In the title molecule, C
8H
7BrClNO
2, 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
CCDC reference: 1815604
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(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
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
C8H7BrClNO2 | Z = 2 |
Mr = 264.51 | F(000) = 260 |
Triclinic, P1 | Dx = 1.841 Mg m−3 |
a = 4.6637 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.4598 (6) Å | Cell parameters from 2127 reflections |
c = 11.9898 (7) Å | θ = 5.1–74.1° |
α = 111.639 (5)° | µ = 8.19 mm−1 |
β = 101.035 (5)° | T = 150 K |
γ = 93.712 (5)° | Block, colourless |
V = 477.25 (5) Å3 | 0.31 × 0.20 × 0.15 mm |
Data collection top
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 1777 reflections with I > 2σ(I) |
ω scans | Rint = 0.019 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014) | θmax = 74.0°, θmin = 4.1° |
Tmin = 0.776, Tmax = 0.891 | h = −5→5 |
2938 measured reflections | k = −10→11 |
1847 independent reflections | l = −14→11 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-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 reflections | Δρmax = 0.30 e Å−3 |
119 parameters | Δρmin = −0.61 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 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) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 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) top
C1—C6 | 1.400 (3) | C5—H5 | 0.9500 |
C1—N1 | 1.401 (3) | C6—H6 | 0.9500 |
C1—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) |
C3—C4 | 1.381 (3) | C8—O2 | 1.439 (3) |
C3—H3 | 0.9500 | C8—H8A | 0.9800 |
C4—C5 | 1.381 (3) | C8—H8B | 0.9800 |
C4—Cl1 | 1.744 (2) | C8—H8C | 0.9800 |
C5—C6 | 1.384 (3) | N1—H1 | 0.8800 |
| | | |
C6—C1—N1 | 122.34 (18) | C5—C6—H6 | 119.3 |
C6—C1—C2 | 117.59 (19) | C1—C6—H6 | 119.3 |
N1—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 | 109.5 |
C4—C3—C2 | 119.0 (2) | O2—C8—H8B | 109.5 |
C4—C3—H3 | 120.5 | H8A—C8—H8B | 109.5 |
C2—C3—H3 | 120.5 | O2—C8—H8C | 109.5 |
C5—C4—C3 | 121.44 (19) | H8A—C8—H8C | 109.5 |
C5—C4—Cl1 | 119.54 (17) | H8B—C8—H8C | 109.5 |
C3—C4—Cl1 | 119.02 (17) | C7—N1—C1 | 124.53 (17) |
C4—C5—C6 | 119.14 (19) | C7—N1—H1 | 117.7 |
C4—C5—H5 | 120.4 | C1—N1—H1 | 117.7 |
C6—C5—H5 | 120.4 | C7—O2—C8 | 115.05 (17) |
C5—C6—C1 | 121.39 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 | 2.19 | 2.885 (2) | 135 |
Symmetry code: (i) x+1, y, z. |