Literature DB >> 21581684

1,3-Dimeth-oxy-2,3-dihydro-1H-isoindole-2-carbothio-amide.

Bushra Maliha, Muhammad Ilyas Tariq, M Nawaz Tahir, Ishtiaq Hussain, Muhammad Ali.   

Abstract

In the mol-ecule of the title compound, C(11)H(14)N(2)O(2)S, the five-membered ring adopts an envelope conformation and an intramolecular N-H⋯O hydrogen bond occurs. Intra-molecular N-H⋯O, C-H⋯S and C-H⋯N hydrogen bonds result in the formation of two five- and one six-membered rings, having twisted conformations. In the crystal structure, inter-molecular N-H⋯O, N-H⋯S and C-H⋯S hydrogen bonds link the mol-ecules, forming polymeric sheets. The π-π contacts between the isoindole ring systems, [centroid-centroid distances = 3.5883 (8) and 4.0619 (8) Å] may further stabilize the structure. A C-H⋯π inter-actions also occur.

Entities:  

Year:  2008        PMID： 21581684      PMCID： PMC2967958          DOI： 10.1107/S1600536808040075

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007 ▶); Toru et al. (1986 ▶). For related structures, see: Maliha et al. (2007 ▶); Maliha, Hussain et al. (2008 ▶); Maliha, Tariq et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14N2O2S M = 238.30 Monoclinic, a = 15.4577 (8) Å b = 8.6455 (5) Å c = 18.2184 (10) Å β = 107.322 (2)° V = 2324.3 (2) Å3 Z = 8 Mo Kα radiation μ = 0.27 mm−1 T = 100 (2) K 0.20 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.945, T max = 0.969 18083 measured reflections 2894 independent reflections 2471 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.110 S = 1.01 2894 reflections 159 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.44 e Å−3 Δρmin = −0.37 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808040075/hk2586sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040075/hk2586Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C11H14N2O2SF(000) = 1008
Mr = 238.30Dx = 1.362 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1295 reflections
a = 15.4577 (8) Åθ = 2.3–28.3°
b = 8.6455 (5) ŵ = 0.27 mm−1
c = 18.2184 (10) ÅT = 100 K
β = 107.322 (2)°Prismatic, red
V = 2324.3 (2) Å30.20 × 0.16 × 0.12 mm
Z = 8
Bruker Kappa APEXII CCD diffractometer2894 independent reflections
Radiation source: fine-focus sealed tube2471 reflections with I > 2σ(I)
graphiteRint = 0.032
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.3°
ω scansh = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −11→11
Tmin = 0.945, Tmax = 0.969l = −24→23
18083 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0799P)2 + 0.660P] where P = (Fo2 + 2Fc2)/3
2894 reflections(Δ/σ)max = 0.002
159 parametersΔρmax = 0.44 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
S10.11517 (2)0.49877 (3)0.21266 (2)0.0204 (1)
O10.14785 (6)−0.02891 (10)0.15401 (5)0.0138 (2)
O2−0.01835 (6)0.30468 (10)0.05803 (5)0.0171 (2)
N10.07220 (7)0.20405 (11)0.17484 (6)0.0120 (3)
N20.21825 (7)0.25081 (12)0.24928 (6)0.0148 (3)
C10.08273 (8)0.03577 (13)0.18556 (7)0.0110 (3)
C2−0.01336 (8)−0.02006 (14)0.15260 (7)0.0117 (3)
C3−0.04573 (8)−0.17035 (14)0.15157 (7)0.0154 (3)
C4−0.13922 (9)−0.19328 (15)0.12533 (8)0.0174 (3)
C5−0.19841 (9)−0.06902 (15)0.10138 (7)0.0167 (3)
C6−0.16516 (8)0.08113 (14)0.10175 (7)0.0141 (3)
C7−0.07174 (8)0.10380 (13)0.12693 (7)0.0119 (3)
C8−0.01925 (8)0.25238 (13)0.13215 (7)0.0128 (3)
C90.12812 (10)−0.01421 (17)0.07232 (8)0.0221 (4)
C10−0.08727 (10)0.41497 (17)0.02569 (9)0.0275 (4)
C110.13705 (8)0.30768 (14)0.21217 (7)0.0125 (3)
H10.1091 (11)0.0123 (16)0.2398 (10)0.0132*
H1N0.2602 (11)0.318 (2)0.2748 (9)0.0178*
H2N0.2325 (11)0.160 (2)0.2447 (9)0.0178*
H3−0.00537−0.254870.168250.0184*
H4−0.16291−0.295030.123740.0208*
H5−0.26194−0.086730.084670.0201*
H6−0.205330.165940.085190.0169*
H8−0.0393 (10)0.3344 (18)0.1604 (9)0.0153*
H9A0.07524−0.077790.046760.0265*
H9B0.18042−0.049090.056810.0265*
H9C0.115200.094290.057530.0265*
H10A−0.146790.368070.019250.0330*
H10B−0.082900.44837−0.024490.0330*
H10C−0.079670.504560.059980.0330*
U11U22U33U12U13U23
S10.0134 (2)0.0095 (2)0.0347 (2)0.0004 (1)0.0018 (2)−0.0017 (1)
O10.0126 (4)0.0154 (4)0.0131 (4)0.0039 (3)0.0032 (3)−0.0015 (3)
O20.0180 (4)0.0163 (4)0.0155 (4)0.0019 (3)0.0025 (4)0.0062 (3)
N10.0103 (5)0.0095 (4)0.0144 (5)0.0014 (3)0.0010 (4)0.0007 (4)
N20.0121 (5)0.0107 (5)0.0195 (5)0.0001 (4)0.0013 (4)−0.0006 (4)
C10.0115 (5)0.0089 (5)0.0119 (5)0.0016 (4)0.0024 (4)0.0000 (4)
C20.0105 (5)0.0133 (5)0.0109 (5)0.0006 (4)0.0025 (4)−0.0007 (4)
C30.0161 (6)0.0124 (5)0.0162 (6)0.0005 (4)0.0026 (5)−0.0008 (4)
C40.0182 (6)0.0145 (6)0.0184 (6)−0.0043 (4)0.0040 (5)−0.0014 (5)
C50.0123 (5)0.0208 (6)0.0160 (6)−0.0035 (5)0.0027 (5)−0.0001 (5)
C60.0126 (5)0.0160 (6)0.0130 (6)0.0016 (4)0.0027 (4)0.0011 (4)
C70.0134 (5)0.0121 (5)0.0098 (5)0.0006 (4)0.0030 (4)−0.0004 (4)
C80.0113 (5)0.0116 (5)0.0138 (5)0.0013 (4)0.0013 (4)0.0011 (4)
C90.0224 (7)0.0315 (8)0.0134 (6)0.0055 (5)0.0069 (5)−0.0018 (5)
C100.0194 (6)0.0282 (7)0.0313 (8)0.0045 (5)0.0021 (6)0.0163 (6)
C110.0127 (5)0.0127 (5)0.0126 (5)−0.0006 (4)0.0046 (4)0.0003 (4)
S1—C111.6869 (12)C5—C61.3954 (18)
O1—C11.4145 (16)C6—C71.3927 (18)
O1—C91.4331 (16)C7—C81.5072 (17)
O2—C81.4280 (15)C1—H10.972 (17)
O2—C101.4204 (18)C3—H30.9500
N1—C11.4705 (15)C4—H40.9500
N1—C81.4571 (17)C5—H50.9500
N1—C111.3653 (16)C6—H60.9500
N2—C111.3300 (17)C8—H80.979 (16)
N2—H1N0.891 (17)C9—H9A0.9800
N2—H2N0.826 (17)C9—H9B0.9800
C1—C21.5062 (18)C9—H9C0.9800
C2—C71.3887 (17)C10—H10A0.9800
C2—C31.3905 (17)C10—H10B0.9800
C3—C41.3946 (19)C10—H10C0.9800
C4—C51.3942 (19)
S1···O23.3984 (10)C6···H10A2.9600
S1···N2i3.2857 (11)C6···H1vi2.819 (17)
S1···H3ii2.7900C6···H9Biv2.8400
S1···H82.697 (16)C7···H1vi2.773 (17)
S1···H2Ni2.646 (17)C7···H10A3.0100
O1···N22.9867 (14)C10···H10Bv2.8900
O1···N2iii2.9738 (14)C10···H5vii2.9800
O2···S13.3984 (10)H1···N22.637 (16)
O1···H1Niii2.087 (17)H1···H2N2.28 (2)
O1···H2N2.413 (17)H1···C2vi2.800 (18)
O2···H9C2.7500H1···C3vi2.920 (17)
O2···H9Aiv2.7000H1···C4vi2.955 (16)
O2···H10Bv2.8200H1···C5vi2.897 (17)
N2···C6vi3.3938 (16)H1···C6vi2.819 (17)
N2···O12.9867 (14)H1···C7vi2.773 (17)
N2···O1i2.9738 (14)H1N···O1i2.087 (17)
N2···S1iii3.2857 (11)H1N···C1i2.986 (17)
N1···H9C2.6000H2N···O12.413 (17)
N2···H12.637 (16)H2N···C12.488 (17)
C1···C2vi3.4582 (18)H2N···H12.28 (2)
C1···C7vi3.5200 (17)H2N···S1iii2.646 (17)
C2···C2vi3.4486 (17)H3···S1viii2.7900
C2···C1vi3.4582 (18)H5···C10vii2.9800
C3···C3vi3.4413 (17)H6···H10A2.4400
C6···N2vi3.3938 (16)H6···H10Avii2.5200
C6···C9iv3.4352 (19)H8···S12.697 (16)
C6···C103.563 (2)H8···H10C2.2800
C7···C1vi3.5200 (17)H9A···C22.7200
C7···C9iv3.5571 (19)H9A···O2iv2.7000
C9···C7iv3.5571 (19)H9B···C6iv2.8400
C9···C6iv3.4352 (19)H9C···O22.7500
C10···C10v3.438 (2)H9C···N12.6000
C10···C63.563 (2)H10A···C62.9600
C1···H1Niii2.986 (17)H10A···C73.0100
C1···H2N2.488 (17)H10A···H62.4400
C2···H9A2.7200H10A···H6vii2.5200
C2···H1vi2.800 (18)H10B···O2v2.8200
C3···H1vi2.920 (17)H10B···C10v2.8900
C4···H1vi2.955 (16)H10C···H82.2800
C5···H1vi2.897 (17)
C1—O1—C9115.45 (10)O1—C1—H1101.4 (10)
C8—O2—C10112.80 (10)N1—C1—H1109.8 (8)
C1—N1—C8113.96 (10)C2—C1—H1113.8 (10)
C1—N1—C11123.18 (10)C2—C3—H3121.00
C8—N1—C11121.97 (10)C4—C3—H3121.00
H1N—N2—H2N119.8 (16)C3—C4—H4120.00
C11—N2—H1N117.0 (11)C5—C4—H4120.00
C11—N2—H2N122.7 (12)C4—C5—H5120.00
O1—C1—N1113.65 (10)C6—C5—H5120.00
O1—C1—C2116.61 (10)C5—C6—H6121.00
N1—C1—C2101.95 (10)C7—C6—H6121.00
C1—C2—C3127.81 (11)O2—C8—H8111.2 (9)
C3—C2—C7121.39 (12)N1—C8—H8109.6 (9)
C1—C2—C7110.61 (10)C7—C8—H8113.7 (9)
C2—C3—C4118.00 (12)O1—C9—H9A109.00
C3—C4—C5120.95 (12)O1—C9—H9B109.00
C4—C5—C6120.59 (13)O1—C9—H9C109.00
C5—C6—C7118.48 (11)H9A—C9—H9B109.00
C2—C7—C6120.56 (11)H9A—C9—H9C109.00
C2—C7—C8110.63 (11)H9B—C9—H9C109.00
C6—C7—C8128.80 (11)O2—C10—H10A109.00
N1—C8—C7101.99 (9)O2—C10—H10B109.00
O2—C8—N1108.33 (10)O2—C10—H10C109.00
O2—C8—C7111.52 (10)H10A—C10—H10B109.00
S1—C11—N1121.78 (10)H10A—C10—H10C109.00
S1—C11—N2121.31 (10)H10B—C10—H10C109.00
N1—C11—N2116.90 (11)
C9—O1—C1—N1−62.73 (14)N1—C1—C2—C3−175.58 (12)
C9—O1—C1—C255.45 (14)N1—C1—C2—C7−0.62 (13)
C10—O2—C8—N1−153.14 (10)C1—C2—C3—C4173.19 (12)
C10—O2—C8—C795.39 (12)C7—C2—C3—C4−1.28 (19)
C8—N1—C1—O1120.77 (11)C1—C2—C7—C6−173.11 (11)
C8—N1—C1—C2−5.57 (13)C1—C2—C7—C86.27 (14)
C11—N1—C1—O1−69.90 (15)C3—C2—C7—C62.22 (19)
C11—N1—C1—C2163.77 (11)C3—C2—C7—C8−178.40 (11)
C1—N1—C8—O2−108.78 (11)C2—C3—C4—C5−0.45 (19)
C1—N1—C8—C78.96 (13)C3—C4—C5—C61.3 (2)
C11—N1—C8—O281.74 (13)C4—C5—C6—C7−0.33 (19)
C11—N1—C8—C7−160.52 (11)C5—C6—C7—C2−1.37 (18)
C1—N1—C11—S1−167.45 (9)C5—C6—C7—C8179.37 (12)
C1—N1—C11—N211.57 (18)C2—C7—C8—O2106.35 (12)
C8—N1—C11—S11.05 (17)C2—C7—C8—N1−9.08 (13)
C8—N1—C11—N2−179.93 (11)C6—C7—C8—O2−74.34 (16)
O1—C1—C2—C360.04 (17)C6—C7—C8—N1170.24 (12)
O1—C1—C2—C7−125.00 (11)
D—H···AD—HH···AD···AD—H···A
N2—H1N···O1i0.891 (17)2.087 (17)2.9738 (14)172.9 (15)
N2—H2N···O10.826 (17)2.413 (17)2.9867 (14)127.3 (14)
N2—H2N···S1iii0.826 (17)2.646 (17)3.2857 (11)135.4 (15)
C3—H3···S1viii0.95002.79003.7362 (13)178.00
C8—H8···S10.979 (16)2.697 (16)3.0318 (12)100.5 (11)
C9—H9C···N10.98002.60002.9593 (18)102.00
C1—H1···CgBvi0.98002.500 (17)3.4059 (13)155.1 (1)
C9—H9C···CgA0.98002.742.9052 (16)90
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H1N⋯O1i0.891 (17)2.087 (17)2.9738 (14)172.9 (15)
N2—H2N⋯O10.826 (17)2.413 (17)2.9867 (14)127.3 (14)
N2—H2N⋯S1ii0.826 (17)2.646 (17)3.2857 (11)135.4 (15)
C3—H3⋯S1iii0.952.793.7362 (13)178
C1—H1⋯CgBiv0.982.500 (17)3.4059 (13)155.1 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . CgB is the centroids of the N1/C1/C2/C7/C8 ring.

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