1,3,5-Tri­chloro-1λ⁶,2,4,6-thia­triazin-1-one

In the title compound, C₂Cl₃N₃OS, there are four independent mol­ecules in the asymmetric unit; their geometries are the same within experimental error. The six atoms of the thia­triazine ring and the 3,5-chloro atoms are all essentially coplanar.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](N-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.075
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1A   ..  N3A     ..       2.93 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.681     0.795
            Tmin and Tmax expected:      0.538     0.789
            RR =      1.256
            Please check that your absorption correction is appropriate.
PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound ..          ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.27
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1C   ..  O1A     ..       3.04 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1D   ..  O1B     ..       3.08 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2B   ..  N1B     ..       3.25 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2C   ..  N3C     ..       3.29 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2D   ..  N3C     ..       3.22 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3A   ..  N3D     ..       3.20 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3B   ..  N3B     ..       3.10 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3D   ..  N1A     ..       3.16 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1B    ..  C2D     ..       2.98 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1C    ..  C2C     ..       2.98 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1997-2003); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,3,5-Trichloro-1λ⁶,2,4,6-thiatriazin-1-one

Crystal data

C2Cl3N3OS	F(000) = 1728
Mr = 220.46	Dx = 2.027 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19673 reflections
a = 18.6270 (3) Å	θ = 2.6–27.5°
b = 7.3160 (1) Å	µ = 1.48 mm^−1
c = 21.2340 (5) Å	T = 150 K
β = 93.1840 (7)°	Plate, white
V = 2889.20 (9) Å^3	0.43 × 0.38 × 0.16 mm
Z = 16

Data collection

Nonius KappaCCD diffractometer	6606 independent reflections
Radiation source: fine-focus sealed tube	5166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.8°
φ scans and ω scans with κ offsets	h = −24→24
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −9→9
Tmin = 0.681, Tmax = 0.795	l = −20→27
19673 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.032	Secondary atom site location: difference Fourier map
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0235P)^2 + 0.8966P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
6606 reflections	Δρmax = 0.38 e Å^−3
362 parameters	Δρmin = −0.43 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

- 0.8725 (0.0073) x - 0.7635 (0.0025) y + 21.1173 (0.0009) z = 18.2115 (0.0037)

* 0.0252 (0.0011) S1A * 0.0058 (0.0016) N1A * -0.0192 (0.0015) N2A * -0.0134 (0.0016) N3A * -0.0088 (0.0018) C1A * 0.0010 (0.0020) C2A * 0.0083 (0.0010) Cl1A * 0.0010 (0.0011) Cl3A

Rms deviation of fitted atoms = 0.0131

- 1.2175 (0.0053) x + 3.9267 (0.0023) y + 17.9120 (0.0043) z = 13.6859 (0.0036)

Angle to previous plane (with approximate e.s.d.) = 38.49 (0.02)

* 0.0068 (0.0009) S1B * 0.0497 (0.0015) N1B * -0.0228 (0.0013) N2B * -0.0033 (0.0014) N3B * 0.0091 (0.0018) C1B * 0.0195 (0.0018) C2B * -0.0223 (0.0009) Cl1B * -0.0368 (0.0010) Cl3B

Rms deviation of fitted atoms = 0.0259

5.7275 (0.0051) x + 4.0123 (0.0024) y + 16.1237 (0.0049) z = 16.8501 (0.0029)

Angle to previous plane (with approximate e.s.d.) = 21.81 (0.04)

* -0.0246 (0.0010) S1C * 0.0329 (0.0014) N1C * 0.0290 (0.0014) N2C * -0.0866 (0.0015) N3C * -0.0237 (0.0018) C1C * -0.0210 (0.0018) C2C * 0.0467 (0.0010) Cl1C * 0.0474 (0.0009) Cl3C

Rms deviation of fitted atoms = 0.0439

7.9325 (0.0051) x - 4.3321 (0.0024) y + 14.0018 (0.0057) z = 10.5685 (0.0043)

Angle to previous plane (with approximate e.s.d.) = 70.23 (0.02)

* 0.0764 (0.0010) S1D * 0.0942 (0.0016) N1D * -0.1045 (0.0014) N2D * -0.0194 (0.0014) N3D * 0.0006 (0.0019) C1D * 0.0201 (0.0019) C2D * -0.0079 (0.0010) Cl1D * -0.0596 (0.0010) Cl3D

Rms deviation of fitted atoms = 0.0613

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Cl1A	0.46836 (3)	1.16492 (7)	0.92426 (3)	0.03069 (15)
Cl2A	0.58836 (3)	0.60828 (8)	0.82751 (3)	0.02941 (14)
Cl3A	0.33045 (4)	0.56048 (9)	0.89636 (3)	0.04118 (17)
S1A	0.54442 (3)	0.65218 (7)	0.90966 (3)	0.02540 (14)
O1A	0.59067 (10)	0.5702 (2)	0.95665 (8)	0.0380 (5)
N1A	0.40886 (11)	0.8490 (3)	0.91026 (9)	0.0268 (4)
N2A	0.53844 (11)	0.8669 (2)	0.91508 (9)	0.0264 (4)
N3A	0.46784 (11)	0.5596 (3)	0.90133 (11)	0.0328 (5)
C1A	0.47243 (13)	0.9331 (3)	0.91524 (10)	0.0227 (5)
C2A	0.41205 (13)	0.6694 (3)	0.90367 (11)	0.0266 (5)
Cl1B	0.56508 (3)	0.11527 (7)	0.77596 (3)	0.02760 (14)
Cl2B	0.40911 (3)	0.68225 (7)	0.74322 (3)	0.02751 (14)
Cl3B	0.29050 (3)	0.05962 (8)	0.76868 (3)	0.03489 (16)
S1B	0.41431 (3)	0.44791 (7)	0.69441 (3)	0.01954 (13)
O1B	0.41034 (9)	0.5013 (2)	0.63024 (7)	0.0274 (4)
N1B	0.42677 (10)	0.1177 (2)	0.77005 (9)	0.0223 (4)
N2B	0.48815 (10)	0.3584 (2)	0.71739 (9)	0.0210 (4)
N3B	0.34766 (10)	0.3317 (2)	0.71480 (9)	0.0247 (4)
C1B	0.48397 (12)	0.2082 (3)	0.75182 (10)	0.0198 (5)
C2B	0.36338 (12)	0.1848 (3)	0.74935 (11)	0.0220 (5)
Cl1C	0.82440 (3)	0.72893 (9)	0.57371 (3)	0.03527 (16)
Cl2C	0.70117 (3)	0.15260 (8)	0.64321 (3)	0.03180 (15)
Cl3C	0.57192 (3)	0.76398 (8)	0.65472 (3)	0.03276 (15)
S1C	0.72626 (3)	0.38444 (7)	0.68987 (3)	0.02360 (14)
O1C	0.75337 (10)	0.3278 (2)	0.75035 (8)	0.0357 (4)
N1C	0.78386 (10)	0.4802 (3)	0.64914 (10)	0.0268 (5)
N2C	0.65410 (10)	0.4979 (2)	0.69060 (9)	0.0248 (4)
N3C	0.69789 (10)	0.7098 (2)	0.61513 (9)	0.0215 (4)
C1C	0.76103 (12)	0.6272 (3)	0.61718 (11)	0.0228 (5)
C2C	0.65057 (12)	0.6422 (3)	0.65284 (11)	0.0217 (5)
Cl1D	0.54085 (3)	0.36538 (10)	0.56087 (3)	0.04021 (17)
Cl2D	0.64993 (4)	−0.17801 (8)	0.47251 (3)	0.03842 (17)
Cl3D	0.77259 (3)	0.41874 (9)	0.44240 (3)	0.03777 (17)
S1D	0.61442 (3)	0.04320 (7)	0.42553 (3)	0.02126 (13)
O1D	0.57826 (9)	−0.0190 (2)	0.36924 (7)	0.0285 (4)
N1D	0.65706 (10)	0.3591 (3)	0.50037 (9)	0.0241 (4)
N2D	0.56357 (10)	0.1417 (3)	0.47189 (9)	0.0255 (4)
N3D	0.68466 (10)	0.1593 (2)	0.41480 (9)	0.0242 (4)
C1D	0.59390 (13)	0.2787 (3)	0.50460 (11)	0.0240 (5)
C2D	0.69609 (12)	0.2977 (3)	0.45398 (11)	0.0242 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0420 (4)	0.0179 (3)	0.0325 (3)	0.0059 (2)	0.0053 (3)	−0.0035 (2)
Cl2A	0.0295 (3)	0.0308 (3)	0.0286 (3)	0.0005 (2)	0.0074 (3)	−0.0058 (2)
Cl3A	0.0311 (4)	0.0381 (4)	0.0555 (5)	−0.0092 (3)	0.0131 (3)	0.0038 (3)
S1A	0.0289 (3)	0.0201 (3)	0.0277 (3)	0.0065 (2)	0.0057 (3)	0.0003 (2)
O1A	0.0495 (12)	0.0357 (10)	0.0284 (10)	0.0225 (9)	0.0003 (9)	0.0009 (7)
N1A	0.0277 (12)	0.0244 (10)	0.0288 (12)	0.0039 (9)	0.0076 (9)	0.0023 (8)
N2A	0.0278 (12)	0.0200 (10)	0.0317 (12)	0.0029 (8)	0.0048 (9)	−0.0027 (8)
N3A	0.0309 (12)	0.0196 (10)	0.0490 (14)	0.0007 (9)	0.0131 (10)	0.0054 (9)
C1A	0.0315 (14)	0.0191 (11)	0.0178 (12)	0.0044 (10)	0.0043 (10)	−0.0006 (8)
C2A	0.0293 (14)	0.0251 (13)	0.0265 (13)	−0.0003 (10)	0.0101 (11)	0.0042 (9)
Cl1B	0.0215 (3)	0.0270 (3)	0.0339 (3)	0.0055 (2)	−0.0010 (2)	0.0034 (2)
Cl2B	0.0320 (3)	0.0212 (3)	0.0296 (3)	0.0046 (2)	0.0045 (3)	−0.0034 (2)
Cl3B	0.0232 (3)	0.0337 (3)	0.0489 (4)	−0.0067 (3)	0.0123 (3)	0.0045 (3)
S1B	0.0185 (3)	0.0188 (3)	0.0215 (3)	0.0023 (2)	0.0035 (2)	0.0001 (2)
O1B	0.0299 (10)	0.0319 (9)	0.0206 (9)	0.0062 (7)	0.0025 (7)	0.0025 (7)
N1B	0.0251 (11)	0.0234 (10)	0.0188 (10)	−0.0008 (8)	0.0037 (8)	0.0006 (7)
N2B	0.0172 (10)	0.0199 (9)	0.0259 (11)	0.0009 (7)	0.0026 (8)	0.0019 (8)
N3B	0.0181 (10)	0.0225 (10)	0.0342 (12)	0.0003 (8)	0.0059 (9)	0.0015 (8)
C1B	0.0202 (12)	0.0199 (11)	0.0195 (12)	0.0011 (9)	0.0026 (9)	−0.0043 (9)
C2B	0.0206 (12)	0.0234 (12)	0.0224 (12)	−0.0022 (9)	0.0062 (10)	−0.0046 (9)
Cl1C	0.0297 (3)	0.0377 (4)	0.0392 (4)	−0.0101 (3)	0.0087 (3)	0.0062 (3)
Cl2C	0.0406 (4)	0.0201 (3)	0.0343 (4)	−0.0039 (2)	−0.0020 (3)	0.0003 (2)
Cl3C	0.0236 (3)	0.0265 (3)	0.0482 (4)	0.0032 (2)	0.0026 (3)	−0.0017 (3)
S1C	0.0254 (3)	0.0207 (3)	0.0242 (3)	−0.0020 (2)	−0.0028 (2)	0.0037 (2)
O1C	0.0452 (11)	0.0332 (10)	0.0274 (10)	−0.0006 (8)	−0.0100 (8)	0.0059 (7)
N1C	0.0211 (11)	0.0239 (10)	0.0353 (12)	−0.0024 (8)	0.0003 (9)	0.0028 (8)
N2C	0.0244 (11)	0.0227 (10)	0.0273 (11)	−0.0028 (8)	0.0024 (8)	0.0041 (8)
N3C	0.0209 (10)	0.0221 (10)	0.0211 (10)	−0.0022 (8)	−0.0012 (8)	0.0023 (7)
C1C	0.0252 (13)	0.0224 (12)	0.0205 (12)	−0.0046 (10)	−0.0006 (10)	−0.0007 (9)
C2C	0.0189 (12)	0.0210 (11)	0.0245 (13)	−0.0028 (9)	−0.0044 (10)	−0.0035 (9)
Cl1D	0.0301 (4)	0.0590 (4)	0.0324 (4)	0.0023 (3)	0.0099 (3)	−0.0184 (3)
Cl2D	0.0410 (4)	0.0290 (3)	0.0442 (4)	0.0013 (3)	−0.0072 (3)	0.0136 (3)
Cl3D	0.0290 (3)	0.0354 (4)	0.0499 (4)	−0.0109 (3)	0.0117 (3)	−0.0057 (3)
S1D	0.0238 (3)	0.0200 (3)	0.0198 (3)	0.0004 (2)	0.0008 (2)	−0.0007 (2)
O1D	0.0338 (10)	0.0293 (9)	0.0218 (9)	−0.0002 (7)	−0.0045 (7)	−0.0044 (7)
N1D	0.0224 (11)	0.0272 (11)	0.0227 (11)	−0.0010 (8)	0.0001 (8)	−0.0045 (8)
N2D	0.0218 (11)	0.0309 (11)	0.0241 (11)	−0.0037 (8)	0.0051 (8)	−0.0051 (8)
N3D	0.0229 (11)	0.0230 (10)	0.0273 (11)	−0.0002 (8)	0.0050 (9)	−0.0020 (8)
C1D	0.0235 (13)	0.0286 (12)	0.0202 (12)	0.0035 (10)	0.0027 (10)	−0.0022 (9)
C2D	0.0232 (13)	0.0240 (12)	0.0253 (13)	−0.0003 (10)	0.0007 (10)	0.0024 (9)

Geometric parameters (Å, º)

Cl1A—C1A	1.709 (2)	Cl1C—C1C	1.709 (2)
Cl2A—S1A	1.9935 (8)	Cl2C—S1C	2.0064 (8)
Cl3A—C2A	1.716 (2)	Cl3C—C2C	1.717 (2)
S1A—O1A	1.4149 (18)	S1C—O1C	1.4155 (17)
S1A—N2A	1.5798 (19)	S1C—N1C	1.579 (2)
S1A—N3A	1.580 (2)	S1C—N2C	1.581 (2)
N1A—C2A	1.323 (3)	N1C—C1C	1.328 (3)
N1A—C1A	1.333 (3)	N2C—C2C	1.325 (3)
N2A—C1A	1.321 (3)	N3C—C2C	1.320 (3)
N3A—C2A	1.317 (3)	N3C—C1C	1.321 (3)
Cl1B—C1B	1.709 (2)	Cl1D—C1D	1.714 (2)
Cl2B—S1B	2.0084 (8)	Cl2D—S1D	1.9947 (8)
Cl3B—C2B	1.706 (2)	Cl3D—C2D	1.707 (2)
S1B—O1B	1.4154 (16)	S1D—O1D	1.4142 (16)
S1B—N2B	1.5760 (18)	S1D—N2D	1.578 (2)
S1B—N3B	1.5847 (19)	S1D—N3D	1.5867 (19)
N1B—C1B	1.330 (3)	N1D—C1D	1.323 (3)
N1B—C2B	1.331 (3)	N1D—C2D	1.334 (3)
N2B—C1B	1.325 (3)	N2D—C1D	1.328 (3)
N3B—C2B	1.325 (3)	N3D—C2D	1.321 (3)
O1A—S1A—N2A	114.39 (11)	O1C—S1C—N1C	114.08 (11)
O1A—S1A—N3A	114.07 (12)	O1C—S1C—N2C	113.93 (11)
N2A—S1A—N3A	111.55 (11)	N1C—S1C—N2C	112.11 (10)
O1A—S1A—Cl2A	106.58 (8)	O1C—S1C—Cl2C	105.18 (8)
N2A—S1A—Cl2A	104.95 (8)	N1C—S1C—Cl2C	104.56 (8)
N3A—S1A—Cl2A	104.17 (9)	N2C—S1C—Cl2C	105.89 (8)
C2A—N1A—C1A	114.9 (2)	C1C—N1C—S1C	115.53 (17)
C1A—N2A—S1A	115.70 (16)	C2C—N2C—S1C	115.22 (17)
C2A—N3A—S1A	116.36 (17)	C2C—N3C—C1C	115.58 (19)
N2A—C1A—N1A	130.8 (2)	N3C—C1C—N1C	130.3 (2)
N2A—C1A—Cl1A	114.25 (17)	N3C—C1C—Cl1C	115.03 (17)
N1A—C1A—Cl1A	114.97 (17)	N1C—C1C—Cl1C	114.67 (17)
N3A—C2A—N1A	130.6 (2)	N3C—C2C—N2C	130.8 (2)
N3A—C2A—Cl3A	114.22 (17)	N3C—C2C—Cl3C	114.78 (16)
N1A—C2A—Cl3A	115.22 (18)	N2C—C2C—Cl3C	114.40 (17)
O1B—S1B—N2B	114.24 (10)	O1D—S1D—N2D	113.58 (10)
O1B—S1B—N3B	114.27 (10)	O1D—S1D—N3D	114.12 (10)
N2B—S1B—N3B	112.09 (10)	N2D—S1D—N3D	111.94 (10)
O1B—S1B—Cl2B	105.06 (7)	O1D—S1D—Cl2D	106.90 (7)
N2B—S1B—Cl2B	105.13 (7)	N2D—S1D—Cl2D	104.62 (8)
N3B—S1B—Cl2B	104.84 (8)	N3D—S1D—Cl2D	104.64 (8)
C1B—N1B—C2B	115.50 (19)	C1D—N1D—C2D	115.08 (19)
C1B—N2B—S1B	116.00 (16)	C1D—N2D—S1D	114.74 (16)
C2B—N3B—S1B	115.74 (16)	C2D—N3D—S1D	115.17 (17)
N2B—C1B—N1B	130.3 (2)	N1D—C1D—N2D	130.9 (2)
N2B—C1B—Cl1B	114.67 (16)	N1D—C1D—Cl1D	115.62 (17)
N1B—C1B—Cl1B	115.05 (16)	N2D—C1D—Cl1D	113.52 (17)
N3B—C2B—N1B	130.3 (2)	N3D—C2D—N1D	130.4 (2)
N3B—C2B—Cl3B	114.47 (17)	N3D—C2D—Cl3D	114.44 (18)
N1B—C2B—Cl3B	115.20 (17)	N1D—C2D—Cl3D	115.18 (17)