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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618000548/sj4153sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314618000548/sj4153Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314618000548/sj4153Isup3.cml
Supplementary material

CCDC reference: 1815604

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.024
  • wR factor = 0.063
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 20 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.005 Degree PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 69 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

Methyl N-(2-bromo-4-chlorophenyl)carbamate top
Crystal data top
C8H7BrClNO2Z = 2
Mr = 264.51F(000) = 260
Triclinic, P1Dx = 1.841 Mg m3
a = 4.6637 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.4598 (6) ÅCell parameters from 2127 reflections
c = 11.9898 (7) Åθ = 5.1–74.1°
α = 111.639 (5)°µ = 8.19 mm1
β = 101.035 (5)°T = 150 K
γ = 93.712 (5)°Block, colourless
V = 477.25 (5) Å30.31 × 0.20 × 0.15 mm
Data collection top
Agilent SuperNova, Dual, Cu at zero, Atlas
diffractometer
1777 reflections with I > 2σ(I)
ω scansRint = 0.019
Absorption correction: gaussian
(CrysAlis PRO; Agilent, 2014)
θmax = 74.0°, θmin = 4.1°
Tmin = 0.776, Tmax = 0.891h = 55
2938 measured reflectionsk = 1011
1847 independent reflectionsl = 1411
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.040P)2 + 0.157P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1847 reflectionsΔρmax = 0.30 e Å3
119 parametersΔρmin = 0.61 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5832 (4)0.2508 (2)0.08977 (18)0.0178 (4)
C20.7774 (4)0.3658 (2)0.19208 (19)0.0189 (4)
C30.7777 (5)0.3806 (2)0.31131 (19)0.0226 (4)
H30.91150.45850.37960.027*
C40.5803 (5)0.2806 (3)0.3295 (2)0.0242 (4)
C50.3866 (5)0.1654 (2)0.2315 (2)0.0230 (4)
H50.25250.09730.24550.028*
C60.3903 (5)0.1504 (2)0.1125 (2)0.0210 (4)
H60.25920.07040.04490.025*
C70.3560 (5)0.1832 (2)0.12754 (19)0.0194 (4)
C80.2102 (6)0.1130 (3)0.3419 (2)0.0324 (5)
H8A0.14010.00580.35810.049*
H8B0.28820.11740.41100.049*
H8C0.04590.17260.33230.049*
N10.5916 (4)0.2373 (2)0.02987 (16)0.0204 (3)
H10.76180.26610.04240.024*
O10.1036 (3)0.14673 (18)0.12501 (14)0.0242 (3)
O20.4400 (3)0.17650 (19)0.23043 (14)0.0264 (3)
Cl10.57621 (15)0.30115 (7)0.47984 (5)0.03750 (16)
Br11.04171 (4)0.50705 (2)0.16904 (2)0.02356 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0170 (9)0.0181 (9)0.0196 (10)0.0047 (7)0.0063 (7)0.0075 (7)
C20.0177 (9)0.0181 (9)0.0223 (10)0.0019 (7)0.0058 (8)0.0091 (8)
C30.0241 (10)0.0215 (9)0.0200 (10)0.0003 (8)0.0033 (8)0.0070 (8)
C40.0310 (11)0.0269 (11)0.0194 (10)0.0054 (9)0.0097 (8)0.0121 (8)
C50.0239 (10)0.0219 (10)0.0264 (11)0.0013 (8)0.0099 (8)0.0115 (8)
C60.0202 (10)0.0197 (9)0.0222 (10)0.0002 (7)0.0058 (8)0.0072 (8)
C70.0208 (10)0.0194 (9)0.0194 (10)0.0048 (7)0.0066 (8)0.0079 (8)
C80.0341 (12)0.0413 (13)0.0194 (10)0.0026 (10)0.0017 (9)0.0117 (10)
N10.0157 (8)0.0256 (9)0.0198 (8)0.0002 (6)0.0058 (6)0.0084 (7)
O10.0159 (7)0.0315 (8)0.0243 (8)0.0010 (6)0.0052 (6)0.0101 (6)
O20.0219 (8)0.0402 (9)0.0198 (7)0.0013 (6)0.0049 (6)0.0152 (7)
Cl10.0549 (4)0.0381 (3)0.0208 (3)0.0052 (3)0.0122 (2)0.0132 (2)
Br10.02532 (14)0.02146 (14)0.02454 (14)0.00329 (9)0.00644 (9)0.01045 (10)
Geometric parameters (Å, º) top
C1—C61.400 (3)C5—H50.9500
C1—N11.401 (3)C6—H60.9500
C1—C21.404 (3)C7—O11.214 (3)
C2—C31.384 (3)C7—O21.345 (2)
C2—Br11.890 (2)C7—N11.354 (3)
C3—C41.381 (3)C8—O21.439 (3)
C3—H30.9500C8—H8A0.9800
C4—C51.381 (3)C8—H8B0.9800
C4—Cl11.744 (2)C8—H8C0.9800
C5—C61.384 (3)N1—H10.8800
C6—C1—N1122.34 (18)C5—C6—H6119.3
C6—C1—C2117.59 (19)C1—C6—H6119.3
N1—C1—C2120.06 (18)O1—C7—O2123.82 (19)
C3—C2—C1121.46 (19)O1—C7—N1126.17 (19)
C3—C2—Br1118.43 (15)O2—C7—N1110.00 (17)
C1—C2—Br1120.11 (15)O2—C8—H8A109.5
C4—C3—C2119.0 (2)O2—C8—H8B109.5
C4—C3—H3120.5H8A—C8—H8B109.5
C2—C3—H3120.5O2—C8—H8C109.5
C5—C4—C3121.44 (19)H8A—C8—H8C109.5
C5—C4—Cl1119.54 (17)H8B—C8—H8C109.5
C3—C4—Cl1119.02 (17)C7—N1—C1124.53 (17)
C4—C5—C6119.14 (19)C7—N1—H1117.7
C4—C5—H5120.4C1—N1—H1117.7
C6—C5—H5120.4C7—O2—C8115.05 (17)
C5—C6—C1121.39 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.192.885 (2)135
Symmetry code: (i) x+1, y, z.
 

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