organic compounds
(E)-6-Bromo-3-{2-[2-(2-methoxybenzylidene)hydrazinyl]-1,3-thiazol-4-yl}-2H-chromen-2-one
aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the title compound, C20H14BrN3O3S, the molecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thiazole ring are approximately planar [maximum deviations = 0.029 (3) and 0.007 (3) Å, respectively]. The chromene ring system is inclined at angles of 7.37 (12) and 13.90 (13)° with respect to the thiazole and benzene rings, respectively, while the thiazole ring makes a dihedral angle of 12.58 (15)° with the benzene ring. In the crystal, molecules are connected by N—H⋯O hydrogen bonds, forming C(8) supramolecular chains along the c axis.
Related literature
For related structures, further synthetic details and background references, see: Arshad et al. (2011a,b).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536811024536/hb5923sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811024536/hb5923Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811024536/hb5923Isup3.cml
The title compound was synthesized by the same procedure as mentioned in our previous papers (Arshad et al., 2011a,b). 2-Methoxy benzylidene thiosemicarbazone was reacted with 6-bromo-3- (2-bromoacetyl)-2H-chromen-2-one in chloroform-ethanol (2:1) mixture. The reaction mixture was refluxed for 2–3 hours at 60°C to get dense yellow precipitates. It was cooled in ice bath and basified with ammonia to pH 7–8. The title compound (I) was recrystallized from CHCl3–EtOH (1:1) as golden yellow needles.
All hydrogen atoms were positioned geometrically [N–H = 0.9449 Å and C–H = 0.93 or 0.96 Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C20H14BrN3O3S | F(000) = 920 |
Mr = 456.31 | Dx = 1.649 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2197 reflections |
a = 7.2802 (12) Å | θ = 3.0–22.4° |
b = 19.551 (3) Å | µ = 2.38 mm−1 |
c = 14.0638 (18) Å | T = 296 K |
β = 113.352 (7)° | Needle, yellow |
V = 1837.8 (5) Å3 | 0.43 × 0.07 × 0.04 mm |
Z = 4 |
Bruker APEXII DUO CCD diffractometer | 4266 independent reflections |
Radiation source: fine-focus sealed tube | 2786 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ϕ and ω scans | θmax = 27.7°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.427, Tmax = 0.921 | k = −25→24 |
11951 measured reflections | l = −18→18 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.488P] where P = (Fo2 + 2Fc2)/3 |
4266 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C20H14BrN3O3S | V = 1837.8 (5) Å3 |
Mr = 456.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2802 (12) Å | µ = 2.38 mm−1 |
b = 19.551 (3) Å | T = 296 K |
c = 14.0638 (18) Å | 0.43 × 0.07 × 0.04 mm |
β = 113.352 (7)° |
Bruker APEXII DUO CCD diffractometer | 4266 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2786 reflections with I > 2σ(I) |
Tmin = 0.427, Tmax = 0.921 | Rint = 0.036 |
11951 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.30 e Å−3 |
4266 reflections | Δρmin = −0.29 e Å−3 |
253 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.24394 (5) | 1.084300 (17) | 0.06129 (3) | 0.06481 (13) | |
S1 | 0.21746 (11) | 0.61887 (3) | 0.38892 (5) | 0.04655 (18) | |
O1 | 0.2719 (3) | 0.92795 (9) | 0.43367 (12) | 0.0453 (4) | |
O2 | 0.2679 (3) | 0.83501 (10) | 0.51902 (14) | 0.0567 (5) | |
O3 | 0.2197 (3) | 0.37198 (9) | 0.04438 (13) | 0.0518 (5) | |
N1 | 0.2186 (3) | 0.71059 (10) | 0.25691 (15) | 0.0403 (5) | |
N2 | 0.2131 (3) | 0.59752 (10) | 0.19923 (16) | 0.0459 (6) | |
H1 | 0.2264 | 0.6102 | 0.1375 | 0.055* | |
N3 | 0.2291 (3) | 0.53132 (10) | 0.23123 (16) | 0.0397 (5) | |
C1 | 0.2567 (4) | 0.85797 (13) | 0.43706 (19) | 0.0402 (6) | |
C2 | 0.2663 (4) | 0.96192 (13) | 0.34700 (19) | 0.0407 (6) | |
C3 | 0.2939 (4) | 1.03179 (15) | 0.3551 (2) | 0.0515 (7) | |
H3A | 0.3160 | 1.0541 | 0.4171 | 0.062* | |
C4 | 0.2880 (4) | 1.06785 (14) | 0.2703 (2) | 0.0523 (7) | |
H4A | 0.3068 | 1.1150 | 0.2744 | 0.063* | |
C5 | 0.2538 (4) | 1.03353 (14) | 0.1781 (2) | 0.0446 (6) | |
C6 | 0.2293 (4) | 0.96446 (14) | 0.1706 (2) | 0.0439 (6) | |
H6A | 0.2081 | 0.9424 | 0.1085 | 0.053* | |
C7 | 0.2358 (4) | 0.92670 (12) | 0.25618 (18) | 0.0372 (6) | |
C8 | 0.2190 (4) | 0.85417 (13) | 0.25783 (19) | 0.0401 (6) | |
H8A | 0.1991 | 0.8297 | 0.1978 | 0.048* | |
C9 | 0.2310 (4) | 0.81934 (13) | 0.34368 (18) | 0.0372 (6) | |
C10 | 0.2232 (4) | 0.74489 (13) | 0.34487 (18) | 0.0366 (6) | |
C11 | 0.2234 (4) | 0.70361 (13) | 0.42228 (19) | 0.0430 (6) | |
H11A | 0.2264 | 0.7192 | 0.4854 | 0.052* | |
C12 | 0.2177 (4) | 0.64534 (12) | 0.27085 (18) | 0.0363 (6) | |
C13 | 0.2343 (4) | 0.48370 (12) | 0.17014 (19) | 0.0375 (6) | |
H13A | 0.2209 | 0.4934 | 0.1030 | 0.045* | |
C14 | 0.2620 (4) | 0.41341 (12) | 0.20920 (18) | 0.0348 (5) | |
C15 | 0.3017 (4) | 0.40043 (13) | 0.3125 (2) | 0.0445 (6) | |
H15A | 0.3043 | 0.4367 | 0.3559 | 0.053* | |
C16 | 0.3374 (5) | 0.33511 (14) | 0.3522 (2) | 0.0544 (8) | |
H16A | 0.3618 | 0.3275 | 0.4215 | 0.065* | |
C17 | 0.3368 (5) | 0.28129 (14) | 0.2896 (2) | 0.0557 (8) | |
H17A | 0.3650 | 0.2374 | 0.3170 | 0.067* | |
C18 | 0.2947 (4) | 0.29182 (13) | 0.1862 (2) | 0.0479 (7) | |
H18A | 0.2917 | 0.2550 | 0.1437 | 0.057* | |
C19 | 0.2572 (4) | 0.35707 (13) | 0.14584 (18) | 0.0376 (6) | |
C20 | 0.2017 (5) | 0.31519 (14) | −0.0228 (2) | 0.0530 (7) | |
H20A | 0.1687 | 0.3315 | −0.0920 | 0.080* | |
H20B | 0.0979 | 0.2852 | −0.0220 | 0.080* | |
H20C | 0.3262 | 0.2908 | 0.0005 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0782 (2) | 0.0614 (2) | 0.0665 (2) | −0.00399 (17) | 0.04110 (19) | 0.01182 (16) |
S1 | 0.0669 (5) | 0.0376 (4) | 0.0421 (4) | −0.0001 (3) | 0.0291 (3) | 0.0017 (3) |
O1 | 0.0660 (12) | 0.0354 (10) | 0.0349 (10) | 0.0021 (9) | 0.0203 (9) | −0.0065 (8) |
O2 | 0.0930 (16) | 0.0460 (11) | 0.0367 (11) | 0.0041 (10) | 0.0315 (11) | −0.0039 (9) |
O3 | 0.0867 (14) | 0.0353 (10) | 0.0391 (10) | −0.0008 (10) | 0.0310 (10) | −0.0042 (8) |
N1 | 0.0546 (13) | 0.0317 (12) | 0.0366 (12) | −0.0013 (10) | 0.0202 (10) | −0.0057 (9) |
N2 | 0.0760 (16) | 0.0297 (12) | 0.0394 (12) | −0.0014 (11) | 0.0307 (12) | −0.0028 (9) |
N3 | 0.0529 (13) | 0.0285 (11) | 0.0404 (12) | −0.0002 (10) | 0.0213 (10) | −0.0002 (9) |
C1 | 0.0459 (15) | 0.0371 (15) | 0.0377 (14) | 0.0032 (12) | 0.0167 (12) | −0.0057 (12) |
C2 | 0.0451 (15) | 0.0357 (15) | 0.0408 (15) | 0.0018 (12) | 0.0166 (12) | −0.0033 (12) |
C3 | 0.0630 (19) | 0.0439 (17) | 0.0441 (16) | −0.0017 (14) | 0.0176 (14) | −0.0127 (13) |
C4 | 0.0640 (19) | 0.0327 (15) | 0.0591 (18) | −0.0057 (14) | 0.0234 (16) | −0.0050 (13) |
C5 | 0.0454 (16) | 0.0408 (16) | 0.0516 (16) | 0.0001 (13) | 0.0235 (13) | 0.0055 (13) |
C6 | 0.0511 (16) | 0.0444 (16) | 0.0398 (15) | −0.0008 (13) | 0.0219 (13) | −0.0045 (12) |
C7 | 0.0410 (14) | 0.0340 (14) | 0.0366 (14) | 0.0012 (11) | 0.0155 (12) | −0.0064 (11) |
C8 | 0.0481 (16) | 0.0386 (15) | 0.0349 (14) | −0.0009 (12) | 0.0179 (12) | −0.0093 (11) |
C9 | 0.0400 (14) | 0.0367 (14) | 0.0359 (14) | 0.0016 (11) | 0.0159 (12) | −0.0077 (11) |
C10 | 0.0391 (14) | 0.0369 (14) | 0.0336 (13) | 0.0012 (11) | 0.0141 (11) | −0.0066 (11) |
C11 | 0.0578 (17) | 0.0398 (15) | 0.0356 (14) | 0.0011 (13) | 0.0231 (13) | −0.0046 (11) |
C12 | 0.0444 (15) | 0.0334 (14) | 0.0324 (13) | −0.0006 (11) | 0.0165 (12) | −0.0026 (11) |
C13 | 0.0485 (15) | 0.0327 (14) | 0.0336 (13) | −0.0012 (12) | 0.0187 (12) | −0.0011 (11) |
C14 | 0.0400 (13) | 0.0296 (13) | 0.0376 (14) | −0.0030 (11) | 0.0184 (11) | −0.0013 (11) |
C15 | 0.0605 (18) | 0.0359 (15) | 0.0404 (15) | −0.0032 (13) | 0.0236 (14) | −0.0031 (12) |
C16 | 0.082 (2) | 0.0437 (17) | 0.0405 (16) | 0.0001 (15) | 0.0280 (16) | 0.0043 (13) |
C17 | 0.079 (2) | 0.0344 (15) | 0.0556 (18) | 0.0057 (15) | 0.0293 (17) | 0.0109 (13) |
C18 | 0.0691 (19) | 0.0311 (15) | 0.0502 (16) | −0.0027 (13) | 0.0309 (15) | −0.0047 (12) |
C19 | 0.0454 (15) | 0.0337 (14) | 0.0380 (14) | −0.0032 (11) | 0.0211 (12) | −0.0013 (11) |
C20 | 0.073 (2) | 0.0473 (17) | 0.0419 (16) | −0.0035 (15) | 0.0259 (15) | −0.0133 (13) |
Br1—C5 | 1.896 (3) | C6—H6A | 0.9300 |
S1—C11 | 1.718 (3) | C7—C8 | 1.424 (3) |
S1—C12 | 1.740 (2) | C8—C9 | 1.359 (3) |
O1—C2 | 1.375 (3) | C8—H8A | 0.9300 |
O1—C1 | 1.375 (3) | C9—C10 | 1.457 (3) |
O2—C1 | 1.209 (3) | C10—C11 | 1.355 (3) |
O3—C19 | 1.374 (3) | C11—H11A | 0.9300 |
O3—C20 | 1.430 (3) | C13—C14 | 1.464 (3) |
N1—C12 | 1.291 (3) | C13—H13A | 0.9300 |
N1—C10 | 1.396 (3) | C14—C15 | 1.387 (3) |
N2—N3 | 1.360 (3) | C14—C19 | 1.409 (3) |
N2—C12 | 1.365 (3) | C15—C16 | 1.377 (4) |
N2—H1 | 0.9449 | C15—H15A | 0.9300 |
N3—C13 | 1.277 (3) | C16—C17 | 1.371 (4) |
C1—C9 | 1.461 (3) | C16—H16A | 0.9300 |
C2—C3 | 1.379 (4) | C17—C18 | 1.377 (4) |
C2—C7 | 1.389 (3) | C17—H17A | 0.9300 |
C3—C4 | 1.371 (4) | C18—C19 | 1.379 (3) |
C3—H3A | 0.9300 | C18—H18A | 0.9300 |
C4—C5 | 1.392 (4) | C20—H20A | 0.9600 |
C4—H4A | 0.9300 | C20—H20B | 0.9600 |
C5—C6 | 1.361 (4) | C20—H20C | 0.9600 |
C6—C7 | 1.397 (3) | ||
C11—S1—C12 | 87.96 (12) | C11—C10—C9 | 128.1 (2) |
C2—O1—C1 | 122.48 (18) | N1—C10—C9 | 117.2 (2) |
C19—O3—C20 | 116.75 (19) | C10—C11—S1 | 111.30 (18) |
C12—N1—C10 | 109.9 (2) | C10—C11—H11A | 124.4 |
N3—N2—C12 | 115.7 (2) | S1—C11—H11A | 124.4 |
N3—N2—H1 | 121.9 | N1—C12—N2 | 124.4 (2) |
C12—N2—H1 | 121.1 | N1—C12—S1 | 116.16 (17) |
C13—N3—N2 | 119.5 (2) | N2—C12—S1 | 119.44 (18) |
O2—C1—O1 | 115.2 (2) | N3—C13—C14 | 117.9 (2) |
O2—C1—C9 | 126.9 (2) | N3—C13—H13A | 121.0 |
O1—C1—C9 | 117.8 (2) | C14—C13—H13A | 121.0 |
O1—C2—C3 | 116.9 (2) | C15—C14—C19 | 117.5 (2) |
O1—C2—C7 | 120.9 (2) | C15—C14—C13 | 120.3 (2) |
C3—C2—C7 | 122.1 (2) | C19—C14—C13 | 122.1 (2) |
C4—C3—C2 | 118.9 (2) | C16—C15—C14 | 121.5 (2) |
C4—C3—H3A | 120.5 | C16—C15—H15A | 119.3 |
C2—C3—H3A | 120.5 | C14—C15—H15A | 119.3 |
C3—C4—C5 | 119.6 (3) | C17—C16—C15 | 119.9 (3) |
C3—C4—H4A | 120.2 | C17—C16—H16A | 120.0 |
C5—C4—H4A | 120.2 | C15—C16—H16A | 120.0 |
C6—C5—C4 | 121.4 (2) | C16—C17—C18 | 120.4 (3) |
C6—C5—Br1 | 119.5 (2) | C16—C17—H17A | 119.8 |
C4—C5—Br1 | 119.1 (2) | C18—C17—H17A | 119.8 |
C5—C6—C7 | 119.9 (2) | C17—C18—C19 | 119.8 (2) |
C5—C6—H6A | 120.0 | C17—C18—H18A | 120.1 |
C7—C6—H6A | 120.0 | C19—C18—H18A | 120.1 |
C2—C7—C6 | 118.0 (2) | O3—C19—C18 | 123.3 (2) |
C2—C7—C8 | 117.5 (2) | O3—C19—C14 | 115.9 (2) |
C6—C7—C8 | 124.5 (2) | C18—C19—C14 | 120.8 (2) |
C9—C8—C7 | 122.5 (2) | O3—C20—H20A | 109.5 |
C9—C8—H8A | 118.7 | O3—C20—H20B | 109.5 |
C7—C8—H8A | 118.7 | H20A—C20—H20B | 109.5 |
C8—C9—C10 | 121.4 (2) | O3—C20—H20C | 109.5 |
C8—C9—C1 | 118.7 (2) | H20A—C20—H20C | 109.5 |
C10—C9—C1 | 119.9 (2) | H20B—C20—H20C | 109.5 |
C11—C10—N1 | 114.7 (2) | ||
C12—N2—N3—C13 | −177.2 (2) | C1—C9—C10—C11 | 4.9 (4) |
C2—O1—C1—O2 | 178.6 (2) | C8—C9—C10—N1 | 4.9 (4) |
C2—O1—C1—C9 | −0.9 (3) | C1—C9—C10—N1 | −173.7 (2) |
C1—O1—C2—C3 | −176.6 (2) | N1—C10—C11—S1 | −0.1 (3) |
C1—O1—C2—C7 | 2.9 (4) | C9—C10—C11—S1 | −178.8 (2) |
O1—C2—C3—C4 | −179.5 (3) | C12—S1—C11—C10 | 0.6 (2) |
C7—C2—C3—C4 | 1.0 (4) | C10—N1—C12—N2 | 179.9 (2) |
C2—C3—C4—C5 | 0.3 (4) | C10—N1—C12—S1 | 1.2 (3) |
C3—C4—C5—C6 | −1.1 (4) | N3—N2—C12—N1 | 174.9 (2) |
C3—C4—C5—Br1 | 179.5 (2) | N3—N2—C12—S1 | −6.4 (3) |
C4—C5—C6—C7 | 0.8 (4) | C11—S1—C12—N1 | −1.1 (2) |
Br1—C5—C6—C7 | −179.84 (19) | C11—S1—C12—N2 | −179.8 (2) |
O1—C2—C7—C6 | 179.2 (2) | N2—N3—C13—C14 | 176.9 (2) |
C3—C2—C7—C6 | −1.3 (4) | N3—C13—C14—C15 | −6.5 (4) |
O1—C2—C7—C8 | −2.6 (4) | N3—C13—C14—C19 | 176.0 (2) |
C3—C2—C7—C8 | 176.9 (2) | C19—C14—C15—C16 | 0.7 (4) |
C5—C6—C7—C2 | 0.4 (4) | C13—C14—C15—C16 | −177.0 (3) |
C5—C6—C7—C8 | −177.7 (2) | C14—C15—C16—C17 | 0.9 (5) |
C2—C7—C8—C9 | 0.3 (4) | C15—C16—C17—C18 | −2.0 (5) |
C6—C7—C8—C9 | 178.4 (3) | C16—C17—C18—C19 | 1.4 (5) |
C7—C8—C9—C10 | −176.9 (2) | C20—O3—C19—C18 | 5.8 (4) |
C7—C8—C9—C1 | 1.7 (4) | C20—O3—C19—C14 | −176.2 (2) |
O2—C1—C9—C8 | 179.2 (3) | C17—C18—C19—O3 | 178.1 (3) |
O1—C1—C9—C8 | −1.4 (4) | C17—C18—C19—C14 | 0.2 (4) |
O2—C1—C9—C10 | −2.1 (4) | C15—C14—C19—O3 | −179.3 (2) |
O1—C1—C9—C10 | 177.3 (2) | C13—C14—C19—O3 | −1.7 (4) |
C12—N1—C10—C11 | −0.7 (3) | C15—C14—C19—C18 | −1.3 (4) |
C12—N1—C10—C9 | 178.2 (2) | C13—C14—C19—C18 | 176.4 (2) |
C8—C9—C10—C11 | −176.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O2i | 0.94 | 2.10 | 3.021 (3) | 164 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H14BrN3O3S |
Mr | 456.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.2802 (12), 19.551 (3), 14.0638 (18) |
β (°) | 113.352 (7) |
V (Å3) | 1837.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.38 |
Crystal size (mm) | 0.43 × 0.07 × 0.04 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.427, 0.921 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11951, 4266, 2786 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.653 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.089, 1.01 |
No. of reflections | 4266 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.29 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O2i | 0.94 | 2.10 | 3.021 (3) | 164 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
Acknowledgements
AA, HO, CKL thank the Malaysian Government and Universiti Sains Malaysia (USM) for a grant [1001/PKimia/811133] to conduct this work. AA also thanks Universiti Sains Malaysia for a fellowship. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.
References
Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011a). Acta Cryst. E67, o1072–o1073. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, A., Osman, H., Lam, C. K., Hemamalini, M. & Fun, H.-K. (2011b). Acta Cryst. E67, o1007–o1008. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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As part of our ongoing studies of substituted coumarins (Arshad et al., 2011a,b) we now present the crystal structure of the title compound, (I).
In (I), the molecule adopts an E configuration about the central C13═N3 double bond. The chromene (O1/C1–C9) and the thiazole (S1/N1/C10–C12) rings are approximately planar [maximum deviations of 0.029 (3) Å for atom C4 and 0.007 (3) Å for atom C12, respectively]. The chromene (O1/C1–C9) ring system is inclined at angles of 7.37 (12)° and 13.90 (13)° with respect to the thiazole (S1/N1/C10–C12) and benzene (C14–C19) rings, respectively, while the thiazole (S1/N1/C10–C12) ring makes a dihedral angle of 12.58 (15)° with the benzene ((C14–C19) ring.
In the crystal (Fig. 2), the molecules are connected by N2—H1···O2 (Table 1) hydrogen bonds forming supramolecular chains along the c-axis.