Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methyl­benzene­sulfonyl)glycine hydrazone derivatives

The crystal structures of N-(4-methyl­benzene­sulfon­yl)glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzyl­idene)hydrazin­yl]-2-oxoeth­yl}-4-methyl­benzene­sul­fon­amide, C₁₆H₁₇N₃O₃S, (I), (E)-N-{2-[2-(4-bromo­benzyl­idene)hydrazin­yl]-2-oxoeth­yl}-4-methyl­benzene­sulfonamide, C₁₆H₁₆BrN₃O₃S, (II), (E)-N-{2-[2-(4-chloro­benzyl­idene)hydrazin­yl]-2-oxoeth­yl}-4-methyl­benzene­sulfonamide, C₁₆H₁₆ClN₃O₃S, (III), (E)-N-(2-{2-[4-(di­methyl­amino)­benzyl­idene]hydrazin­yl}-2-oxoeth­yl)-4-methyl­benzenesulfonamide, C₁₈H₂₂N₄O₃S, (IV), and (E)-N-{2-[2-(4-meth­oxy­benzyl­idene)hydrazin­yl]-2-oxoeth­yl}-4-methyl­benzene­sulfonamide, C₁₇H₁₉N₃O₄S, (V). The mol­ecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the mol­ecule, i.e. C—C—N—N=C, is almost linear in all the structures, with the C—C—N—N torsion angles ranging from −178.3 (1) to −180.0 (2)° and the C—N—N=C torsion angles ranging from −178.5 (4) to −179.8 (3)°. The conformation of the N—H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R₂²(8) ring motifs are observed, which are further augmented by C—H...O inter­actions. A common feature of each of (I)–(V) is the formation of sulfonamide and hydrazone dimers with an R₂²(8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H...H, O...H/H...O, N...H/H...N, C...H/H...C and other contacts. The H...H ­contacts show large surfaces, whereas the O...H plots show the presence of O...H/O...H contacts with the two characteristic long sharp spikes.

Computing details

For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009). Program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008) for (I), (II), (III); SHELXS2014 (Sheldrick, 2008) for (IV), (V). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXS97 and SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009) for (I); PLATON (Spek, 2009) for (II), (III), (IV), (V). For all structures, software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(E)-N-{2-[2-(Benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (I)

Crystal data

C16H17N3O3S	F(000) = 1392
Mr = 331.38	Dx = 1.321 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.764 (2) Å	Cell parameters from 1656 reflections
b = 6.6904 (6) Å	θ = 2.5–27.9°
c = 24.174 (3) Å	µ = 0.21 mm^−1
β = 97.10 (1)°	T = 293 K
V = 3332.5 (6) Å^3	Prism, colourless
Z = 8	0.48 × 0.36 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur single crystal X-ray diffractometer with Sapphire CCD detector	2266 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.031
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −25→25
Tmin = 0.905, Tmax = 0.979	k = −7→8
6193 measured reflections	l = −30→23
3366 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 6.2303P] where P = (Fo^2 + 2Fc^2)/3
S = 1.24	(Δ/σ)max = 0.006
3366 reflections	Δρmax = 0.23 e Å^−3
214 parameters	Δρmin = −0.27 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
C1	0.22673 (16)	−0.1645 (5)	0.37267 (15)	0.0505 (9)
C2	0.2178 (2)	−0.3652 (6)	0.37919 (17)	0.0682 (11)
H2	0.2301	−0.4253	0.4136	0.082*
C3	0.1905 (2)	−0.4783 (7)	0.33453 (18)	0.0767 (12)
H3	0.1845	−0.6147	0.3394	0.092*
C4	0.1717 (2)	−0.3945 (7)	0.28268 (17)	0.0697 (11)
C5	0.1830 (2)	−0.1953 (7)	0.27661 (18)	0.0806 (13)
H5	0.1721	−0.1363	0.2419	0.097*
C6	0.2102 (2)	−0.0783 (6)	0.32058 (17)	0.0710 (12)
H6	0.2174	0.0572	0.3153	0.085*
C7	0.14367 (16)	0.1516 (5)	0.44609 (15)	0.0551 (9)
H7A	0.1367	0.1473	0.4057	0.066*
H7B	0.1544	0.2878	0.4575	0.066*
C8	0.08323 (17)	0.0860 (5)	0.46934 (14)	0.0484 (9)
C9	−0.01756 (17)	0.4847 (5)	0.42378 (14)	0.0515 (9)
H9A	−0.0529	0.4431	0.4410	0.062*
C10	−0.02253 (17)	0.6693 (5)	0.39126 (14)	0.0503 (9)
C11	−0.07651 (18)	0.7915 (6)	0.39166 (15)	0.0577 (10)
H11	−0.1095	0.7543	0.4123	0.069*
C12	−0.0817 (2)	0.9684 (6)	0.36161 (17)	0.0707 (12)
H12	−0.1179	1.0494	0.3625	0.085*
C13	−0.0344 (2)	1.0243 (7)	0.33102 (18)	0.0789 (13)
H13	−0.0382	1.1431	0.3109	0.095*
C14	0.0192 (2)	0.9048 (7)	0.32970 (18)	0.0797 (13)
H14	0.0515	0.9429	0.3084	0.096*
C15	0.02543 (19)	0.7297 (6)	0.35951 (16)	0.0676 (11)
H15	0.0621	0.6506	0.3584	0.081*
C16	0.1377 (3)	−0.5184 (8)	0.23573 (19)	0.1069 (18)
H16A	0.1343	−0.6541	0.2480	0.160*
H16B	0.0951	−0.4655	0.2249	0.160*
H16C	0.1621	−0.5146	0.2045	0.160*
N1	0.19652 (14)	0.0184 (5)	0.46682 (12)	0.0541 (8)
H1N	0.1874 (17)	−0.088 (4)	0.4835 (14)	0.065*
N2	0.03162 (15)	0.2082 (5)	0.46076 (13)	0.0548 (8)
H2N	−0.0033 (12)	0.169 (5)	0.4737 (14)	0.066*
N3	0.03396 (14)	0.3792 (4)	0.42910 (11)	0.0495 (7)
O1	0.30389 (11)	−0.1281 (4)	0.46530 (11)	0.0690 (8)
O2	0.27192 (12)	0.1752 (4)	0.41009 (11)	0.0680 (8)
O3	0.08143 (12)	−0.0711 (4)	0.49543 (10)	0.0609 (7)
S1	0.25579 (4)	−0.01549 (14)	0.43089 (4)	0.0546 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0473 (19)	0.052 (2)	0.053 (2)	0.0079 (17)	0.0095 (16)	0.0108 (18)
C2	0.088 (3)	0.056 (2)	0.058 (3)	0.003 (2)	−0.001 (2)	0.017 (2)
C3	0.102 (3)	0.055 (2)	0.071 (3)	−0.002 (2)	0.001 (2)	0.006 (2)
C4	0.072 (3)	0.074 (3)	0.062 (3)	0.009 (2)	0.002 (2)	0.000 (2)
C5	0.103 (4)	0.087 (3)	0.051 (3)	0.013 (3)	0.004 (2)	0.015 (2)
C6	0.093 (3)	0.058 (2)	0.062 (3)	0.007 (2)	0.008 (2)	0.021 (2)
C7	0.055 (2)	0.054 (2)	0.057 (2)	0.0067 (18)	0.0077 (17)	0.0112 (19)
C8	0.055 (2)	0.050 (2)	0.0395 (19)	0.0045 (17)	0.0025 (16)	0.0003 (17)
C9	0.054 (2)	0.054 (2)	0.046 (2)	−0.0003 (19)	0.0078 (16)	0.0049 (18)
C10	0.052 (2)	0.055 (2)	0.043 (2)	0.0018 (18)	0.0010 (16)	−0.0005 (17)
C11	0.056 (2)	0.064 (2)	0.052 (2)	0.005 (2)	−0.0001 (17)	−0.007 (2)
C12	0.073 (3)	0.064 (3)	0.070 (3)	0.020 (2)	−0.012 (2)	0.001 (2)
C13	0.090 (3)	0.071 (3)	0.069 (3)	0.003 (3)	−0.015 (3)	0.023 (2)
C14	0.080 (3)	0.090 (3)	0.068 (3)	0.001 (3)	0.010 (2)	0.031 (3)
C15	0.061 (2)	0.078 (3)	0.064 (3)	0.014 (2)	0.006 (2)	0.019 (2)
C16	0.120 (4)	0.116 (4)	0.079 (3)	0.000 (4)	−0.010 (3)	−0.015 (3)
N1	0.0549 (17)	0.0556 (19)	0.0512 (18)	0.0071 (16)	0.0037 (14)	0.0118 (16)
N2	0.0576 (19)	0.0547 (19)	0.0538 (19)	0.0062 (16)	0.0130 (15)	0.0135 (16)
N3	0.0565 (17)	0.0481 (17)	0.0436 (16)	0.0065 (15)	0.0048 (13)	0.0069 (14)
O1	0.0486 (14)	0.0775 (19)	0.0767 (18)	0.0077 (14)	−0.0087 (13)	0.0196 (15)
O2	0.0573 (15)	0.0586 (16)	0.087 (2)	−0.0097 (13)	0.0067 (14)	0.0184 (15)
O3	0.0660 (16)	0.0541 (15)	0.0647 (17)	0.0112 (13)	0.0161 (13)	0.0179 (14)
S1	0.0446 (5)	0.0556 (6)	0.0620 (6)	0.0009 (5)	0.0007 (4)	0.0145 (5)

Geometric parameters (Å, º)

C1—C2	1.367 (5)	C10—C11	1.389 (5)
C1—C6	1.389 (5)	C10—C15	1.390 (5)
C1—S1	1.769 (4)	C11—C12	1.386 (5)
C2—C3	1.382 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.352 (6)
C3—C4	1.385 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.373 (6)
C4—C5	1.365 (6)	C13—H13	0.9300
C4—C16	1.509 (6)	C14—C15	1.374 (5)
C5—C6	1.383 (6)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16A	0.9600
C7—N1	1.454 (4)	C16—H16B	0.9600
C7—C8	1.503 (5)	C16—H16C	0.9600
C7—H7A	0.9700	N1—S1	1.608 (3)
C7—H7B	0.9700	N1—H1N	0.852 (18)
C8—O3	1.229 (4)	N2—N3	1.381 (4)
C8—N2	1.343 (4)	N2—H2N	0.865 (18)
C9—N3	1.275 (4)	O1—S1	1.432 (2)
C9—C10	1.460 (5)	O2—S1	1.426 (3)
C9—H9A	0.9300
C2—C1—C6	119.4 (4)	C12—C11—H11	119.7
C2—C1—S1	120.0 (3)	C10—C11—H11	119.7
C6—C1—S1	120.6 (3)	C13—C12—C11	120.6 (4)
C1—C2—C3	119.8 (4)	C13—C12—H12	119.7
C1—C2—H2	120.1	C11—C12—H12	119.7
C3—C2—H2	120.1	C12—C13—C14	119.8 (4)
C2—C3—C4	121.8 (4)	C12—C13—H13	120.1
C2—C3—H3	119.1	C14—C13—H13	120.1
C4—C3—H3	119.1	C13—C14—C15	120.6 (4)
C5—C4—C3	117.4 (4)	C13—C14—H14	119.7
C5—C4—C16	121.8 (4)	C15—C14—H14	119.7
C3—C4—C16	120.8 (4)	C14—C15—C10	120.7 (4)
C4—C5—C6	122.0 (4)	C14—C15—H15	119.7
C4—C5—H5	119.0	C10—C15—H15	119.7
C6—C5—H5	119.0	C4—C16—H16A	109.5
C5—C6—C1	119.6 (4)	C4—C16—H16B	109.5
C5—C6—H6	120.2	H16A—C16—H16B	109.5
C1—C6—H6	120.2	C4—C16—H16C	109.5
N1—C7—C8	108.8 (3)	H16A—C16—H16C	109.5
N1—C7—H7A	109.9	H16B—C16—H16C	109.5
C8—C7—H7A	109.9	C7—N1—S1	119.7 (2)
N1—C7—H7B	109.9	C7—N1—H1N	118 (3)
C8—C7—H7B	109.9	S1—N1—H1N	112 (3)
H7A—C7—H7B	108.3	C8—N2—N3	120.5 (3)
O3—C8—N2	121.7 (3)	C8—N2—H2N	117 (3)
O3—C8—C7	121.4 (3)	N3—N2—H2N	123 (3)
N2—C8—C7	116.8 (3)	C9—N3—N2	115.3 (3)
N3—C9—C10	121.7 (3)	O2—S1—O1	119.87 (16)
N3—C9—H9A	119.2	O2—S1—N1	107.05 (16)
C10—C9—H9A	119.2	O1—S1—N1	106.59 (16)
C11—C10—C15	117.8 (4)	O2—S1—C1	107.20 (17)
C11—C10—C9	119.8 (3)	O1—S1—C1	108.08 (17)
C15—C10—C9	122.3 (3)	N1—S1—C1	107.49 (16)
C12—C11—C10	120.6 (4)
C6—C1—C2—C3	−2.2 (6)	C12—C13—C14—C15	−0.5 (7)
S1—C1—C2—C3	175.1 (3)	C13—C14—C15—C10	0.4 (7)
C1—C2—C3—C4	0.2 (7)	C11—C10—C15—C14	0.0 (6)
C2—C3—C4—C5	1.9 (7)	C9—C10—C15—C14	−179.7 (4)
C2—C3—C4—C16	−175.7 (4)	C8—C7—N1—S1	152.9 (3)
C3—C4—C5—C6	−2.0 (7)	O3—C8—N2—N3	−177.0 (3)
C16—C4—C5—C6	175.6 (4)	C7—C8—N2—N3	3.7 (5)
C4—C5—C6—C1	0.0 (7)	C10—C9—N3—N2	−179.7 (3)
C2—C1—C6—C5	2.2 (6)	C8—N2—N3—C9	−179.8 (3)
S1—C1—C6—C5	−175.1 (3)	C7—N1—S1—O2	42.2 (3)
N1—C7—C8—O3	−8.2 (5)	C7—N1—S1—O1	171.6 (3)
N1—C7—C8—N2	171.1 (3)	C7—N1—S1—C1	−72.7 (3)
N3—C9—C10—C11	−172.7 (3)	C2—C1—S1—O2	169.1 (3)
N3—C9—C10—C15	7.0 (5)	C6—C1—S1—O2	−13.6 (4)
C15—C10—C11—C12	−0.5 (5)	C2—C1—S1—O1	38.6 (4)
C9—C10—C11—C12	179.2 (3)	C6—C1—S1—O1	−144.1 (3)
C10—C11—C12—C13	0.5 (6)	C2—C1—S1—N1	−76.1 (3)
C11—C12—C13—C14	0.0 (7)	C6—C1—S1—N1	101.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.85 (2)	2.26 (2)	3.084 (4)	163 (3)
N1—H1N···O3	0.85 (2)	2.26 (4)	2.637 (4)	107 (3)
N2—H2N···O3^ii	0.87 (2)	1.98 (2)	2.844 (4)	178 (4)

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

(E)-N-{2-[2-(4-Bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (II)

Crystal data

C16H16BrN3O3S	Z = 2
Mr = 410.29	F(000) = 416
Triclinic, P1	Dx = 1.528 Mg m^−3
a = 6.7308 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.322 (1) Å	Cell parameters from 3588 reflections
c = 13.723 (2) Å	θ = 3.1–27.4°
α = 75.562 (8)°	µ = 2.44 mm^−1
β = 85.556 (9)°	T = 293 K
γ = 75.046 (8)°	Rod, colourless
V = 891.94 (19) Å^3	0.52 × 0.34 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur single crystal X-ray diffractometer with Sapphire CCD detector	2855 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.051
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.363, Tmax = 0.668	k = −11→12
5760 measured reflections	l = −17→17
3645 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.208	w = 1/[σ^2(Fo^2) + (0.1153P)^2 + 0.7752P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3645 reflections	Δρmax = 0.94 e Å^−3
224 parameters	Δρmin = −1.01 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
Br1	−0.20339 (9)	0.57194 (9)	0.10166 (4)	0.0953 (3)
S1	1.28730 (15)	−0.02081 (9)	0.38669 (8)	0.0445 (3)
O1	1.1118 (5)	−0.0558 (3)	0.3579 (3)	0.0576 (8)
O2	1.4295 (5)	−0.1215 (3)	0.4567 (2)	0.0589 (8)
O3	1.1442 (5)	0.3354 (3)	0.4968 (2)	0.0556 (7)
N1	1.2011 (5)	0.1081 (3)	0.4366 (3)	0.0474 (8)
H1N	1.299 (6)	0.126 (5)	0.461 (3)	0.057*
N2	0.8305 (5)	0.4350 (3)	0.4310 (3)	0.0480 (8)
H2N	0.819 (8)	0.506 (3)	0.453 (4)	0.058*
N3	0.6785 (5)	0.4316 (3)	0.3702 (3)	0.0449 (7)
C1	1.4255 (6)	0.0332 (4)	0.2760 (3)	0.0462 (8)
C2	1.3419 (8)	0.0558 (6)	0.1830 (4)	0.0627 (11)
H2	1.2144	0.0388	0.1779	0.075*
C3	1.4493 (9)	0.1039 (6)	0.0974 (4)	0.0728 (14)
H3	1.3917	0.1197	0.0347	0.087*
C4	1.6395 (9)	0.1292 (6)	0.1023 (4)	0.0706 (13)
C5	1.7183 (8)	0.1063 (7)	0.1958 (4)	0.0766 (15)
H5	1.8454	0.1239	0.2009	0.092*
C6	1.6157 (8)	0.0581 (6)	0.2830 (4)	0.0642 (12)
H6	1.6736	0.0426	0.3455	0.077*
C7	1.0185 (6)	0.2139 (4)	0.3981 (3)	0.0423 (8)
H7A	0.8973	0.1779	0.4151	0.051*
H7B	1.0283	0.2442	0.3255	0.051*
C8	1.0042 (6)	0.3327 (4)	0.4459 (3)	0.0420 (8)
C9	0.5226 (6)	0.5345 (4)	0.3590 (3)	0.0479 (9)
H9	0.5174	0.6050	0.3909	0.057*
C10	0.3521 (6)	0.5425 (4)	0.2965 (3)	0.0433 (8)
C11	0.3568 (7)	0.4457 (4)	0.2404 (4)	0.0549 (10)
H11	0.4730	0.3730	0.2425	0.066*
C12	0.1944 (8)	0.4554 (5)	0.1823 (4)	0.0580 (10)
H12	0.1998	0.3904	0.1452	0.070*
C13	0.0231 (7)	0.5633 (5)	0.1800 (3)	0.0573 (11)
C14	0.0112 (7)	0.6600 (5)	0.2330 (4)	0.0609 (11)
H14	−0.1062	0.7319	0.2304	0.073*
C15	0.1764 (7)	0.6501 (4)	0.2910 (4)	0.0543 (10)
H15	0.1696	0.7166	0.3269	0.065*
C16	1.7529 (13)	0.1854 (9)	0.0072 (6)	0.111 (3)
H16A	1.8960	0.1380	0.0121	0.166*
H16B	1.7386	0.2823	−0.0003	0.166*
H16C	1.6957	0.1712	−0.0501	0.166*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0571 (4)	0.1590 (8)	0.0725 (4)	−0.0313 (4)	−0.0170 (3)	−0.0229 (4)
S1	0.0415 (5)	0.0401 (5)	0.0563 (6)	−0.0111 (4)	−0.0044 (4)	−0.0172 (4)
O1	0.0469 (16)	0.0546 (16)	0.082 (2)	−0.0194 (13)	−0.0044 (15)	−0.0285 (15)
O2	0.0578 (18)	0.0475 (16)	0.069 (2)	−0.0120 (13)	−0.0107 (15)	−0.0077 (14)
O3	0.0468 (16)	0.0561 (16)	0.0724 (19)	−0.0062 (12)	−0.0159 (14)	−0.0330 (15)
N1	0.0423 (18)	0.0519 (18)	0.0554 (19)	−0.0098 (14)	−0.0048 (14)	−0.0270 (15)
N2	0.0430 (18)	0.0445 (17)	0.063 (2)	−0.0067 (14)	−0.0118 (15)	−0.0251 (15)
N3	0.0419 (17)	0.0465 (17)	0.0500 (17)	−0.0117 (13)	−0.0089 (13)	−0.0149 (14)
C1	0.041 (2)	0.0419 (19)	0.057 (2)	−0.0078 (15)	−0.0052 (16)	−0.0156 (16)
C2	0.050 (2)	0.084 (3)	0.059 (3)	−0.017 (2)	−0.004 (2)	−0.024 (2)
C3	0.072 (3)	0.093 (4)	0.054 (3)	−0.019 (3)	−0.005 (2)	−0.019 (3)
C4	0.065 (3)	0.075 (3)	0.067 (3)	−0.012 (2)	0.012 (2)	−0.018 (2)
C5	0.052 (3)	0.103 (4)	0.081 (4)	−0.031 (3)	0.010 (2)	−0.026 (3)
C6	0.053 (3)	0.087 (3)	0.059 (3)	−0.027 (2)	−0.004 (2)	−0.020 (2)
C7	0.044 (2)	0.0437 (19)	0.0452 (19)	−0.0153 (15)	−0.0014 (15)	−0.0172 (15)
C8	0.043 (2)	0.0416 (18)	0.0445 (19)	−0.0107 (15)	−0.0037 (15)	−0.0154 (15)
C9	0.046 (2)	0.046 (2)	0.057 (2)	−0.0123 (16)	−0.0029 (17)	−0.0205 (17)
C10	0.042 (2)	0.0406 (18)	0.049 (2)	−0.0108 (15)	−0.0046 (15)	−0.0108 (15)
C11	0.052 (2)	0.046 (2)	0.066 (3)	−0.0069 (18)	−0.0077 (19)	−0.0163 (19)
C12	0.062 (3)	0.062 (3)	0.059 (2)	−0.022 (2)	−0.008 (2)	−0.020 (2)
C13	0.051 (2)	0.072 (3)	0.049 (2)	−0.023 (2)	−0.0079 (18)	−0.004 (2)
C14	0.046 (2)	0.063 (3)	0.066 (3)	−0.003 (2)	−0.003 (2)	−0.012 (2)
C15	0.050 (2)	0.049 (2)	0.068 (3)	−0.0106 (18)	0.0013 (19)	−0.023 (2)
C16	0.105 (6)	0.134 (6)	0.084 (4)	−0.039 (5)	0.036 (4)	−0.010 (4)

Geometric parameters (Å, º)

Br1—C13	1.903 (4)	C5—H5	0.9300
S1—O1	1.430 (3)	C6—H6	0.9300
S1—O2	1.432 (3)	C7—C8	1.508 (5)
S1—N1	1.603 (3)	C7—H7A	0.9700
S1—C1	1.763 (4)	C7—H7B	0.9700
O3—C8	1.225 (5)	C9—C10	1.459 (6)
N1—C7	1.450 (5)	C9—H9	0.9300
N1—H1N	0.843 (19)	C10—C15	1.390 (6)
N2—C8	1.347 (5)	C10—C11	1.398 (6)
N2—N3	1.382 (4)	C11—C12	1.371 (6)
N2—H2N	0.850 (19)	C11—H11	0.9300
N3—C9	1.273 (5)	C12—C13	1.377 (7)
C1—C2	1.376 (6)	C12—H12	0.9300
C1—C6	1.383 (6)	C13—C14	1.357 (7)
C2—C3	1.383 (7)	C14—C15	1.385 (7)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.381 (8)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.369 (8)	C16—H16B	0.9600
C4—C16	1.523 (8)	C16—H16C	0.9600
C5—C6	1.381 (7)
O1—S1—O2	119.49 (19)	N1—C7—H7B	110.2
O1—S1—N1	106.59 (18)	C8—C7—H7B	110.2
O2—S1—N1	106.38 (19)	H7A—C7—H7B	108.5
O1—S1—C1	107.7 (2)	O3—C8—N2	121.5 (3)
O2—S1—C1	107.90 (19)	O3—C8—C7	121.3 (3)
N1—S1—C1	108.41 (18)	N2—C8—C7	117.2 (3)
C7—N1—S1	120.8 (3)	N3—C9—C10	120.4 (3)
C7—N1—H1N	122 (3)	N3—C9—H9	119.8
S1—N1—H1N	110 (3)	C10—C9—H9	119.8
C8—N2—N3	120.2 (3)	C15—C10—C11	117.6 (4)
C8—N2—H2N	120 (4)	C15—C10—C9	119.7 (4)
N3—N2—H2N	119 (4)	C11—C10—C9	122.7 (4)
C9—N3—N2	115.4 (3)	C12—C11—C10	121.6 (4)
C2—C1—C6	119.9 (4)	C12—C11—H11	119.2
C2—C1—S1	120.4 (3)	C10—C11—H11	119.2
C6—C1—S1	119.6 (3)	C11—C12—C13	118.6 (4)
C1—C2—C3	119.4 (5)	C11—C12—H12	120.7
C1—C2—H2	120.3	C13—C12—H12	120.7
C3—C2—H2	120.3	C14—C13—C12	122.0 (4)
C4—C3—C2	121.8 (5)	C14—C13—Br1	120.1 (4)
C4—C3—H3	119.1	C12—C13—Br1	117.9 (3)
C2—C3—H3	119.1	C13—C14—C15	119.1 (4)
C5—C4—C3	117.5 (5)	C13—C14—H14	120.5
C5—C4—C16	121.5 (6)	C15—C14—H14	120.5
C3—C4—C16	121.0 (6)	C14—C15—C10	121.1 (4)
C4—C5—C6	122.3 (5)	C14—C15—H15	119.4
C4—C5—H5	118.8	C10—C15—H15	119.4
C6—C5—H5	118.8	C4—C16—H16A	109.5
C5—C6—C1	119.1 (5)	C4—C16—H16B	109.5
C5—C6—H6	120.5	H16A—C16—H16B	109.5
C1—C6—H6	120.5	C4—C16—H16C	109.5
N1—C7—C8	107.4 (3)	H16A—C16—H16C	109.5
N1—C7—H7A	110.2	H16B—C16—H16C	109.5
C8—C7—H7A	110.2
O1—S1—N1—C7	−36.3 (4)	S1—C1—C6—C5	−177.1 (4)
O2—S1—N1—C7	−164.8 (3)	S1—N1—C7—C8	−168.5 (3)
C1—S1—N1—C7	79.4 (3)	N3—N2—C8—O3	177.5 (4)
C8—N2—N3—C9	−178.5 (4)	N3—N2—C8—C7	−3.0 (6)
O1—S1—C1—C2	9.9 (4)	N1—C7—C8—O3	8.2 (5)
O2—S1—C1—C2	140.1 (4)	N1—C7—C8—N2	−171.4 (3)
N1—S1—C1—C2	−105.0 (4)	N2—N3—C9—C10	−180.0 (4)
O1—S1—C1—C6	−172.6 (4)	N3—C9—C10—C15	175.2 (4)
O2—S1—C1—C6	−42.4 (4)	N3—C9—C10—C11	−5.0 (6)
N1—S1—C1—C6	72.4 (4)	C15—C10—C11—C12	−0.3 (7)
C6—C1—C2—C3	−0.3 (7)	C9—C10—C11—C12	179.9 (4)
S1—C1—C2—C3	177.2 (4)	C10—C11—C12—C13	−0.2 (7)
C1—C2—C3—C4	0.5 (8)	C11—C12—C13—C14	0.3 (7)
C2—C3—C4—C5	−0.7 (9)	C11—C12—C13—Br1	−178.4 (4)
C2—C3—C4—C16	−178.5 (6)	C12—C13—C14—C15	0.1 (7)
C3—C4—C5—C6	0.9 (9)	Br1—C13—C14—C15	178.8 (4)
C16—C4—C5—C6	178.6 (6)	C13—C14—C15—C10	−0.7 (7)
C4—C5—C6—C1	−0.7 (9)	C11—C10—C15—C14	0.8 (7)
C2—C1—C6—C5	0.4 (7)	C9—C10—C15—C14	−179.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.84 (2)	2.20 (2)	3.031 (5)	167 (5)
N2—H2N···O3^ii	0.85 (2)	2.00 (2)	2.834 (4)	168 (5)
C15—H15···O1^iii	0.93	2.42	3.301 (5)	158

Symmetry codes: (i) −x+3, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y+1, z.

(E)-N-{2-[2-(4-Chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (III)

Crystal data

C16H16ClN3O3S	Z = 2
Mr = 365.83	F(000) = 380
Triclinic, P1	Dx = 1.382 Mg m^−3
a = 6.7101 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.359 (1) Å	Cell parameters from 2986 reflections
c = 13.500 (1) Å	θ = 2.9–27.7°
α = 76.049 (8)°	µ = 0.36 mm^−1
β = 85.846 (9)°	T = 293 K
γ = 74.823 (8)°	Prism, colourless
V = 878.90 (13) Å^3	0.44 × 0.42 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur single crystal X-ray diffractometer with Sapphire CCD detector	2984 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.015
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.859, Tmax = 0.883	k = −11→12
5740 measured reflections	l = −16→12
3580 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 0.3439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3580 reflections	Δρmax = 0.30 e Å^−3
224 parameters	Δρmin = −0.35 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
Cl1	−0.69451 (11)	0.56991 (10)	0.10339 (6)	0.0985 (3)
S1	0.78525 (7)	−0.02006 (5)	0.38459 (4)	0.04606 (15)
O1	0.9302 (2)	−0.12017 (14)	0.45436 (12)	0.0606 (4)
O2	0.6100 (2)	−0.05535 (15)	0.35447 (12)	0.0586 (4)
O3	0.6445 (2)	0.33557 (15)	0.49653 (12)	0.0576 (4)
N1	0.6980 (2)	0.10762 (17)	0.43598 (12)	0.0483 (4)
H1N	0.786 (3)	0.127 (2)	0.4633 (16)	0.058*
N2	0.3297 (2)	0.43565 (17)	0.42952 (13)	0.0500 (4)
H2N	0.322 (3)	0.5079 (19)	0.4504 (16)	0.060*
N3	0.1766 (2)	0.43233 (16)	0.36805 (12)	0.0465 (4)
C1	0.9220 (3)	0.03486 (19)	0.27256 (15)	0.0471 (4)
C2	0.8354 (4)	0.0603 (3)	0.17817 (17)	0.0659 (6)
H2	0.7071	0.0441	0.1726	0.079*
C3	0.9407 (4)	0.1099 (3)	0.09201 (19)	0.0796 (7)
H3	0.8817	0.1272	0.0284	0.096*
C4	1.1316 (4)	0.1344 (3)	0.0979 (2)	0.0736 (7)
C5	1.2133 (4)	0.1075 (3)	0.1931 (2)	0.0813 (8)
H5	1.3414	0.1239	0.1987	0.098*
C6	1.1137 (3)	0.0573 (3)	0.28006 (19)	0.0693 (6)
H6	1.1743	0.0385	0.3435	0.083*
C7	0.5155 (3)	0.21426 (19)	0.39697 (14)	0.0445 (4)
H7A	0.3932	0.1798	0.4139	0.053*
H7B	0.5252	0.2437	0.3233	0.053*
C8	0.5024 (3)	0.33313 (19)	0.44529 (14)	0.0439 (4)
C9	0.0198 (3)	0.5356 (2)	0.35626 (15)	0.0488 (4)
H9	0.0151	0.6061	0.3886	0.059*
C10	−0.1532 (3)	0.54426 (19)	0.29231 (14)	0.0460 (4)
C11	−0.1453 (3)	0.4472 (2)	0.23547 (16)	0.0554 (5)
H11	−0.0273	0.3756	0.2369	0.067*
C12	−0.3103 (4)	0.4563 (2)	0.17729 (17)	0.0612 (5)
H12	−0.3040	0.3913	0.1393	0.073*
C13	−0.4852 (3)	0.5621 (2)	0.17554 (16)	0.0590 (5)
C14	−0.4966 (3)	0.6590 (2)	0.22985 (17)	0.0632 (6)
H14	−0.6150	0.7304	0.2277	0.076*
C15	−0.3297 (3)	0.6502 (2)	0.28847 (17)	0.0554 (5)
H15	−0.3368	0.7162	0.3255	0.066*
C16	1.2435 (6)	0.1909 (4)	0.0027 (3)	0.1171 (12)
H16A	1.1727	0.1905	−0.0565	0.176*
H16B	1.3822	0.1347	0.0024	0.176*
H16C	1.2467	0.2833	0.0017	0.176*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0651 (4)	0.1592 (8)	0.0727 (4)	−0.0320 (4)	−0.0227 (3)	−0.0194 (4)
S1	0.0449 (3)	0.0419 (2)	0.0540 (3)	−0.01103 (18)	−0.00405 (19)	−0.0150 (2)
O1	0.0596 (9)	0.0485 (8)	0.0689 (9)	−0.0082 (6)	−0.0123 (7)	−0.0071 (7)
O2	0.0531 (8)	0.0571 (8)	0.0754 (10)	−0.0215 (7)	−0.0036 (7)	−0.0250 (7)
O3	0.0502 (8)	0.0571 (8)	0.0719 (9)	−0.0061 (6)	−0.0168 (7)	−0.0301 (7)
N1	0.0444 (8)	0.0530 (9)	0.0522 (9)	−0.0093 (7)	−0.0059 (7)	−0.0226 (7)
N2	0.0480 (9)	0.0493 (9)	0.0579 (10)	−0.0079 (7)	−0.0117 (7)	−0.0237 (8)
N3	0.0450 (8)	0.0499 (9)	0.0473 (9)	−0.0111 (7)	−0.0078 (7)	−0.0151 (7)
C1	0.0442 (9)	0.0454 (10)	0.0525 (11)	−0.0067 (8)	−0.0015 (8)	−0.0173 (8)
C2	0.0545 (12)	0.0874 (16)	0.0586 (13)	−0.0150 (11)	−0.0043 (10)	−0.0240 (12)
C3	0.0757 (16)	0.105 (2)	0.0516 (13)	−0.0107 (14)	−0.0043 (11)	−0.0176 (13)
C4	0.0696 (15)	0.0782 (16)	0.0657 (15)	−0.0138 (12)	0.0144 (12)	−0.0128 (12)
C5	0.0594 (14)	0.112 (2)	0.0755 (17)	−0.0333 (14)	0.0072 (12)	−0.0174 (15)
C6	0.0536 (12)	0.0975 (18)	0.0609 (13)	−0.0280 (12)	−0.0044 (10)	−0.0154 (12)
C7	0.0454 (9)	0.0466 (10)	0.0448 (10)	−0.0135 (8)	−0.0027 (7)	−0.0142 (8)
C8	0.0433 (9)	0.0476 (10)	0.0431 (9)	−0.0114 (8)	−0.0031 (7)	−0.0138 (8)
C9	0.0500 (10)	0.0491 (10)	0.0521 (11)	−0.0123 (8)	−0.0041 (8)	−0.0197 (8)
C10	0.0462 (10)	0.0455 (10)	0.0460 (10)	−0.0114 (8)	−0.0042 (8)	−0.0093 (8)
C11	0.0546 (11)	0.0501 (11)	0.0615 (12)	−0.0055 (9)	−0.0102 (9)	−0.0184 (9)
C12	0.0684 (13)	0.0649 (13)	0.0565 (12)	−0.0205 (11)	−0.0102 (10)	−0.0189 (10)
C13	0.0516 (11)	0.0778 (15)	0.0466 (11)	−0.0219 (11)	−0.0081 (9)	−0.0041 (10)
C14	0.0474 (11)	0.0678 (14)	0.0632 (13)	−0.0017 (10)	−0.0050 (9)	−0.0066 (11)
C15	0.0536 (11)	0.0512 (11)	0.0608 (12)	−0.0082 (9)	−0.0008 (9)	−0.0173 (9)
C16	0.113 (3)	0.144 (3)	0.081 (2)	−0.038 (2)	0.0284 (19)	−0.004 (2)

Geometric parameters (Å, º)

Cl1—C13	1.740 (2)	C5—H5	0.9300
S1—O1	1.4292 (15)	C6—H6	0.9300
S1—O2	1.4313 (14)	C7—C8	1.507 (2)
S1—N1	1.5974 (16)	C7—H7A	0.9700
S1—C1	1.764 (2)	C7—H7B	0.9700
O3—C8	1.227 (2)	C9—C10	1.467 (2)
N1—C7	1.450 (2)	C9—H9	0.9300
N1—H1N	0.811 (15)	C10—C15	1.382 (3)
N2—C8	1.341 (2)	C10—C11	1.393 (3)
N2—N3	1.379 (2)	C11—C12	1.374 (3)
N2—H2N	0.849 (16)	C11—H11	0.9300
N3—C9	1.276 (2)	C12—C13	1.377 (3)
C1—C2	1.377 (3)	C12—H12	0.9300
C1—C6	1.380 (3)	C13—C14	1.363 (3)
C2—C3	1.378 (3)	C14—C15	1.389 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.381 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.370 (4)	C16—H16B	0.9600
C4—C16	1.511 (4)	C16—H16C	0.9600
C5—C6	1.368 (3)
O1—S1—O2	119.66 (9)	N1—C7—H7B	110.1
O1—S1—N1	106.70 (9)	C8—C7—H7B	110.1
O2—S1—N1	106.80 (9)	H7A—C7—H7B	108.5
O1—S1—C1	107.61 (9)	O3—C8—N2	121.73 (17)
O2—S1—C1	107.43 (9)	O3—C8—C7	121.09 (16)
N1—S1—C1	108.21 (9)	N2—C8—C7	117.18 (15)
C7—N1—S1	121.12 (12)	N3—C9—C10	120.77 (17)
C7—N1—H1N	119.1 (17)	N3—C9—H9	119.6
S1—N1—H1N	113.6 (17)	C10—C9—H9	119.6
C8—N2—N3	120.21 (15)	C15—C10—C11	118.66 (18)
C8—N2—H2N	119.7 (16)	C15—C10—C9	119.73 (18)
N3—N2—H2N	119.5 (16)	C11—C10—C9	121.61 (17)
C9—N3—N2	115.61 (16)	C12—C11—C10	120.60 (19)
C2—C1—C6	120.0 (2)	C12—C11—H11	119.7
C2—C1—S1	120.38 (16)	C10—C11—H11	119.7
C6—C1—S1	119.59 (16)	C11—C12—C13	119.6 (2)
C1—C2—C3	119.3 (2)	C11—C12—H12	120.2
C1—C2—H2	120.3	C13—C12—H12	120.2
C3—C2—H2	120.3	C14—C13—C12	121.1 (2)
C2—C3—C4	121.6 (2)	C14—C13—Cl1	120.01 (18)
C2—C3—H3	119.2	C12—C13—Cl1	118.93 (18)
C4—C3—H3	119.2	C13—C14—C15	119.4 (2)
C5—C4—C3	117.4 (2)	C13—C14—H14	120.3
C5—C4—C16	121.7 (3)	C15—C14—H14	120.3
C3—C4—C16	120.9 (3)	C10—C15—C14	120.7 (2)
C6—C5—C4	122.5 (2)	C10—C15—H15	119.7
C6—C5—H5	118.8	C14—C15—H15	119.7
C4—C5—H5	118.8	C4—C16—H16A	109.5
C5—C6—C1	119.2 (2)	C4—C16—H16B	109.5
C5—C6—H6	120.4	H16A—C16—H16B	109.5
C1—C6—H6	120.4	C4—C16—H16C	109.5
N1—C7—C8	107.79 (14)	H16A—C16—H16C	109.5
N1—C7—H7A	110.1	H16B—C16—H16C	109.5
C8—C7—H7A	110.1
O1—S1—N1—C7	−166.15 (14)	S1—C1—C6—C5	−176.3 (2)
O2—S1—N1—C7	−37.09 (17)	S1—N1—C7—C8	−167.41 (13)
C1—S1—N1—C7	78.30 (16)	N3—N2—C8—O3	177.30 (17)
C8—N2—N3—C9	−178.84 (18)	N3—N2—C8—C7	−2.5 (3)
O1—S1—C1—C2	141.34 (18)	N1—C7—C8—O3	8.7 (2)
O2—S1—C1—C2	11.3 (2)	N1—C7—C8—N2	−171.55 (16)
N1—S1—C1—C2	−103.71 (18)	N2—N3—C9—C10	179.80 (16)
O1—S1—C1—C6	−41.1 (2)	N3—C9—C10—C15	173.79 (19)
O2—S1—C1—C6	−171.16 (18)	N3—C9—C10—C11	−5.6 (3)
N1—S1—C1—C6	73.87 (19)	C15—C10—C11—C12	−0.4 (3)
C6—C1—C2—C3	−0.9 (3)	C9—C10—C11—C12	179.0 (2)
S1—C1—C2—C3	176.7 (2)	C10—C11—C12—C13	−0.2 (3)
C1—C2—C3—C4	0.2 (4)	C11—C12—C13—C14	0.7 (3)
C2—C3—C4—C5	0.0 (4)	C11—C12—C13—Cl1	−178.75 (17)
C2—C3—C4—C16	−179.1 (3)	C12—C13—C14—C15	−0.5 (3)
C3—C4—C5—C6	0.4 (4)	Cl1—C13—C14—C15	178.91 (17)
C16—C4—C5—C6	179.5 (3)	C11—C10—C15—C14	0.6 (3)
C4—C5—C6—C1	−1.1 (4)	C9—C10—C15—C14	−178.87 (19)
C2—C1—C6—C5	1.3 (4)	C13—C14—C15—C10	−0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.81 (2)	2.26 (2)	2.611 (2)	107 (2)
N1—H1N···O1^i	0.81 (2)	2.25 (2)	3.038 (2)	164 (2)
N2—H2N···O3^ii	0.85 (2)	1.99 (2)	2.833 (2)	170 (2)
C15—H15···O2^iii	0.93	2.42	3.298 (3)	157

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

(E)-N-(2-{2-[4-(Dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzene-sulfonamide (IV)

Crystal data

C18H22N4O3S	Z = 2
Mr = 374.45	F(000) = 396
Triclinic, P1	Dx = 1.315 Mg m^−3
a = 6.931 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.076 (2) Å	Cell parameters from 1366 reflections
c = 12.935 (3) Å	θ = 3.2–27.7°
α = 87.37 (2)°	µ = 0.20 mm^−1
β = 81.44 (2)°	T = 293 K
γ = 74.42 (2)°	Plate, colourless
V = 945.8 (3) Å^3	0.28 × 0.24 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur single crystal X-ray diffractometer with Sapphire CCD detector	3353 independent reflections
Radiation source: fine-focus sealed tube	1688 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.947, Tmax = 0.992	k = −13→13
5774 measured reflections	l = −15→15

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.082	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.0365P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
3353 reflections	Δρmax = 0.17 e Å^−3
244 parameters	Δρmin = −0.18 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
C1	0.4968 (6)	0.4649 (3)	0.2674 (3)	0.0567 (11)
C2	0.4537 (7)	0.4330 (4)	0.1735 (4)	0.0735 (13)
H2	0.3204	0.4401	0.1645	0.088*
C3	0.6067 (9)	0.3911 (4)	0.0936 (4)	0.0817 (15)
H3	0.5751	0.3700	0.0306	0.098*
C4	0.8060 (8)	0.3790 (4)	0.1029 (4)	0.0728 (13)
C5	0.8455 (8)	0.4135 (5)	0.1966 (5)	0.0874 (15)
H5	0.9785	0.4086	0.2046	0.105*
C6	0.6957 (8)	0.4548 (4)	0.2785 (4)	0.0776 (14)
H6	0.7276	0.4760	0.3414	0.093*
C7	0.2189 (6)	0.2955 (4)	0.4156 (3)	0.0678 (12)
H7A	0.2276	0.2956	0.3401	0.081*
H7B	0.0780	0.3086	0.4455	0.081*
C8	0.3422 (6)	0.1716 (4)	0.4525 (3)	0.0559 (11)
C9	0.0781 (6)	−0.0230 (4)	0.3656 (3)	0.0587 (11)
H9	0.1537	−0.0957	0.3943	0.070*
C10	−0.0821 (6)	−0.0319 (4)	0.3087 (3)	0.0516 (10)
C11	−0.1155 (6)	−0.1479 (4)	0.2963 (3)	0.0605 (11)
H11	−0.0325	−0.2186	0.3241	0.073*
C12	−0.2663 (6)	−0.1619 (4)	0.2447 (3)	0.0635 (12)
H12	−0.2834	−0.2415	0.2379	0.076*
C13	−0.3949 (6)	−0.0588 (4)	0.2021 (3)	0.0595 (11)
C14	−0.3584 (6)	0.0579 (4)	0.2128 (3)	0.0661 (12)
H14	−0.4393	0.1285	0.1840	0.079*
C15	−0.2068 (6)	0.0710 (4)	0.2646 (3)	0.0618 (12)
H15	−0.1869	0.1501	0.2704	0.074*
C16	0.9745 (8)	0.3300 (5)	0.0144 (4)	0.1084 (18)
H16A	0.9441	0.3764	−0.0483	0.163*
H16B	0.9868	0.2429	0.0036	0.163*
H16C	1.0995	0.3395	0.0318	0.163*
C17	−0.5904 (7)	−0.1930 (5)	0.1474 (4)	0.1037 (18)
H17A	−0.6108	−0.2263	0.2168	0.156*
H17B	−0.4769	−0.2490	0.1070	0.156*
H17C	−0.7094	−0.1843	0.1150	0.156*
C18	−0.6898 (7)	0.0372 (5)	0.1135 (4)	0.0934 (16)
H18A	−0.6170	0.0770	0.0596	0.140*
H18B	−0.7507	0.0950	0.1697	0.140*
H18C	−0.7934	0.0118	0.0854	0.140*
N1	0.2971 (5)	0.3960 (3)	0.4481 (3)	0.0657 (10)
H1N	0.396 (4)	0.371 (4)	0.480 (3)	0.079*
N2	0.2812 (5)	0.0705 (3)	0.4335 (3)	0.0601 (10)
H2N	0.351 (5)	−0.002 (2)	0.455 (3)	0.072*
N3	0.1207 (5)	0.0814 (3)	0.3783 (3)	0.0583 (9)
N4	−0.5515 (6)	−0.0720 (4)	0.1526 (3)	0.0807 (11)
O1	0.1148 (4)	0.5467 (2)	0.3287 (2)	0.0788 (9)
O2	0.3534 (4)	0.6048 (2)	0.4299 (2)	0.0804 (9)
O3	0.4883 (4)	0.1648 (2)	0.4977 (2)	0.0680 (8)
S1	0.30085 (18)	0.51416 (10)	0.37183 (10)	0.0659 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.071 (3)	0.042 (2)	0.066 (3)	−0.020 (2)	−0.029 (3)	0.003 (2)
C2	0.074 (3)	0.077 (3)	0.082 (4)	−0.030 (3)	−0.032 (3)	−0.003 (3)
C3	0.094 (4)	0.088 (4)	0.074 (4)	−0.033 (3)	−0.032 (4)	−0.007 (3)
C4	0.088 (4)	0.059 (3)	0.073 (4)	−0.024 (3)	−0.011 (3)	0.003 (3)
C5	0.076 (4)	0.108 (4)	0.087 (4)	−0.034 (3)	−0.023 (4)	0.000 (3)
C6	0.086 (4)	0.090 (4)	0.071 (4)	−0.038 (3)	−0.031 (3)	−0.001 (3)
C7	0.080 (3)	0.055 (3)	0.078 (3)	−0.028 (2)	−0.020 (3)	−0.002 (2)
C8	0.069 (3)	0.053 (3)	0.050 (3)	−0.025 (2)	−0.007 (2)	−0.002 (2)
C9	0.068 (3)	0.053 (3)	0.056 (3)	−0.018 (2)	−0.008 (2)	−0.002 (2)
C10	0.056 (3)	0.049 (3)	0.050 (3)	−0.017 (2)	−0.005 (2)	−0.005 (2)
C11	0.067 (3)	0.049 (3)	0.068 (3)	−0.017 (2)	−0.014 (3)	−0.003 (2)
C12	0.074 (3)	0.050 (3)	0.071 (3)	−0.025 (2)	−0.003 (3)	−0.014 (2)
C13	0.060 (3)	0.064 (3)	0.058 (3)	−0.022 (3)	−0.003 (2)	−0.009 (2)
C14	0.066 (3)	0.055 (3)	0.077 (3)	−0.016 (2)	−0.011 (3)	0.006 (2)
C15	0.068 (3)	0.044 (3)	0.078 (3)	−0.025 (2)	−0.005 (3)	0.000 (2)
C16	0.109 (4)	0.116 (5)	0.096 (4)	−0.026 (3)	−0.006 (4)	−0.005 (4)
C17	0.082 (3)	0.110 (4)	0.133 (5)	−0.043 (3)	−0.015 (3)	−0.043 (4)
C18	0.072 (3)	0.134 (5)	0.075 (4)	−0.024 (3)	−0.016 (3)	0.001 (3)
N1	0.085 (3)	0.050 (2)	0.071 (3)	−0.023 (2)	−0.028 (2)	0.0001 (19)
N2	0.069 (3)	0.051 (2)	0.067 (3)	−0.0207 (19)	−0.023 (2)	0.0010 (19)
N3	0.067 (2)	0.057 (2)	0.058 (2)	−0.0253 (18)	−0.010 (2)	−0.0045 (18)
N4	0.073 (3)	0.087 (3)	0.091 (3)	−0.028 (2)	−0.024 (2)	−0.005 (2)
O1	0.0741 (17)	0.0577 (18)	0.107 (3)	−0.0083 (15)	−0.0369 (16)	−0.0026 (17)
O2	0.106 (2)	0.0501 (18)	0.096 (2)	−0.0249 (16)	−0.0373 (19)	−0.0178 (16)
O3	0.077 (2)	0.0608 (19)	0.077 (2)	−0.0268 (16)	−0.0317 (18)	−0.0012 (16)
S1	0.0777 (8)	0.0441 (7)	0.0820 (9)	−0.0150 (6)	−0.0313 (7)	−0.0053 (6)

Geometric parameters (Å, º)

C1—C2	1.376 (5)	C12—C13	1.395 (5)
C1—C6	1.381 (5)	C12—H12	0.9300
C1—S1	1.758 (4)	C13—N4	1.382 (5)
C2—C3	1.365 (6)	C13—C14	1.398 (5)
C2—H2	0.9300	C14—C15	1.369 (5)
C3—C4	1.374 (6)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.374 (6)	C16—H16A	0.9600
C4—C16	1.512 (6)	C16—H16B	0.9600
C5—C6	1.368 (6)	C16—H16C	0.9600
C5—H5	0.9300	C17—N4	1.443 (5)
C6—H6	0.9300	C17—H17A	0.9600
C7—N1	1.465 (4)	C17—H17B	0.9600
C7—C8	1.507 (5)	C17—H17C	0.9600
C7—H7A	0.9700	C18—N4	1.449 (5)
C7—H7B	0.9700	C18—H18A	0.9600
C8—O3	1.226 (4)	C18—H18B	0.9600
C8—N2	1.343 (5)	C18—H18C	0.9600
C9—N3	1.291 (4)	N1—S1	1.606 (4)
C9—C10	1.446 (5)	N1—H1N	0.828 (18)
C9—H9	0.9300	N2—N3	1.385 (4)
C10—C11	1.386 (5)	N2—H2N	0.875 (18)
C10—C15	1.389 (5)	O1—S1	1.432 (3)
C11—C12	1.366 (5)	O2—S1	1.433 (3)
C11—H11	0.9300
C2—C1—C6	119.0 (5)	C12—C13—C14	116.7 (4)
C2—C1—S1	120.0 (4)	C15—C14—C13	121.8 (4)
C6—C1—S1	121.0 (4)	C15—C14—H14	119.1
C3—C2—C1	119.9 (4)	C13—C14—H14	119.1
C3—C2—H2	120.1	C14—C15—C10	121.0 (4)
C1—C2—H2	120.1	C14—C15—H15	119.5
C2—C3—C4	122.3 (5)	C10—C15—H15	119.5
C2—C3—H3	118.8	C4—C16—H16A	109.5
C4—C3—H3	118.8	C4—C16—H16B	109.5
C3—C4—C5	116.9 (5)	H16A—C16—H16B	109.5
C3—C4—C16	121.8 (5)	C4—C16—H16C	109.5
C5—C4—C16	121.4 (5)	H16A—C16—H16C	109.5
C6—C5—C4	122.2 (5)	H16B—C16—H16C	109.5
C6—C5—H5	118.9	N4—C17—H17A	109.5
C4—C5—H5	118.9	N4—C17—H17B	109.5
C5—C6—C1	119.7 (4)	H17A—C17—H17B	109.5
C5—C6—H6	120.1	N4—C17—H17C	109.5
C1—C6—H6	120.1	H17A—C17—H17C	109.5
N1—C7—C8	109.0 (3)	H17B—C17—H17C	109.5
N1—C7—H7A	109.9	N4—C18—H18A	109.5
C8—C7—H7A	109.9	N4—C18—H18B	109.5
N1—C7—H7B	109.9	H18A—C18—H18B	109.5
C8—C7—H7B	109.9	N4—C18—H18C	109.5
H7A—C7—H7B	108.3	H18A—C18—H18C	109.5
O3—C8—N2	122.6 (4)	H18B—C18—H18C	109.5
O3—C8—C7	121.5 (3)	C7—N1—S1	119.3 (3)
N2—C8—C7	115.9 (4)	C7—N1—H1N	114 (3)
N3—C9—C10	122.9 (4)	S1—N1—H1N	116 (3)
N3—C9—H9	118.6	C8—N2—N3	120.8 (3)
C10—C9—H9	118.6	C8—N2—H2N	117 (3)
C11—C10—C15	117.2 (4)	N3—N2—H2N	122 (3)
C11—C10—C9	119.5 (4)	C9—N3—N2	114.4 (3)
C15—C10—C9	123.3 (4)	C13—N4—C17	120.4 (4)
C12—C11—C10	122.1 (4)	C13—N4—C18	120.4 (4)
C12—C11—H11	118.9	C17—N4—C18	119.0 (4)
C10—C11—H11	118.9	O1—S1—O2	120.08 (18)
C11—C12—C13	121.0 (4)	O1—S1—N1	107.07 (17)
C11—C12—H12	119.5	O2—S1—N1	106.80 (19)
C13—C12—H12	119.5	O1—S1—C1	107.0 (2)
N4—C13—C12	121.2 (4)	O2—S1—C1	107.52 (19)
N4—C13—C14	122.0 (4)	N1—S1—C1	107.87 (18)
C6—C1—C2—C3	0.6 (6)	C13—C14—C15—C10	0.1 (6)
S1—C1—C2—C3	−178.0 (3)	C11—C10—C15—C14	1.2 (6)
C1—C2—C3—C4	0.0 (7)	C9—C10—C15—C14	−179.0 (4)
C2—C3—C4—C5	−1.2 (7)	C8—C7—N1—S1	143.3 (3)
C2—C3—C4—C16	178.8 (4)	O3—C8—N2—N3	−177.2 (3)
C3—C4—C5—C6	1.8 (7)	C7—C8—N2—N3	3.2 (5)
C16—C4—C5—C6	−178.2 (4)	C10—C9—N3—N2	−179.0 (3)
C4—C5—C6—C1	−1.2 (7)	C8—N2—N3—C9	180.0 (4)
C2—C1—C6—C5	0.0 (6)	C12—C13—N4—C17	2.4 (6)
S1—C1—C6—C5	178.6 (3)	C14—C13—N4—C17	−177.0 (4)
N1—C7—C8—O3	−3.1 (5)	C12—C13—N4—C18	176.8 (4)
N1—C7—C8—N2	176.5 (3)	C14—C13—N4—C18	−2.6 (6)
N3—C9—C10—C11	178.5 (4)	C7—N1—S1—O1	41.3 (4)
N3—C9—C10—C15	−1.4 (6)	C7—N1—S1—O2	171.1 (3)
C15—C10—C11—C12	−1.1 (6)	C7—N1—S1—C1	−73.6 (3)
C9—C10—C11—C12	179.0 (4)	C2—C1—S1—O1	−16.5 (4)
C10—C11—C12—C13	−0.2 (6)	C6—C1—S1—O1	164.9 (3)
C11—C12—C13—N4	−178.0 (4)	C2—C1—S1—O2	−146.8 (3)
C11—C12—C13—C14	1.4 (6)	C6—C1—S1—O2	34.6 (4)
N4—C13—C14—C15	178.1 (4)	C2—C1—S1—N1	98.4 (3)
C12—C13—C14—C15	−1.4 (6)	C6—C1—S1—N1	−80.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.83 (2)	2.21 (4)	2.647 (4)	113 (3)
N1—H1N···O2^i	0.83 (2)	2.31 (2)	3.079 (4)	154 (4)
N2—H2N···O3^ii	0.88 (2)	1.97 (2)	2.848 (4)	179 (4)
C11—H11···O1^iii	0.93	2.53	3.366 (5)	150

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

(E)-N-{2-[2-(4-Methoxybenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide (V)

Crystal data

C17H19N3O4S	Z = 2
Mr = 361.41	F(000) = 380
Triclinic, P1	Dx = 1.358 Mg m^−3
a = 6.8887 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.778 (1) Å	Cell parameters from 2806 reflections
c = 12.411 (2) Å	θ = 3.1–27.8°
α = 95.26 (1)°	µ = 0.21 mm^−1
β = 93.43 (1)°	T = 293 K
γ = 104.82 (1)°	Prism, colourless
V = 883.7 (2) Å^3	0.44 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur single crystal X-ray diffractometer with a Sapphire CCD detector	2853 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.012
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.913, Tmax = 0.959	k = −13→9
5894 measured reflections	l = −15→15
3596 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.2083P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3596 reflections	Δρmax = 0.19 e Å^−3
234 parameters	Δρmin = −0.32 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
S1	0.72164 (7)	0.50669 (4)	0.36944 (4)	0.05041 (16)
O1	0.6623 (2)	0.60588 (13)	0.43308 (13)	0.0672 (4)
O2	0.91650 (19)	0.53392 (13)	0.32930 (12)	0.0623 (4)
O3	0.5196 (2)	0.16384 (13)	0.49645 (11)	0.0571 (3)
O4	1.6156 (2)	−0.08436 (16)	0.12733 (12)	0.0712 (4)
N1	0.7093 (2)	0.39129 (15)	0.44328 (13)	0.0524 (4)
H1N	0.606 (3)	0.372 (2)	0.4722 (17)	0.063*
N2	0.7338 (2)	0.05660 (15)	0.42950 (12)	0.0484 (4)
H2N	0.659 (3)	−0.0135 (16)	0.4514 (16)	0.058*
N3	0.9004 (2)	0.06101 (15)	0.37213 (12)	0.0460 (3)
C1	0.5432 (3)	0.45130 (17)	0.25545 (16)	0.0486 (4)
C2	0.5994 (3)	0.4058 (2)	0.15765 (17)	0.0596 (5)
H2	0.7331	0.4055	0.1511	0.072*
C3	0.4591 (4)	0.3612 (2)	0.06992 (18)	0.0673 (6)
H3	0.4993	0.3305	0.0047	0.081*
C4	0.2604 (3)	0.3609 (2)	0.07671 (19)	0.0647 (5)
C5	0.2070 (3)	0.4064 (3)	0.1753 (2)	0.0796 (7)
H5	0.0733	0.4067	0.1817	0.096*
C6	0.3442 (3)	0.4512 (2)	0.26401 (19)	0.0704 (6)
H6	0.3036	0.4812	0.3293	0.085*
C7	0.7942 (3)	0.28483 (17)	0.40979 (16)	0.0515 (4)
H7A	0.9328	0.3033	0.4404	0.062*
H7B	0.7927	0.2735	0.3313	0.062*
C8	0.6707 (3)	0.16375 (17)	0.44900 (13)	0.0443 (4)
C9	0.9493 (3)	−0.04493 (17)	0.35479 (14)	0.0465 (4)
H9	0.8735	−0.1189	0.3806	0.056*
C10	1.1234 (3)	−0.05145 (17)	0.29473 (14)	0.0431 (4)
C11	1.2409 (3)	0.05608 (18)	0.25395 (15)	0.0507 (4)
H11	1.2083	0.1346	0.2649	0.061*
C12	1.4047 (3)	0.04863 (19)	0.19770 (16)	0.0531 (5)
H12	1.4807	0.1214	0.1703	0.064*
C13	1.4561 (3)	−0.06753 (19)	0.18207 (14)	0.0504 (4)
C14	1.3416 (3)	−0.17487 (19)	0.22223 (16)	0.0556 (5)
H14	1.3754	−0.2530	0.2119	0.067*
C15	1.1768 (3)	−0.16688 (18)	0.27770 (15)	0.0512 (4)
H15	1.1002	−0.2402	0.3041	0.061*
C16	0.1075 (4)	0.3138 (3)	−0.0204 (2)	0.0925 (8)
H16A	0.0427	0.3803	−0.0348	0.139*
H16B	0.0083	0.2383	−0.0056	0.139*
H16C	0.1742	0.2930	−0.0827	0.139*
C17	1.7505 (3)	0.0267 (3)	0.09505 (19)	0.0754 (7)
H17A	1.6794	0.0657	0.0448	0.113*
H17B	1.8582	0.0019	0.0607	0.113*
H17C	1.8049	0.0875	0.1578	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0483 (3)	0.0369 (2)	0.0658 (3)	0.00984 (19)	0.0167 (2)	0.0007 (2)
O1	0.0723 (9)	0.0433 (7)	0.0862 (10)	0.0174 (7)	0.0212 (8)	−0.0075 (7)
O2	0.0470 (7)	0.0510 (8)	0.0865 (10)	0.0054 (6)	0.0199 (7)	0.0068 (7)
O3	0.0576 (8)	0.0544 (8)	0.0671 (8)	0.0229 (6)	0.0236 (7)	0.0112 (6)
O4	0.0622 (9)	0.0819 (10)	0.0730 (10)	0.0232 (8)	0.0269 (8)	0.0003 (8)
N1	0.0551 (10)	0.0471 (9)	0.0586 (10)	0.0176 (8)	0.0193 (8)	0.0032 (7)
N2	0.0502 (9)	0.0486 (9)	0.0523 (9)	0.0187 (7)	0.0160 (7)	0.0113 (7)
N3	0.0465 (8)	0.0507 (8)	0.0442 (8)	0.0180 (7)	0.0086 (6)	0.0055 (6)
C1	0.0496 (10)	0.0400 (9)	0.0614 (11)	0.0163 (8)	0.0185 (9)	0.0109 (8)
C2	0.0530 (11)	0.0672 (13)	0.0658 (13)	0.0248 (10)	0.0197 (10)	0.0095 (10)
C3	0.0732 (14)	0.0756 (14)	0.0590 (13)	0.0287 (12)	0.0159 (11)	0.0068 (11)
C4	0.0641 (13)	0.0592 (12)	0.0715 (14)	0.0144 (10)	0.0043 (11)	0.0165 (10)
C5	0.0484 (12)	0.107 (2)	0.0858 (17)	0.0266 (13)	0.0126 (12)	0.0042 (15)
C6	0.0509 (12)	0.0933 (17)	0.0710 (14)	0.0266 (11)	0.0192 (11)	−0.0017 (12)
C7	0.0503 (10)	0.0476 (10)	0.0599 (11)	0.0169 (8)	0.0140 (9)	0.0058 (8)
C8	0.0461 (9)	0.0492 (10)	0.0402 (9)	0.0173 (8)	0.0054 (8)	0.0035 (7)
C9	0.0490 (10)	0.0463 (10)	0.0460 (10)	0.0148 (8)	0.0058 (8)	0.0078 (8)
C10	0.0446 (9)	0.0450 (9)	0.0409 (9)	0.0142 (7)	0.0034 (7)	0.0039 (7)
C11	0.0526 (10)	0.0431 (10)	0.0595 (11)	0.0169 (8)	0.0082 (9)	0.0079 (8)
C12	0.0519 (11)	0.0492 (10)	0.0571 (11)	0.0083 (8)	0.0108 (9)	0.0106 (9)
C13	0.0477 (10)	0.0612 (12)	0.0424 (9)	0.0161 (9)	0.0058 (8)	0.0000 (8)
C14	0.0651 (12)	0.0474 (10)	0.0591 (11)	0.0235 (9)	0.0134 (10)	0.0013 (9)
C15	0.0590 (11)	0.0417 (9)	0.0541 (11)	0.0138 (8)	0.0107 (9)	0.0064 (8)
C16	0.0863 (18)	0.097 (2)	0.0876 (18)	0.0153 (15)	−0.0100 (15)	0.0115 (15)
C17	0.0561 (13)	0.1071 (19)	0.0633 (13)	0.0170 (13)	0.0206 (11)	0.0145 (13)

Geometric parameters (Å, º)

S1—O1	1.4286 (13)	C6—H6	0.9300
S1—O2	1.4288 (13)	C7—C8	1.504 (2)
S1—N1	1.5995 (17)	C7—H7A	0.9700
S1—C1	1.770 (2)	C7—H7B	0.9700
O3—C8	1.226 (2)	C9—C10	1.462 (2)
O4—C13	1.368 (2)	C9—H9	0.9300
O4—C17	1.421 (3)	C10—C15	1.387 (2)
N1—C7	1.455 (2)	C10—C11	1.390 (2)
N1—H1N	0.804 (15)	C11—C12	1.378 (3)
N2—C8	1.341 (2)	C11—H11	0.9300
N2—N3	1.379 (2)	C12—C13	1.386 (3)
N2—H2N	0.875 (15)	C12—H12	0.9300
N3—C9	1.274 (2)	C13—C14	1.377 (3)
C1—C6	1.381 (3)	C14—C15	1.379 (3)
C1—C2	1.381 (3)	C14—H14	0.9300
C2—C3	1.375 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.376 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.381 (3)	C17—H17A	0.9600
C4—C16	1.511 (3)	C17—H17B	0.9600
C5—C6	1.373 (3)	C17—H17C	0.9600
C5—H5	0.9300
O1—S1—O2	119.74 (9)	H7A—C7—H7B	108.3
O1—S1—N1	106.56 (9)	O3—C8—N2	122.00 (16)
O2—S1—N1	106.79 (9)	O3—C8—C7	121.17 (15)
O1—S1—C1	107.83 (9)	N2—C8—C7	116.83 (15)
O2—S1—C1	106.92 (9)	N3—C9—C10	120.72 (16)
N1—S1—C1	108.63 (9)	N3—C9—H9	119.6
C13—O4—C17	118.06 (17)	C10—C9—H9	119.6
C7—N1—S1	120.25 (13)	C15—C10—C11	117.91 (16)
C7—N1—H1N	115.5 (16)	C15—C10—C9	120.18 (16)
S1—N1—H1N	113.7 (16)	C11—C10—C9	121.90 (16)
C8—N2—N3	119.50 (15)	C12—C11—C10	121.30 (17)
C8—N2—H2N	115.8 (13)	C12—C11—H11	119.4
N3—N2—H2N	124.6 (13)	C10—C11—H11	119.4
C9—N3—N2	116.07 (15)	C11—C12—C13	119.84 (17)
C6—C1—C2	119.1 (2)	C11—C12—H12	120.1
C6—C1—S1	120.04 (16)	C13—C12—H12	120.1
C2—C1—S1	120.80 (15)	O4—C13—C14	116.34 (17)
C3—C2—C1	120.42 (19)	O4—C13—C12	124.06 (18)
C3—C2—H2	119.8	C14—C13—C12	119.59 (17)
C1—C2—H2	119.8	C13—C14—C15	120.22 (17)
C2—C3—C4	121.3 (2)	C13—C14—H14	119.9
C2—C3—H3	119.4	C15—C14—H14	119.9
C4—C3—H3	119.4	C14—C15—C10	121.14 (17)
C3—C4—C5	117.4 (2)	C14—C15—H15	119.4
C3—C4—C16	121.1 (2)	C10—C15—H15	119.4
C5—C4—C16	121.5 (2)	C4—C16—H16A	109.5
C6—C5—C4	122.3 (2)	C4—C16—H16B	109.5
C6—C5—H5	118.8	H16A—C16—H16B	109.5
C4—C5—H5	118.8	C4—C16—H16C	109.5
C5—C6—C1	119.4 (2)	H16A—C16—H16C	109.5
C5—C6—H6	120.3	H16B—C16—H16C	109.5
C1—C6—H6	120.3	O4—C17—H17A	109.5
N1—C7—C8	108.83 (15)	O4—C17—H17B	109.5
N1—C7—H7A	109.9	H17A—C17—H17B	109.5
C8—C7—H7A	109.9	O4—C17—H17C	109.5
N1—C7—H7B	109.9	H17A—C17—H17C	109.5
C8—C7—H7B	109.9	H17B—C17—H17C	109.5
O1—S1—N1—C7	−169.02 (15)	S1—N1—C7—C8	−147.88 (14)
O2—S1—N1—C7	−39.95 (17)	N3—N2—C8—O3	177.55 (16)
C1—S1—N1—C7	75.04 (16)	N3—N2—C8—C7	−2.4 (2)
C8—N2—N3—C9	−178.66 (16)	N1—C7—C8—O3	3.0 (2)
O1—S1—C1—C6	−32.11 (19)	N1—C7—C8—N2	−176.96 (16)
O2—S1—C1—C6	−162.08 (17)	N2—N3—C9—C10	179.96 (15)
N1—S1—C1—C6	83.00 (18)	N3—C9—C10—C15	179.09 (17)
O1—S1—C1—C2	148.94 (16)	N3—C9—C10—C11	−0.3 (3)
O2—S1—C1—C2	18.96 (18)	C15—C10—C11—C12	0.4 (3)
N1—S1—C1—C2	−95.95 (17)	C9—C10—C11—C12	179.86 (17)
C6—C1—C2—C3	0.1 (3)	C10—C11—C12—C13	−0.7 (3)
S1—C1—C2—C3	179.02 (16)	C17—O4—C13—C14	−173.20 (19)
C1—C2—C3—C4	0.3 (3)	C17—O4—C13—C12	7.4 (3)
C2—C3—C4—C5	−0.5 (3)	C11—C12—C13—O4	179.94 (17)
C2—C3—C4—C16	179.0 (2)	C11—C12—C13—C14	0.5 (3)
C3—C4—C5—C6	0.3 (4)	O4—C13—C14—C15	−179.46 (17)
C16—C4—C5—C6	−179.1 (2)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C1	0.0 (4)	C13—C14—C15—C10	−0.3 (3)
C2—C1—C6—C5	−0.2 (3)	C11—C10—C15—C14	0.1 (3)
S1—C1—C6—C5	−179.16 (19)	C9—C10—C15—C14	−179.34 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.80 (2)	2.30 (2)	3.067 (2)	160 (2)
N1—H1N···O3	0.80 (2)	2.22 (2)	2.629 (2)	112 (2)
N2—H2N···O3^ii	0.88 (2)	1.96 (2)	2.830 (2)	177 (2)
C15—H15···O2^iii	0.93	2.50	3.403 (2)	165

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