1-(2-Bromo-4-methyl­phen­yl)-3,3-di­methyl­thio­urea

The bromo­methyl­phenyl and di­methyl­thio­urea groups of the mol­ecule of the title compound, C₁₀H₁₃BrN₂S, are inclined to one another at an inter­planar angle of 55.13 (6)°. In the crystal, mol­ecules are stacked along the b axis and inter­molecular N—H...S contacts form chains of mol­ecules along [010].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.115
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   0 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

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Computing details

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).

1-(2-Bromo-4-methylphenyl)-3,3-dimethylthiourea

Crystal data

C10H13BrN2S	F(000) = 552
Mr = 273.19	Dx = 1.566 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 12.2617 (7) Å	Cell parameters from 3751 reflections
b = 8.0222 (4) Å	θ = 4.2–73.6°
c = 12.7397 (7) Å	µ = 6.22 mm^−1
β = 112.380 (6)°	T = 296 K
V = 1158.76 (12) Å^3	Block, colourless
Z = 4	0.22 × 0.12 × 0.05 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	2035 reflections with I > 2σ(I)
ω scans	Rint = 0.030
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θmax = 74.1°, θmin = 4.3°
Tmin = 0.926, Tmax = 0.976	h = −14→15
7605 measured reflections	k = −9→9
2318 independent reflections	l = −12→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.072P)^2 + 0.3056P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2318 reflections	Δρmax = 0.54 e Å^−3
130 parameters	Δρmin = −0.64 e Å^−3

Special 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.26065 (3)	0.22909 (5)	0.48048 (3)	0.06494 (17)
S1	0.18412 (6)	0.22540 (8)	0.06795 (5)	0.0495 (2)
C2	0.1250 (2)	0.1405 (3)	0.3645 (2)	0.0454 (5)
N1	0.24617 (18)	0.0533 (3)	0.26170 (17)	0.0477 (5)
H1	0.2981	−0.0043	0.3139	0.057*
C1	0.1340 (2)	0.0699 (3)	0.26865 (19)	0.0416 (5)
N2	0.3930 (2)	0.0961 (3)	0.19709 (19)	0.0511 (5)
C8	0.2794 (2)	0.1197 (3)	0.18062 (19)	0.0422 (5)
C6	0.0329 (2)	0.0058 (3)	0.1861 (2)	0.0473 (6)
H6	0.0372	−0.0438	0.1218	0.057*
C10	0.4382 (3)	0.1476 (5)	0.1115 (3)	0.0662 (8)
H10A	0.3850	0.1113	0.0380	0.099*
H10B	0.5144	0.0984	0.1281	0.099*
H10C	0.4450	0.2668	0.1120	0.099*
C5	−0.0743 (2)	0.0146 (4)	0.1981 (2)	0.0495 (6)
H5	−0.1414	−0.0287	0.1415	0.059*
C3	0.0176 (3)	0.1482 (4)	0.3771 (2)	0.0524 (6)
H3	0.0137	0.1948	0.4424	0.063*
C4	−0.0834 (2)	0.0873 (4)	0.2936 (2)	0.0509 (6)
C9	0.4791 (2)	0.0276 (4)	0.3016 (3)	0.0614 (7)
H9A	0.4670	0.0750	0.3655	0.092*
H9B	0.5573	0.0538	0.3063	0.092*
H9C	0.4699	−0.0912	0.3019	0.092*
C7	−0.2015 (3)	0.0970 (5)	0.3057 (4)	0.0756 (9)
H7A	−0.1911	0.0734	0.3828	0.113*
H7B	−0.2545	0.0169	0.2562	0.113*
H7C	−0.2337	0.2069	0.2857	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0668 (3)	0.0716 (3)	0.0472 (2)	−0.01503 (14)	0.01142 (17)	−0.00997 (12)
S1	0.0580 (4)	0.0512 (4)	0.0351 (3)	−0.0007 (3)	0.0132 (3)	0.0014 (2)
C2	0.0495 (13)	0.0465 (13)	0.0379 (11)	−0.0033 (10)	0.0139 (10)	−0.0002 (9)
N1	0.0414 (10)	0.0630 (13)	0.0398 (10)	0.0077 (9)	0.0166 (9)	0.0107 (9)
C1	0.0420 (11)	0.0471 (12)	0.0380 (11)	0.0036 (9)	0.0179 (9)	0.0049 (9)
N2	0.0460 (11)	0.0609 (13)	0.0501 (11)	−0.0049 (10)	0.0226 (9)	0.0027 (10)
C8	0.0458 (12)	0.0453 (12)	0.0360 (11)	−0.0041 (9)	0.0161 (9)	−0.0058 (9)
C6	0.0494 (13)	0.0545 (14)	0.0372 (11)	0.0016 (11)	0.0155 (10)	−0.0024 (10)
C10	0.0652 (17)	0.081 (2)	0.0662 (18)	−0.0097 (16)	0.0408 (15)	−0.0004 (16)
C5	0.0405 (12)	0.0562 (14)	0.0474 (13)	0.0003 (10)	0.0117 (10)	0.0027 (11)
C3	0.0627 (15)	0.0547 (15)	0.0486 (13)	0.0032 (12)	0.0311 (12)	−0.0037 (11)
C4	0.0475 (13)	0.0550 (15)	0.0549 (14)	0.0060 (11)	0.0248 (11)	0.0075 (11)
C9	0.0436 (13)	0.0743 (19)	0.0638 (17)	−0.0032 (13)	0.0178 (12)	0.0084 (15)
C7	0.0566 (17)	0.091 (3)	0.090 (2)	0.0030 (16)	0.0412 (17)	0.000 (2)

Geometric parameters (Å, º)

Br1—C2	1.893 (2)	C10—H10B	0.9600
S1—C8	1.693 (2)	C10—H10C	0.9600
C2—C3	1.388 (4)	C5—C4	1.392 (4)
C2—C1	1.388 (3)	C5—H5	0.9300
N1—C8	1.355 (3)	C3—C4	1.379 (4)
N1—C1	1.418 (3)	C3—H3	0.9300
N1—H1	0.8600	C4—C7	1.515 (4)
C1—C6	1.383 (4)	C9—H9A	0.9600
N2—C8	1.340 (3)	C9—H9B	0.9600
N2—C9	1.456 (4)	C9—H9C	0.9600
N2—C10	1.459 (3)	C7—H7A	0.9600
C6—C5	1.382 (4)	C7—H7B	0.9600
C6—H6	0.9300	C7—H7C	0.9600
C10—H10A	0.9600
C3—C2—C1	121.1 (2)	H10B—C10—H10C	109.5
C3—C2—Br1	118.91 (19)	C6—C5—C4	121.0 (2)
C1—C2—Br1	119.99 (19)	C6—C5—H5	119.5
C8—N1—C1	126.2 (2)	C4—C5—H5	119.5
C8—N1—H1	116.9	C4—C3—C2	120.5 (2)
C1—N1—H1	116.9	C4—C3—H3	119.7
C6—C1—C2	118.2 (2)	C2—C3—H3	119.7
C6—C1—N1	121.8 (2)	C3—C4—C5	118.4 (2)
C2—C1—N1	119.8 (2)	C3—C4—C7	121.0 (3)
C8—N2—C9	123.0 (2)	C5—C4—C7	120.5 (3)
C8—N2—C10	120.7 (2)	N2—C9—H9A	109.5
C9—N2—C10	116.1 (2)	N2—C9—H9B	109.5
N2—C8—N1	114.9 (2)	H9A—C9—H9B	109.5
N2—C8—S1	122.94 (19)	N2—C9—H9C	109.5
N1—C8—S1	122.14 (19)	H9A—C9—H9C	109.5
C5—C6—C1	120.7 (2)	H9B—C9—H9C	109.5
C5—C6—H6	119.6	C4—C7—H7A	109.5
C1—C6—H6	119.6	C4—C7—H7B	109.5
N2—C10—H10A	109.5	H7A—C7—H7B	109.5
N2—C10—H10B	109.5	C4—C7—H7C	109.5
H10A—C10—H10B	109.5	H7A—C7—H7C	109.5
N2—C10—H10C	109.5	H7B—C7—H7C	109.5
H10A—C10—H10C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1^i	0.86	2.60	3.309 (2)	140

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.