5)
N3—C201.360 (4)C15—H150.93
N3—C241.443 (5)C16—H160.93
N3—C231.448 (5)C17—C221.400 (4)
C1—C171.430 (4)C17—C181.402 (4)
C1—H10.93C18—C191.368 (4)
C2—C31.384 (4)C18—H180.93
C3—C91.438 (4)C19—C201.402 (4)
C3—C101.483 (4)C19—H190.93
C4—C51.494 (5)C20—C211.411 (4)
C4—C91.507 (4)C21—C221.362 (4)
C4—H4A0.97C21—H210.93
C4—H4B0.97C22—H220.93
C5—C61.324 (7)C23—H23A0.96
C5—H50.93C23—H23B0.96
C6—C71.451 (6)C23—H23C0.96
C6—H60.93C24—H24A0.96
C7—C81.505 (5)C24—H24B0.96
C7—H7A0.97C24—H24C0.96
C7—H7B0.97
C8—S1—C291.75 (15)C16—C11—N2123.2 (3)
C1—N1—C2121.7 (3)C13—C12—C11121.9 (3)
C10—N2—C11126.4 (3)C13—C12—Cl1118.9 (3)
C10—N2—H2116.8C11—C12—Cl1119.2 (3)
C11—N2—H2116.8C14—C13—C12119.0 (4)
C20—N3—C24121.7 (3)C14—C13—H13120.5
C20—N3—C23121.3 (3)C12—C13—H13120.5
C24—N3—C23117.0 (3)C15—C14—C13120.1 (4)
N1—C1—C17124.2 (3)C15—C14—H14120.0
N1—C1—H1117.9C13—C14—H14120.0
C17—C1—H1117.9C14—C15—C16120.7 (4)
N1—C2—C3126.9 (3)C14—C15—H15119.6
N1—C2—S1122.1 (2)C16—C15—H15119.6
C3—C2—S1110.8 (2)C15—C16—C11120.9 (3)
C2—C3—C9112.4 (3)C15—C16—H16119.6
C2—C3—C10125.3 (3)C11—C16—H16119.6
C9—C3—C10122.3 (3)C22—C17—C18116.5 (3)
C5—C4—C9112.8 (3)C22—C17—C1122.4 (3)
C5—C4—H4A109.0C18—C17—C1121.0 (3)
C9—C4—H4A109.0C19—C18—C17122.0 (3)
C5—C4—H4B109.0C19—C18—H18119.0
C9—C4—H4B109.0C17—C18—H18119.0
H4A—C4—H4B107.8C18—C19—C20121.2 (3)
C6—C5—C4123.7 (4)C18—C19—H19119.4
C6—C5—H5118.1C20—C19—H19119.4
C4—C5—H5118.1N3—C20—C19122.0 (3)
C5—C6—C7125.3 (4)N3—C20—C21120.9 (3)
C5—C6—H6117.3C19—C20—C21117.1 (3)
C7—C6—H6117.3C22—C21—C20121.0 (3)
C6—C7—C8111.1 (3)C22—C21—H21119.5
C6—C7—H7A109.4C20—C21—H21119.5
C8—C7—H7A109.4C21—C22—C17122.2 (3)
C6—C7—H7B109.4C21—C22—H22118.9
C8—C7—H7B109.4C17—C22—H22118.9
H7A—C7—H7B108.0N3—C23—H23A109.5
C9—C8—C7126.0 (3)N3—C23—H23B109.5
C9—C8—S1112.4 (2)H23A—C23—H23B109.5
C7—C8—S1121.6 (3)N3—C23—H23C109.5
C8—C9—C3112.6 (3)H23A—C23—H23C109.5
C8—C9—C4120.3 (3)H23B—C23—H23C109.5
C3—C9—C4127.1 (3)N3—C24—H24A109.5
O1—C10—N2121.9 (3)N3—C24—H24B109.5
O1—C10—C3122.3 (3)H24A—C24—H24B109.5
N2—C10—C3115.8 (3)N3—C24—H24C109.5
C12—C11—C16117.4 (3)H24A—C24—H24C109.5
C12—C11—N2119.3 (3)H24B—C24—H24C109.5
C2—N1—C1—C17171.8 (3)C9—C3—C10—N2177.0 (3)
C1—N1—C2—C3157.3 (3)C10—N2—C11—C12152.1 (3)
C1—N1—C2—S127.1 (4)C10—N2—C11—C1631.5 (5)
C8—S1—C2—N1175.8 (3)C16—C11—C12—C130.3 (5)
C8—S1—C2—C30.4 (2)N2—C11—C12—C13176.3 (3)
N1—C2—C3—C9175.9 (3)C16—C11—C12—Cl1178.7 (2)
S1—C2—C3—C90.0 (3)N2—C11—C12—Cl12.1 (4)
N1—C2—C3—C105.0 (5)C11—C12—C13—C140.2 (5)
S1—C2—C3—C10179.0 (2)Cl1—C12—C13—C14178.2 (3)
C9—C4—C5—C610.3 (9)C12—C13—C14—C150.6 (6)
C4—C5—C6—C710.1 (12)C13—C14—C15—C160.5 (6)
C5—C6—C7—C83.6 (10)C14—C15—C16—C110.0 (6)
C6—C7—C8—C91.6 (7)C12—C11—C16—C150.4 (5)
C6—C7—C8—S1177.3 (4)N2—C11—C16—C15176.1 (3)
C2—S1—C8—C90.8 (3)N1—C1—C17—C2211.6 (5)
C2—S1—C8—C7178.3 (3)N1—C1—C17—C18171.5 (3)
C7—C8—C9—C3178.1 (3)C22—C17—C18—C190.1 (5)
S1—C8—C9—C30.9 (4)C1—C17—C18—C19177.3 (3)
C7—C8—C9—C40.4 (5)C17—C18—C19—C200.6 (5)
S1—C8—C9—C4178.6 (2)C24—N3—C20—C19178.7 (4)
C2—C3—C9—C80.5 (4)C23—N3—C20—C192.2 (5)
C10—C3—C9—C8179.6 (3)C24—N3—C20—C211.2 (5)
C2—C3—C9—C4178.1 (3)C23—N3—C20—C21177.9 (3)
C10—C3—C9—C42.9 (5)C18—C19—C20—N3179.3 (3)
C5—C4—C9—C85.0 (5)C18—C19—C20—C210.6 (5)
C5—C4—C9—C3172.3 (4)N3—C20—C21—C22179.6 (3)
C11—N2—C10—O13.3 (5)C19—C20—C21—C220.3 (5)
C11—N2—C10—C3177.6 (3)C20—C21—C22—C170.1 (5)
C2—C3—C10—O1175.0 (3)C18—C17—C22—C210.2 (5)
C9—C3—C10—O13.9 (4)C1—C17—C22—C21176.9 (3)
C2—C3—C10—N24.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···Cl10.862.582.939 (3)106
N2—H2···N10.862.012.743 (4)143
C1—H1···S10.932.703.066 (3)104
C16—H16···O10.932.412.893 (4)113
 

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