In the title molecule, C8H7BrClNO2, the bromochlorophenyl ring is inclined to

the methylcarbamate unit by 32.73 (7). In the crystal, N—HO hydrogen

bonds form chains of molecules parallel to [100]

Alshammari, Mohammed B.

El-Hiti, Gamal A.

Hegazy, Amany S.

Kariuki, Benson M.

Smith, Keith

In the title molecule, C8H7BrClNO2, the bromochlorophenyl ring is inclined to the methylcarbamate unit by 32.73 (7)°. In the crystal, N—H...O hydrogen bonds form chains of molecules parallel to [100].</jats:p

Gamal A. El-Hiti

Keith Smith

Amany S. Hegazy

Mohammed B. Alshammari

Benson M. Kariuki

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IUCrData

Methyl<i>N</i>-(2-bromo-4-chlorophenyl)carbamate

In the title molecule, C8H7BrClNO2, the bromochlorophenyl ring is inclined to the methylcarbamate unit by 32.73 (7)°. In the crystal, N—H...O hydrogen bonds form chains of molecules parallel to [100]

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Methyl N-(2-bromo-4-chlorophenyl)carbamate

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data reportsIUCrData (2018). 3, x180054 https://doi.org/10.1107/S2414314618000548 1 of 2Methyl N-(2-bromo-4-chlorophenyl)carbamateGamal A. El-Hiti,a* Keith Smith,b Amany S. Hegazy,b Mohammed B. Alshammaricand Benson M. Kariukib‡aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box10219, Riyadh 11433, Saudi Arabia, bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF103AT, Wales, and cChemistry Department, College of Sciences and Humanities, Prince Sattam bin Abdulaziz University,PO Box 83, Al-Kharij 11942, Saudi Arabia. *Correspondence e-mail: gelhiti@ksu.edu.saIn the title molecule, C8H7BrClNO2, the bromochlorophenyl ring is inclined tothe methylcarbamate unit by 32.73 (7). In the crystal, N—H  O hydrogenbonds form chains of molecules parallel to [100].Structure descriptionCarbamate derivatives show a variety of biological activities (Krátký et al., 2014; Smith etal., 2014; Yang et al., 2012). They can be synthesized using a variety of convenientprocesses (Blaser et al., 2012; Smith et al., 2012; Ibrahim et al., 2011; Porzelle et al., 2009;Lee et al., 2009; Lebel & Leogane, 2006; Caddick et al., 2003). The X-ray crystal structureof the related tert-butyl 2-phenylethylcarbamate was published recently (El-Hiti et al.,2016).In the title molecule (Fig. 1), the dihedral angle between the bromochlorophenyl andmethylcarbamate groups is 32.73 (7). In the crystal, N—H  O hydrogen bonds, Table 1,form chains parallel to [100], (Fig. 2).Synthesis and crystallizationThe title compound was synthesized from the reaction of 2-bromo-4-chloroaniline anddimethyl dicarbonate in dichloromethane in the presence of triethylamine. Recrystalli-zation of the crude product from diethyl ether solution gave the title compound ascolourless crystals, m.p. 88–89C (lit. 86–89 C; Moghaddam et al., 2016).Received 5 January 2018Accepted 9 January 2018Edited by J. Simpson, University of Otago, NewZealand‡ Additional corresponding author, e-mail:kariukib@cardiff.ac.uk.Keywords: crystal structure; hydrogen bond;carbamate.CCDC reference: 1815604Structural data: full structural data are availablefrom iucrdata.iucr.orgISSN 2414-31462 of 2 El-Hiti et al.  C8H7BrClNO2 IUCrData (2018). 3, x180054data reportsRefinementCrystal data, data collection and structure refinement detailsare summarized in Table 2.Funding informationThis project was supported by King Saud University, Deanshipof Scientific Research, Research Chairs and Cardiff Univer-sity.ReferencesAgilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton,England.Blaser, A., Palmer, B. D., Sutherland, H. S., Kmentova, I., Franzblau,S. G., Wan, B., Wang, Y., Ma, Z., Thompson, A. M. & Denny, W. A.(2012). J. Med. Chem. 55, 312–326.Caddick, S., Judd, D. B., Lewis, A. K. de K., Reich, M. T. & Williams,M. R. V. (2003). Tetrahedron, 59, 5417–5423.Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge SoftCorporation, Cambridge, Massachusetts, USA.El-Hiti, G. A., Smith, K., Alshammari, M. B., Ajarim, M. D. &Kariuki, M. B. (2016). Z. Kristallogr. New Cryst. Struct. 231, 1105–1107.Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.Ibrahim, T., Tala, S. R., El-Feky, S. A., Abdel-Samii, Z. K. &Katritzky, A. R. (2011). Synlett, pp. 2013–2016.Krátký, M., Volková, M., Novotná, E., Trejtnar, E., Stolařı́ková, J. &Vinšová, J. (2014). Bioorg. Med. Chem. 22, 4073–4082.Lebel, H. & Leogane, O. (2006). Org. Lett. 8, 5717–5720.Lee, H.-G., Kim, M.-J., Park, S.-E., Kim, J.-J., Kim, B., Lee, S. & Yoon,Y. (2009). Synlett, pp. 2809–2814.Moghaddam, F. M., Tavakoli, G., Saeednia, B., Langer, P. & Jafari, B.(2016). J. Org. Chem. 81, 3868–3876.Porzelle, A., Woodrow, M. D. & Tomkinson, N. C. O. (2009). Synlett,pp. 798–802.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.Smith, K., El-Hiti, G. A. & Alshammari, M. B. (2012). J. Org. Chem.77, 11210–11215.Smith, K., El-Hiti, G. A. & Alshammari, M. B. (2014). Synthesis, 46,394–402.Yang, Y. H., Voak, A., Wilkinson, S. R. & Hu, L. Q. (2012). Bioorg.Med. Chem. Lett. 22, 6583–6586.Table 2Experimental details.Crystal dataChemical formula C8H7BrClNO2Mr 264.51Crystal system, space group Triclinic, P1Temperature (K) 150a, b, c (Å) 4.6637 (3), 9.4598 (6), 11.9898 (7), ,  () 111.639 (5), 101.035 (5), 93.712 (5)V (Å3) 477.25 (5)Z 2Radiation type Cu K (mm1) 8.19Crystal size (mm) 0.31  0.20  0.15Data collectionDiffractometer Agilent SuperNova, Dual, Cu atzero, AtlasAbsorption correction Gaussian (CrysAlis PRO; Agilent,2014)Tmin, Tmax 0.776, 0.891No. of measured, independent andobserved [I > 2(I)] reflections2938, 1847, 1777Rint 0.019(sin /)max (Å1) 0.623RefinementR[F 2 > 2(F 2)], wR(F 2), S 0.024, 0.063, 1.08No. of reflections 1847No. of parameters 119H-atom treatment H-atom parameters constrained	max, 	min (e Å3) 0.30, 0.61Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS2013 (Sheldrick, 2008),SHELXL2013 (Sheldrick, 2015), ORTEP-3 for Windows and WinGX (Farrugia, 2012)and CHEMDRAW Ultra (Cambridge Soft, 2001).Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AN1—H1  O1i 0.88 2.19 2.885 (2) 135Symmetry code: (i) xþ 1; y; z.Figure 1An ORTEP representation (50% probability level) of the title molecule.Figure 2A segment of the crystal structure, viewed along b, showing the N—H  O hydrogen bonds as dotted lines.data reportsdata-1IUCrData (2018). 3, x180054    full crystallographic dataIUCrData (2018). 3, x180054    [https://doi.org/10.1107/S2414314618000548]Methyl N-(2-bromo-4-chlorophenyl)carbamateGamal A. El-Hiti, Keith Smith, Amany S. Hegazy, Mohammed B. Alshammari and Benson M. KariukiMethyl N-(2-bromo-4-chlorophenyl)carbamate Crystal data C8H7BrClNO2Mr = 264.51Triclinic, P1a = 4.6637 (3) Åb = 9.4598 (6) Åc = 11.9898 (7) Åα = 111.639 (5)°β = 101.035 (5)°γ = 93.712 (5)°V = 477.25 (5) Å3Z = 2F(000) = 260Dx = 1.841 Mg m−3Cu Kα radiation, λ = 1.54184 ÅCell parameters from 2127 reflectionsθ = 5.1–74.1°µ = 8.19 mm−1T = 150 KBlock, colourless0.31 × 0.20 × 0.15 mmData collection Agilent SuperNova, Dual, Cu at zero, Atlas diffractometerω scansAbsorption correction: gaussian (CrysAlis PRO; Agilent, 2014)Tmin = 0.776, Tmax = 0.8912938 measured reflections1847 independent reflections1777 reflections with I > 2σ(I)Rint = 0.019θmax = 74.0°, θmin = 4.1°h = −5→5k = −10→11l = −14→11Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.024wR(F2) = 0.063S = 1.081847 reflections119 parameters0 restraintsHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.040P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.30 e Å−3Δρmin = −0.61 e Å−3Special details 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.data reportsdata-2IUCrData (2018). 3, x180054    Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqC1 0.5832 (4) 0.2508 (2) 0.08977 (18) 0.0178 (4)C2 0.7774 (4) 0.3658 (2) 0.19208 (19) 0.0189 (4)C3 0.7777 (5) 0.3806 (2) 0.31131 (19) 0.0226 (4)H3 0.9115 0.4585 0.3796 0.027*C4 0.5803 (5) 0.2806 (3) 0.3295 (2) 0.0242 (4)C5 0.3866 (5) 0.1654 (2) 0.2315 (2) 0.0230 (4)H5 0.2525 0.0973 0.2455 0.028*C6 0.3903 (5) 0.1504 (2) 0.1125 (2) 0.0210 (4)H6 0.2592 0.0704 0.0449 0.025*C7 0.3560 (5) 0.1832 (2) −0.12754 (19) 0.0194 (4)C8 0.2102 (6) 0.1130 (3) −0.3419 (2) 0.0324 (5)H8A 0.1401 0.0058 −0.3581 0.049*H8B 0.2882 0.1174 −0.4110 0.049*H8C 0.0459 0.1726 −0.3323 0.049*N1 0.5916 (4) 0.2373 (2) −0.02987 (16) 0.0204 (3)H1 0.7618 0.2661 −0.0424 0.024*O1 0.1036 (3) 0.14673 (18) −0.12501 (14) 0.0242 (3)O2 0.4400 (3) 0.17650 (19) −0.23043 (14) 0.0264 (3)Cl1 0.57621 (15) 0.30115 (7) 0.47984 (5) 0.03750 (16)Br1 1.04171 (4) 0.50705 (2) 0.16904 (2) 0.02356 (10)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0170 (9) 0.0181 (9) 0.0196 (10) 0.0047 (7) 0.0063 (7) 0.0075 (7)C2 0.0177 (9) 0.0181 (9) 0.0223 (10) 0.0019 (7) 0.0058 (8) 0.0091 (8)C3 0.0241 (10) 0.0215 (9) 0.0200 (10) −0.0003 (8) 0.0033 (8) 0.0070 (8)C4 0.0310 (11) 0.0269 (11) 0.0194 (10) 0.0054 (9) 0.0097 (8) 0.0121 (8)C5 0.0239 (10) 0.0219 (10) 0.0264 (11) 0.0013 (8) 0.0099 (8) 0.0115 (8)C6 0.0202 (10) 0.0197 (9) 0.0222 (10) 0.0002 (7) 0.0058 (8) 0.0072 (8)C7 0.0208 (10) 0.0194 (9) 0.0194 (10) 0.0048 (7) 0.0066 (8) 0.0079 (8)C8 0.0341 (12) 0.0413 (13) 0.0194 (10) 0.0026 (10) 0.0017 (9) 0.0117 (10)N1 0.0157 (8) 0.0256 (9) 0.0198 (8) −0.0002 (6) 0.0058 (6) 0.0084 (7)O1 0.0159 (7) 0.0315 (8) 0.0243 (8) 0.0010 (6) 0.0052 (6) 0.0101 (6)O2 0.0219 (8) 0.0402 (9) 0.0198 (7) 0.0013 (6) 0.0049 (6) 0.0152 (7)Cl1 0.0549 (4) 0.0381 (3) 0.0208 (3) −0.0052 (3) 0.0122 (2) 0.0132 (2)Br1 0.02532 (14) 0.02146 (14) 0.02454 (14) −0.00329 (9) 0.00644 (9) 0.01045 (10)Geometric parameters (Å, º) C1—C6 1.400 (3) C5—H5 0.9500C1—N1 1.401 (3) C6—H6 0.9500C1—C2 1.404 (3) C7—O1 1.214 (3)C2—C3 1.384 (3) C7—O2 1.345 (2)C2—Br1 1.890 (2) C7—N1 1.354 (3)data reportsdata-3IUCrData (2018). 3, x180054    C3—C4 1.381 (3) C8—O2 1.439 (3)C3—H3 0.9500 C8—H8A 0.9800C4—C5 1.381 (3) C8—H8B 0.9800C4—Cl1 1.744 (2) C8—H8C 0.9800C5—C6 1.384 (3) N1—H1 0.8800C6—C1—N1 122.34 (18) C5—C6—H6 119.3C6—C1—C2 117.59 (19) C1—C6—H6 119.3N1—C1—C2 120.06 (18) O1—C7—O2 123.82 (19)C3—C2—C1 121.46 (19) O1—C7—N1 126.17 (19)C3—C2—Br1 118.43 (15) O2—C7—N1 110.00 (17)C1—C2—Br1 120.11 (15) O2—C8—H8A 109.5C4—C3—C2 119.0 (2) O2—C8—H8B 109.5C4—C3—H3 120.5 H8A—C8—H8B 109.5C2—C3—H3 120.5 O2—C8—H8C 109.5C5—C4—C3 121.44 (19) H8A—C8—H8C 109.5C5—C4—Cl1 119.54 (17) H8B—C8—H8C 109.5C3—C4—Cl1 119.02 (17) C7—N1—C1 124.53 (17)C4—C5—C6 119.14 (19) C7—N1—H1 117.7C4—C5—H5 120.4 C1—N1—H1 117.7C6—C5—H5 120.4 C7—O2—C8 115.05 (17)C5—C6—C1 121.39 (19)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AN1—H1···O1i 0.88 2.19 2.885 (2) 135Symmetry code: (i) x+1, y, z.

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Methyl N-(2-bromo-4-chlorophenyl)carbamate

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