1-Acetyl-5-meth-oxy-4-(phenyl-sulfan-yl)imidazolidin-2-one.

The title compound, C12H14N2O3S, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The five-membered imidazolidin-2-one rings in both mol-ecules are twisted about the C-C bond. In the crystal, the A and B mol-ecules are associated via pairs of N-H⋯O hydrogen bonds, forming A-B dimers. These dimers are linked via C-H⋯S hydrogen bonds, forming double dimers, which are in turn linked via C-H⋯O hydrogen bonds forming two-dimensional networks lying parallel to (001). There are also C-H⋯π inter-actions present, which consolide the layers and link them, so forming a three-dimensional structure.

Related literature

For the anti­tumor activity of imidazolidinones, see: Abdel-Aziz et al. (2012 ▶); Lee et al. (2000 ▶); Kim et al. (2003 ▶). For related crystal structures, see: Park et al. (2000 ▶); Abdel-Aziz et al. (2012 ▶); Kapon & Reisner (1989 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H14N2O3S

M = 266.31

Triclinic,

a = 9.0371 (8) Å

b = 12.0642 (10) Å

c = 12.8369 (11) Å

α = 93.066 (1)°

β = 105.869 (1)°

γ = 111.574 (1)°

V = 1233.20 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.25 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.847, T max = 0.974

22009 measured reflections

6246 independent reflections

5490 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.03

6246 reflections

329 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814000117/su2683sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000117/su2683Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000117/su2683Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H14N2O3S	Z = 4
Mr = 266.31	F(000) = 560
Triclinic, P1	Dx = 1.434 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0371 (8) Å	Cell parameters from 9891 reflections
b = 12.0642 (10) Å	θ = 2.3–29.1°
c = 12.8369 (11) Å	µ = 0.26 mm−1
α = 93.066 (1)°	T = 100 K
β = 105.869 (1)°	Rod, colourless
γ = 111.574 (1)°	0.25 × 0.14 × 0.10 mm
V = 1233.20 (18) Å3

Bruker SMART APEX CCD diffractometer	6246 independent reflections
Radiation source: fine-focus sealed tube	5490 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 29.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −12→11
Tmin = 0.847, Tmax = 0.974	k = −16→16
22009 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.3898P] where P = (Fo2 + 2Fc2)/3
6246 reflections	(Δ/σ)max = 0.001
329 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	0.04876 (4)	0.16574 (3)	0.33282 (2)	0.01531 (8)
O1	0.00144 (11)	−0.07345 (8)	0.32035 (7)	0.01676 (18)
O2	0.08977 (13)	−0.24894 (9)	0.16722 (8)	0.0265 (2)
O3	−0.25546 (11)	−0.12264 (8)	−0.01801 (7)	0.01828 (18)
N1	−0.09455 (13)	0.04366 (9)	0.11887 (8)	0.0155 (2)
H1N	−0.1380	0.0929	0.0891	0.019*
N2	−0.03201 (12)	−0.11728 (9)	0.13027 (8)	0.0144 (2)
C1	0.11335 (15)	0.31463 (10)	0.30058 (9)	0.0145 (2)
C2	0.28336 (16)	0.38990 (11)	0.33308 (11)	0.0193 (2)
H2	0.3646	0.3607	0.3696	0.023*
C3	0.33403 (16)	0.50771 (12)	0.31202 (12)	0.0228 (3)
H3	0.4501	0.5583	0.3330	0.027*
C4	0.21611 (17)	0.55186 (12)	0.26060 (11)	0.0205 (3)
H4	0.2510	0.6327	0.2472	0.025*
C5	0.04669 (16)	0.47702 (12)	0.22883 (10)	0.0197 (2)
H5	−0.0342	0.5070	0.1934	0.024*
C6	−0.00562 (15)	0.35878 (11)	0.24838 (10)	0.0178 (2)
H6	−0.1218	0.3081	0.2264	0.021*
C7	0.05695 (14)	0.08366 (10)	0.21295 (9)	0.0131 (2)
H7	0.1554	0.1347	0.1912	0.016*
C8	0.07070 (14)	−0.03672 (10)	0.23658 (9)	0.0137 (2)
H8	0.1896	−0.0288	0.2567	0.016*
C9	−0.14064 (15)	−0.06988 (10)	0.06753 (9)	0.0137 (2)
C10	−0.01687 (16)	−0.22561 (11)	0.10365 (10)	0.0172 (2)
C11	−0.13220 (18)	−0.30806 (11)	−0.00263 (11)	0.0217 (3)
H11A	−0.1031	−0.3779	−0.0115	0.033*
H11B	−0.1205	−0.2641	−0.0639	0.033*
H11C	−0.2483	−0.3360	−0.0019	0.033*
C12	0.05831 (19)	−0.15414 (13)	0.38084 (11)	0.0250 (3)
H12A	−0.0011	−0.2364	0.3385	0.037*
H12B	0.0359	−0.1526	0.4513	0.037*
H12C	0.1791	−0.1286	0.3942	0.037*
S2	0.45632 (4)	0.91180 (3)	0.63984 (2)	0.01550 (8)
O4	0.47788 (11)	1.14846 (8)	0.66767 (7)	0.01680 (18)
O5	0.38711 (12)	1.30406 (8)	0.81309 (8)	0.0219 (2)
O6	0.70722 (12)	1.16581 (8)	1.01055 (7)	0.02057 (19)
N3	0.57467 (13)	1.01168 (9)	0.86090 (8)	0.0165 (2)
H3N	0.6113	0.9619	0.8987	0.020*
N4	0.50197 (13)	1.16831 (9)	0.85376 (8)	0.0147 (2)
C13	0.38049 (15)	0.75462 (11)	0.64573 (10)	0.0156 (2)
C14	0.27394 (16)	0.67501 (12)	0.54824 (10)	0.0209 (3)
H14	0.2400	0.7059	0.4835	0.025*
C15	0.21730 (17)	0.55073 (12)	0.54547 (11)	0.0231 (3)
H15	0.1459	0.4971	0.4786	0.028*
C16	0.26439 (17)	0.50477 (12)	0.63972 (12)	0.0226 (3)
H16	0.2245	0.4198	0.6379	0.027*
C17	0.37027 (18)	0.58348 (12)	0.73695 (11)	0.0216 (3)
H17	0.4022	0.5520	0.8017	0.026*
C18	0.42995 (16)	0.70802 (11)	0.74040 (10)	0.0185 (2)
H18	0.5041	0.7613	0.8069	0.022*
C19	0.43039 (15)	0.97353 (10)	0.76257 (9)	0.0134 (2)
H19	0.3302	0.9139	0.7771	0.016*
C20	0.40610 (14)	1.09291 (10)	0.74557 (9)	0.0139 (2)
H20	0.2851	1.0794	0.7258	0.017*
C21	0.60722 (15)	1.11992 (11)	0.91856 (9)	0.0149 (2)
C22	0.49203 (16)	1.27940 (11)	0.87707 (10)	0.0164 (2)
C23	0.61395 (18)	1.36279 (12)	0.98098 (11)	0.0233 (3)
H23A	0.5917	1.4359	0.9886	0.035*
H23B	0.7285	1.3850	0.9784	0.035*
H23C	0.6014	1.3220	1.0440	0.035*
C24	0.35893 (17)	1.16093 (12)	0.57410 (10)	0.0222 (3)
H24A	0.2766	1.0806	0.5347	0.033*
H24B	0.4175	1.2038	0.5250	0.033*
H24C	0.3014	1.2069	0.5986	0.033*

	U11	U22	U33	U12	U13	U23
S1	0.01895 (15)	0.01327 (14)	0.01343 (13)	0.00573 (11)	0.00561 (11)	0.00232 (10)
O1	0.0190 (4)	0.0173 (4)	0.0165 (4)	0.0087 (3)	0.0062 (3)	0.0084 (3)
O2	0.0328 (5)	0.0231 (5)	0.0284 (5)	0.0198 (4)	0.0046 (4)	0.0058 (4)
O3	0.0205 (4)	0.0160 (4)	0.0159 (4)	0.0085 (4)	0.0008 (3)	0.0003 (3)
N1	0.0187 (5)	0.0136 (5)	0.0135 (4)	0.0094 (4)	0.0001 (4)	0.0020 (4)
N2	0.0154 (5)	0.0123 (5)	0.0154 (4)	0.0070 (4)	0.0028 (4)	0.0022 (4)
C1	0.0172 (5)	0.0122 (5)	0.0143 (5)	0.0061 (4)	0.0055 (4)	0.0009 (4)
C2	0.0166 (6)	0.0163 (6)	0.0263 (6)	0.0088 (5)	0.0058 (5)	0.0028 (5)
C3	0.0165 (6)	0.0156 (6)	0.0360 (7)	0.0056 (5)	0.0089 (5)	0.0042 (5)
C4	0.0245 (6)	0.0155 (6)	0.0268 (6)	0.0101 (5)	0.0124 (5)	0.0061 (5)
C5	0.0212 (6)	0.0193 (6)	0.0218 (6)	0.0117 (5)	0.0064 (5)	0.0049 (5)
C6	0.0158 (5)	0.0181 (6)	0.0181 (5)	0.0065 (5)	0.0041 (4)	0.0019 (5)
C7	0.0143 (5)	0.0122 (5)	0.0132 (5)	0.0059 (4)	0.0039 (4)	0.0029 (4)
C8	0.0132 (5)	0.0132 (5)	0.0146 (5)	0.0058 (4)	0.0032 (4)	0.0035 (4)
C9	0.0155 (5)	0.0140 (5)	0.0137 (5)	0.0076 (4)	0.0053 (4)	0.0042 (4)
C10	0.0212 (6)	0.0141 (5)	0.0201 (6)	0.0089 (5)	0.0094 (5)	0.0051 (5)
C11	0.0295 (7)	0.0140 (6)	0.0223 (6)	0.0101 (5)	0.0077 (5)	0.0008 (5)
C12	0.0337 (7)	0.0231 (7)	0.0226 (6)	0.0147 (6)	0.0092 (6)	0.0140 (5)
S2	0.01739 (15)	0.01489 (15)	0.01454 (14)	0.00679 (11)	0.00530 (11)	0.00111 (11)
O4	0.0169 (4)	0.0185 (4)	0.0150 (4)	0.0068 (3)	0.0048 (3)	0.0056 (3)
O5	0.0236 (5)	0.0193 (4)	0.0261 (5)	0.0132 (4)	0.0063 (4)	0.0056 (4)
O6	0.0254 (5)	0.0183 (4)	0.0159 (4)	0.0120 (4)	−0.0006 (4)	−0.0010 (3)
N3	0.0202 (5)	0.0145 (5)	0.0140 (4)	0.0103 (4)	0.0000 (4)	0.0007 (4)
N4	0.0166 (5)	0.0139 (5)	0.0140 (4)	0.0079 (4)	0.0033 (4)	0.0015 (4)
C13	0.0144 (5)	0.0149 (5)	0.0190 (5)	0.0072 (4)	0.0062 (4)	0.0006 (4)
C14	0.0215 (6)	0.0206 (6)	0.0190 (6)	0.0104 (5)	0.0022 (5)	−0.0012 (5)
C15	0.0191 (6)	0.0187 (6)	0.0265 (6)	0.0064 (5)	0.0030 (5)	−0.0061 (5)
C16	0.0226 (6)	0.0146 (6)	0.0332 (7)	0.0068 (5)	0.0142 (5)	0.0002 (5)
C17	0.0278 (7)	0.0205 (6)	0.0225 (6)	0.0126 (5)	0.0126 (5)	0.0051 (5)
C18	0.0204 (6)	0.0177 (6)	0.0174 (5)	0.0076 (5)	0.0062 (5)	0.0002 (5)
C19	0.0143 (5)	0.0128 (5)	0.0132 (5)	0.0061 (4)	0.0038 (4)	0.0014 (4)
C20	0.0139 (5)	0.0137 (5)	0.0139 (5)	0.0058 (4)	0.0038 (4)	0.0023 (4)
C21	0.0170 (5)	0.0144 (5)	0.0149 (5)	0.0077 (5)	0.0050 (4)	0.0029 (4)
C22	0.0194 (6)	0.0138 (5)	0.0188 (5)	0.0072 (5)	0.0090 (5)	0.0040 (4)
C23	0.0322 (7)	0.0152 (6)	0.0211 (6)	0.0114 (5)	0.0042 (5)	−0.0001 (5)
C24	0.0257 (7)	0.0235 (6)	0.0161 (5)	0.0112 (5)	0.0021 (5)	0.0063 (5)

S1—C1	1.7830 (12)	S2—C13	1.7775 (13)
S1—C7	1.8186 (12)	S2—C19	1.8157 (12)
O1—C8	1.3998 (14)	O4—C20	1.4059 (14)
O1—C12	1.4301 (15)	O4—C24	1.4329 (14)
O2—C10	1.2115 (15)	O5—C22	1.2124 (15)
O3—C9	1.2264 (14)	O6—C21	1.2232 (15)
N1—C9	1.3483 (15)	N3—C21	1.3545 (15)
N1—C7	1.4538 (14)	N3—C19	1.4496 (14)
N1—H1N	0.8764	N3—H3N	0.8921
N2—C10	1.3975 (15)	N4—C22	1.3980 (15)
N2—C9	1.4032 (14)	N4—C21	1.4017 (15)
N2—C8	1.4733 (15)	N4—C20	1.4609 (15)
C1—C2	1.3936 (17)	C13—C14	1.3957 (17)
C1—C6	1.3978 (17)	C13—C18	1.3977 (17)
C2—C3	1.3903 (18)	C14—C15	1.3897 (18)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.3875 (18)	C15—C16	1.384 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.3886 (18)	C16—C17	1.3882 (19)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.3887 (18)	C17—C18	1.3907 (18)
C5—H5	0.9500	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.5413 (16)	C19—C20	1.5524 (16)
C7—H7	1.0000	C19—H19	1.0000
C8—H8	1.0000	C20—H20	1.0000
C10—C11	1.5006 (18)	C22—C23	1.4976 (17)
C11—H11A	0.9800	C23—H23A	0.9800
C11—H11B	0.9800	C23—H23B	0.9800
C11—H11C	0.9800	C23—H23C	0.9800
C12—H12A	0.9800	C24—H24A	0.9800
C12—H12B	0.9800	C24—H24B	0.9800
C12—H12C	0.9800	C24—H24C	0.9800
C1—S1—C7	99.86 (5)	C13—S2—C19	101.64 (6)
C8—O1—C12	115.46 (10)	C20—O4—C24	113.52 (9)
C9—N1—C7	113.25 (10)	C21—N3—C19	113.13 (10)
C9—N1—H1N	122.1	C21—N3—H3N	116.4
C7—N1—H1N	123.2	C19—N3—H3N	125.0
C10—N2—C9	128.26 (10)	C22—N4—C21	128.30 (10)
C10—N2—C8	121.10 (10)	C22—N4—C20	119.61 (10)
C9—N2—C8	110.62 (9)	C21—N4—C20	111.81 (9)
C2—C1—C6	119.69 (11)	C14—C13—C18	119.31 (11)
C2—C1—S1	119.75 (9)	C14—C13—S2	117.24 (10)
C6—C1—S1	120.47 (9)	C18—C13—S2	123.35 (9)
C3—C2—C1	119.98 (11)	C15—C14—C13	120.31 (12)
C3—C2—H2	120.0	C15—C14—H14	119.8
C1—C2—H2	120.0	C13—C14—H14	119.8
C4—C3—C2	120.41 (12)	C16—C15—C14	120.29 (12)
C4—C3—H3	119.8	C16—C15—H15	119.9
C2—C3—H3	119.8	C14—C15—H15	119.9
C3—C4—C5	119.56 (12)	C15—C16—C17	119.66 (12)
C3—C4—H4	120.2	C15—C16—H16	120.2
C5—C4—H4	120.2	C17—C16—H16	120.2
C4—C5—C6	120.64 (12)	C16—C17—C18	120.61 (12)
C4—C5—H5	119.7	C16—C17—H17	119.7
C6—C5—H5	119.7	C18—C17—H17	119.7
C5—C6—C1	119.71 (11)	C17—C18—C13	119.81 (11)
C5—C6—H6	120.1	C17—C18—H18	120.1
C1—C6—H6	120.1	C13—C18—H18	120.1
N1—C7—C8	102.27 (9)	N3—C19—C20	102.59 (9)
N1—C7—S1	114.45 (8)	N3—C19—S2	115.63 (8)
C8—C7—S1	111.08 (8)	C20—C19—S2	109.31 (8)
N1—C7—H7	109.6	N3—C19—H19	109.7
C8—C7—H7	109.6	C20—C19—H19	109.7
S1—C7—H7	109.6	S2—C19—H19	109.7
O1—C8—N2	111.86 (9)	O4—C20—N4	108.69 (9)
O1—C8—C7	108.49 (9)	O4—C20—C19	111.93 (9)
N2—C8—C7	101.79 (9)	N4—C20—C19	101.96 (9)
O1—C8—H8	111.4	O4—C20—H20	111.3
N2—C8—H8	111.4	N4—C20—H20	111.3
C7—C8—H8	111.4	C19—C20—H20	111.3
O3—C9—N1	126.89 (11)	O6—C21—N3	126.56 (11)
O3—C9—N2	125.95 (11)	O6—C21—N4	126.45 (11)
N1—C9—N2	107.15 (10)	N3—C21—N4	106.99 (10)
O2—C10—N2	118.56 (11)	O5—C22—N4	119.20 (11)
O2—C10—C11	122.56 (11)	O5—C22—C23	123.21 (11)
N2—C10—C11	118.88 (11)	N4—C22—C23	117.59 (11)
C10—C11—H11A	109.5	C22—C23—H23A	109.5
C10—C11—H11B	109.5	C22—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C10—C11—H11C	109.5	C22—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
O1—C12—H12A	109.5	O4—C24—H24A	109.5
O1—C12—H12B	109.5	O4—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
O1—C12—H12C	109.5	O4—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5
C7—S1—C1—C2	−88.48 (10)	C19—S2—C13—C14	135.75 (10)
C7—S1—C1—C6	95.09 (10)	C19—S2—C13—C18	−48.11 (12)
C6—C1—C2—C3	−0.98 (19)	C18—C13—C14—C15	0.18 (19)
S1—C1—C2—C3	−177.44 (10)	S2—C13—C14—C15	176.47 (10)
C1—C2—C3—C4	1.2 (2)	C13—C14—C15—C16	0.8 (2)
C2—C3—C4—C5	−0.9 (2)	C14—C15—C16—C17	−0.8 (2)
C3—C4—C5—C6	0.22 (19)	C15—C16—C17—C18	−0.3 (2)
C4—C5—C6—C1	0.03 (19)	C16—C17—C18—C13	1.24 (19)
C2—C1—C6—C5	0.35 (18)	C14—C13—C18—C17	−1.19 (19)
S1—C1—C6—C5	176.78 (9)	S2—C13—C18—C17	−177.25 (10)
C9—N1—C7—C8	−17.42 (13)	C21—N3—C19—C20	17.05 (13)
C9—N1—C7—S1	−137.63 (9)	C21—N3—C19—S2	135.93 (9)
C1—S1—C7—N1	−85.84 (9)	C13—S2—C19—N3	92.14 (9)
C1—S1—C7—C8	158.98 (8)	C13—S2—C19—C20	−152.75 (8)
C12—O1—C8—N2	91.43 (12)	C24—O4—C20—N4	−128.97 (10)
C12—O1—C8—C7	−157.09 (10)	C24—O4—C20—C19	119.19 (11)
C10—N2—C8—O1	−82.90 (13)	C22—N4—C20—O4	70.60 (13)
C9—N2—C8—O1	95.95 (11)	C21—N4—C20—O4	−103.86 (11)
C10—N2—C8—C7	161.46 (10)	C22—N4—C20—C19	−171.06 (10)
C9—N2—C8—C7	−19.68 (12)	C21—N4—C20—C19	14.49 (12)
N1—C7—C8—O1	−97.00 (10)	N3—C19—C20—O4	98.13 (10)
S1—C7—C8—O1	25.53 (11)	S2—C19—C20—O4	−25.09 (12)
N1—C7—C8—N2	21.08 (11)	N3—C19—C20—N4	−17.87 (11)
S1—C7—C8—N2	143.61 (8)	S2—C19—C20—N4	−141.09 (8)
C7—N1—C9—O3	−174.34 (12)	C19—N3—C21—O6	170.27 (12)
C7—N1—C9—N2	5.55 (13)	C19—N3—C21—N4	−8.52 (14)
C10—N2—C9—O3	8.5 (2)	C22—N4—C21—O6	2.6 (2)
C8—N2—C9—O3	−170.27 (11)	C20—N4—C21—O6	176.49 (12)
C10—N2—C9—N1	−171.40 (11)	C22—N4—C21—N3	−178.58 (12)
C8—N2—C9—N1	9.84 (13)	C20—N4—C21—N3	−4.72 (13)
C9—N2—C10—O2	177.09 (12)	C21—N4—C22—O5	−176.52 (12)
C8—N2—C10—O2	−4.27 (18)	C20—N4—C22—O5	10.04 (17)
C9—N2—C10—C11	−2.51 (19)	C21—N4—C22—C23	3.76 (19)
C8—N2—C10—C11	176.13 (11)	C20—N4—C22—C23	−169.67 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6i	0.88	1.99	2.8483 (13)	165
N3—H3N···O3ii	0.89	1.99	2.8623 (13)	167
C8—H8···S2iii	1.00	2.86	3.7891 (12)	156
C7—H7···O3iv	1.00	2.63	3.4150 (15)	135
C18—H18···O3ii	0.95	2.55	3.4790 (15)	167
C20—H20···O1v	1.00	2.47	3.4604 (15)	173
C2—H2···Cg2iii	0.95	2.83	3.5830 (17)	137
C15—H15···Cg1	0.95	2.68	3.4496 (15)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1–C6 and C13–C18, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6i	0.88	1.99	2.8483 (13)	165
N3—H3N⋯O3ii	0.89	1.99	2.8623 (13)	167
C8—H8⋯S2iii	1.00	2.86	3.7891 (12)	156
C7—H7⋯O3iv	1.00	2.63	3.4150 (15)	135
C18—H18⋯O3ii	0.95	2.55	3.4790 (15)	167
C20—H20⋯O1v	1.00	2.47	3.4604 (15)	173
C2—H2⋯Cg2iii	0.95	2.83	3.5830 (17)	137
C15—H15⋯Cg1	0.95	2.68	3.4496 (15)	138

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