2-Amino-5-(p-nitro­phenyl­sulfonyl)-1,3-thia­zole

In the mol­ecule of the title compound, C₉H₇N₃O₄S₂, the thia­zole ring is oriented with respect to the benzene ring at a dihedral angle of 67.85 (5)°. Mol­ecules are linked by inter­molecular N—H...O and N—H...N hydrogen bonds between the amino H atoms and O and N atoms of the sulfonyl group and thia­zole ring, respectively, forming infinite sheets.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.105
• Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

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

   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Amino-5-(p-nitrophenylsulfonyl)-1,3-thiazole

Crystal data

C9H7N3O4S2	F(000) = 584
Mr = 285.30	Dx = 1.637 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5980 reflections
a = 8.6310 (2) Å	θ = 2.1–30.5°
b = 12.4943 (3) Å	µ = 0.47 mm^−1
c = 11.4911 (4) Å	T = 296 K
β = 110.874 (2)°	Needle, yellow
V = 1157.85 (6) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID-S diffractometer	3314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 30.6°, θmin = 2.5°
ω scans	h = −12→12
22950 measured reflections	k = −16→17
3543 independent reflections	l = −16→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	All H-atom parameters refined
S = 1.16	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 0.3858P] where P = (Fo^2 + 2Fc^2)/3
3543 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.26 e Å^−3
1 restraint	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.

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
S1	0.34542 (5)	0.31628 (3)	0.71182 (4)	0.03790 (12)
S2	0.40853 (5)	0.12202 (3)	0.57648 (3)	0.03312 (11)
O1	0.58132 (15)	0.13928 (10)	0.64556 (13)	0.0457 (3)
O2	0.35521 (17)	0.08579 (10)	0.44973 (11)	0.0450 (3)
O3	0.2490 (2)	−0.18866 (15)	0.98565 (16)	0.0708 (5)
O4	0.08179 (19)	−0.26177 (14)	0.81838 (17)	0.0658 (4)
N	0.1498 (2)	0.49068 (13)	0.67542 (16)	0.0481 (4)
N1	0.1849 (2)	−0.19488 (14)	0.87233 (16)	0.0490 (4)
C2	0.19032 (17)	0.40406 (12)	0.62471 (15)	0.0336 (3)
N3	0.11720 (17)	0.37688 (11)	0.50598 (13)	0.0380 (3)
C4	0.18200 (19)	0.28385 (13)	0.48162 (15)	0.0364 (3)
C5	0.30465 (18)	0.23931 (12)	0.57884 (14)	0.0332 (3)
C6	0.33786 (19)	0.02858 (12)	0.66269 (14)	0.0339 (3)
C7	0.3783 (2)	0.04535 (14)	0.78999 (16)	0.0436 (4)
C8	0.3247 (2)	−0.02768 (16)	0.85822 (16)	0.0451 (4)
C9	0.2370 (2)	−0.11637 (14)	0.79797 (16)	0.0395 (3)
C10	0.1995 (2)	−0.13523 (16)	0.67283 (18)	0.0446 (4)
C11	0.2500 (2)	−0.06080 (15)	0.60365 (16)	0.0412 (4)
H1	0.082 (3)	0.535 (2)	0.624 (2)	0.062 (7)*
H2	0.212 (3)	0.513 (2)	0.7503 (17)	0.067 (7)*
H4	0.140 (2)	0.2543 (16)	0.4044 (19)	0.037 (5)*
H7	0.430 (3)	0.109 (2)	0.832 (2)	0.070 (7)*
H8	0.346 (3)	−0.0129 (19)	0.943 (2)	0.055 (6)*
H10	0.146 (3)	−0.1983 (18)	0.638 (2)	0.052 (6)*
H11	0.224 (3)	−0.076 (2)	0.515 (2)	0.060 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0391 (2)	0.0353 (2)	0.0317 (2)	0.00923 (14)	0.00340 (14)	−0.00421 (14)
S2	0.03998 (19)	0.02969 (19)	0.03069 (19)	0.00601 (13)	0.01382 (14)	0.00120 (13)
O1	0.0370 (6)	0.0423 (7)	0.0568 (8)	0.0058 (5)	0.0155 (5)	0.0032 (6)
O2	0.0676 (8)	0.0389 (6)	0.0309 (6)	0.0070 (6)	0.0207 (5)	−0.0004 (5)
O3	0.0981 (13)	0.0729 (11)	0.0497 (9)	−0.0039 (9)	0.0367 (9)	0.0133 (8)
O4	0.0554 (8)	0.0693 (10)	0.0749 (11)	−0.0113 (7)	0.0258 (7)	0.0151 (8)
N	0.0521 (8)	0.0394 (8)	0.0425 (8)	0.0158 (7)	0.0041 (7)	−0.0073 (6)
N1	0.0511 (8)	0.0523 (9)	0.0514 (9)	0.0070 (7)	0.0279 (7)	0.0111 (7)
C2	0.0307 (6)	0.0308 (7)	0.0365 (8)	0.0034 (5)	0.0085 (5)	0.0007 (6)
N3	0.0375 (6)	0.0371 (7)	0.0340 (7)	0.0080 (5)	0.0060 (5)	0.0014 (5)
C4	0.0391 (7)	0.0358 (8)	0.0303 (7)	0.0029 (6)	0.0077 (6)	−0.0006 (6)
C5	0.0376 (7)	0.0304 (7)	0.0298 (7)	0.0038 (5)	0.0099 (5)	−0.0010 (5)
C6	0.0408 (7)	0.0317 (7)	0.0283 (7)	0.0045 (6)	0.0113 (6)	0.0013 (6)
C7	0.0624 (10)	0.0343 (8)	0.0305 (8)	−0.0003 (7)	0.0124 (7)	−0.0010 (6)
C8	0.0620 (10)	0.0437 (9)	0.0307 (8)	0.0061 (8)	0.0179 (7)	0.0022 (7)
C9	0.0414 (8)	0.0414 (9)	0.0402 (9)	0.0054 (6)	0.0200 (7)	0.0066 (7)
C10	0.0447 (9)	0.0477 (10)	0.0427 (9)	−0.0109 (7)	0.0173 (7)	−0.0055 (8)
C11	0.0450 (8)	0.0455 (9)	0.0327 (8)	−0.0051 (7)	0.0135 (6)	−0.0045 (7)

Geometric parameters (Å, º)

S1—C2	1.7442 (15)	C4—H4	0.91 (2)
S1—C5	1.7322 (15)	C5—C4	1.355 (2)
S2—O1	1.4343 (13)	C6—C7	1.393 (2)
S2—O2	1.4354 (12)	C6—C11	1.384 (2)
S2—C5	1.7231 (15)	C7—H7	0.95 (3)
S2—C6	1.7740 (16)	C8—C7	1.386 (3)
N—H1	0.87 (2)	C8—H8	0.95 (2)
N—H2	0.883 (16)	C9—N1	1.472 (2)
N1—O3	1.223 (2)	C9—C8	1.381 (3)
N1—O4	1.217 (2)	C9—C10	1.377 (2)
C2—N	1.333 (2)	C10—H10	0.93 (2)
N3—C2	1.327 (2)	C11—C10	1.391 (3)
N3—C4	1.361 (2)	C11—H11	0.98 (2)
C5—S1—C2	88.26 (7)	C4—C5—S1	110.66 (12)
O1—S2—O2	120.21 (8)	S2—C5—S1	122.87 (9)
O1—S2—C5	107.92 (8)	C11—C6—C7	121.64 (15)
O2—S2—C5	107.68 (7)	C11—C6—S2	119.64 (12)
O1—S2—C6	106.64 (8)	C7—C6—S2	118.68 (13)
O2—S2—C6	108.02 (8)	C8—C7—C6	119.06 (17)
C5—S2—C6	105.46 (8)	C8—C7—H7	117.1 (16)
C2—N—H1	116.3 (16)	C6—C7—H7	123.4 (16)
C2—N—H2	121.8 (17)	C9—C8—C7	118.60 (16)
H1—N—H2	119 (2)	C9—C8—H8	123.0 (14)
O4—N1—O3	123.89 (18)	C7—C8—H8	118.4 (14)
O4—N1—C9	118.74 (17)	C10—C9—C8	122.93 (16)
O3—N1—C9	117.37 (17)	C10—C9—N1	119.03 (17)
N3—C2—N	123.66 (14)	C8—C9—N1	118.03 (16)
N3—C2—S1	114.56 (11)	C9—C10—C11	118.52 (17)
N—C2—S1	121.78 (13)	C9—C10—H10	119.6 (14)
C2—N3—C4	110.50 (13)	C11—C10—H10	121.8 (14)
C5—C4—N3	116.02 (14)	C6—C11—C10	119.21 (16)
C5—C4—H4	124.2 (12)	C6—C11—H11	123.0 (15)
N3—C4—H4	119.7 (12)	C10—C11—H11	117.8 (15)
C4—C5—S2	126.47 (12)
C2—S1—C5—C4	0.26 (13)	C4—N3—C2—S1	0.80 (18)
C2—S1—C5—S2	−179.14 (11)	S2—C5—C4—N3	179.51 (12)
C5—S1—C2—N3	−0.62 (13)	S1—C5—C4—N3	0.1 (2)
C5—S1—C2—N	178.99 (16)	C7—C6—C11—C10	0.6 (3)
O1—S2—C5—C4	137.55 (16)	S2—C6—C11—C10	178.08 (14)
O2—S2—C5—C4	6.39 (18)	S2—C6—C7—C8	−179.51 (14)
C6—S2—C5—C4	−108.76 (16)	C11—C6—C7—C8	−2.0 (3)
O1—S2—C5—S1	−43.15 (13)	C9—C8—C7—C6	1.9 (3)
O2—S2—C5—S1	−174.31 (10)	C8—C9—C10—C11	−1.0 (3)
C6—S2—C5—S1	70.54 (12)	N1—C9—C10—C11	−179.69 (16)
O1—S2—C6—C11	−129.60 (14)	C10—C9—C8—C7	−0.4 (3)
O2—S2—C6—C11	0.91 (16)	N1—C9—C8—C7	178.30 (16)
C5—S2—C6—C11	115.83 (14)	C10—C9—N1—O4	−15.2 (2)
O1—S2—C6—C7	47.92 (15)	C8—C9—N1—O4	166.04 (17)
O2—S2—C6—C7	178.43 (13)	C10—C9—N1—O3	164.65 (18)
C5—S2—C6—C7	−66.66 (15)	C8—C9—N1—O3	−14.1 (2)
C2—N3—C4—C5	−0.6 (2)	C6—C11—C10—C9	0.9 (3)
C4—N3—C2—N	−178.80 (17)