(4E)-4-[(2-Hy-droxy-anilino)methyl-idene]-1-phenyl-pyrazolidine-3,5-dione dimethyl sulfoxide hemisolvate.

The asymmetric unit of the title compound, C16H13N3O3·0.5C2H6OS, is composed of two independent pyrazolidine-3,5-dione mol-ecules and one dimethyl sulfoxide solvent mol-ecule. In each pyrazolidine-3,5-dione mol-ecule, an intra-molecular N-H⋯O hydrogen bond forms an S(5)S(6) motif. In the crystal, pairs of each independent pyrazolidine-3,5-dione mol-ecule are linked by N-H⋯O hydrogen bonds, forming dimers with R 2 (2)(8) motifs. These dimers are connected with the other mol-ecules through the solvent mol-ecules via O-H⋯O hydrogen bonds, forming ribbons along the b-axis direction. C-H⋯π inter-actions connect the ribbons. C-H⋯O interactions also occur.

Related literature

For the significant role of pyrazolidinediones in the synthesis of various heterocyclic compounds, see: Elnagdy & Ohta (1973 ▶); Abdel-Rahman et al. (2004 ▶); Khodairy (2007 ▶). For the diverse biological actvities of pyrazolidinedione-containing compounds, see: D’Alo et al. (1978 ▶); Tawab et al. (1960 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13N3O3·0.5C2H6OS

M = 334.37

Triclinic,

a = 5.7740 (2) Å

b = 14.9402 (6) Å

c = 19.2441 (7) Å

α = 106.060 (1)°

β = 93.459 (1)°

γ = 92.653 (1)°

V = 1588.96 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.47 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.973, T max = 0.990

25749 measured reflections

7370 independent reflections

5874 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.112

S = 1.02

7370 reflections

453 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813022034/hg5338sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022034/hg5338Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022034/hg5338Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13N3O3·0.5C2H6OS	Z = 4
Mr = 334.37	F(000) = 700
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7740 (2) Å	Cell parameters from 9951 reflections
b = 14.9402 (6) Å	θ = 2.8–27.6°
c = 19.2441 (7) Å	µ = 0.16 mm−1
α = 106.060 (1)°	T = 100 K
β = 93.459 (1)°	Prism, colourless
γ = 92.653 (1)°	0.47 × 0.14 × 0.06 mm
V = 1588.96 (10) Å3

Bruker APEXII CCD diffractometer	7370 independent reflections
Radiation source: sealed tube	5874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −7→6
Tmin = 0.973, Tmax = 0.990	k = −19→19
25749 measured reflections	l = −24→25

Refinement on F2	6 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	W = 1/[Σ2(FO2) + (0.0457P)2 + 1.0131P] WHERE P = (FO2 + 2FC2)/3
wR(F2) = 0.112	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.40 e Å−3
7370 reflections	Δρmin = −0.51 e Å−3
453 parameters

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O1	1.0470 (2)	0.31031 (8)	0.80151 (7)	0.0235 (3)
O2	0.65665 (19)	−0.04836 (8)	0.93836 (7)	0.0239 (4)
O3	1.2614 (2)	0.09699 (8)	0.84559 (7)	0.0249 (4)
N1	0.8575 (2)	0.19791 (9)	0.86858 (7)	0.0176 (4)
N2	1.0350 (2)	−0.07965 (9)	0.91086 (7)	0.0165 (4)
N3	1.2123 (2)	−0.04078 (9)	0.87775 (8)	0.0187 (4)
C1	0.8647 (3)	0.34333 (11)	0.83966 (8)	0.0182 (4)
C2	0.7821 (3)	0.43089 (11)	0.84613 (9)	0.0236 (5)
C3	0.5912 (3)	0.45743 (11)	0.88502 (10)	0.0258 (5)
C4	0.4791 (3)	0.39733 (11)	0.91716 (9)	0.0236 (5)
C5	0.5609 (3)	0.30982 (11)	0.91163 (9)	0.0203 (4)
C6	0.7542 (3)	0.28328 (10)	0.87382 (8)	0.0166 (4)
C7	0.7803 (3)	0.12843 (10)	0.89313 (8)	0.0174 (4)
C8	0.9069 (3)	0.05182 (10)	0.89051 (8)	0.0162 (4)
C9	0.8422 (3)	−0.02722 (10)	0.91639 (8)	0.0162 (4)
C10	1.1384 (3)	0.04256 (10)	0.86849 (9)	0.0178 (4)
C11	1.0542 (3)	−0.17105 (10)	0.91722 (8)	0.0154 (4)
C12	0.8869 (3)	−0.21227 (11)	0.95024 (8)	0.0184 (4)
C13	0.9161 (3)	−0.30103 (11)	0.95758 (9)	0.0217 (5)
C14	1.1073 (3)	−0.34943 (11)	0.93344 (9)	0.0228 (5)
C15	1.2715 (3)	−0.30817 (11)	0.90057 (10)	0.0238 (5)
C16	1.2464 (3)	−0.21971 (11)	0.89186 (9)	0.0200 (5)
O4	0.3509 (2)	0.22169 (9)	0.47285 (7)	0.0331 (4)
O5	1.2172 (2)	0.43434 (8)	0.73963 (6)	0.0242 (4)
O6	0.8410 (2)	0.39366 (8)	0.50665 (6)	0.0230 (3)
N4	0.6176 (2)	0.29482 (9)	0.59083 (7)	0.0197 (4)
N5	1.2770 (2)	0.49105 (9)	0.64119 (7)	0.0179 (4)
N6	1.1791 (2)	0.47253 (10)	0.56906 (7)	0.0195 (4)
C17	0.2873 (3)	0.19598 (12)	0.53154 (9)	0.0244 (5)
C18	0.0972 (3)	0.13555 (13)	0.53120 (10)	0.0299 (5)
C19	0.0470 (3)	0.11388 (13)	0.59430 (11)	0.0321 (6)
C20	0.1841 (3)	0.15263 (13)	0.65813 (10)	0.0305 (6)
C21	0.3754 (3)	0.21364 (12)	0.65940 (9)	0.0248 (5)
C22	0.4276 (3)	0.23438 (11)	0.59601 (9)	0.0206 (5)
C23	0.7898 (3)	0.33169 (11)	0.64012 (9)	0.0188 (4)
C24	0.9671 (3)	0.38897 (11)	0.62757 (8)	0.0181 (4)
C25	1.1586 (3)	0.43738 (10)	0.67724 (8)	0.0182 (4)
C26	0.9804 (3)	0.41578 (11)	0.56190 (8)	0.0186 (4)
C27	1.4860 (3)	0.54793 (10)	0.66204 (8)	0.0176 (4)
C28	1.5761 (3)	0.57334 (12)	0.73415 (9)	0.0228 (5)
C29	1.7817 (3)	0.62903 (12)	0.75405 (10)	0.0270 (5)
C30	1.8980 (3)	0.66043 (12)	0.70351 (10)	0.0250 (5)
C31	1.8058 (3)	0.63606 (12)	0.63225 (9)	0.0232 (5)
C32	1.6008 (3)	0.58009 (11)	0.61100 (9)	0.0206 (5)
S1	0.71959 (8)	0.90279 (3)	0.71557 (2)	0.0305 (2)
O7	0.8621 (2)	0.87145 (9)	0.65113 (7)	0.0334 (4)
C33	0.4512 (4)	0.83276 (15)	0.69636 (13)	0.0416 (7)
C34	0.6075 (4)	1.00954 (15)	0.70907 (12)	0.0418 (7)
H1	0.990 (3)	0.1921 (13)	0.8499 (10)	0.0210*
H1A	1.108 (4)	0.3515 (13)	0.7841 (11)	0.0350*
H2	0.85680	0.47250	0.82380	0.0280*
H3	0.53640	0.51760	0.88970	0.0310*
H3A	1.352 (3)	−0.0388 (13)	0.8987 (10)	0.0220*
H4	0.34620	0.41580	0.94300	0.0280*
H5	0.48430	0.26840	0.93370	0.0240*
H7	0.63340	0.13150	0.91310	0.0210*
H12	0.75470	−0.17990	0.96750	0.0220*
H13	0.80170	−0.32920	0.97980	0.0260*
H14	1.12570	−0.40990	0.93930	0.0270*
H15	1.40370	−0.34080	0.88370	0.0290*
H16	1.35980	−0.19250	0.86870	0.0240*
H4A	0.627 (3)	0.3061 (13)	0.5487 (9)	0.0240*
H4B	0.269 (4)	0.1914 (16)	0.4344 (10)	0.0500*
H6	1.177 (3)	0.5205 (11)	0.5509 (10)	0.0230*
H18	0.00160	0.10910	0.48770	0.0360*
H19	−0.08260	0.07210	0.59380	0.0390*
H20	0.14760	0.13760	0.70120	0.0370*
H21	0.46890	0.24070	0.70320	0.0300*
H23	0.79180	0.31840	0.68570	0.0230*
H28	1.49740	0.55270	0.76940	0.0270*
H29	1.84370	0.64590	0.80310	0.0320*
H30	2.03920	0.69820	0.71760	0.0300*
H31	1.88370	0.65790	0.59740	0.0280*
H32	1.53910	0.56380	0.56190	0.0250*
H33A	0.38080	0.83310	0.64880	0.0620*
H33B	0.34500	0.85820	0.73370	0.0620*
H33C	0.48070	0.76860	0.69600	0.0620*
H34A	0.73610	1.05680	0.71500	0.0630*
H34B	0.50090	1.03090	0.74710	0.0630*
H34C	0.52370	0.99960	0.66140	0.0630*

	U11	U22	U33	U12	U13	U23
O1	0.0266 (6)	0.0209 (6)	0.0281 (6)	0.0018 (5)	0.0080 (5)	0.0139 (5)
O2	0.0160 (6)	0.0201 (6)	0.0412 (7)	0.0035 (4)	0.0091 (5)	0.0161 (5)
O3	0.0213 (6)	0.0220 (6)	0.0378 (7)	0.0022 (5)	0.0096 (5)	0.0174 (5)
N1	0.0173 (7)	0.0149 (6)	0.0222 (7)	0.0021 (5)	0.0031 (5)	0.0075 (5)
N2	0.0139 (6)	0.0140 (6)	0.0243 (7)	0.0008 (5)	0.0050 (5)	0.0090 (5)
N3	0.0135 (6)	0.0177 (6)	0.0290 (7)	0.0021 (5)	0.0062 (6)	0.0124 (6)
C1	0.0208 (8)	0.0168 (7)	0.0170 (8)	−0.0007 (6)	−0.0019 (6)	0.0059 (6)
C2	0.0320 (9)	0.0171 (8)	0.0248 (9)	0.0001 (7)	0.0017 (7)	0.0115 (6)
C3	0.0376 (10)	0.0145 (8)	0.0274 (9)	0.0065 (7)	0.0013 (7)	0.0088 (6)
C4	0.0277 (9)	0.0195 (8)	0.0246 (9)	0.0073 (7)	0.0046 (7)	0.0065 (6)
C5	0.0233 (8)	0.0163 (7)	0.0236 (8)	0.0017 (6)	0.0031 (7)	0.0091 (6)
C6	0.0198 (8)	0.0121 (7)	0.0175 (8)	0.0003 (6)	−0.0029 (6)	0.0047 (6)
C7	0.0159 (7)	0.0147 (7)	0.0217 (8)	0.0001 (6)	0.0003 (6)	0.0058 (6)
C8	0.0158 (7)	0.0141 (7)	0.0190 (8)	−0.0011 (6)	0.0010 (6)	0.0056 (6)
C9	0.0152 (7)	0.0141 (7)	0.0200 (8)	0.0015 (6)	0.0014 (6)	0.0057 (6)
C10	0.0185 (8)	0.0148 (7)	0.0209 (8)	0.0015 (6)	0.0028 (6)	0.0061 (6)
C11	0.0168 (7)	0.0119 (7)	0.0176 (7)	−0.0001 (6)	−0.0024 (6)	0.0052 (5)
C12	0.0179 (8)	0.0183 (7)	0.0202 (8)	0.0018 (6)	0.0026 (6)	0.0073 (6)
C13	0.0241 (8)	0.0197 (8)	0.0235 (8)	−0.0024 (6)	0.0008 (7)	0.0108 (6)
C14	0.0262 (9)	0.0157 (7)	0.0283 (9)	0.0010 (6)	−0.0041 (7)	0.0103 (6)
C15	0.0194 (8)	0.0169 (8)	0.0350 (10)	0.0046 (6)	0.0004 (7)	0.0071 (7)
C16	0.0161 (8)	0.0167 (7)	0.0288 (9)	0.0007 (6)	0.0016 (6)	0.0089 (6)
O4	0.0378 (8)	0.0395 (8)	0.0194 (6)	−0.0165 (6)	−0.0023 (6)	0.0081 (5)
O5	0.0292 (7)	0.0270 (6)	0.0188 (6)	−0.0069 (5)	−0.0028 (5)	0.0126 (5)
O6	0.0244 (6)	0.0276 (6)	0.0176 (6)	−0.0066 (5)	−0.0017 (5)	0.0095 (5)
N4	0.0226 (7)	0.0205 (7)	0.0174 (7)	−0.0027 (5)	0.0025 (6)	0.0079 (5)
N5	0.0202 (7)	0.0210 (7)	0.0137 (6)	−0.0012 (5)	0.0004 (5)	0.0077 (5)
N6	0.0222 (7)	0.0236 (7)	0.0137 (6)	−0.0039 (6)	−0.0011 (5)	0.0085 (5)
C17	0.0282 (9)	0.0221 (8)	0.0219 (8)	−0.0017 (7)	0.0047 (7)	0.0043 (6)
C18	0.0293 (10)	0.0280 (9)	0.0275 (9)	−0.0079 (7)	0.0025 (7)	0.0012 (7)
C19	0.0299 (10)	0.0266 (9)	0.0373 (11)	−0.0098 (7)	0.0108 (8)	0.0048 (8)
C20	0.0343 (10)	0.0294 (9)	0.0302 (10)	−0.0033 (8)	0.0123 (8)	0.0114 (7)
C21	0.0262 (9)	0.0252 (9)	0.0237 (9)	−0.0004 (7)	0.0039 (7)	0.0079 (7)
C22	0.0204 (8)	0.0171 (8)	0.0249 (8)	−0.0006 (6)	0.0050 (7)	0.0063 (6)
C23	0.0233 (8)	0.0171 (7)	0.0178 (8)	0.0023 (6)	0.0036 (6)	0.0073 (6)
C24	0.0213 (8)	0.0171 (7)	0.0164 (8)	0.0013 (6)	0.0022 (6)	0.0056 (6)
C25	0.0214 (8)	0.0161 (7)	0.0185 (8)	0.0006 (6)	0.0035 (6)	0.0070 (6)
C26	0.0197 (8)	0.0182 (7)	0.0185 (8)	0.0004 (6)	0.0027 (6)	0.0061 (6)
C27	0.0180 (8)	0.0162 (7)	0.0191 (8)	0.0018 (6)	0.0024 (6)	0.0057 (6)
C28	0.0271 (9)	0.0242 (8)	0.0187 (8)	−0.0026 (7)	0.0022 (7)	0.0092 (6)
C29	0.0297 (10)	0.0286 (9)	0.0223 (9)	−0.0059 (7)	−0.0057 (7)	0.0095 (7)
C30	0.0206 (8)	0.0245 (8)	0.0299 (9)	−0.0047 (7)	−0.0009 (7)	0.0092 (7)
C31	0.0232 (8)	0.0244 (8)	0.0240 (9)	−0.0003 (7)	0.0069 (7)	0.0093 (7)
C32	0.0224 (8)	0.0224 (8)	0.0173 (8)	0.0000 (6)	0.0029 (6)	0.0061 (6)
S1	0.0324 (3)	0.0342 (3)	0.0215 (2)	0.0017 (2)	0.0025 (2)	0.0020 (2)
O7	0.0256 (7)	0.0396 (8)	0.0272 (7)	−0.0041 (6)	0.0038 (5)	−0.0030 (6)
C33	0.0305 (11)	0.0439 (12)	0.0501 (13)	0.0012 (9)	0.0145 (10)	0.0106 (10)
C34	0.0533 (14)	0.0372 (11)	0.0369 (11)	0.0086 (10)	0.0160 (10)	0.0102 (9)

S1—C34	1.782 (2)	C2—H2	0.9500
S1—O7	1.5072 (13)	C3—H3	0.9500
S1—C33	1.789 (2)	C4—H4	0.9500
O1—C1	1.353 (2)	C5—H5	0.9500
O2—C9	1.234 (2)	C7—H7	0.9500
O3—C10	1.242 (2)	C12—H12	0.9500
O1—H1A	0.85 (2)	C13—H13	0.9500
O4—C17	1.355 (2)	C14—H14	0.9500
O5—C25	1.2412 (19)	C15—H15	0.9500
O6—C26	1.2511 (19)	C16—H16	0.9500
O4—H4B	0.85 (2)	C17—C22	1.402 (2)
N1—C7	1.324 (2)	C17—C18	1.387 (3)
N1—C6	1.414 (2)	C18—C19	1.384 (3)
N2—C11	1.413 (2)	C19—C20	1.385 (3)
N2—N3	1.4212 (18)	C20—C21	1.394 (3)
N2—C9	1.383 (2)	C21—C22	1.386 (2)
N3—C10	1.388 (2)	C23—C24	1.379 (2)
N1—H1	0.863 (18)	C24—C25	1.441 (2)
N3—H3A	0.875 (18)	C24—C26	1.433 (2)
N4—C23	1.318 (2)	C27—C32	1.395 (2)
N4—C22	1.414 (2)	C27—C28	1.394 (2)
N5—C27	1.413 (2)	C28—C29	1.388 (3)
N5—N6	1.4146 (18)	C29—C30	1.385 (3)
N5—C25	1.381 (2)	C30—C31	1.384 (2)
N6—C26	1.371 (2)	C31—C32	1.389 (2)
N4—H4A	0.877 (17)	C18—H18	0.9500
N6—H6	0.880 (17)	C19—H19	0.9500
C1—C6	1.403 (2)	C20—H20	0.9500
C1—C2	1.389 (2)	C21—H21	0.9500
C2—C3	1.381 (2)	C23—H23	0.9500
C3—C4	1.382 (2)	C28—H28	0.9500
C4—C5	1.389 (2)	C29—H29	0.9500
C5—C6	1.383 (2)	C30—H30	0.9500
C7—C8	1.377 (2)	C31—H31	0.9500
C8—C10	1.428 (2)	C32—H32	0.9500
C8—C9	1.445 (2)	C33—H33A	0.9800
C11—C16	1.394 (2)	C33—H33B	0.9800
C11—C12	1.397 (2)	C33—H33C	0.9800
C12—C13	1.389 (2)	C34—H34A	0.9800
C13—C14	1.381 (2)	C34—H34B	0.9800
C14—C15	1.383 (2)	C34—H34C	0.9800
C15—C16	1.390 (2)
O7—S1—C33	107.82 (9)	C15—C14—H14	121.00
O7—S1—C34	105.34 (9)	C14—C15—H15	119.00
C33—S1—C34	97.86 (11)	C16—C15—H15	119.00
C1—O1—H1A	110.7 (15)	C15—C16—H16	120.00
C17—O4—H4B	111.6 (15)	C11—C16—H16	120.00
C6—N1—C7	127.16 (13)	O4—C17—C18	124.48 (16)
N3—N2—C9	110.49 (13)	O4—C17—C22	115.99 (15)
N3—N2—C11	118.54 (12)	C18—C17—C22	119.53 (16)
C9—N2—C11	129.12 (13)	C17—C18—C19	119.91 (17)
N2—N3—C10	107.55 (12)	C18—C19—C20	120.53 (17)
C7—N1—H1	116.5 (13)	C19—C20—C21	120.25 (17)
C6—N1—H1	116.2 (13)	C20—C21—C22	119.24 (16)
C10—N3—H3A	116.6 (13)	C17—C22—C21	120.52 (16)
N2—N3—H3A	114.2 (12)	N4—C22—C21	124.13 (15)
C22—N4—C23	127.91 (14)	N4—C22—C17	115.34 (15)
C25—N5—C27	130.40 (13)	N4—C23—C24	121.98 (15)
N6—N5—C25	110.15 (12)	C23—C24—C26	124.17 (15)
N6—N5—C27	118.85 (12)	C23—C24—C25	127.93 (14)
N5—N6—C26	108.04 (12)	C25—C24—C26	107.76 (14)
C22—N4—H4A	116.0 (12)	N5—C25—C24	105.83 (13)
C23—N4—H4A	116.0 (12)	O5—C25—N5	124.06 (15)
N5—N6—H6	116.1 (12)	O5—C25—C24	130.11 (15)
C26—N6—H6	119.1 (11)	N6—C26—C24	107.70 (14)
O1—C1—C2	124.32 (15)	O6—C26—C24	128.32 (16)
O1—C1—C6	116.43 (15)	O6—C26—N6	123.98 (14)
C2—C1—C6	119.25 (15)	N5—C27—C28	119.95 (14)
C1—C2—C3	119.97 (16)	C28—C27—C32	119.75 (16)
C2—C3—C4	120.71 (16)	N5—C27—C32	120.29 (14)
C3—C4—C5	119.95 (16)	C27—C28—C29	119.51 (16)
C4—C5—C6	119.72 (16)	C28—C29—C30	121.06 (17)
C1—C6—C5	120.38 (15)	C29—C30—C31	119.12 (16)
N1—C6—C1	115.82 (14)	C30—C31—C32	120.86 (16)
N1—C6—C5	123.78 (14)	C27—C32—C31	119.69 (15)
N1—C7—C8	121.87 (15)	C19—C18—H18	120.00
C7—C8—C10	124.68 (15)	C17—C18—H18	120.00
C9—C8—C10	108.23 (14)	C18—C19—H19	120.00
C7—C8—C9	126.77 (16)	C20—C19—H19	120.00
N2—C9—C8	105.69 (14)	C19—C20—H20	120.00
O2—C9—N2	124.45 (14)	C21—C20—H20	120.00
O2—C9—C8	129.85 (16)	C22—C21—H21	120.00
N3—C10—C8	107.75 (13)	C20—C21—H21	120.00
O3—C10—C8	128.75 (15)	C24—C23—H23	119.00
O3—C10—N3	123.49 (15)	N4—C23—H23	119.00
N2—C11—C16	119.35 (14)	C27—C28—H28	120.00
N2—C11—C12	121.03 (15)	C29—C28—H28	120.00
C12—C11—C16	119.60 (15)	C28—C29—H29	119.00
C11—C12—C13	119.25 (16)	C30—C29—H29	119.00
C12—C13—C14	121.64 (16)	C31—C30—H30	120.00
C13—C14—C15	118.67 (16)	C29—C30—H30	120.00
C14—C15—C16	121.10 (16)	C30—C31—H31	120.00
C11—C16—C15	119.73 (16)	C32—C31—H31	120.00
C1—C2—H2	120.00	C27—C32—H32	120.00
C3—C2—H2	120.00	C31—C32—H32	120.00
C2—C3—H3	120.00	S1—C33—H33A	109.00
C4—C3—H3	120.00	S1—C33—H33B	109.00
C5—C4—H4	120.00	S1—C33—H33C	109.00
C3—C4—H4	120.00	H33A—C33—H33B	109.00
C6—C5—H5	120.00	H33A—C33—H33C	109.00
C4—C5—H5	120.00	H33B—C33—H33C	109.00
C8—C7—H7	119.00	S1—C34—H34A	109.00
N1—C7—H7	119.00	S1—C34—H34B	110.00
C13—C12—H12	120.00	S1—C34—H34C	109.00
C11—C12—H12	120.00	H34A—C34—H34B	110.00
C14—C13—H13	119.00	H34A—C34—H34C	109.00
C12—C13—H13	119.00	H34B—C34—H34C	109.00
C13—C14—H14	121.00
C6—N1—C7—C8	−174.14 (15)	C7—C8—C9—N2	−172.41 (15)
C7—N1—C6—C5	5.4 (2)	C10—C8—C9—O2	−177.61 (16)
C7—N1—C6—C1	−176.59 (15)	C7—C8—C10—O3	−3.3 (3)
C9—N2—C11—C12	−18.0 (2)	C7—C8—C10—N3	175.97 (15)
C11—N2—N3—C10	171.57 (13)	C7—C8—C9—O2	8.7 (3)
C11—N2—C9—O2	10.8 (3)	C9—C8—C10—O3	−177.15 (17)
N3—N2—C11—C16	0.8 (2)	C9—C8—C10—N3	2.08 (18)
C9—N2—C11—C16	163.72 (15)	N2—C11—C16—C15	177.38 (15)
C9—N2—N3—C10	5.64 (17)	C12—C11—C16—C15	−0.9 (2)
C11—N2—C9—C8	−168.25 (14)	N2—C11—C12—C13	−177.88 (14)
N3—N2—C11—C12	179.05 (14)	C16—C11—C12—C13	0.4 (2)
N3—N2—C9—O2	174.78 (15)	C11—C12—C13—C14	0.4 (2)
N3—N2—C9—C8	−4.22 (16)	C12—C13—C14—C15	−0.7 (3)
N2—N3—C10—C8	−4.60 (17)	C13—C14—C15—C16	0.1 (3)
N2—N3—C10—O3	174.69 (15)	C14—C15—C16—C11	0.7 (3)
C23—N4—C22—C17	−171.75 (16)	O4—C17—C22—C21	179.01 (16)
C22—N4—C23—C24	179.09 (16)	C18—C17—C22—N4	179.75 (16)
C23—N4—C22—C21	9.1 (3)	O4—C17—C22—N4	−0.2 (2)
N6—N5—C27—C28	174.88 (15)	O4—C17—C18—C19	−179.90 (17)
N6—N5—C27—C32	−4.1 (2)	C22—C17—C18—C19	0.2 (3)
C27—N5—C25—C24	−175.58 (15)	C18—C17—C22—C21	−1.1 (3)
N6—N5—C25—O5	174.60 (15)	C17—C18—C19—C20	0.5 (3)
C25—N5—C27—C28	−15.0 (3)	C18—C19—C20—C21	−0.4 (3)
C27—N5—C25—O5	3.8 (3)	C19—C20—C21—C22	−0.5 (3)
C25—N5—C27—C32	166.08 (16)	C20—C21—C22—C17	1.2 (3)
C27—N5—N6—C26	179.47 (14)	C20—C21—C22—N4	−179.68 (16)
C25—N5—N6—C26	7.45 (17)	N4—C23—C24—C26	1.5 (3)
N6—N5—C25—C24	−4.77 (17)	N4—C23—C24—C25	176.69 (16)
N5—N6—C26—O6	172.99 (15)	C26—C24—C25—N5	0.50 (18)
N5—N6—C26—C24	−6.87 (18)	C23—C24—C26—O6	0.2 (3)
C2—C1—C6—N1	−176.10 (14)	C23—C24—C26—N6	−179.97 (16)
O1—C1—C6—N1	4.4 (2)	C25—C24—C26—O6	−175.85 (17)
O1—C1—C6—C5	−177.50 (15)	C25—C24—C26—N6	4.01 (19)
C6—C1—C2—C3	−0.9 (2)	C23—C24—C25—O5	5.4 (3)
O1—C1—C2—C3	178.54 (16)	C23—C24—C25—N5	−175.32 (17)
C2—C1—C6—C5	2.0 (2)	C26—C24—C25—O5	−178.81 (17)
C1—C2—C3—C4	−0.7 (3)	N5—C27—C28—C29	179.85 (15)
C2—C3—C4—C5	1.2 (3)	C32—C27—C28—C29	−1.2 (3)
C3—C4—C5—C6	−0.1 (3)	N5—C27—C32—C31	179.89 (16)
C4—C5—C6—N1	176.44 (15)	C28—C27—C32—C31	0.9 (3)
C4—C5—C6—C1	−1.5 (2)	C27—C28—C29—C30	0.5 (3)
N1—C7—C8—C10	6.4 (2)	C28—C29—C30—C31	0.4 (3)
N1—C7—C8—C9	179.11 (15)	C29—C30—C31—C32	−0.7 (3)
C10—C8—C9—N2	1.32 (17)	C30—C31—C32—C27	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	2.23 (2)	2.6235 (18)	107 (2)
N1—H1···O3	0.86 (2)	2.15 (2)	2.8265 (17)	135 (2)
O1—H1A···O5	0.85 (2)	1.80 (2)	2.6479 (17)	174 (2)
N3—H3A···O2i	0.88 (2)	1.90 (2)	2.7740 (17)	174 (2)
N4—H4A···O4	0.88 (2)	2.19 (2)	2.6019 (18)	109 (2)
N4—H4A···O6	0.88 (2)	2.11 (2)	2.8050 (18)	136 (2)
O4—H4B···S1ii	0.85 (2)	2.85 (2)	3.5767 (14)	145 (2)
O4—H4B···O7ii	0.85 (2)	1.76 (2)	2.6061 (18)	172 (2)
N6—H6···O6iii	0.88 (2)	1.92 (2)	2.7831 (19)	169 (2)
C7—H7···O3iv	0.95	2.40	3.055 (2)	126
C12—H12···O2	0.95	2.27	2.897 (2)	122
C16—H16···N3	0.95	2.42	2.775 (2)	102
C28—H28···O5	0.95	2.27	2.893 (2)	123
C32—H32···N6	0.95	2.46	2.801 (2)	101
C34—H34B···O3v	0.98	2.43	3.403 (3)	175
C29—H29···Cg3vi	0.95	2.64	3.548 (2)	160
C33—H33C···Cg6iv	0.98	2.74	3.690 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg6 are the centroids of the C11–C16 and C27–C32 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86 (2)	2.15 (2)	2.8265 (17)	135 (2)
O1—H1A⋯O5	0.85 (2)	1.80 (2)	2.6479 (17)	174 (2)
N3—H3A⋯O2i	0.88 (2)	1.90 (2)	2.7740 (17)	174 (2)
N4—H4A⋯O6	0.88 (2)	2.11 (2)	2.8050 (18)	136 (2)
O4—H4B⋯O7ii	0.85 (2)	1.76 (2)	2.6061 (18)	172 (2)
N6—H6⋯O6iii	0.88 (2)	1.92 (2)	2.7831 (19)	169 (2)
C34—H34B⋯O3iv	0.98	2.43	3.403 (3)	175
C29—H29⋯Cg3v	0.95	2.64	3.548 (2)	160
C33—H33C⋯Cg6vi	0.98	2.74	3.690 (2)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .