Pyridine and 3-methyl­pyridine solvates of the triple sulfa drug constitutent sulfamethazine

Sulfonamides display a wide variety of pharmacological activities. Sulfamethazine [abbreviated as SMZ; systematic name 4-amino-N-(4,6-di­methyl­pyrimidin-2-yl)benzene­sulfonamide], one of the constitutents of the triple sulfa drugs, has wide clinical use. Pharmaceutical solvates are crystalline solids of active pharmaceutical ingredients (APIs) incorporating one or more solvent mol­ecules in the crystal lattice, and these have received special attention, as the solvent molecule can impart characteristic physicochemical properties to APIs and solvates, therefore playing a significant role in drug development. The ability of SMZ to form solvates has been investigated. Both pyridine and 3-methyl­pyridine form solvates with SMZ in 1:1 molar ratios. The pyridine monosolvate, C₁₂H₁₄N₄O₂S·C₅H₅N, crystallizes in the ortho­rhom­bic space group Pna2₁, with Z = 8 and two mol­ecules per assymetric unit, whereas the 3-methyl­pyridine monosolvate, C₁₂H₁₄N₄O₂S·C₆H₇N, crystallizes in the ortho­rhom­bic space group P2₁2₁2₁, with Z = 4. Crystal structure analysis reveals intra­molecular N—H...N hydrogen bonds between the mol­ecules of SMZ and the pyridine solvent mol­ecules. The solvent mol­ecules in both structures play an active part in strong inter­molecular inter­actions, thereby contributing significantly to the stability of both structures. Three-dimensional hydrogen-bonding networks exist in both structures involving at least one sulfonyl O atom and the amine N atom. In the pyridine solvate, there is a short π–π inter­action [centroid–centroid distance = 3.926 (3) Å] involving the centroids of the pyridine rings of two solvent mol­ecules and a weak inter­molecular C—H...π inter­action also contributes to the stability of the crystal packing.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) for (1); SHELXL2016 (Sheldrick, 2015) for (2). For both compounds, molecular graphics: PLATON (Spek, 2009) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(1) 4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide pyridine monosolvate

Crystal data

C12H14N4O2S·C5H5N	Dx = 1.273 Mg m^−3
Mr = 357.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 4378 reflections
a = 30.5388 (9) Å	θ = 2.7–21.2°
b = 8.0984 (2) Å	µ = 0.19 mm^−1
c = 15.0810 (4) Å	T = 293 K
V = 3729.76 (17) Å^3	Needle, colourless
Z = 8	0.65 × 0.30 × 0.25 mm
F(000) = 1504

Data collection

Bruker Kappa APEXII CCD diffractometer	Rint = 0.035
φ and ω scans	θmax = 27.4°, θmin = 1.3°
18564 measured reflections	h = −26→39
6825 independent reflections	k = −10→8
4494 reflections with I > 2σ(I)	l = −19→11

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0506P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.047	(Δ/σ)max = 0.005
wR(F^2) = 0.105	Δρmax = 0.19 e Å^−3
S = 1.00	Δρmin = −0.19 e Å^−3
6825 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
517 parameters	Extinction coefficient: 0.0016 (4)
1 restraint	Absolute structure: Refined as an inversion twin (Flack, 1983)
Hydrogen site location: mixed	Absolute structure parameter: 0.04 (8)

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.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq
N20A	−0.30004 (15)	0.8913 (5)	0.2996 (3)	0.0820 (13)
C25A	−0.3316 (2)	0.8679 (7)	0.3576 (4)	0.0906 (17)
H25A	−0.324254	0.873117	0.417375	0.109*
C24A	−0.3736 (2)	0.8368 (9)	0.3368 (6)	0.115 (2)
H24A	−0.394463	0.819105	0.380762	0.138*
C21A	−0.3108 (2)	0.8853 (10)	0.2166 (5)	0.123 (2)
H21A	−0.289126	0.904116	0.174472	0.147*
C22A	−0.3520 (3)	0.8528 (13)	0.1880 (6)	0.167 (4)
H22A	−0.358288	0.844580	0.127862	0.200*
C23A	−0.3845 (3)	0.8322 (11)	0.2516 (9)	0.158 (3)
H23A	−0.413451	0.815444	0.234656	0.189*
S1B	0.02690 (3)	0.27065 (11)	0.43631 (7)	0.0441 (3)
S1A	−0.20516 (3)	0.95563 (13)	0.46009 (7)	0.0536 (3)
O3B	−0.00381 (8)	0.3942 (3)	0.46281 (19)	0.0526 (7)
N17B	0.05700 (11)	0.3537 (4)	0.6183 (2)	0.0497 (8)
O2B	0.03220 (9)	0.2389 (3)	0.34374 (18)	0.0573 (8)
C10B	0.02973 (14)	−0.0611 (5)	0.4606 (3)	0.0533 (11)
C7A	−0.12822 (12)	0.4776 (5)	0.4602 (3)	0.0489 (9)
C4A	−0.17513 (12)	0.7738 (4)	0.4598 (3)	0.0442 (9)
C12B	0.08850 (13)	0.3473 (4)	0.5573 (3)	0.0436 (9)
N11B	0.07562 (11)	0.3225 (4)	0.4690 (2)	0.0481 (8)
O3A	−0.17959 (11)	1.0823 (3)	0.5007 (2)	0.0653 (8)
C10A	−0.19598 (14)	0.6254 (5)	0.4419 (3)	0.0532 (11)
N17A	−0.14181 (12)	1.0502 (4)	0.3192 (2)	0.0578 (9)
C6A	−0.10755 (14)	0.6291 (5)	0.4763 (3)	0.0512 (11)
N8A	−0.10533 (17)	0.3354 (6)	0.4608 (4)	0.0746 (13)
N13B	0.13131 (11)	0.3637 (4)	0.5687 (2)	0.0541 (9)
C5A	−0.13036 (14)	0.7736 (5)	0.4765 (3)	0.0513 (11)
N11A	−0.21463 (13)	1.0049 (5)	0.3560 (3)	0.0583 (10)
C4B	0.01261 (12)	0.0878 (4)	0.4906 (3)	0.0400 (9)
C6B	−0.02321 (14)	−0.0545 (5)	0.6085 (3)	0.0530 (11)
O2A	−0.24790 (9)	0.9224 (3)	0.4943 (2)	0.0667 (9)
N13A	−0.19812 (13)	1.0397 (5)	0.2096 (3)	0.0705 (11)
C16B	0.07060 (15)	0.3713 (5)	0.7036 (3)	0.0518 (11)
C15B	0.11458 (17)	0.3878 (6)	0.7215 (3)	0.0639 (12)
C5B	−0.01422 (13)	0.0901 (5)	0.5644 (3)	0.0512 (10)
C12A	−0.18292 (14)	1.0333 (5)	0.2928 (3)	0.0503 (10)
C9B	0.02067 (15)	−0.2048 (6)	0.5052 (3)	0.0600 (12)
N8B	−0.01412 (18)	−0.3465 (6)	0.6281 (4)	0.0688 (13)
C15A	−0.1248 (2)	1.0851 (7)	0.1674 (4)	0.0804 (17)
C16A	−0.11190 (16)	1.0772 (5)	0.2545 (4)	0.0656 (13)
C7B	−0.00593 (13)	−0.2046 (5)	0.5817 (3)	0.0525 (11)
C19B	0.03641 (17)	0.3704 (7)	0.7725 (3)	0.0792 (15)
H191	0.049730	0.383666	0.829738	0.119*
H192	0.016349	0.459635	0.762120	0.119*
H193	0.020867	0.267458	0.770616	0.119*
C9A	−0.17331 (13)	0.4795 (5)	0.4425 (3)	0.0549 (10)
C14B	0.14401 (15)	0.3858 (6)	0.6528 (3)	0.0596 (12)
C18B	0.19249 (16)	0.4075 (8)	0.6669 (4)	0.0966 (19)
H183	0.198278	0.422347	0.728971	0.145*
H182	0.207671	0.311243	0.646000	0.145*
H181	0.202439	0.502674	0.634770	0.145*
C14A	−0.1681 (2)	1.0682 (6)	0.1464 (3)	0.0781 (16)
C19A	−0.06528 (16)	1.0934 (7)	0.2830 (4)	0.0945 (18)
H19X	−0.047145	1.112204	0.231963	0.142*
H19Z	−0.062509	1.184781	0.323170	0.142*
H19Y	−0.056193	0.993779	0.312124	0.142*
C18A	−0.1855 (2)	1.0738 (10)	0.0532 (4)	0.135 (3)
H18Z	−0.161873	1.094631	0.012719	0.202*
H18X	−0.198941	0.969936	0.038944	0.202*
H18Y	−0.206839	1.160412	0.048313	0.202*
N20B	0.14115 (12)	0.2099 (5)	0.3505 (3)	0.0682 (10)
C21B	0.18363 (18)	0.2129 (6)	0.3658 (4)	0.0786 (15)
H21B	0.193231	0.251730	0.420524	0.094*
C25B	0.1298 (2)	0.1555 (10)	0.2723 (4)	0.125 (3)
H25B	0.100148	0.155104	0.258292	0.150*
C23B	0.2015 (2)	0.1057 (9)	0.2257 (5)	0.110 (2)
H23B	0.221605	0.072602	0.183023	0.132*
C24B	0.1583 (2)	0.0993 (11)	0.2099 (4)	0.140 (3)
H24B	0.147917	0.056723	0.156685	0.168*
C22B	0.21464 (17)	0.1617 (7)	0.3053 (5)	0.0904 (17)
H22B	0.244274	0.165852	0.319309	0.108*
H9A	−0.1899 (12)	0.378 (5)	0.427 (3)	0.059 (12)*
H82A	−0.1168 (14)	0.252 (5)	0.449 (3)	0.058 (16)*
H5A	−0.1172 (12)	0.881 (5)	0.484 (2)	0.049 (11)*
H10B	0.0500 (11)	−0.054 (4)	0.411 (3)	0.046 (10)*
H5B	−0.0245 (12)	0.199 (5)	0.591 (3)	0.061 (12)*
H10A	−0.2265 (13)	0.628 (4)	0.429 (3)	0.055 (11)*
H15B	0.1231 (12)	0.389 (4)	0.784 (3)	0.049 (11)*
H9B	0.0287 (13)	−0.307 (5)	0.484 (3)	0.066 (14)*
H81A	−0.0789 (16)	0.342 (5)	0.465 (4)	0.071 (16)*
H6A	−0.0789 (13)	0.625 (4)	0.490 (3)	0.056 (12)*
H6B	−0.0404 (14)	−0.059 (5)	0.654 (3)	0.068 (15)*
H11B	0.0926 (12)	0.286 (4)	0.434 (3)	0.047 (12)*
H11A	−0.2393 (15)	0.974 (5)	0.346 (3)	0.067 (16)*
H81B	−0.0035 (14)	−0.430 (6)	0.606 (3)	0.064 (16)*
H15A	−0.1058 (19)	1.108 (7)	0.127 (5)	0.11 (2)*
H82B	−0.025 (2)	−0.347 (8)	0.674 (5)	0.10 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N20A	0.078 (3)	0.100 (3)	0.068 (3)	−0.010 (2)	−0.003 (3)	0.015 (2)
C25A	0.093 (4)	0.107 (4)	0.072 (4)	−0.027 (3)	−0.004 (4)	0.012 (3)
C24A	0.086 (5)	0.145 (6)	0.113 (6)	−0.036 (4)	0.002 (5)	0.000 (5)
C21A	0.091 (5)	0.204 (8)	0.073 (5)	−0.020 (5)	0.002 (4)	0.009 (5)
C22A	0.143 (8)	0.276 (12)	0.082 (6)	−0.057 (8)	−0.039 (6)	0.017 (6)
C23A	0.092 (6)	0.215 (9)	0.165 (10)	−0.041 (6)	−0.032 (7)	0.015 (8)
S1B	0.0428 (5)	0.0524 (6)	0.0373 (5)	−0.0013 (4)	−0.0031 (5)	0.0002 (5)
S1A	0.0545 (6)	0.0593 (6)	0.0471 (7)	0.0040 (5)	0.0064 (6)	0.0056 (5)
O3B	0.0523 (15)	0.0511 (14)	0.0544 (18)	0.0066 (12)	−0.0028 (15)	0.0054 (13)
N17B	0.051 (2)	0.060 (2)	0.038 (2)	−0.0011 (17)	0.0039 (18)	0.0018 (16)
O2B	0.0572 (17)	0.0802 (19)	0.0344 (16)	−0.0083 (14)	−0.0048 (14)	−0.0008 (14)
C10B	0.056 (2)	0.057 (3)	0.048 (3)	−0.002 (2)	0.010 (3)	−0.009 (2)
C7A	0.045 (2)	0.055 (2)	0.047 (2)	0.004 (2)	0.002 (2)	0.004 (2)
C4A	0.044 (2)	0.055 (2)	0.034 (2)	−0.0043 (18)	0.0018 (19)	0.002 (2)
C12B	0.053 (3)	0.041 (2)	0.037 (2)	−0.0071 (18)	0.002 (2)	0.0013 (17)
N11B	0.0394 (19)	0.072 (2)	0.0333 (19)	−0.0053 (16)	0.0031 (18)	−0.0053 (17)
O3A	0.081 (2)	0.0565 (17)	0.058 (2)	0.0004 (16)	0.0001 (17)	−0.0046 (13)
C10A	0.041 (2)	0.063 (3)	0.056 (3)	−0.002 (2)	−0.006 (2)	0.008 (2)
N17A	0.052 (2)	0.069 (2)	0.052 (2)	−0.0009 (18)	0.005 (2)	0.0056 (17)
C6A	0.034 (2)	0.072 (3)	0.048 (3)	0.000 (2)	−0.005 (2)	−0.001 (2)
N8A	0.055 (3)	0.060 (3)	0.109 (4)	0.005 (2)	−0.004 (3)	−0.005 (3)
N13B	0.043 (2)	0.079 (2)	0.040 (2)	−0.0167 (17)	−0.0072 (17)	0.0001 (17)
C5A	0.055 (3)	0.051 (3)	0.048 (3)	−0.010 (2)	−0.005 (2)	0.0015 (19)
N11A	0.046 (2)	0.076 (3)	0.053 (3)	0.003 (2)	0.000 (2)	0.0191 (19)
C4B	0.0341 (18)	0.044 (2)	0.042 (2)	0.0022 (17)	0.0003 (18)	−0.0006 (16)
C6B	0.048 (3)	0.061 (3)	0.051 (3)	0.004 (2)	0.012 (2)	0.006 (2)
O2A	0.0549 (17)	0.0802 (19)	0.065 (2)	0.0100 (15)	0.0162 (16)	0.0102 (15)
N13A	0.074 (3)	0.083 (3)	0.055 (3)	0.015 (2)	−0.004 (2)	0.017 (2)
C16B	0.066 (3)	0.055 (2)	0.034 (2)	0.002 (2)	0.001 (2)	−0.0030 (18)
C15B	0.068 (3)	0.085 (3)	0.039 (3)	−0.010 (2)	−0.011 (3)	0.000 (2)
C5B	0.047 (2)	0.052 (3)	0.055 (3)	0.007 (2)	0.007 (2)	0.000 (2)
C12A	0.056 (3)	0.051 (2)	0.044 (3)	0.007 (2)	0.000 (2)	0.009 (2)
C9B	0.070 (3)	0.046 (3)	0.064 (3)	0.005 (2)	0.005 (3)	−0.011 (2)
N8B	0.086 (3)	0.049 (3)	0.071 (3)	0.002 (2)	0.005 (3)	0.012 (3)
C15A	0.089 (5)	0.097 (4)	0.055 (4)	−0.001 (3)	0.024 (4)	0.017 (3)
C16A	0.061 (3)	0.067 (3)	0.069 (4)	−0.004 (2)	0.014 (3)	−0.003 (2)
C7B	0.049 (2)	0.055 (3)	0.053 (3)	0.000 (2)	−0.010 (2)	−0.001 (2)
C19B	0.084 (4)	0.105 (4)	0.049 (3)	0.009 (3)	0.012 (3)	−0.002 (3)
C9A	0.046 (2)	0.053 (3)	0.065 (3)	−0.005 (2)	−0.001 (2)	0.004 (2)
C14B	0.055 (3)	0.074 (3)	0.050 (3)	−0.018 (2)	−0.008 (3)	0.002 (2)
C18B	0.071 (4)	0.149 (5)	0.070 (4)	−0.033 (3)	−0.021 (3)	0.002 (3)
C14A	0.099 (4)	0.090 (4)	0.045 (3)	0.019 (3)	0.007 (3)	0.016 (3)
C19A	0.063 (4)	0.126 (5)	0.094 (4)	−0.023 (3)	0.019 (3)	−0.017 (3)
C18A	0.152 (6)	0.196 (7)	0.056 (4)	0.017 (5)	−0.008 (5)	0.035 (4)
N20B	0.054 (2)	0.105 (3)	0.046 (2)	−0.003 (2)	−0.001 (2)	−0.009 (2)
C21B	0.073 (4)	0.095 (4)	0.068 (4)	−0.008 (3)	−0.012 (3)	−0.005 (3)
C25B	0.063 (4)	0.250 (8)	0.062 (4)	0.030 (5)	−0.007 (3)	−0.053 (5)
C23B	0.076 (5)	0.167 (6)	0.086 (5)	0.034 (4)	0.021 (4)	−0.017 (4)
C24B	0.078 (5)	0.284 (10)	0.057 (4)	0.055 (5)	−0.006 (4)	−0.054 (5)
C22B	0.050 (3)	0.109 (4)	0.113 (6)	0.007 (3)	0.002 (4)	−0.015 (4)

Geometric parameters (Å, º)

N20A—C21A	1.294 (8)	C6B—C5B	1.374 (6)
N20A—C25A	1.314 (7)	C6B—C7B	1.385 (6)
C25A—C24A	1.347 (8)	C6B—H6B	0.87 (4)
C25A—H25A	0.9300	N13A—C12A	1.339 (5)
C24A—C23A	1.327 (11)	N13A—C14A	1.342 (6)
C24A—H24A	0.9300	C16B—C15B	1.377 (6)
C21A—C22A	1.356 (10)	C16B—C19B	1.473 (6)
C21A—H21A	0.9300	C15B—C14B	1.372 (6)
C22A—C23A	1.390 (12)	C15B—H15B	0.98 (4)
C22A—H22A	0.9300	C5B—H5B	1.02 (4)
C23A—H23A	0.9300	C9B—C7B	1.412 (6)
S1B—O3B	1.428 (3)	C9B—H9B	0.92 (4)
S1B—O2B	1.429 (3)	N8B—C7B	1.368 (6)
S1B—N11B	1.623 (3)	N8B—H81B	0.82 (4)
S1B—C4B	1.747 (4)	N8B—H82B	0.76 (6)
S1A—O3A	1.427 (3)	C15A—C14A	1.367 (8)
S1A—O2A	1.429 (3)	C15A—C16A	1.373 (8)
S1A—N11A	1.645 (4)	C15A—H15A	0.86 (6)
S1A—C4A	1.735 (4)	C16A—C19A	1.493 (7)
N17B—C12B	1.332 (5)	C19B—H191	0.9600
N17B—C16B	1.359 (5)	C19B—H192	0.9600
C10B—C9B	1.372 (6)	C19B—H193	0.9600
C10B—C4B	1.389 (5)	C9A—H9A	1.00 (4)
C10B—H10B	0.97 (4)	C14B—C18B	1.506 (6)
C7A—N8A	1.347 (5)	C18B—H183	0.9600
C7A—C6A	1.401 (5)	C18B—H182	0.9600
C7A—C9A	1.403 (5)	C18B—H181	0.9600
C4A—C10A	1.387 (5)	C14A—C18A	1.505 (8)
C4A—C5A	1.390 (5)	C19A—H19X	0.9600
C12B—N13B	1.325 (5)	C19A—H19Z	0.9600
C12B—N11B	1.403 (5)	C19A—H19Y	0.9600
N11B—H11B	0.80 (4)	C18A—H18Z	0.9600
C10A—C9A	1.369 (6)	C18A—H18X	0.9600
C10A—H10A	0.95 (4)	C18A—H18Y	0.9600
N17A—C12A	1.324 (5)	N20B—C25B	1.306 (7)
N17A—C16A	1.354 (6)	N20B—C21B	1.318 (6)
C6A—C5A	1.362 (6)	C21B—C22B	1.380 (7)
C6A—H6A	0.90 (4)	C21B—H21B	0.9300
N8A—H82A	0.78 (4)	C25B—C24B	1.360 (8)
N8A—H81A	0.81 (5)	C25B—H25B	0.9300
N13B—C14B	1.338 (5)	C23B—C24B	1.340 (8)
C5A—H5A	0.96 (4)	C23B—C22B	1.345 (8)
N11A—C12A	1.379 (5)	C23B—H23B	0.9300
N11A—H11A	0.81 (4)	C24B—H24B	0.9300
C4B—C5B	1.383 (5)	C22B—H22B	0.9300
C21A—N20A—C25A	116.9 (5)	C14B—C15B—H15B	124 (2)
N20A—C25A—C24A	124.8 (6)	C16B—C15B—H15B	117 (2)
N20A—C25A—H25A	117.6	C6B—C5B—C4B	119.8 (4)
C24A—C25A—H25A	117.6	C6B—C5B—H5B	119 (2)
C23A—C24A—C25A	118.0 (8)	C4B—C5B—H5B	121 (2)
C23A—C24A—H24A	121.0	N17A—C12A—N13A	127.3 (4)
C25A—C24A—H24A	121.0	N17A—C12A—N11A	118.4 (4)
N20A—C21A—C22A	123.4 (7)	N13A—C12A—N11A	114.3 (4)
N20A—C21A—H21A	118.3	C10B—C9B—C7B	121.0 (4)
C22A—C21A—H21A	118.3	C10B—C9B—H9B	123 (3)
C21A—C22A—C23A	117.8 (8)	C7B—C9B—H9B	116 (3)
C21A—C22A—H22A	121.1	C7B—N8B—H81B	114 (3)
C23A—C22A—H22A	121.1	C7B—N8B—H82B	123 (5)
C24A—C23A—C22A	119.0 (7)	H81B—N8B—H82B	122 (6)
C24A—C23A—H23A	120.5	C14A—C15A—C16A	119.6 (5)
C22A—C23A—H23A	120.5	C14A—C15A—H15A	121 (4)
O3B—S1B—O2B	118.29 (17)	C16A—C15A—H15A	120 (4)
O3B—S1B—N11B	109.62 (18)	N17A—C16A—C15A	120.3 (5)
O2B—S1B—N11B	103.88 (18)	N17A—C16A—C19A	116.7 (5)
O3B—S1B—C4B	107.37 (17)	C15A—C16A—C19A	123.0 (5)
O2B—S1B—C4B	109.47 (17)	N8B—C7B—C6B	121.2 (5)
N11B—S1B—C4B	107.80 (18)	N8B—C7B—C9B	121.5 (4)
O3A—S1A—O2A	118.69 (19)	C6B—C7B—C9B	117.3 (4)
O3A—S1A—N11A	109.4 (2)	C16B—C19B—H191	109.5
O2A—S1A—N11A	103.3 (2)	C16B—C19B—H192	109.5
O3A—S1A—C4A	108.77 (18)	H191—C19B—H192	109.5
O2A—S1A—C4A	108.91 (16)	C16B—C19B—H193	109.5
N11A—S1A—C4A	107.25 (19)	H191—C19B—H193	109.5
C12B—N17B—C16B	115.9 (3)	H192—C19B—H193	109.5
C9B—C10B—C4B	120.1 (4)	C10A—C9A—C7A	120.5 (4)
C9B—C10B—H10B	124 (2)	C10A—C9A—H9A	117 (2)
C4B—C10B—H10B	116 (2)	C7A—C9A—H9A	122 (2)
N8A—C7A—C6A	120.9 (4)	N13B—C14B—C15B	121.8 (4)
N8A—C7A—C9A	121.3 (4)	N13B—C14B—C18B	115.8 (4)
C6A—C7A—C9A	117.8 (4)	C15B—C14B—C18B	122.4 (4)
C10A—C4A—C5A	119.1 (4)	C14B—C18B—H183	109.5
C10A—C4A—S1A	119.6 (3)	C14B—C18B—H182	109.5
C5A—C4A—S1A	121.4 (3)	H183—C18B—H182	109.5
N13B—C12B—N17B	128.2 (4)	C14B—C18B—H181	109.5
N13B—C12B—N11B	114.5 (4)	H183—C18B—H181	109.5
N17B—C12B—N11B	117.3 (3)	H182—C18B—H181	109.5
C12B—N11B—S1B	125.6 (3)	N13A—C14A—C15A	121.0 (5)
C12B—N11B—H11B	120 (3)	N13A—C14A—C18A	115.3 (6)
S1B—N11B—H11B	107 (3)	C15A—C14A—C18A	123.7 (6)
C9A—C10A—C4A	121.0 (4)	C16A—C19A—H19X	109.5
C9A—C10A—H10A	121 (2)	C16A—C19A—H19Z	109.5
C4A—C10A—H10A	118 (2)	H19X—C19A—H19Z	109.5
C12A—N17A—C16A	116.1 (4)	C16A—C19A—H19Y	109.5
C5A—C6A—C7A	121.5 (4)	H19X—C19A—H19Y	109.5
C5A—C6A—H6A	122 (2)	H19Z—C19A—H19Y	109.5
C7A—C6A—H6A	117 (2)	C14A—C18A—H18Z	109.5
C7A—N8A—H82A	120 (3)	C14A—C18A—H18X	109.5
C7A—N8A—H81A	117 (3)	H18Z—C18A—H18X	109.5
H82A—N8A—H81A	121 (5)	C14A—C18A—H18Y	109.5
C12B—N13B—C14B	115.0 (4)	H18Z—C18A—H18Y	109.5
C6A—C5A—C4A	120.2 (4)	H18X—C18A—H18Y	109.5
C6A—C5A—H5A	124 (2)	C25B—N20B—C21B	115.2 (5)
C4A—C5A—H5A	116 (2)	N20B—C21B—C22B	123.6 (5)
C12A—N11A—S1A	125.2 (3)	N20B—C21B—H21B	118.2
C12A—N11A—H11A	125 (4)	C22B—C21B—H21B	118.2
S1A—N11A—H11A	106 (4)	N20B—C25B—C24B	124.6 (6)
C5B—C4B—C10B	119.8 (4)	N20B—C25B—H25B	117.7
C5B—C4B—S1B	120.9 (3)	C24B—C25B—H25B	117.7
C10B—C4B—S1B	119.3 (3)	C24B—C23B—C22B	117.8 (6)
C5B—C6B—C7B	122.0 (5)	C24B—C23B—H23B	121.1
C5B—C6B—H6B	123 (3)	C22B—C23B—H23B	121.1
C7B—C6B—H6B	115 (3)	C23B—C24B—C25B	119.6 (6)
C12A—N13A—C14A	115.8 (4)	C23B—C24B—H24B	120.2
N17B—C16B—C15B	119.6 (4)	C25B—C24B—H24B	120.2
N17B—C16B—C19B	116.8 (4)	C23B—C22B—C21B	119.1 (5)
C15B—C16B—C19B	123.6 (4)	C23B—C22B—H22B	120.4
C14B—C15B—C16B	119.4 (4)	C21B—C22B—H22B	120.4
C21A—N20A—C25A—C24A	0.7 (9)	C12B—N17B—C16B—C15B	2.5 (5)
N20A—C25A—C24A—C23A	−1.2 (11)	C12B—N17B—C16B—C19B	−177.1 (4)
C25A—N20A—C21A—C22A	−1.5 (11)	N17B—C16B—C15B—C14B	−0.2 (6)
N20A—C21A—C22A—C23A	2.9 (15)	C19B—C16B—C15B—C14B	179.4 (4)
C25A—C24A—C23A—C22A	2.6 (13)	C7B—C6B—C5B—C4B	0.4 (6)
C21A—C22A—C23A—C24A	−3.3 (15)	C10B—C4B—C5B—C6B	1.0 (6)
O3A—S1A—C4A—C10A	166.0 (3)	S1B—C4B—C5B—C6B	−176.8 (3)
O2A—S1A—C4A—C10A	35.2 (4)	C16A—N17A—C12A—N13A	0.1 (6)
N11A—S1A—C4A—C10A	−75.9 (4)	C16A—N17A—C12A—N11A	179.7 (4)
O3A—S1A—C4A—C5A	−14.6 (4)	C14A—N13A—C12A—N17A	−0.8 (7)
O2A—S1A—C4A—C5A	−145.3 (3)	C14A—N13A—C12A—N11A	179.6 (4)
N11A—S1A—C4A—C5A	103.6 (4)	S1A—N11A—C12A—N17A	−12.0 (6)
C16B—N17B—C12B—N13B	−3.5 (5)	S1A—N11A—C12A—N13A	167.6 (3)
C16B—N17B—C12B—N11B	177.5 (3)	C4B—C10B—C9B—C7B	−0.1 (6)
N13B—C12B—N11B—S1B	170.0 (3)	C12A—N17A—C16A—C15A	−0.3 (6)
N17B—C12B—N11B—S1B	−10.8 (5)	C12A—N17A—C16A—C19A	−178.9 (4)
O3B—S1B—N11B—C12B	60.5 (4)	C14A—C15A—C16A—N17A	1.1 (8)
O2B—S1B—N11B—C12B	−172.2 (3)	C14A—C15A—C16A—C19A	179.6 (5)
C4B—S1B—N11B—C12B	−56.1 (4)	C5B—C6B—C7B—N8B	177.9 (4)
C5A—C4A—C10A—C9A	1.6 (7)	C5B—C6B—C7B—C9B	−1.6 (6)
S1A—C4A—C10A—C9A	−179.0 (4)	C10B—C9B—C7B—N8B	−178.1 (4)
N8A—C7A—C6A—C5A	−179.5 (4)	C10B—C9B—C7B—C6B	1.5 (6)
C9A—C7A—C6A—C5A	1.2 (6)	C4A—C10A—C9A—C7A	−0.9 (7)
N17B—C12B—N13B—C14B	1.6 (6)	N8A—C7A—C9A—C10A	−179.7 (5)
N11B—C12B—N13B—C14B	−179.4 (3)	C6A—C7A—C9A—C10A	−0.5 (7)
C7A—C6A—C5A—C4A	−0.6 (6)	C12B—N13B—C14B—C15B	1.2 (6)
C10A—C4A—C5A—C6A	−0.8 (6)	C12B—N13B—C14B—C18B	−179.0 (4)
S1A—C4A—C5A—C6A	179.7 (3)	C16B—C15B—C14B—N13B	−1.8 (7)
O3A—S1A—N11A—C12A	58.8 (4)	C16B—C15B—C14B—C18B	178.4 (5)
O2A—S1A—N11A—C12A	−173.9 (4)	C12A—N13A—C14A—C15A	1.5 (7)
C4A—S1A—N11A—C12A	−58.9 (4)	C12A—N13A—C14A—C18A	179.6 (5)
C9B—C10B—C4B—C5B	−1.2 (6)	C16A—C15A—C14A—N13A	−1.7 (8)
C9B—C10B—C4B—S1B	176.7 (3)	C16A—C15A—C14A—C18A	−179.6 (5)
O3B—S1B—C4B—C5B	−18.3 (4)	C25B—N20B—C21B—C22B	−0.6 (8)
O2B—S1B—C4B—C5B	−147.9 (3)	C21B—N20B—C25B—C24B	2.2 (11)
N11B—S1B—C4B—C5B	99.7 (3)	C22B—C23B—C24B—C25B	2.9 (13)
O3B—S1B—C4B—C10B	163.9 (3)	N20B—C25B—C24B—C23B	−3.4 (14)
O2B—S1B—C4B—C10B	34.3 (4)	C24B—C23B—C22B—C21B	−1.4 (11)
N11B—S1B—C4B—C10B	−78.1 (4)	N20B—C21B—C22B—C23B	0.2 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8A—H81A···O3B	0.81 (5)	2.34 (5)	3.176 (6)	172 (5)
N8A—H82A···O3A	0.78 (4)	2.49 (4)	3.168 (6)	139 (4)
N8B—H81B···O3B^i	0.82 (5)	2.59 (5)	3.275 (6)	142 (4)
N8B—H81B···N17B^i	0.82 (5)	2.55 (5)	3.261 (6)	145 (4)
N11A—H11A···N20A	0.81 (4)	2.09 (5)	2.894 (6)	171 (5)
N11B—H11B···N20B	0.80 (4)	2.04 (4)	2.834 (5)	174 (3)

Symmetry code: (i) x, y−1, z.

(2) 4-Amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide pyridine monosolvate

Crystal data

C12H14N4O2S·C6H7N	Dx = 1.267 Mg m^−3
Mr = 371.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 6058 reflections
a = 9.6920 (2) Å	θ = 2.3–27.5°
b = 25.1673 (6) Å	µ = 0.19 mm^−1
c = 7.9853 (2) Å	T = 296 K
V = 1947.79 (8) Å^3	Needle, colorless
Z = 4	0.65 × 0.60 × 0.35 mm
F(000) = 784

Data collection

Bruker Kappa APEXII CCD diffractometer	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 1.6°
10022 measured reflections	h = −7→12
4438 independent reflections	k = −32→28
4082 reflections with I > 2σ(I)	l = −9→10

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.1007P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.23 e Å^−3
4438 reflections	Δρmin = −0.28 e Å^−3
270 parameters	Absolute structure: Refined as an inversion twin.
0 restraints	Absolute structure parameter: −0.01 (9)

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.

Refinement. Refined as a 2-component inversion twin

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

	x	y	z	Uiso*/Ueq
S1	0.44885 (5)	0.65278 (2)	0.74692 (7)	0.04252 (15)
O2	0.31271 (17)	0.63361 (8)	0.7099 (2)	0.0599 (5)
O3	0.4646 (2)	0.69307 (7)	0.8725 (2)	0.0568 (5)
N13	0.7158 (2)	0.54388 (8)	0.8259 (3)	0.0539 (5)
C6	0.6878 (3)	0.73158 (9)	0.4223 (3)	0.0495 (5)
N11	0.5299 (2)	0.59874 (7)	0.8069 (3)	0.0440 (4)
N8	0.7199 (3)	0.72280 (10)	0.1257 (3)	0.0609 (6)
C4	0.5271 (2)	0.67515 (8)	0.5639 (3)	0.0388 (4)
C5	0.6251 (3)	0.71551 (9)	0.5680 (3)	0.0460 (5)
N17	0.74845 (19)	0.63772 (7)	0.8302 (2)	0.0436 (4)
C7	0.6565 (2)	0.70779 (8)	0.2691 (3)	0.0442 (5)
C12	0.6727 (2)	0.59385 (8)	0.8216 (3)	0.0401 (4)
C9	0.5570 (3)	0.66678 (9)	0.2682 (3)	0.0496 (5)
C10	0.4941 (3)	0.65099 (9)	0.4133 (3)	0.0451 (5)
C16	0.8857 (2)	0.63022 (11)	0.8340 (3)	0.0511 (5)
C15	0.9413 (3)	0.58014 (12)	0.8330 (4)	0.0642 (7)
C24	0.4181 (4)	0.40510 (12)	0.7755 (4)	0.0715 (8)
N20	0.4000 (2)	0.49939 (9)	0.7369 (4)	0.0648 (6)
C21	0.2893 (3)	0.49161 (15)	0.6425 (5)	0.0752 (9)
H21	0.244679	0.520952	0.596926	0.090*
C25	0.4616 (3)	0.45649 (11)	0.8002 (4)	0.0652 (7)
H25	0.539742	0.461726	0.865845	0.078*
C19	0.9738 (3)	0.67906 (13)	0.8382 (5)	0.0723 (8)
H19A	0.975191	0.693219	0.949842	0.108*
H19B	0.936751	0.705135	0.762881	0.108*
H19C	1.066083	0.670151	0.804634	0.108*
C14	0.8535 (3)	0.53738 (11)	0.8339 (5)	0.0657 (8)
C22	0.2380 (4)	0.44171 (19)	0.6095 (5)	0.0879 (11)
H22	0.160184	0.437432	0.542666	0.105*
C26	0.4937 (6)	0.35923 (15)	0.8538 (8)	0.125 (2)
H26A	0.449231	0.326556	0.823323	0.187*
H26B	0.587379	0.358838	0.814647	0.187*
H26C	0.492866	0.363021	0.973420	0.187*
C18	0.9020 (4)	0.48042 (14)	0.8406 (9)	0.1108 (17)
H18A	0.877941	0.462790	0.738079	0.166*
H18B	0.858499	0.462644	0.932975	0.166*
H18C	1.000285	0.479600	0.855061	0.166*
C23	0.3029 (4)	0.39881 (15)	0.6761 (5)	0.0830 (11)
H23	0.269328	0.364876	0.654559	0.100*
H5	0.648 (3)	0.7310 (10)	0.679 (3)	0.041 (6)*
H9	0.531 (3)	0.6502 (13)	0.167 (4)	0.066 (8)*
H6	0.748 (3)	0.7616 (13)	0.425 (4)	0.065 (9)*
H8B	0.692 (3)	0.7089 (13)	0.031 (4)	0.062 (9)*
H10	0.424 (4)	0.6244 (14)	0.414 (4)	0.068 (8)*
H8A	0.782 (3)	0.7477 (12)	0.132 (4)	0.054 (8)*
H11	0.481 (3)	0.5667 (14)	0.780 (4)	0.074 (9)*
H15	1.031 (4)	0.5753 (13)	0.844 (4)	0.074 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0365 (3)	0.0450 (3)	0.0461 (3)	0.0105 (2)	0.0038 (2)	0.0067 (2)
O2	0.0322 (8)	0.0758 (12)	0.0717 (11)	0.0089 (8)	0.0035 (7)	0.0193 (9)
O3	0.0677 (12)	0.0560 (10)	0.0466 (8)	0.0166 (9)	0.0066 (9)	−0.0011 (7)
N13	0.0430 (11)	0.0420 (9)	0.0767 (13)	0.0055 (8)	−0.0122 (10)	0.0026 (10)
C6	0.0558 (15)	0.0391 (11)	0.0535 (12)	−0.0099 (11)	−0.0007 (11)	−0.0010 (10)
N11	0.0339 (9)	0.0384 (8)	0.0596 (10)	0.0031 (7)	−0.0027 (8)	0.0098 (8)
N8	0.0699 (16)	0.0616 (14)	0.0511 (12)	−0.0179 (12)	0.0136 (11)	−0.0072 (10)
C4	0.0402 (11)	0.0355 (9)	0.0406 (9)	0.0042 (8)	0.0025 (9)	0.0038 (8)
C5	0.0596 (15)	0.0351 (10)	0.0434 (10)	−0.0022 (9)	−0.0046 (11)	−0.0038 (9)
N17	0.0376 (9)	0.0435 (9)	0.0496 (10)	0.0009 (7)	0.0028 (8)	−0.0002 (8)
C7	0.0475 (11)	0.0371 (9)	0.0481 (11)	0.0008 (8)	0.0022 (10)	0.0020 (9)
C12	0.0346 (10)	0.0416 (10)	0.0440 (10)	0.0036 (8)	−0.0032 (9)	0.0048 (9)
C9	0.0587 (13)	0.0483 (11)	0.0417 (11)	−0.0094 (10)	−0.0021 (11)	−0.0067 (9)
C10	0.0470 (12)	0.0403 (10)	0.0480 (10)	−0.0077 (9)	−0.0042 (9)	0.0004 (10)
C16	0.0377 (12)	0.0607 (14)	0.0548 (12)	−0.0026 (11)	−0.0001 (10)	−0.0054 (11)
C15	0.0355 (12)	0.0691 (16)	0.0880 (19)	0.0097 (13)	−0.0086 (14)	−0.0101 (15)
C24	0.081 (2)	0.0565 (14)	0.0769 (19)	−0.0125 (14)	0.0183 (17)	−0.0003 (14)
N20	0.0543 (12)	0.0563 (12)	0.0838 (16)	−0.0073 (10)	−0.0075 (12)	0.0001 (13)
C21	0.0542 (17)	0.085 (2)	0.087 (2)	−0.0046 (16)	−0.0100 (15)	−0.0019 (18)
C25	0.0632 (17)	0.0558 (14)	0.0767 (17)	−0.0085 (13)	−0.0096 (14)	0.0002 (13)
C19	0.0449 (15)	0.0752 (18)	0.097 (2)	−0.0154 (13)	0.0101 (15)	−0.0133 (18)
C14	0.0503 (15)	0.0541 (14)	0.093 (2)	0.0195 (12)	−0.0156 (15)	−0.0038 (15)
C22	0.060 (2)	0.116 (3)	0.088 (2)	−0.026 (2)	−0.0038 (17)	−0.024 (2)
C26	0.174 (6)	0.060 (2)	0.140 (4)	0.007 (3)	0.011 (4)	0.019 (3)
C18	0.072 (2)	0.0599 (18)	0.201 (5)	0.0315 (17)	−0.028 (3)	−0.009 (3)
C23	0.083 (2)	0.076 (2)	0.089 (2)	−0.035 (2)	0.025 (2)	−0.0230 (19)

Geometric parameters (Å, º)

S1—O3	1.4342 (18)	C16—C19	1.497 (4)
S1—O2	1.4357 (19)	C15—C14	1.372 (4)
S1—N11	1.6421 (18)	C15—H15	0.88 (4)
S1—C4	1.740 (2)	C24—C25	1.375 (4)
N13—C12	1.326 (3)	C24—C23	1.379 (6)
N13—C14	1.346 (3)	C24—C26	1.504 (6)
C6—C5	1.373 (4)	N20—C21	1.325 (4)
C6—C7	1.396 (3)	N20—C25	1.334 (4)
C6—H6	0.96 (3)	C21—C22	1.376 (5)
N11—C12	1.394 (3)	C21—H21	0.9300
N11—H11	0.96 (4)	C25—H25	0.9300
N8—C7	1.354 (3)	C19—H19A	0.9600
N8—H8B	0.88 (3)	C19—H19B	0.9600
N8—H8A	0.87 (3)	C19—H19C	0.9600
C4—C10	1.385 (3)	C14—C18	1.509 (4)
C4—C5	1.392 (3)	C22—C23	1.358 (6)
C5—H5	0.99 (3)	C22—H22	0.9300
N17—C12	1.328 (3)	C26—H26A	0.9600
N17—C16	1.344 (3)	C26—H26B	0.9600
C7—C9	1.412 (3)	C26—H26C	0.9600
C9—C10	1.369 (3)	C18—H18A	0.9600
C9—H9	0.94 (3)	C18—H18B	0.9600
C10—H10	0.95 (3)	C18—H18C	0.9600
C16—C15	1.371 (4)	C23—H23	0.9300
O3—S1—O2	118.66 (12)	C16—C15—H15	121 (2)
O3—S1—N11	109.31 (11)	C14—C15—H15	120 (2)
O2—S1—N11	102.80 (11)	C25—C24—C23	116.1 (3)
O3—S1—C4	108.19 (11)	C25—C24—C26	120.9 (4)
O2—S1—C4	109.64 (11)	C23—C24—C26	123.1 (3)
N11—S1—C4	107.72 (10)	C21—N20—C25	117.3 (3)
C12—N13—C14	115.4 (2)	N20—C21—C22	122.4 (3)
C5—C6—C7	121.3 (2)	N20—C21—H21	118.8
C5—C6—H6	119 (2)	C22—C21—H21	118.8
C7—C6—H6	119 (2)	N20—C25—C24	124.7 (3)
C12—N11—S1	124.94 (16)	N20—C25—H25	117.6
C12—N11—H11	116 (2)	C24—C25—H25	117.6
S1—N11—H11	113 (2)	C16—C19—H19A	109.5
C7—N8—H8B	119 (2)	C16—C19—H19B	109.5
C7—N8—H8A	118 (2)	H19A—C19—H19B	109.5
H8B—N8—H8A	123 (3)	C16—C19—H19C	109.5
C10—C4—C5	119.9 (2)	H19A—C19—H19C	109.5
C10—C4—S1	119.13 (17)	H19B—C19—H19C	109.5
C5—C4—S1	120.96 (17)	N13—C14—C15	121.3 (2)
C6—C5—C4	119.8 (2)	N13—C14—C18	115.2 (3)
C6—C5—H5	122.9 (15)	C15—C14—C18	123.5 (3)
C4—C5—H5	117.2 (15)	C23—C22—C21	118.9 (3)
C12—N17—C16	115.6 (2)	C23—C22—H22	120.6
N8—C7—C6	121.5 (2)	C21—C22—H22	120.6
N8—C7—C9	120.6 (2)	C24—C26—H26A	109.5
C6—C7—C9	117.8 (2)	C24—C26—H26B	109.5
N13—C12—N17	127.8 (2)	H26A—C26—H26B	109.5
N13—C12—N11	113.5 (2)	C24—C26—H26C	109.5
N17—C12—N11	118.68 (19)	H26A—C26—H26C	109.5
C10—C9—C7	120.8 (2)	H26B—C26—H26C	109.5
C10—C9—H9	118 (2)	C14—C18—H18A	109.5
C7—C9—H9	121 (2)	C14—C18—H18B	109.5
C9—C10—C4	120.3 (2)	H18A—C18—H18B	109.5
C9—C10—H10	122 (2)	C14—C18—H18C	109.5
C4—C10—H10	118 (2)	H18A—C18—H18C	109.5
N17—C16—C15	121.2 (2)	H18B—C18—H18C	109.5
N17—C16—C19	116.7 (2)	C22—C23—C24	120.6 (3)
C15—C16—C19	122.0 (2)	C22—C23—H23	119.7
C16—C15—C14	118.5 (2)	C24—C23—H23	119.7
O3—S1—N11—C12	−67.8 (2)	C6—C7—C9—C10	−0.1 (4)
O2—S1—N11—C12	165.2 (2)	C7—C9—C10—C4	0.0 (4)
C4—S1—N11—C12	49.5 (2)	C5—C4—C10—C9	−0.3 (4)
O3—S1—C4—C10	−162.20 (18)	S1—C4—C10—C9	−178.1 (2)
O2—S1—C4—C10	−31.4 (2)	C12—N17—C16—C15	−1.5 (4)
N11—S1—C4—C10	79.7 (2)	C12—N17—C16—C19	178.1 (2)
O3—S1—C4—C5	20.0 (2)	N17—C16—C15—C14	−2.2 (4)
O2—S1—C4—C5	150.80 (19)	C19—C16—C15—C14	178.2 (3)
N11—S1—C4—C5	−98.0 (2)	C25—N20—C21—C22	0.1 (5)
C7—C6—C5—C4	−0.7 (4)	C21—N20—C25—C24	−0.5 (5)
C10—C4—C5—C6	0.6 (4)	C23—C24—C25—N20	0.7 (5)
S1—C4—C5—C6	178.42 (19)	C26—C24—C25—N20	−179.3 (4)
C5—C6—C7—N8	−178.7 (3)	C12—N13—C14—C15	−1.7 (5)
C5—C6—C7—C9	0.5 (4)	C12—N13—C14—C18	179.4 (4)
C14—N13—C12—N17	−2.6 (4)	C16—C15—C14—N13	3.9 (5)
C14—N13—C12—N11	177.7 (3)	C16—C15—C14—C18	−177.2 (4)
C16—N17—C12—N13	4.2 (4)	N20—C21—C22—C23	0.1 (6)
C16—N17—C12—N11	−176.1 (2)	C21—C22—C23—C24	0.1 (6)
S1—N11—C12—N13	−162.20 (19)	C25—C24—C23—C22	−0.5 (5)
S1—N11—C12—N17	18.1 (3)	C26—C24—C23—C22	179.5 (4)
N8—C7—C9—C10	179.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8A···O3^i	0.87	2.31	3.1792 (3)	173
N8—H8B···O3^ii	0.88	2.57	3.2821 (3)	139
N8—H8B···N17^ii	0.88	2.46	3.1984 (3)	141
N11—H11···N20	0.96	1.90	2.8550 (3)	174

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