Literature DB >> 21582121

3-[(Methyl-carbamo-yl)amino]-1H-isoindolium chloride.

Bushra Maliha, Muhammad Ilyas Tariq, M Nawaz Tahir, Ishtiaq Hussain, Hamid Latif Siddiqui.   

Abstract

The title compound, C(10)H(12)N(3)O(+)·Cl(-), is a derivative of o-phthaldehyde and methyl-thio-urea. The mol-ecules form dimers through intra- and inter-molecular N-H⋯O hydrogen bonds. The dimers are further linked into chains through one C-H⋯Cl and two N-H⋯Cl hydrogen bonds.

Entities:  

Year:  2009        PMID： 21582121      PMCID： PMC2968434          DOI： 10.1107/S1600536809003699

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


Related literature

For applications of iminium salts, see: Page et al. (2008 ▶); Skalkos et al. (1994 ▶) Tariq et al. (2008 ▶). For the formation of derivatives of o-phthaldehyde with different ureas, see: Maliha, Tariq, Tahir, Hussain & Ali (2009 ▶); Maliha, Tariq, Tahir, Hussain & Siddiqui (2009 ▶); Maliha et al. (2008 ▶). For a related structure, see: Arfan et al. (2008 ▶).

Experimental

Crystal data

C10H12N3O+·Cl− M = 225.68 Triclinic, a = 7.1171 (5) Å b = 7.7900 (6) Å c = 10.3033 (8) Å α = 89.484 (3)° β = 69.997 (2)° γ = 74.613 (4)° V = 515.43 (7) Å3 Z = 2 Mo Kα radiation μ = 0.35 mm−1 T = 296 (2) K 0.30 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.989 8853 measured reflections 2369 independent reflections 2210 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.101 S = 1.01 2369 reflections 146 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.69 e Å−3 Δρmin = −0.22 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 (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003699/ez2156sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003699/ez2156Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H12N3O+·Cl−Z = 2
Mr = 225.68F(000) = 236
Triclinic, P1Dx = 1.454 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1171 (5) ÅCell parameters from 2369 reflections
b = 7.7900 (6) Åθ = 3.1–27.5°
c = 10.3033 (8) ŵ = 0.35 mm−1
α = 89.484 (3)°T = 296 K
β = 69.997 (2)°Needle, light yellow
γ = 74.613 (4)°0.30 × 0.10 × 0.06 mm
V = 515.43 (7) Å3
Bruker Kappa APEXII CCD diffractometer2369 independent reflections
Radiation source: fine-focus sealed tube2210 reflections with I > 2σ(I)
graphiteRint = 0.020
Detector resolution: 7.50 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −10→10
Tmin = 0.982, Tmax = 0.989l = −13→13
8853 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: mixed
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0646P)2 + 0.2853P] where P = (Fo2 + 2Fc2)/3
2369 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.69 e Å−3
0 restraintsΔρmin = −0.21 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 esds 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
O10.29475 (16)0.09740 (13)0.60677 (11)0.0195 (3)
N10.46180 (18)0.25619 (17)0.37719 (12)0.0161 (3)
N20.19866 (18)0.40058 (16)0.58681 (12)0.0155 (3)
N30.05849 (19)0.28726 (17)0.79177 (13)0.0177 (3)
C10.5740 (2)0.29979 (19)0.23859 (15)0.0175 (4)
C20.4836 (2)0.49861 (19)0.24873 (15)0.0165 (4)
C30.5278 (2)0.6215 (2)0.15233 (15)0.0201 (4)
C40.4209 (2)0.8007 (2)0.19298 (17)0.0222 (4)
C50.2750 (2)0.8576 (2)0.32626 (17)0.0214 (4)
C60.2298 (2)0.73562 (19)0.42329 (15)0.0183 (4)
C70.3359 (2)0.55629 (19)0.38103 (14)0.0149 (4)
C80.3263 (2)0.39698 (18)0.45638 (14)0.0147 (3)
C90.1900 (2)0.24711 (19)0.66151 (14)0.0155 (3)
C100.0312 (3)0.1475 (2)0.88541 (15)0.0218 (4)
Cl10.11104 (5)0.28646 (4)0.19897 (3)0.0186 (1)
H1A0.547290.239970.167350.0210*
H1B0.722870.267950.219410.0210*
H1N0.487 (3)0.156 (3)0.401 (2)0.0194*
H2N0.113 (3)0.507 (3)0.631 (2)0.0186*
H30.625470.585100.063600.0242*
H3N−0.007 (3)0.397 (3)0.819 (2)0.0212*
H40.447290.885010.129760.0266*
H50.207290.978640.350360.0256*
H60.133170.772120.512340.0220*
H10A0.012120.049820.839960.0327*
H10B−0.088890.194480.967220.0327*
H10C0.152380.106080.910810.0327*
U11U22U33U12U13U23
O10.0212 (5)0.0138 (5)0.0177 (5)−0.0003 (4)−0.0033 (4)0.0024 (4)
N10.0167 (5)0.0144 (6)0.0145 (6)−0.0019 (4)−0.0039 (4)0.0029 (4)
N20.0166 (5)0.0126 (6)0.0143 (6)−0.0020 (4)−0.0032 (4)0.0016 (4)
N30.0208 (6)0.0145 (6)0.0145 (6)−0.0031 (5)−0.0036 (5)0.0021 (4)
C10.0162 (6)0.0182 (7)0.0149 (6)−0.0030 (5)−0.0029 (5)0.0021 (5)
C20.0146 (6)0.0192 (7)0.0165 (7)−0.0058 (5)−0.0057 (5)0.0024 (5)
C30.0193 (7)0.0251 (8)0.0169 (7)−0.0097 (6)−0.0049 (5)0.0049 (6)
C40.0251 (7)0.0221 (8)0.0249 (7)−0.0130 (6)−0.0111 (6)0.0101 (6)
C50.0245 (7)0.0158 (7)0.0264 (8)−0.0074 (6)−0.0109 (6)0.0047 (6)
C60.0181 (6)0.0176 (7)0.0200 (7)−0.0053 (5)−0.0074 (5)0.0016 (5)
C70.0142 (6)0.0160 (6)0.0164 (7)−0.0055 (5)−0.0067 (5)0.0037 (5)
C80.0140 (6)0.0156 (6)0.0158 (6)−0.0040 (5)−0.0071 (5)0.0018 (5)
C90.0160 (6)0.0156 (6)0.0155 (6)−0.0048 (5)−0.0062 (5)0.0033 (5)
C100.0280 (7)0.0197 (7)0.0156 (7)−0.0068 (6)−0.0050 (6)0.0060 (5)
Cl10.0195 (2)0.0144 (2)0.0192 (2)−0.0041 (1)−0.0040 (1)0.0002 (1)
O1—C91.2234 (17)C4—C51.397 (2)
N1—C11.4654 (19)C5—C61.390 (2)
N1—C81.3096 (19)C6—C71.392 (2)
N2—C81.3356 (18)C7—C81.463 (2)
N2—C91.4197 (19)C1—H1A0.9700
N3—C91.3296 (19)C1—H1B0.9700
N3—C101.456 (2)C3—H30.9300
N1—H1N0.81 (2)C4—H40.9300
N2—H2N0.90 (2)C5—H50.9300
N3—H3N0.86 (2)C6—H60.9300
C1—C21.501 (2)C10—H10A0.9600
C2—C31.390 (2)C10—H10B0.9600
C2—C71.395 (2)C10—H10C0.9600
C3—C41.390 (2)
Cl1···C13.4838 (16)C8···C7vii3.457 (2)
Cl1···C23.6463 (16)C9···C3vii3.539 (2)
Cl1···C5i3.6252 (16)C9···C6ii3.358 (2)
Cl1···N2ii3.0969 (13)C9···C4vii3.513 (2)
Cl1···N3ii3.2082 (13)C9···C5ii3.575 (2)
Cl1···H5i2.9100C10···C4ii3.500 (3)
Cl1···H1A2.9300C10···C5ii3.579 (3)
Cl1···H1Biii2.7400C10···C10ix3.283 (2)
Cl1···H2Nii2.23 (2)C1···H10Bx2.9400
Cl1···H3iv3.0500C5···H10Aii3.0400
Cl1···H3Nii2.40 (2)C6···H2N2.82 (2)
Cl1···H6ii2.9900C9···H1N2.75 (2)
Cl1···H10Av3.0400C10···H10Bix3.0600
O1···O1vi2.9982 (16)C10···H10Cix3.0700
O1···N1vi2.8760 (17)H1A···Cl12.9300
O1···N12.7097 (16)H1B···Cl1xi2.7400
O1···H1Nvi2.15 (2)H1B···H10Bx2.4700
O1···H10A2.6500H1N···O1vi2.15 (2)
O1···H1N2.22 (2)H1N···C92.75 (2)
N1···O12.7097 (16)H1N···O12.22 (2)
N1···O1vi2.8760 (17)H2N···H62.4000
N2···Cl1ii3.0969 (13)H2N···H3N2.11 (3)
N3···C5ii3.436 (2)H2N···C62.82 (2)
N3···C3vii3.433 (2)H2N···Cl1ii2.23 (2)
N3···Cl1ii3.2082 (13)H3···Cl1iv3.0500
N2···H62.9400H3N···H2N2.11 (3)
C1···Cl13.4838 (16)H3N···Cl1ii2.40 (2)
C2···Cl13.6463 (16)H5···Cl1viii2.9100
C3···N3vii3.433 (2)H6···H2N2.4000
C3···C9vii3.539 (2)H6···N22.9400
C4···C9vii3.513 (2)H6···Cl1ii2.9900
C4···C10ii3.500 (3)H10A···O12.6500
C5···N3ii3.436 (2)H10A···Cl1v3.0400
C5···C9ii3.575 (2)H10A···C5ii3.0400
C5···C10ii3.579 (3)H10B···C10ix3.0600
C5···Cl1viii3.6252 (16)H10B···H1Bxii2.4700
C6···C9ii3.358 (2)H10B···C1xii2.9400
C7···C8vii3.457 (2)H10C···C10ix3.0700
C1—N1—C8112.52 (12)N2—C9—N3112.47 (12)
C8—N2—C9124.09 (12)O1—C9—N2121.32 (12)
C9—N3—C10120.48 (13)O1—C9—N3126.20 (13)
C8—N1—H1N125.2 (14)N1—C1—H1A111.00
C1—N1—H1N122.2 (14)N1—C1—H1B111.00
C8—N2—H2N118.4 (13)C2—C1—H1A111.00
C9—N2—H2N117.5 (13)C2—C1—H1B111.00
C10—N3—H3N121.3 (13)H1A—C1—H1B109.00
C9—N3—H3N118.2 (13)C2—C3—H3121.00
N1—C1—C2101.98 (12)C4—C3—H3121.00
C1—C2—C3130.68 (13)C3—C4—H4119.00
C3—C2—C7120.12 (13)C5—C4—H4119.00
C1—C2—C7109.19 (12)C4—C5—H5120.00
C2—C3—C4117.74 (14)C6—C5—H5120.00
C3—C4—C5121.78 (14)C5—C6—H6122.00
C4—C5—C6120.86 (14)C7—C6—H6122.00
C5—C6—C7116.91 (13)N3—C10—H10A109.00
C2—C7—C8106.74 (12)N3—C10—H10B109.00
C2—C7—C6122.59 (13)N3—C10—H10C109.00
C6—C7—C8130.66 (13)H10A—C10—H10B109.00
N1—C8—C7109.54 (12)H10A—C10—H10C109.00
N1—C8—N2126.82 (13)H10B—C10—H10C109.00
N2—C8—C7123.63 (12)
C8—N1—C1—C21.26 (17)C1—C2—C7—C6177.86 (14)
C1—N1—C8—C7−1.95 (18)C1—C2—C7—C8−1.00 (17)
C1—N1—C8—N2178.99 (15)C3—C2—C7—C6−1.0 (2)
C9—N2—C8—N1−0.2 (3)C3—C2—C7—C8−179.83 (14)
C8—N2—C9—N3176.55 (15)C2—C3—C4—C50.6 (2)
C9—N2—C8—C7−179.15 (14)C3—C4—C5—C6−0.6 (2)
C8—N2—C9—O1−3.7 (2)C4—C5—C6—C7−0.1 (2)
C10—N3—C9—O11.4 (3)C5—C6—C7—C8179.48 (16)
C10—N3—C9—N2−178.92 (15)C5—C6—C7—C20.9 (2)
N1—C1—C2—C3178.61 (16)C2—C7—C8—N11.83 (18)
N1—C1—C2—C7−0.06 (17)C6—C7—C8—N1−176.90 (16)
C1—C2—C3—C4−178.36 (16)C6—C7—C8—N22.2 (3)
C7—C2—C3—C40.2 (2)C2—C7—C8—N2−179.07 (15)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.81 (2)2.22 (2)2.7097 (16)119.9 (18)
N1—H1N···O1vi0.81 (2)2.15 (2)2.8760 (17)150 (2)
N2—H2N···Cl1ii0.90 (2)2.23 (2)3.0969 (13)160.5 (18)
N3—H3N···Cl1ii0.86 (2)2.40 (2)3.2082 (13)157.0 (17)
C1—H1B···Cl1xi0.97002.74003.6755 (16)162.00
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O10.81 (2)2.22 (2)2.7097 (16)119.9 (18)
N1—H1N⋯O1i0.81 (2)2.15 (2)2.8760 (17)150 (2)
N2—H2N⋯Cl1ii0.90 (2)2.23 (2)3.0969 (13)160.5 (18)
N3—H3N⋯Cl1ii0.86 (2)2.40 (2)3.2082 (13)157.0 (17)
C1—H1B⋯Cl1iii0.972.743.6755 (16)162

Symmetry codes: (i) ; (ii) ; (iii) .

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