N-(4-Methyl­pyrimidin-2-yl)bis(1,2,3-benzothia­diazole-7-carbonyl)amine

Ai, Y.-W.; Zhang, Y.-G.; Liu, F.-L.; Song, H.-B.; Fan, Z.-J.

doi:10.1107/S1600536805040183

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N-(4-Methylpyrimidin-2-yl)bis(1,2,3-benzothiadiazole-7-carbonyl)amine

Y.-W. Ai, Y.-G. Zhang, F.-L. Liu, H.-B. Song and Z.-J. Fan

The title compound, C₁₉H₁₁N₇O₂S₂, was synthesized as a potential new plant elicitor, by reaction of 2-amino-4-methylpyrimidine with 1,2,3-benzothiadiazole-7-carbonyl chloride. There are two crystallographically independent molecules in the asymmetric unit. In the crystal structure, the molecules are linked by a weak C—H

N hydrogen-bonding interaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040183/rz6144sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040183/rz6144Isup2.hkl Contains datablock I

CCDC reference: 296639

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.107
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found





Alert level A
EXPT001_ALERT_1_A  _exptl_crystal_density_diffrn is missing
            Density calculated from unit cell and contents (Mg m-3).
            The following tests will not be performed.
            DENSD_01,DENSX_01
PLAT044_ALERT_1_A Calculated and Reported Dx Differ ..............          ?

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.60 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.38
           From the CIF: _reflns_number_total               7122
           Count of symmetry unique reflns         4062
           Completeness (_total/calc)            175.33%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3060
           Fraction of Friedel pairs measured     0.753
           Are heavy atom types Z>Si present        yes

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

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Plant elicitors (activators) are a new class of agrochemicals with a new mode of action which have attracted much interest in China (Gozzo, 2003; Fan, Liu & Liu, 2005; Bao, Liu & Fan, 2005). Our research team has synthesized a series of benzothiadiazole derivatives (Liu, 2005), some of which can induce in tobacco a comparatively high resistance to tobacco mosaic virus (TMV). In order to investigate the quantitative structure–activity relationship (QSAR) of this new type of pesticides, we have recently reported the structures of some of them (Bao, Fan et al., 2005; Ai et al., 2005; Liu et al., 2005; Zhao et al., 2006). We report here the crystal structure of the title compound, (I), which represents an example of an N-substituted carboximide derivative of benzothiadiazole.

The asymmetric unit of (I) (Fig. 1) contains two crystallographically independent molecules, A (atoms S1/S2/O1/O2/N1–N7/C1–C19) and B (atoms S3/S4/O3/O4/N8–N14/C20–C38). The bond lengths and angles in (I) are normal (Reference for standard values?), and the values for the two independent molecules agree well with each other (Table 1). In both molecules, the two benzothiadiazole ring systems are essentially planar, forming dihedral angles of 77.5 (1) and 77.8 (1)° in molecules A and B, respectively. The pyrimidine rings are also essentially planar, with a maximum deviation from planarity of 0.027 (4) Å for atom C4. The dihedral angles formed by the pyrimidine rings and the benzothiadiazole rings are 61.6 (1) and 75.2 (1)° in molecule A, and 66.9 (1) and 74.7 (1)° in molecule B.

The crystal structure of (I) is stabilized by a weak C—H···N hydrogen bond (Table 2).

Experimental top

The title compound was synthesized by the reaction of 2-amino-4-methylpyrimidine with 1,2,3-benzothiadiazole-7-carboxylic acid chloride according to the reported precedure of Fan, Liu et al. (2005). Light-yellow [Colourless below?] single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether–ethyl acetate solution (3:1 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

N-(4-Methylpyrimidin-2-yl)di-1,2,3-benzothiadiazole-7-carboximide top

Crystal data top

C₁₉H₁₁N₇O₂S₂	F(000) = 888
M_r = 433.47	D_x = 1.524 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3817 reflections
a = 11.689 (3) Å	θ = 2.4–26.1°
b = 12.283 (3) Å	µ = 0.32 mm⁻¹
c = 13.223 (3) Å	T = 293 K
β = 95.771 (4)°	Prism, colourless
V = 1889.0 (8) Å³	0.28 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	7122 independent reflections
Radiation source: fine-focus sealed tube	5141 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→14
T_min = 0.902, T_max = 0.945	k = −12→15
11005 measured reflections	l = −16→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0511P)² + 0.0505P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
7122 reflections	Δρ_max = 0.32 e Å⁻³
543 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 4042 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

Crystal data top

C₁₉H₁₁N₇O₂S₂	V = 1889.0 (8) Å³
M_r = 433.47	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.689 (3) Å	µ = 0.32 mm⁻¹
b = 12.283 (3) Å	T = 293 K
c = 13.223 (3) Å	0.28 × 0.22 × 0.18 mm
β = 95.771 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7122 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5141 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.945	R_int = 0.026
11005 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.107	Δρ_max = 0.32 e Å⁻³
S = 1.03	Δρ_min = −0.23 e Å⁻³
7122 reflections	Absolute structure: Flack (1983), with 4042 Friedel pairs
543 parameters	Absolute structure parameter: −0.03 (7)
1 restraint

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.64205 (9)	0.80495 (8)	0.02637 (7)	0.0543 (3)
S2	0.58035 (10)	0.77804 (10)	0.64852 (8)	0.0665 (3)
S3	0.13445 (9)	−0.14450 (9)	−0.24325 (7)	0.0574 (3)
S4	0.06695 (11)	−0.12617 (9)	0.37299 (7)	0.0675 (3)
O1	0.4912 (2)	0.7378 (2)	0.1655 (2)	0.0615 (7)
O2	0.6199 (2)	0.7827 (2)	0.42626 (19)	0.0539 (6)
O3	−0.01431 (19)	−0.0520 (2)	−0.11421 (17)	0.0469 (6)
O4	0.1135 (2)	−0.1220 (2)	0.15091 (17)	0.0502 (6)
N1	0.5269 (2)	0.6563 (2)	0.32147 (19)	0.0406 (7)
N2	0.3591 (2)	0.6388 (2)	0.3984 (2)	0.0387 (6)
N3	0.3786 (3)	0.5501 (3)	0.2406 (2)	0.0473 (7)
N4	0.7626 (3)	0.8221 (3)	−0.0345 (2)	0.0618 (9)
N5	0.8543 (3)	0.7876 (3)	0.0158 (2)	0.0528 (8)
N6	0.5913 (4)	0.7315 (5)	0.7708 (3)	0.0869 (13)
N7	0.6050 (3)	0.6288 (5)	0.7763 (3)	0.0775 (12)
N8	0.0207 (2)	0.0090 (2)	0.0499 (2)	0.0395 (7)
N9	−0.1469 (2)	0.0240 (3)	0.1275 (2)	0.0455 (7)
N10	−0.1241 (3)	0.1255 (2)	−0.0225 (2)	0.0492 (8)
N11	0.2550 (4)	−0.1690 (3)	−0.3034 (3)	0.0773 (12)
N12	0.3453 (3)	−0.1354 (3)	−0.2537 (3)	0.0676 (10)
N13	0.0774 (4)	−0.0831 (4)	0.4964 (3)	0.0786 (12)
N14	0.0953 (3)	0.0184 (4)	0.5052 (3)	0.0686 (10)
C1	0.4136 (3)	0.6117 (3)	0.3186 (3)	0.0370 (8)
C2	0.2718 (3)	0.5132 (3)	0.2415 (3)	0.0499 (9)
H2	0.2401	0.4721	0.1867	0.060*
C3	0.2060 (3)	0.5333 (3)	0.3205 (3)	0.0482 (10)
H3	0.1318	0.5057	0.3198	0.058*
C4	0.2537 (3)	0.5955 (3)	0.4001 (3)	0.0461 (9)
C5	0.1941 (4)	0.6186 (4)	0.4925 (3)	0.0728 (14)
H5A	0.2153	0.6898	0.5179	0.109*
H5B	0.2162	0.5652	0.5438	0.109*
H5C	0.1124	0.6156	0.4753	0.109*
C6	0.5605 (3)	0.7026 (3)	0.2301 (3)	0.0400 (8)
C7	0.6854 (3)	0.7013 (2)	0.2179 (2)	0.0342 (7)
C8	0.7694 (3)	0.6533 (3)	0.2830 (2)	0.0381 (8)
H8	0.7488	0.6203	0.3419	0.046*
C9	0.8848 (3)	0.6523 (3)	0.2639 (3)	0.0392 (8)
H9	0.9396	0.6202	0.3104	0.047*
C10	0.9175 (3)	0.6980 (3)	0.1772 (3)	0.0438 (9)
H10	0.9943	0.6980	0.1644	0.053*
C11	0.8343 (3)	0.7443 (3)	0.1087 (3)	0.0384 (8)
C12	0.7188 (3)	0.7481 (3)	0.1286 (2)	0.0368 (7)
C13	0.5797 (3)	0.6922 (3)	0.4166 (2)	0.0391 (8)
C14	0.5884 (3)	0.6120 (3)	0.5015 (2)	0.0367 (8)
C15	0.6004 (3)	0.5018 (3)	0.4864 (3)	0.0475 (9)
H15	0.5978	0.4744	0.4206	0.057*
C16	0.6166 (3)	0.4308 (3)	0.5693 (4)	0.0622 (12)
H16	0.6263	0.3569	0.5577	0.075*
C17	0.6185 (3)	0.4672 (4)	0.6659 (4)	0.0659 (13)
H17	0.6276	0.4191	0.7204	0.079*
C18	0.6065 (3)	0.5781 (4)	0.6819 (3)	0.0532 (10)
C19	0.5920 (3)	0.6497 (3)	0.6005 (3)	0.0428 (8)
C20	−0.0916 (3)	0.0560 (3)	0.0502 (3)	0.0394 (8)
C21	−0.2302 (3)	0.1666 (3)	−0.0182 (3)	0.0565 (10)
H21	−0.2602	0.2140	−0.0690	0.068*
C22	−0.2942 (3)	0.1410 (3)	0.0578 (3)	0.0580 (11)
H22	−0.3668	0.1714	0.0599	0.070*
C23	−0.2515 (3)	0.0701 (4)	0.1314 (3)	0.0485 (9)
C24	−0.3134 (4)	0.0369 (4)	0.2214 (4)	0.0746 (14)
H24A	−0.3409	0.1007	0.2532	0.112*
H24B	−0.2614	−0.0019	0.2694	0.112*
H24C	−0.3773	−0.0092	0.1988	0.112*
C25	0.0560 (3)	−0.0322 (3)	−0.0431 (2)	0.0373 (8)
C26	0.1806 (3)	−0.0392 (3)	−0.0532 (2)	0.0343 (7)
C27	0.2668 (3)	0.0067 (3)	0.0132 (3)	0.0417 (8)
H27	0.2476	0.0405	0.0721	0.050*
C28	0.3815 (3)	0.0033 (3)	−0.0066 (3)	0.0493 (9)
H28	0.4376	0.0329	0.0404	0.059*
C29	0.4131 (3)	−0.0426 (3)	−0.0934 (3)	0.0501 (10)
H29	0.4896	−0.0427	−0.1070	0.060*
C30	0.3290 (3)	−0.0888 (3)	−0.1608 (3)	0.0449 (9)
C31	0.2129 (3)	−0.0863 (3)	−0.1420 (2)	0.0371 (8)
C32	0.0734 (3)	−0.0325 (3)	0.1436 (2)	0.0387 (8)
C33	0.0816 (3)	0.0446 (3)	0.2304 (3)	0.0388 (8)
C34	0.0976 (3)	0.1547 (3)	0.2208 (3)	0.0468 (9)
H34	0.0961	0.1852	0.1563	0.056*
C35	0.1162 (3)	0.2217 (3)	0.3058 (4)	0.0597 (11)
H35	0.1284	0.2957	0.2966	0.072*
C36	0.1172 (3)	0.1823 (4)	0.4015 (4)	0.0608 (12)
H36	0.1294	0.2282	0.4575	0.073*
C37	0.0992 (3)	0.0708 (3)	0.4136 (3)	0.0486 (9)
C38	0.0843 (3)	0.0029 (3)	0.3301 (2)	0.0407 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0595 (6)	0.0639 (6)	0.0382 (5)	−0.0023 (5)	−0.0019 (4)	0.0172 (5)
S2	0.0723 (7)	0.0833 (8)	0.0418 (6)	0.0279 (6)	−0.0049 (5)	−0.0173 (5)
S3	0.0592 (6)	0.0716 (7)	0.0412 (5)	−0.0015 (5)	0.0051 (5)	−0.0143 (5)
S4	0.0957 (9)	0.0660 (7)	0.0389 (5)	−0.0194 (6)	−0.0022 (5)	0.0071 (5)
O1	0.0393 (14)	0.091 (2)	0.0523 (16)	0.0071 (13)	−0.0021 (13)	0.0295 (15)
O2	0.0643 (16)	0.0442 (15)	0.0539 (16)	−0.0060 (14)	0.0095 (13)	−0.0027 (13)
O3	0.0377 (13)	0.0681 (16)	0.0351 (13)	−0.0057 (12)	0.0042 (11)	−0.0056 (12)
O4	0.0698 (17)	0.0423 (14)	0.0392 (13)	0.0104 (13)	0.0093 (12)	−0.0006 (12)
N1	0.0359 (15)	0.0565 (18)	0.0300 (15)	−0.0062 (13)	0.0054 (12)	0.0031 (13)
N2	0.0325 (15)	0.0460 (16)	0.0376 (16)	−0.0007 (13)	0.0043 (13)	−0.0025 (13)
N3	0.0424 (17)	0.064 (2)	0.0358 (16)	−0.0027 (15)	0.0027 (13)	−0.0091 (14)
N4	0.074 (2)	0.070 (2)	0.0423 (18)	−0.0149 (18)	0.0127 (18)	0.0112 (16)
N5	0.060 (2)	0.062 (2)	0.0391 (17)	−0.0100 (17)	0.0137 (16)	0.0055 (16)
N6	0.081 (3)	0.142 (4)	0.037 (2)	0.038 (3)	−0.0027 (19)	−0.006 (2)
N7	0.056 (2)	0.136 (4)	0.040 (2)	0.013 (2)	0.0035 (17)	0.013 (2)
N8	0.0345 (15)	0.0542 (18)	0.0305 (15)	0.0047 (13)	0.0069 (12)	0.0000 (13)
N9	0.0377 (16)	0.0573 (18)	0.0427 (18)	−0.0042 (14)	0.0098 (14)	−0.0100 (14)
N10	0.0461 (18)	0.0520 (19)	0.0488 (19)	0.0064 (15)	0.0018 (14)	0.0037 (15)
N11	0.079 (3)	0.108 (3)	0.047 (2)	0.016 (2)	0.013 (2)	−0.022 (2)
N12	0.064 (2)	0.093 (3)	0.048 (2)	0.027 (2)	0.0227 (18)	0.000 (2)
N13	0.095 (3)	0.106 (3)	0.035 (2)	−0.013 (3)	0.0034 (19)	0.010 (2)
N14	0.073 (2)	0.098 (3)	0.0349 (19)	−0.004 (2)	0.0039 (17)	−0.011 (2)
C1	0.0333 (18)	0.044 (2)	0.0338 (18)	0.0020 (15)	0.0047 (15)	0.0031 (16)
C2	0.052 (2)	0.049 (2)	0.046 (2)	−0.0028 (19)	−0.0069 (18)	−0.0042 (17)
C3	0.039 (2)	0.051 (2)	0.054 (2)	−0.0059 (18)	0.0025 (18)	−0.0047 (18)
C4	0.039 (2)	0.047 (2)	0.054 (2)	0.0039 (17)	0.0114 (18)	0.0064 (18)
C5	0.060 (3)	0.094 (4)	0.069 (3)	−0.007 (3)	0.028 (2)	−0.011 (3)
C6	0.0346 (19)	0.053 (2)	0.0325 (18)	−0.0020 (16)	0.0025 (15)	0.0015 (17)
C7	0.0356 (18)	0.0381 (18)	0.0293 (17)	−0.0014 (14)	0.0046 (14)	0.0003 (14)
C8	0.0407 (19)	0.0423 (19)	0.0322 (18)	−0.0020 (16)	0.0085 (15)	0.0023 (15)
C9	0.039 (2)	0.040 (2)	0.038 (2)	0.0025 (16)	−0.0010 (15)	−0.0011 (15)
C10	0.038 (2)	0.046 (2)	0.048 (2)	−0.0074 (17)	0.0085 (17)	−0.0097 (18)
C11	0.048 (2)	0.0370 (18)	0.0314 (18)	−0.0068 (16)	0.0101 (16)	−0.0050 (15)
C12	0.0423 (19)	0.0355 (18)	0.0321 (17)	−0.0012 (15)	0.0018 (15)	0.0007 (14)
C13	0.0315 (17)	0.052 (2)	0.0354 (18)	0.0023 (16)	0.0094 (14)	0.0003 (16)
C14	0.0259 (17)	0.048 (2)	0.0359 (18)	−0.0036 (14)	0.0040 (14)	−0.0013 (16)
C15	0.041 (2)	0.050 (2)	0.050 (2)	−0.0071 (17)	−0.0012 (18)	−0.0002 (19)
C16	0.057 (3)	0.047 (2)	0.081 (3)	−0.012 (2)	−0.002 (2)	0.011 (2)
C17	0.049 (2)	0.082 (3)	0.065 (3)	−0.017 (2)	−0.005 (2)	0.035 (3)
C18	0.035 (2)	0.080 (3)	0.044 (2)	−0.0051 (19)	−0.0011 (17)	0.011 (2)
C19	0.0272 (17)	0.065 (2)	0.0365 (19)	0.0007 (16)	0.0047 (15)	0.0014 (17)
C20	0.0306 (18)	0.049 (2)	0.0383 (19)	−0.0018 (16)	0.0027 (15)	−0.0096 (16)
C21	0.044 (2)	0.060 (2)	0.063 (3)	0.0069 (19)	−0.006 (2)	−0.005 (2)
C22	0.039 (2)	0.058 (3)	0.077 (3)	0.0074 (19)	0.004 (2)	−0.017 (2)
C23	0.0342 (18)	0.063 (2)	0.049 (2)	−0.0104 (17)	0.0096 (16)	−0.0235 (19)
C24	0.057 (3)	0.106 (4)	0.066 (3)	−0.002 (3)	0.030 (2)	−0.018 (3)
C25	0.0375 (18)	0.045 (2)	0.0300 (17)	−0.0033 (15)	0.0067 (15)	−0.0013 (15)
C26	0.0363 (18)	0.0374 (18)	0.0294 (17)	0.0016 (15)	0.0045 (14)	0.0039 (14)
C27	0.0408 (19)	0.049 (2)	0.0356 (19)	−0.0006 (16)	0.0049 (15)	−0.0008 (16)
C28	0.0321 (19)	0.070 (3)	0.045 (2)	−0.0030 (18)	0.0018 (17)	0.007 (2)
C29	0.0304 (19)	0.070 (3)	0.051 (2)	0.0087 (19)	0.0110 (18)	0.017 (2)
C30	0.047 (2)	0.052 (2)	0.0374 (19)	0.0167 (18)	0.0149 (17)	0.0093 (16)
C31	0.041 (2)	0.0373 (18)	0.0328 (17)	0.0047 (14)	0.0053 (15)	0.0065 (14)
C32	0.0333 (18)	0.049 (2)	0.0349 (19)	−0.0016 (16)	0.0096 (15)	−0.0004 (16)
C33	0.0316 (17)	0.049 (2)	0.0361 (19)	0.0023 (15)	0.0060 (14)	−0.0030 (16)
C34	0.042 (2)	0.044 (2)	0.054 (2)	0.0025 (17)	0.0084 (18)	0.0013 (18)
C35	0.046 (2)	0.046 (2)	0.085 (3)	0.0003 (18)	−0.002 (2)	−0.015 (2)
C36	0.053 (3)	0.067 (3)	0.060 (3)	0.006 (2)	−0.007 (2)	−0.030 (2)
C37	0.0372 (19)	0.069 (3)	0.039 (2)	0.0008 (18)	0.0030 (16)	−0.0154 (19)
C38	0.0360 (19)	0.053 (2)	0.0327 (18)	−0.0016 (16)	0.0008 (15)	−0.0038 (16)

Geometric parameters (Å, º) top

S1—C12	1.696 (3)	C8—C9	1.398 (5)
S1—N4	1.705 (3)	C8—H8	0.9300
S2—N6	1.708 (4)	C9—C10	1.365 (5)
S2—C19	1.711 (4)	C9—H9	0.9300
S3—C31	1.702 (4)	C10—C11	1.383 (5)
S3—N11	1.713 (4)	C10—H10	0.9300
S4—C38	1.703 (4)	C11—C12	1.402 (5)
S4—N13	1.708 (4)	C13—C14	1.489 (5)
O1—C6	1.197 (4)	C14—C15	1.377 (5)
O2—C13	1.209 (4)	C14—C19	1.385 (5)
O3—C25	1.210 (4)	C15—C16	1.399 (5)
O4—C32	1.195 (4)	C15—H15	0.9300
N1—C13	1.414 (4)	C16—C17	1.351 (6)
N1—C6	1.426 (4)	C16—H16	0.9300
N1—C1	1.429 (4)	C17—C18	1.387 (6)
N2—C1	1.329 (4)	C17—H17	0.9300
N2—C4	1.345 (4)	C18—C19	1.387 (5)
N3—C1	1.311 (4)	C21—C22	1.350 (6)
N3—C2	1.329 (5)	C21—H21	0.9300
N4—N5	1.276 (4)	C22—C23	1.362 (6)
N5—C11	1.380 (4)	C22—H22	0.9300
N6—N7	1.273 (6)	C23—C24	1.510 (6)
N7—C18	1.397 (6)	C24—H24A	0.9600
N8—C32	1.423 (4)	C24—H24B	0.9600
N8—C25	1.428 (4)	C24—H24C	0.9600
N8—C20	1.434 (4)	C25—C26	1.479 (4)
N9—C20	1.323 (4)	C26—C27	1.387 (4)
N9—C23	1.354 (5)	C26—C31	1.395 (4)
N10—C20	1.313 (5)	C27—C28	1.392 (5)
N10—C21	1.346 (5)	C27—H27	0.9300
N11—N12	1.257 (5)	C28—C29	1.364 (5)
N12—C30	1.386 (5)	C28—H28	0.9300
N13—N14	1.268 (5)	C29—C30	1.380 (5)
N14—C37	1.376 (5)	C29—H29	0.9300
C2—C3	1.380 (5)	C30—C31	1.404 (5)
C2—H2	0.9300	C32—C33	1.483 (5)
C3—C4	1.372 (5)	C33—C34	1.374 (5)
C3—H3	0.9300	C33—C38	1.412 (5)
C4—C5	1.494 (5)	C34—C35	1.392 (6)
C5—H5A	0.9600	C34—H34	0.9300
C5—H5B	0.9600	C35—C36	1.353 (6)
C5—H5C	0.9600	C35—H35	0.9300
C6—C7	1.485 (5)	C36—C37	1.398 (6)
C7—C8	1.372 (5)	C36—H36	0.9300
C7—C12	1.404 (4)	C37—C38	1.380 (5)

C12—S1—N4	91.79 (17)	C17—C16—H16	119.2
N6—S2—C19	92.4 (2)	C15—C16—H16	119.2
C31—S3—N11	92.06 (18)	C16—C17—C18	118.5 (4)
C38—S4—N13	91.7 (2)	C16—C17—H17	120.8
C13—N1—C6	119.8 (3)	C18—C17—H17	120.8
C13—N1—C1	117.6 (2)	C17—C18—C19	120.7 (4)
C6—N1—C1	117.6 (3)	C17—C18—N7	125.8 (4)
C1—N2—C4	115.3 (3)	C19—C18—N7	113.5 (4)
C1—N3—C2	114.1 (3)	C14—C19—C18	120.8 (4)
N5—N4—S1	113.8 (2)	C14—C19—S2	131.5 (3)
N4—N5—C11	112.6 (3)	C18—C19—S2	107.7 (3)
N7—N6—S2	112.5 (3)	N10—C20—N9	129.1 (3)
N6—N7—C18	113.8 (4)	N10—C20—N8	117.2 (3)
C32—N8—C25	119.0 (3)	N9—C20—N8	113.6 (3)
C32—N8—C20	117.2 (2)	N10—C21—C22	121.7 (4)
C25—N8—C20	119.3 (3)	N10—C21—H21	119.1
C20—N9—C23	114.7 (3)	C22—C21—H21	119.1
C20—N10—C21	114.5 (3)	C21—C22—C23	119.3 (4)
N12—N11—S3	112.7 (3)	C21—C22—H22	120.3
N11—N12—C30	114.6 (3)	C23—C22—H22	120.3
N14—N13—S4	112.8 (3)	N9—C23—C22	120.6 (4)
N13—N14—C37	113.5 (4)	N9—C23—C24	115.0 (4)
N3—C1—N2	129.2 (3)	C22—C23—C24	124.4 (4)
N3—C1—N1	117.2 (3)	C23—C24—H24A	109.5
N2—C1—N1	113.6 (3)	C23—C24—H24B	109.5
N3—C2—C3	122.8 (4)	H24A—C24—H24B	109.5
N3—C2—H2	118.6	C23—C24—H24C	109.5
C3—C2—H2	118.6	H24A—C24—H24C	109.5
C4—C3—C2	117.7 (4)	H24B—C24—H24C	109.5
C4—C3—H3	121.1	O3—C25—N8	120.5 (3)
C2—C3—H3	121.1	O3—C25—C26	121.1 (3)
N2—C4—C3	120.7 (3)	N8—C25—C26	118.1 (3)
N2—C4—C5	116.2 (4)	C27—C26—C31	117.4 (3)
C3—C4—C5	123.1 (4)	C27—C26—C25	125.4 (3)
C4—C5—H5A	109.5	C31—C26—C25	116.9 (3)
C4—C5—H5B	109.5	C26—C27—C28	121.4 (3)
H5A—C5—H5B	109.5	C26—C27—H27	119.3
C4—C5—H5C	109.5	C28—C27—H27	119.3
H5A—C5—H5C	109.5	C29—C28—C27	121.2 (4)
H5B—C5—H5C	109.5	C29—C28—H28	119.4
O1—C6—N1	121.6 (3)	C27—C28—H28	119.4
O1—C6—C7	121.9 (3)	C28—C29—C30	118.5 (3)
N1—C6—C7	116.5 (3)	C28—C29—H29	120.7
C8—C7—C12	117.6 (3)	C30—C29—H29	120.7
C8—C7—C6	125.8 (3)	C29—C30—N12	126.1 (3)
C12—C7—C6	116.5 (3)	C29—C30—C31	121.0 (3)
C7—C8—C9	122.2 (3)	N12—C30—C31	112.8 (3)
C7—C8—H8	118.9	C26—C31—C30	120.4 (3)
C9—C8—H8	118.9	C26—C31—S3	131.8 (3)
C10—C9—C8	120.4 (3)	C30—C31—S3	107.8 (2)
C10—C9—H9	119.8	O4—C32—N8	122.1 (3)
C8—C9—H9	119.8	O4—C32—C33	122.1 (3)
C9—C10—C11	118.7 (3)	N8—C32—C33	115.7 (3)
C9—C10—H10	120.6	C34—C33—C38	116.9 (3)
C11—C10—H10	120.6	C34—C33—C32	123.8 (3)
N5—C11—C10	124.8 (3)	C38—C33—C32	119.0 (3)
N5—C11—C12	114.0 (3)	C33—C34—C35	121.2 (4)
C10—C11—C12	121.3 (3)	C33—C34—H34	119.4
C11—C12—C7	119.9 (3)	C35—C34—H34	119.4
C11—C12—S1	107.9 (2)	C36—C35—C34	122.0 (4)
C7—C12—S1	132.1 (3)	C36—C35—H35	119.0
O2—C13—N1	120.7 (3)	C34—C35—H35	119.0
O2—C13—C14	122.1 (3)	C35—C36—C37	118.0 (4)
N1—C13—C14	117.1 (3)	C35—C36—H36	121.0
C15—C14—C19	118.1 (3)	C37—C36—H36	121.0
C15—C14—C13	122.8 (3)	N14—C37—C38	114.1 (4)
C19—C14—C13	119.0 (3)	N14—C37—C36	125.3 (4)
C14—C15—C16	120.5 (4)	C38—C37—C36	120.6 (4)
C14—C15—H15	119.8	C37—C38—C33	121.2 (3)
C16—C15—H15	119.8	C37—C38—S4	107.8 (3)
C17—C16—C15	121.5 (4)	C33—C38—S4	131.0 (3)

C12—S1—N4—N5	0.5 (3)	C17—C18—C19—S2	−180.0 (3)
S1—N4—N5—C11	−0.1 (4)	N7—C18—C19—S2	1.3 (4)
C19—S2—N6—N7	1.3 (4)	N6—S2—C19—C14	178.2 (3)
S2—N6—N7—C18	−0.8 (5)	N6—S2—C19—C18	−1.4 (3)
C31—S3—N11—N12	−1.0 (4)	C21—N10—C20—N9	−2.1 (6)
S3—N11—N12—C30	1.5 (5)	C21—N10—C20—N8	179.9 (3)
C38—S4—N13—N14	−1.6 (4)	C23—N9—C20—N10	−0.2 (5)
S4—N13—N14—C37	1.6 (5)	C23—N9—C20—N8	177.9 (3)
C2—N3—C1—N2	2.4 (6)	C32—N8—C20—N10	157.5 (3)
C2—N3—C1—N1	−178.7 (3)	C25—N8—C20—N10	−46.3 (4)
C4—N2—C1—N3	1.1 (6)	C32—N8—C20—N9	−20.8 (4)
C4—N2—C1—N1	−177.9 (3)	C25—N8—C20—N9	135.4 (3)
C13—N1—C1—N3	−160.1 (3)	C20—N10—C21—C22	2.7 (5)
C6—N1—C1—N3	45.0 (5)	N10—C21—C22—C23	−1.2 (6)
C13—N1—C1—N2	19.0 (4)	C20—N9—C23—C22	2.0 (5)
C6—N1—C1—N2	−135.9 (3)	C20—N9—C23—C24	−178.0 (3)
C1—N3—C2—C3	−3.3 (5)	C21—C22—C23—N9	−1.3 (6)
N3—C2—C3—C4	1.0 (6)	C21—C22—C23—C24	178.6 (4)
C1—N2—C4—C3	−3.8 (5)	C32—N8—C25—O3	138.0 (3)
C1—N2—C4—C5	175.9 (4)	C20—N8—C25—O3	−17.8 (5)
C2—C3—C4—N2	2.8 (5)	C32—N8—C25—C26	−48.1 (4)
C2—C3—C4—C5	−176.8 (4)	C20—N8—C25—C26	156.1 (3)
C13—N1—C6—O1	−128.9 (4)	O3—C25—C26—C27	162.9 (3)
C1—N1—C6—O1	25.4 (5)	N8—C25—C26—C27	−10.9 (5)
C13—N1—C6—C7	53.0 (4)	O3—C25—C26—C31	−10.2 (5)
C1—N1—C6—C7	−152.7 (3)	N8—C25—C26—C31	176.0 (3)
O1—C6—C7—C8	−173.3 (4)	C31—C26—C27—C28	−1.8 (5)
N1—C6—C7—C8	4.8 (5)	C25—C26—C27—C28	−174.9 (3)
O1—C6—C7—C12	2.7 (5)	C26—C27—C28—C29	1.9 (6)
N1—C6—C7—C12	−179.2 (3)	C27—C28—C29—C30	−1.8 (6)
C12—C7—C8—C9	1.5 (5)	C28—C29—C30—N12	177.7 (4)
C6—C7—C8—C9	177.4 (3)	C28—C29—C30—C31	1.7 (6)
C7—C8—C9—C10	−1.3 (5)	N11—N12—C30—C29	−177.7 (4)
C8—C9—C10—C11	−0.5 (5)	N11—N12—C30—C31	−1.4 (5)
N4—N5—C11—C10	177.8 (3)	C27—C26—C31—C30	1.7 (5)
N4—N5—C11—C12	−0.5 (4)	C25—C26—C31—C30	175.3 (3)
C9—C10—C11—N5	−176.1 (3)	C27—C26—C31—S3	−176.8 (3)
C9—C10—C11—C12	2.1 (5)	C25—C26—C31—S3	−3.1 (5)
N5—C11—C12—C7	176.5 (3)	C29—C30—C31—C26	−1.7 (5)
C10—C11—C12—C7	−1.9 (5)	N12—C30—C31—C26	−178.2 (3)
N5—C11—C12—S1	0.9 (4)	C29—C30—C31—S3	177.1 (3)
C10—C11—C12—S1	−177.5 (3)	N12—C30—C31—S3	0.6 (4)
C8—C7—C12—C11	0.1 (5)	N11—S3—C31—C26	178.8 (3)
C6—C7—C12—C11	−176.2 (3)	N11—S3—C31—C30	0.2 (3)
C8—C7—C12—S1	174.4 (3)	C25—N8—C32—O4	−26.9 (5)
C6—C7—C12—S1	−1.9 (5)	C20—N8—C32—O4	129.4 (3)
N4—S1—C12—C11	−0.8 (2)	C25—N8—C32—C33	149.7 (3)
N4—S1—C12—C7	−175.6 (3)	C20—N8—C32—C33	−54.0 (4)
C6—N1—C13—O2	26.5 (4)	O4—C32—C33—C34	142.9 (4)
C1—N1—C13—O2	−127.9 (3)	N8—C32—C33—C34	−33.6 (4)
C6—N1—C13—C14	−150.5 (3)	O4—C32—C33—C38	−30.7 (5)
C1—N1—C13—C14	55.2 (4)	N8—C32—C33—C38	152.8 (3)
O2—C13—C14—C15	−145.5 (4)	C38—C33—C34—C35	0.3 (5)
N1—C13—C14—C15	31.4 (4)	C32—C33—C34—C35	−173.4 (3)
O2—C13—C14—C19	30.3 (5)	C33—C34—C35—C36	−1.3 (6)
N1—C13—C14—C19	−152.8 (3)	C34—C35—C36—C37	0.3 (6)
C19—C14—C15—C16	−0.5 (5)	N13—N14—C37—C38	−0.7 (5)
C13—C14—C15—C16	175.4 (3)	N13—N14—C37—C36	179.7 (4)
C14—C15—C16—C17	1.4 (6)	C35—C36—C37—N14	−178.7 (4)
C15—C16—C17—C18	−1.4 (6)	C35—C36—C37—C38	1.8 (6)
C16—C17—C18—C19	0.5 (6)	N14—C37—C38—C33	177.6 (3)
C16—C17—C18—N7	179.1 (4)	C36—C37—C38—C33	−2.8 (5)
N6—N7—C18—C17	−179.0 (4)	N14—C37—C38—S4	−0.5 (4)
N6—N7—C18—C19	−0.4 (5)	C36—C37—C38—S4	179.1 (3)
C15—C14—C19—C18	−0.4 (5)	C34—C33—C38—C37	1.7 (5)
C13—C14—C19—C18	−176.4 (3)	C32—C33—C38—C37	175.8 (3)
C15—C14—C19—S2	−180.0 (3)	C34—C33—C38—S4	179.3 (3)
C13—C14—C19—S2	4.1 (5)	C32—C33—C38—S4	−6.7 (5)
C17—C18—C19—C14	0.4 (5)	N13—S4—C38—C37	1.1 (3)
N7—C18—C19—C14	−178.3 (3)	N13—S4—C38—C33	−176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1	0.93	2.62	2.930 (4)	100

Experimental details

Crystal data
Chemical formula	C₁₉H₁₁N₇O₂S₂
M_r	433.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	11.689 (3), 12.283 (3), 13.223 (3)
β (°)	95.771 (4)
V (Å³)	1889.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.902, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	11005, 7122, 5141
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.03
No. of reflections	7122
No. of parameters	543
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23
Absolute structure	Flack (1983), with 4042 Friedel pairs
Absolute structure parameter	−0.03 (7)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top

S1—C12	1.696 (3)	N4—N5	1.276 (4)
S1—N4	1.705 (3)	N5—C11	1.380 (4)
S2—N6	1.708 (4)	N6—N7	1.273 (6)
S2—C19	1.711 (4)	N7—C18	1.397 (6)
S3—C31	1.702 (4)	N8—C32	1.423 (4)
S3—N11	1.713 (4)	N8—C25	1.428 (4)
S4—C38	1.703 (4)	N8—C20	1.434 (4)
S4—N13	1.708 (4)	N9—C20	1.323 (4)
N1—C13	1.414 (4)	N9—C23	1.354 (5)
N1—C6	1.426 (4)	N10—C20	1.313 (5)
N1—C1	1.429 (4)	N10—C21	1.346 (5)
N2—C1	1.329 (4)	N11—N12	1.257 (5)
N2—C4	1.345 (4)	N12—C30	1.386 (5)
N3—C1	1.311 (4)	N13—N14	1.268 (5)
N3—C2	1.329 (5)	N14—C37	1.376 (5)

C12—S1—N4	91.79 (17)	N7—N6—S2	112.5 (3)
N6—S2—C19	92.4 (2)	N6—N7—C18	113.8 (4)
C31—S3—N11	92.06 (18)	C32—N8—C25	119.0 (3)
C38—S4—N13	91.7 (2)	C32—N8—C20	117.2 (2)
C13—N1—C6	119.8 (3)	C25—N8—C20	119.3 (3)
C13—N1—C1	117.6 (2)	C20—N9—C23	114.7 (3)
C6—N1—C1	117.6 (3)	C20—N10—C21	114.5 (3)
C1—N2—C4	115.3 (3)	N12—N11—S3	112.7 (3)
C1—N3—C2	114.1 (3)	N11—N12—C30	114.6 (3)
N5—N4—S1	113.8 (2)	N14—N13—S4	112.8 (3)
N4—N5—C11	112.6 (3)	N13—N14—C37	113.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1	0.93	2.62	2.930 (4)	100

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