Crystal structure of 2-(2,5-di­meth­oxy­phen­yl)benzo[d]thia­zole

The title compound was synthesized efficiently in the solid state by exploiting pepsin catalysis. The ring systems are nearly coplanar. A short intra­molecular S...O=C contact is observed.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.027
• wR factor = 0.084
• Data-to-parameter ratio = 38.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.21 Report
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13      ..O1       .       2.65 Ang.
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        192 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

2-(2,5-Dimethoxyphenyl)benzo[d]thiazole

Crystal data

C15H13NO2S	F(000) = 568
Mr = 271.32	Dx = 1.435 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6666 (2) Å	Cell parameters from 88513 reflections
b = 13.8922 (2) Å	θ = 2.8–38.4°
c = 6.26063 (10) Å	µ = 0.25 mm^−1
β = 100.1273 (14)°	T = 100 K
V = 1255.74 (3) Å^3	Block, colourless
Z = 4	0.22 × 0.22 × 0.15 mm

Data collection

XtaLAB Synergy, HyPix diffractometer	6759 independent reflections
Radiation source: micro-focus sealed X-ray tube	6156 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.023
ω scans	θmax = 38.3°, θmin = 2.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −24→25
Tmin = 0.927, Tmax = 1.000	k = −23→23
123768 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0489P)^2 + 0.2455P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6759 reflections	Δρmax = 0.62 e Å^−3
174 parameters	Δρmin = −0.19 e Å^−3
0 restraints

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.2606 (0.0025) x + 11.3686 (0.0009) y - 3.5208 (0.0006) z = 4.3561 (0.0009)

* -0.0113 (0.0003) S1 * 0.0122 (0.0004) C2 * 0.0073 (0.0004) N3 * -0.0022 (0.0005) C3A * -0.0178 (0.0004) C4 * 0.0029 (0.0005) C5 * 0.0151 (0.0005) C6 * -0.0033 (0.0005) C7 * -0.0029 (0.0005) C7A

Rms deviation of fitted atoms = 0.0101

- 1.6150 (0.0031) x + 11.4261 (0.0017) y - 3.3180 (0.0011) z = 4.1087 (0.0012)

Angle to previous plane (with approximate esd) = 5.381 ( 0.023 )

* -0.0035 (0.0003) C11 * 0.0058 (0.0004) C12 * -0.0025 (0.0004) C13 * -0.0031 (0.0004) C14 * 0.0054 (0.0004) C15 * -0.0020 (0.0004) C16 -0.0003 (0.0008) O1 0.0801 (0.0011) C17 0.0285 (0.0008) O2 0.1636 (0.0010) C18

Rms deviation of fitted atoms = 0.0040

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

	x	y	z	Uiso*/Ueq
S1	0.13465 (2)	0.49165 (2)	0.34350 (2)	0.01451 (4)
C2	0.24674 (4)	0.47726 (4)	0.28209 (8)	0.01188 (8)
N3	0.31247 (3)	0.52002 (3)	0.41668 (7)	0.01347 (7)
C3A	0.27752 (4)	0.56826 (4)	0.57771 (8)	0.01360 (8)
C4	0.33134 (4)	0.62033 (4)	0.74630 (9)	0.01695 (9)
H4	0.396755	0.623486	0.758537	0.020*
C5	0.28692 (5)	0.66707 (4)	0.89466 (9)	0.01963 (10)
H5	0.322334	0.703577	1.008219	0.024*
C6	0.19042 (5)	0.66133 (5)	0.87976 (10)	0.02095 (11)
H6	0.161650	0.694472	0.982862	0.025*
C7	0.13610 (5)	0.60805 (4)	0.71696 (10)	0.01924 (10)
H7	0.071002	0.603042	0.709129	0.023*
C7A	0.18087 (4)	0.56196 (4)	0.56475 (9)	0.01468 (8)
C11	0.26660 (3)	0.42388 (3)	0.09270 (8)	0.01131 (7)
C12	0.19879 (3)	0.37320 (4)	−0.05164 (8)	0.01179 (8)
C13	0.22303 (4)	0.32478 (4)	−0.22766 (8)	0.01295 (8)
H13	0.177114	0.290066	−0.323243	0.016*
C14	0.31402 (4)	0.32648 (4)	−0.26592 (8)	0.01283 (8)
H14	0.329903	0.293120	−0.386674	0.015*
C15	0.38132 (3)	0.37743 (4)	−0.12577 (8)	0.01215 (8)
C16	0.35765 (4)	0.42522 (4)	0.05254 (8)	0.01240 (8)
H16	0.404004	0.459248	0.148423	0.015*
O1	0.11061 (3)	0.37347 (3)	−0.00594 (7)	0.01587 (7)
C17	0.04056 (4)	0.32676 (5)	−0.15693 (10)	0.01998 (10)
H17A	0.036645	0.356648	−0.300050	0.030*
H17B	−0.019153	0.333071	−0.108453	0.030*
H17C	0.056005	0.258430	−0.166186	0.030*
O2	0.47191 (3)	0.38509 (3)	−0.15047 (7)	0.01691 (8)
C18	0.49545 (4)	0.34434 (5)	−0.34295 (10)	0.01952 (10)
H18A	0.454902	0.371139	−0.470203	0.029*
H18B	0.487554	0.274329	−0.340465	0.029*
H18C	0.560067	0.359596	−0.350301	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01415 (6)	0.01602 (6)	0.01373 (6)	0.00148 (4)	0.00352 (4)	−0.00175 (4)
C2	0.01436 (18)	0.01083 (17)	0.01076 (17)	0.00014 (14)	0.00307 (14)	0.00011 (13)
N3	0.01641 (18)	0.01302 (17)	0.01139 (16)	−0.00157 (13)	0.00354 (13)	−0.00175 (13)
C3A	0.0193 (2)	0.01086 (18)	0.01120 (17)	−0.00042 (15)	0.00426 (15)	−0.00038 (14)
C4	0.0236 (2)	0.0142 (2)	0.01336 (19)	−0.00312 (17)	0.00403 (17)	−0.00254 (15)
C5	0.0314 (3)	0.0140 (2)	0.0142 (2)	−0.00201 (19)	0.00606 (19)	−0.00317 (16)
C6	0.0321 (3)	0.0161 (2)	0.0167 (2)	0.0025 (2)	0.0097 (2)	−0.00306 (17)
C7	0.0239 (2)	0.0180 (2)	0.0176 (2)	0.00356 (19)	0.00846 (19)	−0.00219 (18)
C7A	0.0190 (2)	0.01267 (19)	0.01312 (18)	0.00175 (15)	0.00489 (15)	−0.00059 (15)
C11	0.01340 (17)	0.01037 (17)	0.01029 (16)	0.00010 (13)	0.00241 (13)	−0.00034 (13)
C12	0.01206 (17)	0.01134 (18)	0.01187 (17)	0.00064 (13)	0.00182 (14)	−0.00025 (13)
C13	0.01318 (18)	0.01267 (18)	0.01268 (18)	0.00015 (14)	0.00138 (14)	−0.00222 (14)
C14	0.01418 (18)	0.01223 (18)	0.01217 (18)	0.00012 (14)	0.00257 (14)	−0.00183 (14)
C15	0.01276 (18)	0.01177 (18)	0.01232 (17)	−0.00073 (14)	0.00333 (14)	−0.00073 (14)
C16	0.01365 (18)	0.01212 (18)	0.01161 (17)	−0.00128 (14)	0.00273 (14)	−0.00118 (14)
O1	0.01170 (15)	0.01927 (18)	0.01672 (16)	−0.00048 (12)	0.00270 (12)	−0.00411 (13)
C17	0.01240 (19)	0.0272 (3)	0.0192 (2)	−0.00078 (18)	−0.00011 (17)	−0.0035 (2)
O2	0.01379 (16)	0.02132 (19)	0.01681 (17)	−0.00358 (13)	0.00599 (13)	−0.00600 (14)
C18	0.0175 (2)	0.0238 (3)	0.0190 (2)	−0.00194 (19)	0.00813 (18)	−0.00580 (19)

Geometric parameters (Å, º)

S1—C7A	1.7327 (6)	C15—O2	1.3686 (6)
S1—C2	1.7642 (5)	C15—C16	1.3941 (7)
C2—N3	1.3064 (7)	O1—C17	1.4243 (7)
C2—C11	1.4704 (7)	O2—C18	1.4276 (7)
N3—C3A	1.3820 (7)	C4—H4	0.9500
C3A—C4	1.4027 (8)	C5—H5	0.9500
C3A—C7A	1.4082 (8)	C6—H6	0.9500
C4—C5	1.3862 (8)	C7—H7	0.9500
C5—C6	1.4043 (10)	C13—H13	0.9500
C6—C7	1.3912 (9)	C14—H14	0.9500
C7—C7A	1.4032 (8)	C16—H16	0.9500
C11—C16	1.4017 (7)	C17—H17A	0.9800
C11—C12	1.4091 (7)	C17—H17B	0.9800
C12—O1	1.3728 (6)	C17—H17C	0.9800
C12—C13	1.3896 (7)	C18—H18A	0.9800
C13—C14	1.3969 (7)	C18—H18B	0.9800
C14—C15	1.3930 (7)	C18—H18C	0.9800
C7A—S1—C2	89.40 (3)	C15—O2—C18	116.63 (4)
N3—C2—C11	121.40 (5)	C5—C4—H4	120.7
N3—C2—S1	114.72 (4)	C3A—C4—H4	120.7
C11—C2—S1	123.86 (4)	C4—C5—H5	119.5
C2—N3—C3A	111.39 (5)	C6—C5—H5	119.5
N3—C3A—C4	124.55 (5)	C7—C6—H6	119.4
N3—C3A—C7A	115.25 (5)	C5—C6—H6	119.4
C4—C3A—C7A	120.20 (5)	C6—C7—H7	121.2
C5—C4—C3A	118.50 (6)	C7A—C7—H7	121.2
C4—C5—C6	121.05 (6)	C12—C13—H13	119.6
C7—C6—C5	121.30 (5)	C14—C13—H13	119.6
C6—C7—C7A	117.66 (6)	C15—C14—H14	120.2
C7—C7A—C3A	121.26 (5)	C13—C14—H14	120.2
C7—C7A—S1	129.51 (5)	C15—C16—H16	119.5
C3A—C7A—S1	109.23 (4)	C11—C16—H16	119.5
C16—C11—C12	118.61 (4)	O1—C17—H17A	109.5
C16—C11—C2	117.91 (4)	O1—C17—H17B	109.5
C12—C11—C2	123.47 (4)	H17A—C17—H17B	109.5
O1—C12—C13	123.26 (5)	O1—C17—H17C	109.5
O1—C12—C11	116.71 (4)	H17A—C17—H17C	109.5
C13—C12—C11	120.02 (5)	H17B—C17—H17C	109.5
C12—C13—C14	120.88 (5)	O2—C18—H18A	109.5
C15—C14—C13	119.54 (5)	O2—C18—H18B	109.5
O2—C15—C14	124.24 (5)	H18A—C18—H18B	109.5
O2—C15—C16	115.90 (4)	O2—C18—H18C	109.5
C14—C15—C16	119.85 (5)	H18A—C18—H18C	109.5
C15—C16—C11	121.10 (5)	H18B—C18—H18C	109.5
C12—O1—C17	117.16 (4)
C7A—S1—C2—N3	0.85 (4)	S1—C2—C11—C16	174.46 (4)
C7A—S1—C2—C11	−177.67 (4)	N3—C2—C11—C12	177.18 (5)
C11—C2—N3—C3A	177.97 (4)	S1—C2—C11—C12	−4.38 (7)
S1—C2—N3—C3A	−0.60 (6)	C16—C11—C12—O1	179.80 (5)
C2—N3—C3A—C4	179.57 (5)	C2—C11—C12—O1	−1.36 (7)
C2—N3—C3A—C7A	−0.08 (7)	C16—C11—C12—C13	0.89 (7)
N3—C3A—C4—C5	178.64 (5)	C2—C11—C12—C13	179.73 (5)
C7A—C3A—C4—C5	−1.73 (8)	O1—C12—C13—C14	−179.65 (5)
C3A—C4—C5—C6	1.12 (9)	C11—C12—C13—C14	−0.81 (8)
C4—C5—C6—C7	0.50 (10)	C12—C13—C14—C15	−0.03 (8)
C5—C6—C7—C7A	−1.46 (9)	C13—C14—C15—O2	−178.84 (5)
C6—C7—C7A—C3A	0.83 (9)	C13—C14—C15—C16	0.78 (8)
C6—C7—C7A—S1	−179.51 (5)	O2—C15—C16—C11	178.96 (5)
N3—C3A—C7A—C7	−179.57 (5)	C14—C15—C16—C11	−0.69 (8)
C4—C3A—C7A—C7	0.76 (8)	C12—C11—C16—C15	−0.14 (7)
N3—C3A—C7A—S1	0.70 (6)	C2—C11—C16—C15	−179.05 (5)
C4—C3A—C7A—S1	−178.96 (4)	C13—C12—O1—C17	−4.35 (8)
C2—S1—C7A—C7	179.48 (6)	C11—C12—O1—C17	176.78 (5)
C2—S1—C7A—C3A	−0.82 (4)	C14—C15—O2—C18	5.35 (8)
N3—C2—C11—C16	−3.97 (7)	C16—C15—O2—C18	−174.28 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1^i	0.95	2.65	3.5113 (7)	151
C18—H18C···N3^ii	0.98	2.60	3.4867 (8)	151

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