Crystal structure of 1-(1,3-benzo­thia­zol-2-yl)-3-(4-bromo­benzo­yl)thio­urea

Sow, S.; Thiam, M.; Odame, F.; Thiam, E.I.; Diouf, O.; Ellena, J.; Gaye, M.; Tshentu, Z.

doi:10.1107/S2056989024004742

Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea

S. Sow, M. Thiam, F. Odame, E. I. Thiam, O. Diouf, J. Ellena, M. Gaye and Z. Tshentu

A thiourea derivative with two dissimilar functional groups was prepared and characterized. In the crystal, pairs of adjacent molecules interact via intermolecular hydrogen bonds of type C—H

N, C—H

S and N—H

S, resulting in molecular layers parallel to the ac plane.

Keywords: crystal structure; 4-bromobenzoylchloride; 2-benzothiazole; potassium cyanate; thiourea.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024004742/pk2706sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989024004742/pk2706Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024004742/pk2706Isup3.cml Supplementary material

CCDC reference: 2341267

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.024
wR factor = 0.057
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3       ..H15      .       1.91 Ang.
                                                      x,y,z  =      1_555 Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N3       --H3       .     Please Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
              H2    H3
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3       ..S2       .       2.96 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H14      ..S2       .       2.95 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H2A      ..S1       .       3.00 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H5       ..N1       .       2.68 Ang.
PLAT484_ALERT_4_G Round D-H..A Angle Rep for N3       ..S2       .        132 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for N2       ..O1       .        139 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C14      ..S2       .        146 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C2       ..S1       .        161 Degree
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C8 Note
PLAT797_ALERT_4_G N-Atom in CIF Coordinate List Out-of-Sequence ..         N1 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
               -1  0  1,   1  0  1,   0  0  2,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       1.77 Note
              Predicted wR2: Based on SigI   2  3.23 or SHELX Weight  5.74       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

1-(1,3-Benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea top

Crystal data top

C₁₅H₁₀BrN₃OS₂	F(000) = 784
M_r = 392.29	D_x = 1.728 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5009 (5) Å	Cell parameters from 9123 reflections
b = 6.4130 (2) Å	θ = 3.1–33.9°
c = 17.9147 (7) Å	µ = 3.01 mm⁻¹
β = 103.606 (4)°	T = 100 K
V = 1507.54 (10) Å³	Block, light colourless
Z = 4	0.10 × 0.06 × 0.06 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2581 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.041
ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	h = −16→16
T_min = 0.804, T_max = 0.986	k = −8→8
18792 measured reflections	l = −22→21
3074 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0191P)² + 1.3729P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3074 reflections	Δρ_max = 0.35 e Å⁻³
199 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints

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	U_iso*/U_eq
Br1	0.07298 (2)	−0.50717 (3)	0.27034 (2)	0.01865 (7)
S1	0.24869 (4)	0.98772 (8)	0.63447 (3)	0.01659 (12)
S2	0.10718 (4)	0.61809 (8)	0.59446 (3)	0.02191 (13)
O1	0.29683 (11)	0.3918 (2)	0.43225 (8)	0.0182 (3)
N3	0.16341 (14)	0.3897 (3)	0.48987 (10)	0.0172 (4)
H3	0.106967	0.322341	0.490909	0.021*
N1	0.38000 (13)	0.9461 (3)	0.54899 (10)	0.0155 (4)
N2	0.26397 (13)	0.6774 (3)	0.52923 (10)	0.0148 (4)
H2	0.298111	0.627829	0.496902	0.018*
C10	0.18323 (16)	0.1035 (3)	0.40497 (12)	0.0145 (4)
C11	0.24401 (17)	0.0071 (3)	0.36228 (12)	0.0183 (4)
H11	0.307296	0.068130	0.359855	0.022*
C8	0.18301 (16)	0.5657 (3)	0.53592 (12)	0.0167 (4)
C9	0.22053 (16)	0.3057 (3)	0.44251 (12)	0.0152 (4)
C13	0.12063 (17)	−0.2631 (3)	0.32704 (12)	0.0162 (4)
C6	0.40504 (15)	1.1298 (3)	0.59049 (11)	0.0139 (4)
C4	0.49993 (17)	1.4411 (3)	0.62991 (13)	0.0208 (5)
H4	0.553913	1.533414	0.626970	0.025*
C12	0.21305 (17)	−0.1773 (3)	0.32321 (13)	0.0199 (5)
H12	0.254784	−0.243387	0.294303	0.024*
C14	0.05956 (16)	−0.1731 (3)	0.37025 (13)	0.0178 (4)
H14	−0.003263	−0.235813	0.372947	0.021*
C3	0.43652 (17)	1.4872 (3)	0.67971 (13)	0.0200 (5)
H3A	0.448160	1.611081	0.709576	0.024*
C2	0.35797 (17)	1.3570 (3)	0.68620 (12)	0.0196 (5)
H2A	0.315825	1.387679	0.720416	0.023*
C1	0.34260 (16)	1.1782 (3)	0.64059 (12)	0.0158 (4)
C7	0.30166 (16)	0.8612 (3)	0.56641 (12)	0.0144 (4)
C15	0.09165 (17)	0.0100 (3)	0.40956 (13)	0.0185 (4)
H15	0.050806	0.072576	0.439944	0.022*
C5	0.48474 (16)	1.2633 (3)	0.58523 (12)	0.0179 (4)
H5	0.527660	1.232504	0.551582	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02144 (12)	0.01489 (11)	0.01875 (12)	−0.00221 (8)	0.00297 (8)	−0.00376 (8)
S1	0.0190 (3)	0.0164 (2)	0.0168 (3)	−0.0037 (2)	0.0090 (2)	−0.0033 (2)
S2	0.0203 (3)	0.0227 (3)	0.0263 (3)	−0.0068 (2)	0.0127 (2)	−0.0073 (2)
O1	0.0163 (8)	0.0172 (7)	0.0223 (8)	−0.0017 (6)	0.0071 (6)	−0.0016 (6)
N3	0.0164 (9)	0.0160 (9)	0.0212 (10)	−0.0064 (7)	0.0087 (8)	−0.0048 (7)
N1	0.0149 (9)	0.0163 (8)	0.0154 (9)	−0.0014 (7)	0.0036 (7)	0.0004 (7)
N2	0.0159 (9)	0.0147 (8)	0.0158 (9)	−0.0021 (7)	0.0074 (7)	−0.0038 (7)
C10	0.0162 (11)	0.0115 (10)	0.0150 (11)	−0.0002 (8)	0.0020 (9)	0.0018 (8)
C11	0.0174 (11)	0.0187 (11)	0.0199 (11)	−0.0035 (9)	0.0070 (9)	−0.0006 (9)
C8	0.0173 (11)	0.0165 (10)	0.0160 (11)	−0.0008 (8)	0.0035 (9)	0.0001 (8)
C9	0.0150 (11)	0.0161 (10)	0.0136 (11)	0.0012 (8)	0.0014 (9)	0.0034 (8)
C13	0.0204 (12)	0.0114 (9)	0.0147 (11)	−0.0012 (8)	−0.0002 (9)	−0.0008 (8)
C6	0.0139 (11)	0.0141 (10)	0.0123 (10)	0.0006 (8)	0.0004 (8)	0.0003 (8)
C4	0.0182 (12)	0.0189 (11)	0.0231 (12)	−0.0050 (9)	0.0004 (9)	0.0008 (8)
C12	0.0209 (12)	0.0195 (11)	0.0210 (12)	0.0005 (9)	0.0086 (10)	−0.0024 (9)
C14	0.0147 (11)	0.0166 (10)	0.0233 (12)	−0.0020 (8)	0.0066 (9)	0.0003 (8)
C3	0.0231 (12)	0.0151 (10)	0.0185 (11)	−0.0018 (9)	−0.0016 (9)	−0.0037 (8)
C2	0.0219 (12)	0.0198 (11)	0.0161 (11)	0.0002 (9)	0.0026 (9)	−0.0021 (8)
C1	0.0158 (11)	0.0171 (10)	0.0142 (11)	−0.0009 (8)	0.0029 (9)	0.0011 (8)
C7	0.0155 (11)	0.0152 (10)	0.0124 (10)	−0.0002 (8)	0.0031 (8)	0.0013 (8)
C15	0.0187 (11)	0.0175 (10)	0.0210 (12)	−0.0002 (9)	0.0081 (9)	−0.0018 (9)
C5	0.0155 (11)	0.0184 (10)	0.0197 (11)	−0.0024 (8)	0.0037 (9)	−0.0008 (8)

Geometric parameters (Å, º) top

Br1—C13	1.894 (2)	C11—C12	1.388 (3)
S1—C1	1.745 (2)	C13—C12	1.380 (3)
S1—C7	1.751 (2)	C13—C14	1.383 (3)
S2—C8	1.663 (2)	C6—C1	1.403 (3)
O1—C9	1.220 (2)	C6—C5	1.396 (3)
N3—H3	0.8800	C4—H4	0.9500
N3—C8	1.386 (3)	C4—C3	1.406 (3)
N3—C9	1.383 (3)	C4—C5	1.380 (3)
N1—C6	1.392 (3)	C12—H12	0.9500
N1—C7	1.291 (3)	C14—H14	0.9500
N2—H2	0.8800	C14—C15	1.386 (3)
N2—C8	1.335 (3)	C3—H3A	0.9500
N2—C7	1.390 (3)	C3—C2	1.376 (3)
C10—C11	1.391 (3)	C2—H2A	0.9500
C10—C9	1.492 (3)	C2—C1	1.395 (3)
C10—C15	1.394 (3)	C15—H15	0.9500
C11—H11	0.9500	C5—H5	0.9500

C1—S1—C7	87.61 (9)	C5—C4—H4	119.6
C8—N3—H3	115.6	C5—C4—C3	120.8 (2)
C9—N3—H3	115.6	C11—C12—H12	120.6
C9—N3—C8	128.78 (18)	C13—C12—C11	118.89 (19)
C7—N1—C6	109.74 (17)	C13—C12—H12	120.6
C8—N2—H2	115.6	C13—C14—H14	120.6
C8—N2—C7	128.81 (17)	C13—C14—C15	118.80 (19)
C7—N2—H2	115.6	C15—C14—H14	120.6
C11—C10—C9	116.96 (18)	C4—C3—H3A	119.3
C11—C10—C15	119.18 (19)	C2—C3—C4	121.5 (2)
C15—C10—C9	123.85 (18)	C2—C3—H3A	119.3
C10—C11—H11	119.7	C3—C2—H2A	121.3
C12—C11—C10	120.6 (2)	C3—C2—C1	117.4 (2)
C12—C11—H11	119.7	C1—C2—H2A	121.3
N3—C8—S2	118.68 (15)	C6—C1—S1	110.00 (15)
N2—C8—S2	125.92 (16)	C2—C1—S1	128.16 (16)
N2—C8—N3	115.40 (17)	C2—C1—C6	121.83 (19)
O1—C9—N3	121.88 (19)	N1—C7—S1	117.69 (15)
O1—C9—C10	122.19 (18)	N1—C7—N2	118.04 (18)
N3—C9—C10	115.92 (18)	N2—C7—S1	124.26 (15)
C12—C13—Br1	119.98 (16)	C10—C15—H15	119.7
C12—C13—C14	121.79 (19)	C14—C15—C10	120.69 (19)
C14—C13—Br1	118.22 (16)	C14—C15—H15	119.7
N1—C6—C1	114.95 (18)	C6—C5—H5	120.7
N1—C6—C5	125.29 (18)	C4—C5—C6	118.65 (19)
C5—C6—C1	119.76 (18)	C4—C5—H5	120.7
C3—C4—H4	119.6

Br1—C13—C12—C11	176.90 (16)	C12—C13—C14—C15	1.1 (3)
Br1—C13—C14—C15	−177.46 (16)	C14—C13—C12—C11	−1.7 (3)
N1—C6—C1—S1	−0.6 (2)	C3—C4—C5—C6	0.0 (3)
N1—C6—C1—C2	179.95 (19)	C3—C2—C1—S1	−178.55 (17)
N1—C6—C5—C4	179.7 (2)	C3—C2—C1—C6	0.8 (3)
C10—C11—C12—C13	0.4 (3)	C1—S1—C7—N1	0.05 (18)
C11—C10—C9—O1	5.2 (3)	C1—S1—C7—N2	−178.98 (19)
C11—C10—C9—N3	−174.74 (18)	C1—C6—C5—C4	0.0 (3)
C11—C10—C15—C14	−2.0 (3)	C7—S1—C1—C6	0.32 (16)
C8—N3—C9—O1	−4.8 (3)	C7—S1—C1—C2	179.7 (2)
C8—N3—C9—C10	175.1 (2)	C7—N1—C6—C1	0.7 (3)
C8—N2—C7—S1	1.2 (3)	C7—N1—C6—C5	−179.1 (2)
C8—N2—C7—N1	−177.8 (2)	C7—N2—C8—S2	−2.1 (3)
C9—N3—C8—S2	−173.64 (17)	C7—N2—C8—N3	178.90 (19)
C9—N3—C8—N2	5.5 (3)	C15—C10—C11—C12	1.5 (3)
C9—C10—C11—C12	−177.60 (19)	C15—C10—C9—O1	−173.8 (2)
C9—C10—C15—C14	177.0 (2)	C15—C10—C9—N3	6.2 (3)
C13—C14—C15—C10	0.7 (3)	C5—C6—C1—S1	179.10 (16)
C6—N1—C7—S1	−0.4 (2)	C5—C6—C1—C2	−0.3 (3)
C6—N1—C7—N2	178.69 (17)	C5—C4—C3—C2	0.5 (3)
C4—C3—C2—C1	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S2ⁱ	0.88	2.96	3.6102 (19)	132
N2—H2···O1	0.88	1.90	2.633 (2)	139
C14—H14···S2ⁱⁱ	0.95	2.95	3.779 (2)	146
C2—H2A···S1ⁱⁱⁱ	0.95	3.00	3.908 (2)	161
C5—H5···N1^iv	0.95	2.68	3.604 (3)	165

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+1.

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Crystal structure of 1-(1,3-benzo­thia­zol-2-yl)-3-(4-bromo­benzo­yl)thio­urea

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea