Influence of 3-{5-[4-(diethylamino)benzylidene]­rhodanine}propionic acid on the conformation of 5-(4-chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-3H-imidazol-4(5H)-one

The aryl­idene–imidazolone derivatives are a group of compounds of great inter­est in medicinal chemistry due to their various pharmacological actions. In order to study the possible conformations of an aryl­idene–imidazolone derivative, two new crystal structures were determined by X-ray diffraction, namely (Z)-5-(4-chloro­benzyl­idene)-2-(4-methyl­piperazin-1-yl)-3H-imidazol-5(4H)-one, C₁₅H₁₇ClN₄O, (6), and its salt 4-[5-(4-chloro­benzyl­idene)-5-oxo-4,5-di­hydro-3H-imidazol-2-yl]-1-methyl­piperazin-1-ium 3-{5-[4-(di­ethyl­amino)­benzyl­idene]-4-oxo-2-thioxothia­zolidin-3-yl}propionate, C₁₅H₁₈ClN₄O⁺·C₁₇H₁₉N₂O₃S₂⁻, (7). Both com­pounds crystallize in the space group P. The basic form (6) crystallizes with two mol­ecules in the asymmetric unit. In the acid form of (6), the N atom of the piperazine ring is protonated by proton transfer from the carboxyl group of the rhodanine acid derivative. The greatest difference in the conformations of (6) and its protonated form, (6c), is observed in the location of the aryl­idene–imidazolone substituent at the N atom. In the case of (6c), the position of this substituent is close to axial, while for (6), the corresponding position is inter­mediate between equatorial and axial. The crystal packing is dominated by a network of N—H...O hydrogen bonds. Furthermore, the crystal structures are stabilized by numerous inter­molecular contacts of types C—H...N and C—H...Cl in (6), and C—H...O and C—H...S in (7). The geometry with respect to the location of the substituents at the N atoms of the piperazine ring was compared with other crystal structures possessing an N-methyl­piperazine moiety.

Computing details

Data collection: COLLECT (Bruker, 2004) for (6); CrysAlis PRO (Agilent, 2014) for (7). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for (6); CrysAlis PRO (Agilent, 2014) for (7). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (6); CrysAlis PRO (Agilent, 2014) for (7). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (6); SIR97 (Altomare et al., 1999) for (7). For both structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(Z)-4-(4-Chlorobenzylidene)-2-(4-methylpiperazin-1-yl)-1H-imidazol-5(4H)-one (6)

Crystal data

C15H17ClN4O	Z = 4
Mr = 304.77	F(000) = 640
Triclinic, P1	Dx = 1.347 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1010 (6) Å	Cell parameters from 37828 reflections
b = 13.1770 (7) Å	θ = 1.0–27.5°
c = 13.3280 (7) Å	µ = 0.26 mm^−1
α = 70.334 (4)°	T = 130 K
β = 89.469 (3)°	Needle, yellow
γ = 86.582 (4)°	0.55 × 0.08 × 0.05 mm
V = 1502.34 (15) Å^3

Data collection

Nonius KappaCCD diffractometer	6666 independent reflections
Horizonally mounted graphite crystal monochromator	4750 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	Rint = 0.086
CCD scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −11→10
Tmin = 0.975, Tmax = 0.987	k = −16→17
23208 measured reflections	l = −17→17

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)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 0.4874P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.29 e Å^−3
6816 reflections	Δρmin = −0.37 e Å^−3
390 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0086 (11)

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
Cl1A	−0.62763 (8)	0.91644 (5)	0.39818 (5)	0.04953 (19)
C10A	−0.3503 (2)	0.71608 (17)	0.30962 (16)	0.0311 (5)
H10A	−0.2768	0.6608	0.3425	0.037*
C9A	−0.4239 (3)	0.77106 (18)	0.36903 (17)	0.0342 (5)
H9A	−0.3994	0.7545	0.4422	0.041*
C8A	−0.5323 (3)	0.84957 (17)	0.32211 (17)	0.0323 (5)
C7A	−0.5678 (2)	0.87755 (17)	0.21433 (17)	0.0330 (5)
H7A	−0.6423	0.9324	0.1824	0.04*
C6A	−0.4924 (2)	0.82391 (17)	0.15490 (17)	0.0305 (4)
H6A	−0.5149	0.8432	0.0811	0.037*
C5A	−0.3839 (2)	0.74185 (16)	0.20054 (16)	0.0266 (4)
C4A	−0.3107 (2)	0.68754 (16)	0.13374 (16)	0.0277 (4)
H4A	−0.3388	0.7149	0.0606	0.033*
C3A	−0.2090 (2)	0.60420 (16)	0.16019 (15)	0.0262 (4)
N1A	−0.14641 (18)	0.54451 (13)	0.25979 (13)	0.0266 (4)
C1A	−0.0518 (2)	0.47417 (16)	0.24102 (15)	0.0260 (4)
N2A	−0.0439 (2)	0.48136 (14)	0.13419 (13)	0.0276 (4)
C2A	−0.1419 (2)	0.56323 (16)	0.07823 (16)	0.0272 (4)
O1A	−0.16635 (16)	0.59341 (12)	−0.01850 (11)	0.0326 (3)
N3A	0.02685 (19)	0.39613 (14)	0.31594 (13)	0.0293 (4)
C13A	0.0278 (2)	0.39656 (17)	0.42565 (15)	0.0309 (5)
H3AB	−0.0571	0.4423	0.4362	0.037*
H3AA	0.1191	0.4273	0.4393	0.037*
C14A	0.0194 (2)	0.28217 (17)	0.50321 (16)	0.0326 (5)
H4AB	0.0307	0.2822	0.577	0.039*
H4AA	−0.0784	0.2557	0.4967	0.039*
N4A	0.1338 (2)	0.20992 (14)	0.48228 (13)	0.0341 (4)
C12A	0.1162 (3)	0.20739 (17)	0.37445 (16)	0.0322 (5)
H2AA	0.0178	0.1826	0.3664	0.039*
H2AB	0.1914	0.1557	0.3617	0.039*
C11A	0.1326 (2)	0.31860 (17)	0.29359 (16)	0.0297 (4)
H1AB	0.2339	0.3407	0.297	0.036*
H1AA	0.1149	0.3171	0.2209	0.036*
C15A	0.1299 (4)	0.1018 (2)	0.5611 (2)	0.0558 (7)
H5AA	0.0345	0.0726	0.5567	0.084*
H5AB	0.1436	0.1056	0.6326	0.084*
H5AC	0.2088	0.0548	0.5468	0.084*
Cl1B	−0.12179 (8)	0.91476 (5)	−0.17042 (5)	0.04765 (18)
C6B	0.0045 (2)	0.82602 (17)	0.13497 (16)	0.0299 (4)
H6B	−0.0193	0.8465	0.1953	0.036*
C7B	−0.0686 (2)	0.87919 (17)	0.03893 (17)	0.0321 (5)
H7B	−0.1425	0.9349	0.0334	0.039*
C8B	−0.0315 (2)	0.84918 (17)	−0.04867 (16)	0.0316 (5)
C9B	0.0753 (2)	0.76841 (17)	−0.04248 (17)	0.0326 (5)
H9B	0.0996	0.7496	−0.1037	0.039*
C10B	0.1467 (2)	0.71492 (17)	0.05397 (16)	0.0300 (4)
H10B	0.2197	0.6588	0.0588	0.036*
C5B	0.1121 (2)	0.74308 (16)	0.14469 (16)	0.0270 (4)
C4B	0.1849 (2)	0.69003 (16)	0.24720 (15)	0.0277 (4)
H4B	0.1568	0.7177	0.3022	0.033*
C3B	0.2871 (2)	0.60666 (16)	0.27455 (15)	0.0267 (4)
N1B	0.34860 (19)	0.54752 (13)	0.21348 (13)	0.0272 (4)
C1B	0.4450 (2)	0.47685 (16)	0.27680 (15)	0.0266 (4)
N2B	0.4536 (2)	0.48366 (14)	0.37867 (13)	0.0283 (4)
C2B	0.3561 (2)	0.56510 (17)	0.38259 (16)	0.0283 (4)
O1B	0.33332 (16)	0.59502 (12)	0.46016 (11)	0.0335 (3)
N3B	0.5231 (2)	0.40068 (14)	0.25052 (13)	0.0298 (4)
C11B	0.6296 (2)	0.32238 (17)	0.32145 (16)	0.0296 (4)
H1BB	0.6112	0.318	0.3961	0.035*
H1BA	0.7306	0.3459	0.3029	0.035*
C12B	0.6158 (3)	0.21248 (17)	0.31060 (16)	0.0332 (5)
H2BB	0.6915	0.1604	0.3557	0.04*
H2BA	0.5177	0.1861	0.3353	0.04*
N4B	0.6348 (2)	0.21946 (14)	0.19935 (14)	0.0330 (4)
C14B	0.5185 (2)	0.29242 (18)	0.13345 (17)	0.0327 (5)
H4BA	0.4213	0.2642	0.1582	0.039*
H4BB	0.53	0.2955	0.0586	0.039*
C13B	0.5245 (3)	0.40405 (17)	0.13912 (16)	0.0320 (5)
H3BB	0.6151	0.4366	0.1044	0.038*
H3BA	0.4389	0.4498	0.1003	0.038*
C15B	0.6314 (4)	0.1126 (2)	0.1890 (2)	0.0530 (7)
H5BB	0.7114	0.0651	0.2318	0.079*
H5BC	0.6437	0.1189	0.1141	0.079*
H5BA	0.5367	0.0822	0.2142	0.079*
H2A	0.026 (3)	0.451 (2)	0.104 (2)	0.048 (8)*
H2B	0.525 (3)	0.455 (2)	0.425 (2)	0.043 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0667 (4)	0.0423 (3)	0.0392 (3)	0.0138 (3)	0.0113 (3)	−0.0164 (3)
C10A	0.0307 (11)	0.0297 (11)	0.0316 (10)	0.0028 (9)	−0.0013 (9)	−0.0093 (9)
C9A	0.0397 (13)	0.0343 (12)	0.0284 (10)	−0.0015 (10)	0.0023 (9)	−0.0105 (9)
C8A	0.0395 (12)	0.0263 (10)	0.0330 (11)	0.0016 (9)	0.0061 (9)	−0.0131 (9)
C7A	0.0322 (11)	0.0286 (11)	0.0380 (11)	0.0040 (9)	−0.0015 (9)	−0.0118 (9)
C6A	0.0313 (11)	0.0304 (11)	0.0297 (10)	0.0019 (9)	−0.0034 (9)	−0.0106 (9)
C5A	0.0248 (10)	0.0263 (10)	0.0292 (10)	−0.0017 (8)	0.0002 (8)	−0.0097 (8)
C4A	0.0276 (11)	0.0294 (10)	0.0262 (10)	−0.0019 (8)	−0.0013 (8)	−0.0097 (8)
C3A	0.0253 (10)	0.0283 (10)	0.0248 (9)	−0.0023 (8)	0.0002 (8)	−0.0084 (8)
N1A	0.0272 (9)	0.0264 (8)	0.0254 (8)	0.0012 (7)	0.0016 (7)	−0.0084 (7)
C1A	0.0264 (10)	0.0273 (10)	0.0245 (9)	−0.0026 (8)	0.0033 (8)	−0.0088 (8)
N2A	0.0298 (9)	0.0285 (9)	0.0232 (8)	0.0039 (7)	0.0026 (7)	−0.0080 (7)
C2A	0.0227 (10)	0.0296 (10)	0.0299 (10)	−0.0012 (8)	0.0002 (8)	−0.0110 (8)
O1A	0.0342 (8)	0.0376 (8)	0.0252 (7)	0.0060 (7)	−0.0028 (6)	−0.0107 (6)
N3A	0.0322 (10)	0.0302 (9)	0.0235 (8)	0.0071 (8)	0.0004 (7)	−0.0078 (7)
C13A	0.0357 (12)	0.0323 (11)	0.0245 (10)	0.0046 (9)	0.0002 (8)	−0.0104 (9)
C14A	0.0358 (12)	0.0362 (12)	0.0238 (10)	−0.0001 (10)	0.0027 (9)	−0.0079 (9)
N4A	0.0431 (11)	0.0289 (9)	0.0261 (9)	0.0054 (8)	−0.0031 (8)	−0.0048 (7)
C12A	0.0379 (12)	0.0284 (11)	0.0296 (10)	0.0033 (9)	−0.0018 (9)	−0.0096 (9)
C11A	0.0307 (11)	0.0295 (10)	0.0280 (10)	0.0055 (9)	0.0024 (8)	−0.0099 (8)
C15A	0.087 (2)	0.0360 (13)	0.0345 (13)	0.0085 (14)	−0.0042 (13)	−0.0009 (10)
Cl1B	0.0605 (4)	0.0449 (3)	0.0359 (3)	0.0207 (3)	−0.0181 (3)	−0.0149 (3)
C6B	0.0316 (11)	0.0286 (10)	0.0307 (10)	0.0001 (9)	0.0016 (9)	−0.0121 (9)
C7B	0.0327 (12)	0.0283 (11)	0.0345 (11)	0.0040 (9)	−0.0009 (9)	−0.0103 (9)
C8B	0.0354 (12)	0.0277 (10)	0.0309 (10)	0.0019 (9)	−0.0061 (9)	−0.0092 (9)
C9B	0.0360 (12)	0.0343 (11)	0.0288 (10)	0.0029 (9)	−0.0021 (9)	−0.0131 (9)
C10B	0.0286 (11)	0.0310 (11)	0.0303 (10)	0.0030 (9)	−0.0029 (8)	−0.0109 (9)
C5B	0.0257 (10)	0.0259 (10)	0.0288 (10)	−0.0029 (8)	−0.0013 (8)	−0.0082 (8)
C4B	0.0274 (11)	0.0307 (11)	0.0256 (10)	−0.0026 (9)	0.0000 (8)	−0.0100 (8)
C3B	0.0273 (10)	0.0292 (10)	0.0243 (9)	−0.0046 (8)	−0.0002 (8)	−0.0095 (8)
N1B	0.0297 (9)	0.0264 (9)	0.0251 (8)	0.0000 (7)	−0.0031 (7)	−0.0084 (7)
C1B	0.0295 (11)	0.0261 (10)	0.0241 (9)	−0.0026 (8)	−0.0034 (8)	−0.0080 (8)
N2B	0.0304 (9)	0.0301 (9)	0.0242 (8)	0.0011 (8)	−0.0046 (7)	−0.0092 (7)
C2B	0.0265 (11)	0.0306 (11)	0.0272 (10)	−0.0040 (9)	−0.0007 (8)	−0.0087 (8)
O1B	0.0338 (8)	0.0415 (9)	0.0270 (7)	0.0029 (7)	−0.0032 (6)	−0.0149 (7)
N3B	0.0361 (10)	0.0293 (9)	0.0234 (8)	0.0050 (8)	−0.0073 (7)	−0.0089 (7)
C11B	0.0298 (11)	0.0308 (11)	0.0263 (10)	0.0034 (9)	−0.0054 (8)	−0.0080 (8)
C12B	0.0409 (12)	0.0292 (11)	0.0274 (10)	0.0007 (9)	−0.0011 (9)	−0.0070 (8)
N4B	0.0426 (11)	0.0278 (9)	0.0288 (9)	0.0007 (8)	−0.0001 (8)	−0.0104 (7)
C14B	0.0340 (12)	0.0384 (12)	0.0283 (10)	−0.0010 (9)	−0.0028 (9)	−0.0145 (9)
C13B	0.0380 (12)	0.0345 (11)	0.0233 (10)	0.0033 (9)	−0.0045 (9)	−0.0101 (8)
C15B	0.088 (2)	0.0310 (13)	0.0414 (13)	0.0004 (13)	−0.0010 (14)	−0.0145 (11)

Geometric parameters (Å, º)

Cl1A—C8A	1.747 (2)	Cl1B—C8B	1.747 (2)
C10A—C9A	1.385 (3)	C6B—C7B	1.389 (3)
C10A—C5A	1.409 (3)	C6B—C5B	1.397 (3)
C10A—H10A	0.95	C6B—H6B	0.95
C9A—C8A	1.374 (3)	C7B—C8B	1.386 (3)
C9A—H9A	0.95	C7B—H7B	0.95
C8A—C7A	1.393 (3)	C8B—C9B	1.379 (3)
C7A—C6A	1.381 (3)	C9B—C10B	1.387 (3)
C7A—H7A	0.95	C9B—H9B	0.95
C6A—C5A	1.398 (3)	C10B—C5B	1.407 (3)
C6A—H6A	0.95	C10B—H10B	0.95
C5A—C4A	1.453 (3)	C5B—C4B	1.454 (3)
C4A—C3A	1.346 (3)	C4B—C3B	1.349 (3)
C4A—H4A	0.95	C4B—H4B	0.95
C3A—N1A	1.401 (3)	C3B—N1B	1.396 (3)
C3A—C2A	1.484 (3)	C3B—C2B	1.488 (3)
N1A—C1A	1.312 (3)	N1B—C1B	1.318 (3)
C1A—N3A	1.342 (3)	C1B—N3B	1.335 (3)
C1A—N2A	1.396 (2)	C1B—N2B	1.394 (2)
N2A—C2A	1.368 (3)	N2B—C2B	1.365 (3)
N2A—H2A	0.89 (3)	N2B—H2B	0.88 (3)
C2A—O1A	1.233 (2)	C2B—O1B	1.236 (2)
N3A—C11A	1.463 (3)	N3B—C11B	1.462 (3)
N3A—C13A	1.464 (2)	N3B—C13B	1.470 (2)
C13A—C14A	1.520 (3)	C11B—C12B	1.516 (3)
C13A—H3AB	0.99	C11B—H1BB	0.99
C13A—H3AA	0.99	C11B—H1BA	0.99
C14A—N4A	1.457 (3)	C12B—N4B	1.464 (3)
C14A—H4AB	0.99	C12B—H2BB	0.99
C14A—H4AA	0.99	C12B—H2BA	0.99
N4A—C12A	1.459 (3)	N4B—C15B	1.463 (3)
N4A—C15A	1.460 (3)	N4B—C14B	1.464 (3)
C12A—C11A	1.514 (3)	C14B—C13B	1.502 (3)
C12A—H2AA	0.99	C14B—H4BA	0.99
C12A—H2AB	0.99	C14B—H4BB	0.99
C11A—H1AB	0.99	C13B—H3BB	0.99
C11A—H1AA	0.99	C13B—H3BA	0.99
C15A—H5AA	0.98	C15B—H5BB	0.98
C15A—H5AB	0.98	C15B—H5BC	0.98
C15A—H5AC	0.98	C15B—H5BA	0.98
C9A—C10A—C5A	120.3 (2)	C7B—C6B—C5B	121.39 (19)
C9A—C10A—H10A	119.9	C7B—C6B—H6B	119.3
C5A—C10A—H10A	119.9	C5B—C6B—H6B	119.3
C8A—C9A—C10A	120.0 (2)	C8B—C7B—C6B	118.6 (2)
C8A—C9A—H9A	120	C8B—C7B—H7B	120.7
C10A—C9A—H9A	120	C6B—C7B—H7B	120.7
C9A—C8A—C7A	121.28 (19)	C9B—C8B—C7B	121.73 (19)
C9A—C8A—Cl1A	119.76 (17)	C9B—C8B—Cl1B	118.78 (16)
C7A—C8A—Cl1A	118.96 (17)	C7B—C8B—Cl1B	119.50 (17)
C6A—C7A—C8A	118.6 (2)	C8B—C9B—C10B	119.36 (19)
C6A—C7A—H7A	120.7	C8B—C9B—H9B	120.3
C8A—C7A—H7A	120.7	C10B—C9B—H9B	120.3
C7A—C6A—C5A	121.7 (2)	C9B—C10B—C5B	120.6 (2)
C7A—C6A—H6A	119.2	C9B—C10B—H10B	119.7
C5A—C6A—H6A	119.2	C5B—C10B—H10B	119.7
C6A—C5A—C10A	118.18 (19)	C6B—C5B—C10B	118.35 (19)
C6A—C5A—C4A	118.78 (18)	C6B—C5B—C4B	119.07 (18)
C10A—C5A—C4A	123.03 (19)	C10B—C5B—C4B	122.58 (19)
C3A—C4A—C5A	129.53 (19)	C3B—C4B—C5B	128.60 (19)
C3A—C4A—H4A	115.2	C3B—C4B—H4B	115.7
C5A—C4A—H4A	115.2	C5B—C4B—H4B	115.7
C4A—C3A—N1A	129.83 (18)	C4B—C3B—N1B	129.58 (18)
C4A—C3A—C2A	121.24 (18)	C4B—C3B—C2B	121.69 (18)
N1A—C3A—C2A	108.91 (17)	N1B—C3B—C2B	108.72 (17)
C1A—N1A—C3A	105.05 (16)	C1B—N1B—C3B	105.42 (16)
N1A—C1A—N3A	124.97 (18)	N1B—C1B—N3B	124.58 (18)
N1A—C1A—N2A	114.36 (17)	N1B—C1B—N2B	113.87 (18)
N3A—C1A—N2A	120.55 (18)	N3B—C1B—N2B	121.45 (18)
C2A—N2A—C1A	107.39 (17)	C2B—N2B—C1B	107.70 (17)
C2A—N2A—H2A	124.4 (17)	C2B—N2B—H2B	124.7 (17)
C1A—N2A—H2A	126.7 (17)	C1B—N2B—H2B	125.4 (17)
O1A—C2A—N2A	126.30 (18)	O1B—C2B—N2B	126.29 (19)
O1A—C2A—C3A	129.43 (19)	O1B—C2B—C3B	129.42 (19)
N2A—C2A—C3A	104.28 (16)	N2B—C2B—C3B	104.29 (17)
C1A—N3A—C11A	124.28 (16)	C1B—N3B—C11B	124.19 (16)
C1A—N3A—C13A	119.44 (16)	C1B—N3B—C13B	119.67 (16)
C11A—N3A—C13A	115.53 (16)	C11B—N3B—C13B	115.31 (16)
N3A—C13A—C14A	109.99 (17)	N3B—C11B—C12B	109.68 (17)
N3A—C13A—H3AB	109.7	N3B—C11B—H1BB	109.7
C14A—C13A—H3AB	109.7	C12B—C11B—H1BB	109.7
N3A—C13A—H3AA	109.7	N3B—C11B—H1BA	109.7
C14A—C13A—H3AA	109.7	C12B—C11B—H1BA	109.7
H3AB—C13A—H3AA	108.2	H1BB—C11B—H1BA	108.2
N4A—C14A—C13A	111.11 (17)	N4B—C12B—C11B	110.13 (17)
N4A—C14A—H4AB	109.4	N4B—C12B—H2BB	109.6
C13A—C14A—H4AB	109.4	C11B—C12B—H2BB	109.6
N4A—C14A—H4AA	109.4	N4B—C12B—H2BA	109.6
C13A—C14A—H4AA	109.4	C11B—C12B—H2BA	109.6
H4AB—C14A—H4AA	108	H2BB—C12B—H2BA	108.1
C14A—N4A—C12A	109.86 (16)	C15B—N4B—C12B	110.62 (18)
C14A—N4A—C15A	110.54 (19)	C15B—N4B—C14B	110.20 (18)
C12A—N4A—C15A	111.07 (18)	C12B—N4B—C14B	109.58 (17)
N4A—C12A—C11A	110.26 (17)	N4B—C14B—C13B	111.01 (17)
N4A—C12A—H2AA	109.6	N4B—C14B—H4BA	109.4
C11A—C12A—H2AA	109.6	C13B—C14B—H4BA	109.4
N4A—C12A—H2AB	109.6	N4B—C14B—H4BB	109.4
C11A—C12A—H2AB	109.6	C13B—C14B—H4BB	109.4
H2AA—C12A—H2AB	108.1	H4BA—C14B—H4BB	108
N3A—C11A—C12A	109.65 (16)	N3B—C13B—C14B	110.67 (17)
N3A—C11A—H1AB	109.7	N3B—C13B—H3BB	109.5
C12A—C11A—H1AB	109.7	C14B—C13B—H3BB	109.5
N3A—C11A—H1AA	109.7	N3B—C13B—H3BA	109.5
C12A—C11A—H1AA	109.7	C14B—C13B—H3BA	109.5
H1AB—C11A—H1AA	108.2	H3BB—C13B—H3BA	108.1
N4A—C15A—H5AA	109.5	N4B—C15B—H5BB	109.5
N4A—C15A—H5AB	109.5	N4B—C15B—H5BC	109.5
H5AA—C15A—H5AB	109.5	H5BB—C15B—H5BC	109.5
N4A—C15A—H5AC	109.5	N4B—C15B—H5BA	109.5
H5AA—C15A—H5AC	109.5	H5BB—C15B—H5BA	109.5
H5AB—C15A—H5AC	109.5	H5BC—C15B—H5BA	109.5
C5A—C10A—C9A—C8A	1.3 (3)	C5B—C6B—C7B—C8B	−0.7 (3)
C10A—C9A—C8A—C7A	−1.7 (3)	C6B—C7B—C8B—C9B	0.1 (3)
C10A—C9A—C8A—Cl1A	178.51 (17)	C6B—C7B—C8B—Cl1B	179.98 (17)
C9A—C8A—C7A—C6A	0.6 (3)	C7B—C8B—C9B—C10B	0.6 (3)
Cl1A—C8A—C7A—C6A	−179.65 (17)	Cl1B—C8B—C9B—C10B	−179.33 (17)
C8A—C7A—C6A—C5A	1.0 (3)	C8B—C9B—C10B—C5B	−0.6 (3)
C7A—C6A—C5A—C10A	−1.3 (3)	C7B—C6B—C5B—C10B	0.7 (3)
C7A—C6A—C5A—C4A	178.97 (19)	C7B—C6B—C5B—C4B	−179.9 (2)
C9A—C10A—C5A—C6A	0.2 (3)	C9B—C10B—C5B—C6B	0.0 (3)
C9A—C10A—C5A—C4A	179.86 (19)	C9B—C10B—C5B—C4B	−179.44 (19)
C6A—C5A—C4A—C3A	−176.7 (2)	C6B—C5B—C4B—C3B	177.5 (2)
C10A—C5A—C4A—C3A	3.6 (3)	C10B—C5B—C4B—C3B	−3.1 (3)
C5A—C4A—C3A—N1A	1.3 (4)	C5B—C4B—C3B—N1B	−1.4 (4)
C5A—C4A—C3A—C2A	−177.05 (19)	C5B—C4B—C3B—C2B	177.02 (19)
C4A—C3A—N1A—C1A	−178.9 (2)	C4B—C3B—N1B—C1B	178.7 (2)
C2A—C3A—N1A—C1A	−0.3 (2)	C2B—C3B—N1B—C1B	0.1 (2)
C3A—N1A—C1A—N3A	−175.81 (19)	C3B—N1B—C1B—N3B	176.51 (19)
C3A—N1A—C1A—N2A	0.3 (2)	C3B—N1B—C1B—N2B	0.1 (2)
N1A—C1A—N2A—C2A	−0.1 (2)	N1B—C1B—N2B—C2B	−0.2 (2)
N3A—C1A—N2A—C2A	176.17 (18)	N3B—C1B—N2B—C2B	−176.81 (19)
C1A—N2A—C2A—O1A	−179.7 (2)	C1B—N2B—C2B—O1B	−179.8 (2)
C1A—N2A—C2A—C3A	−0.1 (2)	C1B—N2B—C2B—C3B	0.3 (2)
C4A—C3A—C2A—O1A	−1.4 (3)	C4B—C3B—C2B—O1B	1.2 (3)
N1A—C3A—C2A—O1A	179.9 (2)	N1B—C3B—C2B—O1B	179.9 (2)
C4A—C3A—C2A—N2A	178.96 (19)	C4B—C3B—C2B—N2B	−178.95 (19)
N1A—C3A—C2A—N2A	0.3 (2)	N1B—C3B—C2B—N2B	−0.3 (2)
N1A—C1A—N3A—C11A	−179.68 (19)	N1B—C1B—N3B—C11B	−179.8 (2)
N2A—C1A—N3A—C11A	4.5 (3)	N2B—C1B—N3B—C11B	−3.7 (3)
N1A—C1A—N3A—C13A	−10.0 (3)	N1B—C1B—N3B—C13B	11.1 (3)
N2A—C1A—N3A—C13A	174.10 (18)	N2B—C1B—N3B—C13B	−172.75 (18)
C1A—N3A—C13A—C14A	139.4 (2)	C1B—N3B—C11B—C12B	139.4 (2)
C11A—N3A—C13A—C14A	−50.1 (2)	C13B—N3B—C11B—C12B	−51.1 (2)
N3A—C13A—C14A—N4A	53.2 (2)	N3B—C11B—C12B—N4B	56.3 (2)
C13A—C14A—N4A—C12A	−60.3 (2)	C11B—C12B—N4B—C15B	176.3 (2)
C13A—C14A—N4A—C15A	176.73 (19)	C11B—C12B—N4B—C14B	−62.0 (2)
C14A—N4A—C12A—C11A	61.8 (2)	C15B—N4B—C14B—C13B	−177.43 (19)
C15A—N4A—C12A—C11A	−175.6 (2)	C12B—N4B—C14B—C13B	60.6 (2)
C1A—N3A—C11A—C12A	−138.2 (2)	C1B—N3B—C13B—C14B	−140.2 (2)
C13A—N3A—C11A—C12A	51.8 (2)	C11B—N3B—C13B—C14B	49.8 (2)
N4A—C12A—C11A—N3A	−56.2 (2)	N4B—C14B—C13B—N3B	−53.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1A^i	0.89 (3)	1.90 (3)	2.785 (2)	170 (3)
N2B—H2B···O1B^ii	0.88 (3)	1.92 (3)	2.791 (2)	170 (2)
C11A—H1AA···O1A^i	0.99	2.61	3.470 (2)	146
C11B—H1BB···O1B^ii	0.99	2.61	3.459 (2)	144
C9A—H9A···N4A^iii	0.95	2.75	3.386 (3)	125
C7A—H7A···Cl1B^iv	0.95	2.82	3.721 (2)	158
C9B—H9B···N4B^v	0.95	2.71	3.329 (3)	123
C11A—H1AB···N1B	0.99	2.83	3.551 (3)	130
C11A—H1AB···N3B	0.99	2.80	3.760 (3)	164
C11B—H1BA···N1A^vi	0.99	2.78	3.530 (3)	133
C11B—H1BA···N3A^vi	0.99	2.83	3.793 (3)	163
C10A—H10A···N1A	0.95	2.42	3.079 (3)	126
C13A—H3AB···N1A	0.99	2.40	2.828 (3)	105
C10B—H10B···N1B	0.95	2.36	3.032 (3)	127
C13B—H3BA···N1B	0.99	2.40	2.827 (3)	105

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

4-[4-(4-Chlorobenzylidene)-5-oxo-4,5-dihydro-1H-imidazol-2-yl]-1-methylpiperazin-1-ium 3-{5-[4-(diethylamino)benzylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}propionate (7)

Crystal data

C15H18ClN4O^+·C17H19N2O3S2^−	Z = 2
Mr = 669.24	F(000) = 704
Triclinic, P1	Dx = 1.358 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.937 (5) Å	Cell parameters from 8081 reflections
b = 11.384 (5) Å	θ = 2.9–28.7°
c = 14.488 (5) Å	µ = 0.29 mm^−1
α = 77.450 (5)°	T = 293 K
β = 81.731 (5)°	Block, orange
γ = 68.704 (5)°	0.73 × 0.44 × 0.31 mm
V = 1636.3 (12) Å^3

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	7624 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5403 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.044
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.7°, θmin = 2.9°
ω scans	h = −14→14
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	k = −14→15
Tmin = 0.909, Tmax = 0.957	l = −19→19
24554 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 1.1174P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
7624 reflections	Δρmax = 0.37 e Å^−3
417 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
S2C	0.29532 (7)	0.51459 (6)	0.46823 (5)	0.04314 (18)
S1C	0.22340 (6)	0.38262 (6)	0.65738 (4)	0.03392 (15)
Cl1B	0.54731 (8)	−0.43244 (8)	1.23409 (6)	0.0626 (2)
O2C	0.32983 (14)	0.10410 (15)	0.45841 (11)	0.0306 (4)
O3C	0.17516 (14)	0.10814 (15)	0.37266 (10)	0.0292 (3)
N3C	0.13688 (18)	0.37354 (18)	0.50475 (13)	0.0298 (4)
O1B	−0.06244 (16)	−0.37089 (17)	0.85512 (12)	0.0379 (4)
N1B	0.19650 (19)	−0.24601 (19)	0.82770 (13)	0.0319 (4)
N2B	0.02659 (19)	−0.23471 (19)	0.74836 (14)	0.0305 (4)
O1C	0.01463 (16)	0.24140 (18)	0.55524 (12)	0.0399 (4)
N3B	0.16276 (19)	−0.1108 (2)	0.67924 (13)	0.0343 (5)
C16C	0.2289 (2)	0.2978 (2)	0.35296 (15)	0.0274 (5)
H16C	0.2116	0.3127	0.2868	0.033*
H16D	0.3096	0.3134	0.3558	0.033*
N4B	0.34313 (18)	−0.1368 (2)	0.51527 (14)	0.0302 (4)
C1B	0.1326 (2)	−0.1966 (2)	0.75084 (15)	0.0296 (5)
N2C	0.2883 (2)	0.0508 (2)	1.10927 (14)	0.0368 (5)
C17C	0.2459 (2)	0.1593 (2)	0.39721 (14)	0.0242 (4)
C11B	0.1148 (2)	−0.0800 (2)	0.58467 (15)	0.0319 (5)
H11A	0.0961	0.0105	0.5598	0.038*
H11B	0.0337	−0.0977	0.5888	0.038*
C2C	0.2158 (2)	0.4250 (2)	0.53479 (17)	0.0328 (5)
C12B	0.2153 (2)	−0.1577 (2)	0.51802 (16)	0.0322 (5)
H12A	0.2278	−0.2479	0.5393	0.039*
H12B	0.1839	−0.1322	0.4549	0.039*
C5B	0.2463 (2)	−0.3939 (2)	1.03561 (17)	0.0354 (5)
C4B	0.1471 (2)	−0.3858 (2)	0.97460 (17)	0.0353 (5)
H4B	0.0901	−0.43	1.0009	0.042*
C2B	0.0181 (2)	−0.3169 (2)	0.83254 (16)	0.0313 (5)
C6B	0.3553 (2)	−0.3569 (2)	1.00237 (18)	0.0388 (6)
H6B	0.3654	−0.3225	0.9386	0.047*
C7C	0.1390 (2)	0.1761 (3)	0.83913 (16)	0.0354 (5)
C12C	0.1872 (2)	0.2524 (3)	0.87842 (17)	0.0373 (6)
H12C	0.1884	0.3307	0.8432	0.045*
C3B	0.1280 (2)	−0.3223 (2)	0.88513 (16)	0.0316 (5)
C10C	0.2354 (2)	0.0939 (2)	1.02347 (16)	0.0350 (5)
C6C	0.0996 (2)	0.2060 (3)	0.74394 (17)	0.0360 (5)
H6C	0.0479	0.1618	0.7333	0.043*
C4C	0.0837 (2)	0.2945 (2)	0.57422 (17)	0.0322 (5)
C5C	0.1251 (2)	0.2876 (2)	0.66736 (16)	0.0326 (5)
C14B	0.3910 (2)	−0.1716 (2)	0.61215 (17)	0.0358 (6)
H14A	0.4729	−0.1558	0.6096	0.043*
H14B	0.4074	−0.262	0.6362	0.043*
C15C	0.1158 (2)	0.3904 (2)	0.40425 (16)	0.0328 (5)
H25C	0.1067	0.4776	0.3738	0.039*
H25D	0.0346	0.3769	0.3991	0.039*
C7B	0.4488 (3)	−0.3704 (3)	1.06268 (19)	0.0419 (6)
H7B	0.5224	−0.3474	1.0394	0.05*
C8C	0.1339 (2)	0.0620 (3)	0.89766 (17)	0.0390 (6)
H8C	0.0974	0.0121	0.8755	0.047*
C8B	0.4316 (3)	−0.4182 (3)	1.15751 (19)	0.0446 (7)
C13C	0.3488 (2)	0.1232 (3)	1.14759 (17)	0.0377 (6)
H13C	0.3427	0.1015	1.2162	0.045*
H13D	0.3005	0.214	1.1299	0.045*
C14C	0.3111 (3)	−0.0815 (3)	1.15857 (18)	0.0426 (6)
H14C	0.3882	−0.1097	1.1944	0.051*
H14D	0.3294	−0.1363	1.1119	0.051*
C11C	0.2324 (2)	0.2134 (3)	0.96764 (16)	0.0360 (5)
H11C	0.2617	0.2669	0.992	0.043*
C15B	0.4425 (2)	−0.2051 (3)	0.4465 (2)	0.0426 (6)
H15A	0.522	−0.1872	0.445	0.064*
H15B	0.4094	−0.1769	0.3846	0.064*
H15C	0.4604	−0.2957	0.4652	0.064*
C9C	0.1805 (2)	0.0214 (3)	0.98579 (17)	0.0383 (6)
H9C	0.1759	−0.0555	1.0217	0.046*
C10B	0.2329 (3)	−0.4426 (3)	1.13178 (18)	0.0487 (7)
H10B	0.1612	−0.4683	1.1554	0.058*
C18C	0.1960 (3)	−0.0974 (3)	1.22528 (19)	0.0463 (7)
H18C	0.179	−0.0457	1.2731	0.069*
H18D	0.2164	−0.1857	1.2548	0.069*
H18E	0.1194	−0.0708	1.1902	0.069*
C13B	0.2889 (2)	−0.0925 (3)	0.67735 (17)	0.0370 (6)
H13A	0.3188	−0.1174	0.7409	0.044*
H13B	0.2777	−0.0026	0.6557	0.044*
C19C	0.4921 (3)	0.0965 (3)	1.1121 (2)	0.0490 (7)
H19C	0.5416	0.0078	1.1332	0.073*
H19D	0.5265	0.1491	1.1367	0.073*
H19E	0.4989	0.1156	1.0441	0.073*
C9B	0.3240 (3)	−0.4536 (3)	1.19321 (19)	0.0524 (8)
H9B	0.3126	−0.4844	1.2576	0.063*
H2N	−0.031 (3)	−0.205 (3)	0.7090 (19)	0.040 (8)*
H4N	0.333 (3)	−0.051 (3)	0.492 (2)	0.058 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2C	0.0626 (4)	0.0354 (3)	0.0389 (3)	−0.0260 (3)	−0.0131 (3)	0.0002 (3)
S1C	0.0356 (3)	0.0386 (3)	0.0308 (3)	−0.0146 (3)	−0.0094 (2)	−0.0053 (2)
Cl1B	0.0755 (5)	0.0677 (5)	0.0603 (5)	−0.0405 (4)	−0.0416 (4)	0.0083 (4)
O2C	0.0271 (8)	0.0326 (8)	0.0335 (8)	−0.0153 (7)	−0.0096 (7)	0.0047 (7)
O3C	0.0294 (8)	0.0356 (9)	0.0272 (8)	−0.0184 (7)	−0.0060 (6)	0.0002 (7)
N3C	0.0278 (9)	0.0326 (10)	0.0284 (10)	−0.0071 (8)	−0.0067 (8)	−0.0070 (8)
O1B	0.0400 (9)	0.0473 (10)	0.0350 (9)	−0.0302 (8)	−0.0097 (7)	0.0063 (8)
N1B	0.0326 (10)	0.0408 (11)	0.0281 (10)	−0.0226 (9)	−0.0060 (8)	0.0018 (8)
N2B	0.0289 (10)	0.0390 (11)	0.0275 (10)	−0.0201 (9)	−0.0075 (8)	0.0042 (8)
O1C	0.0303 (9)	0.0609 (12)	0.0367 (9)	−0.0226 (8)	−0.0015 (7)	−0.0138 (8)
N3B	0.0317 (10)	0.0507 (12)	0.0271 (10)	−0.0278 (9)	−0.0062 (8)	0.0061 (9)
C16C	0.0305 (11)	0.0299 (11)	0.0251 (11)	−0.0149 (9)	−0.0044 (9)	−0.0023 (9)
N4B	0.0253 (9)	0.0320 (11)	0.0348 (11)	−0.0154 (8)	−0.0038 (8)	0.0021 (8)
C1B	0.0297 (11)	0.0364 (12)	0.0268 (11)	−0.0182 (10)	−0.0041 (9)	−0.0008 (9)
N2C	0.0369 (11)	0.0487 (12)	0.0291 (10)	−0.0216 (10)	−0.0011 (8)	−0.0044 (9)
C17C	0.0223 (10)	0.0305 (11)	0.0210 (10)	−0.0126 (9)	0.0005 (8)	−0.0020 (8)
C11B	0.0251 (11)	0.0441 (13)	0.0286 (11)	−0.0199 (10)	−0.0053 (9)	0.0053 (10)
C2C	0.0345 (12)	0.0263 (11)	0.0357 (12)	−0.0040 (9)	−0.0115 (10)	−0.0071 (9)
C12B	0.0340 (12)	0.0360 (12)	0.0327 (12)	−0.0231 (10)	−0.0085 (10)	0.0049 (10)
C5B	0.0433 (14)	0.0344 (13)	0.0338 (12)	−0.0221 (11)	−0.0149 (11)	0.0060 (10)
C4B	0.0401 (13)	0.0413 (13)	0.0322 (12)	−0.0266 (11)	−0.0099 (10)	0.0046 (10)
C2B	0.0327 (12)	0.0366 (13)	0.0288 (11)	−0.0189 (10)	−0.0042 (9)	−0.0006 (10)
C6B	0.0423 (14)	0.0443 (14)	0.0349 (13)	−0.0230 (12)	−0.0110 (11)	0.0023 (11)
C7C	0.0312 (12)	0.0494 (15)	0.0293 (12)	−0.0182 (11)	0.0010 (10)	−0.0089 (11)
C12C	0.0398 (13)	0.0450 (14)	0.0292 (12)	−0.0198 (11)	−0.0002 (10)	−0.0038 (11)
C3B	0.0331 (12)	0.0374 (13)	0.0306 (12)	−0.0215 (10)	−0.0046 (10)	−0.0013 (10)
C10C	0.0294 (12)	0.0486 (15)	0.0293 (12)	−0.0179 (11)	0.0032 (9)	−0.0076 (11)
C6C	0.0292 (12)	0.0514 (15)	0.0328 (12)	−0.0185 (11)	0.0000 (10)	−0.0117 (11)
C4C	0.0234 (11)	0.0395 (13)	0.0334 (12)	−0.0076 (9)	−0.0023 (9)	−0.0112 (10)
C5C	0.0262 (11)	0.0417 (13)	0.0309 (12)	−0.0104 (10)	−0.0051 (9)	−0.0088 (10)
C14B	0.0291 (12)	0.0383 (13)	0.0412 (14)	−0.0193 (10)	−0.0120 (10)	0.0099 (11)
C15C	0.0337 (12)	0.0333 (12)	0.0302 (12)	−0.0079 (10)	−0.0119 (10)	−0.0036 (10)
C7B	0.0405 (14)	0.0448 (15)	0.0468 (15)	−0.0224 (12)	−0.0125 (12)	−0.0019 (12)
C8C	0.0374 (13)	0.0539 (16)	0.0348 (13)	−0.0257 (12)	0.0022 (10)	−0.0124 (12)
C8B	0.0569 (16)	0.0405 (14)	0.0458 (15)	−0.0260 (13)	−0.0271 (13)	0.0043 (12)
C13C	0.0409 (14)	0.0503 (15)	0.0269 (12)	−0.0211 (12)	−0.0042 (10)	−0.0062 (11)
C14C	0.0450 (15)	0.0489 (16)	0.0346 (13)	−0.0187 (12)	−0.0054 (11)	−0.0026 (12)
C11C	0.0386 (13)	0.0473 (15)	0.0294 (12)	−0.0222 (11)	−0.0005 (10)	−0.0100 (11)
C15B	0.0360 (13)	0.0395 (14)	0.0520 (16)	−0.0145 (11)	0.0036 (12)	−0.0096 (12)
C9C	0.0394 (13)	0.0486 (15)	0.0322 (12)	−0.0239 (12)	0.0017 (10)	−0.0053 (11)
C10B	0.0687 (19)	0.0581 (17)	0.0359 (14)	−0.0472 (15)	−0.0210 (13)	0.0131 (12)
C18C	0.0551 (17)	0.0534 (17)	0.0382 (14)	−0.0308 (14)	−0.0010 (12)	−0.0046 (12)
C13B	0.0356 (13)	0.0527 (15)	0.0318 (12)	−0.0318 (12)	−0.0087 (10)	0.0069 (11)
C19C	0.0394 (14)	0.0641 (19)	0.0490 (16)	−0.0259 (13)	−0.0047 (12)	−0.0063 (14)
C9B	0.080 (2)	0.0572 (18)	0.0363 (14)	−0.0471 (16)	−0.0266 (14)	0.0152 (13)

Geometric parameters (Å, º)

S2C—C2C	1.643 (3)	C7C—C8C	1.404 (4)
S1C—C2C	1.742 (2)	C7C—C12C	1.411 (3)
S1C—C5C	1.755 (3)	C7C—C6C	1.436 (3)
Cl1B—C8B	1.743 (3)	C12C—C11C	1.374 (3)
O2C—C17C	1.263 (2)	C12C—H12C	0.93
O3C—C17C	1.250 (2)	C10C—C9C	1.412 (3)
N3C—C2C	1.366 (3)	C10C—C11C	1.415 (4)
N3C—C4C	1.407 (3)	C6C—C5C	1.350 (3)
N3C—C15C	1.467 (3)	C6C—H6C	0.93
O1B—C2B	1.219 (3)	C4C—C5C	1.462 (3)
N1B—C1B	1.308 (3)	C14B—C13B	1.512 (4)
N1B—C3B	1.409 (3)	C14B—H14A	0.97
N2B—C2B	1.380 (3)	C14B—H14B	0.97
N2B—C1B	1.385 (3)	C15C—H25C	0.97
N2B—H2N	0.84 (3)	C15C—H25D	0.97
O1C—C4C	1.215 (3)	C7B—C8B	1.376 (4)
N3B—C1B	1.355 (3)	C7B—H7B	0.93
N3B—C11B	1.463 (3)	C8C—C9C	1.365 (3)
N3B—C13B	1.464 (3)	C8C—H8C	0.93
C16C—C17C	1.520 (3)	C8B—C9B	1.376 (4)
C16C—C15C	1.524 (3)	C13C—C19C	1.518 (4)
C16C—H16C	0.97	C13C—H13C	0.97
C16C—H16D	0.97	C13C—H13D	0.97
N4B—C15B	1.480 (3)	C14C—C18C	1.514 (4)
N4B—C14B	1.490 (3)	C14C—H14C	0.97
N4B—C12B	1.495 (3)	C14C—H14D	0.97
N4B—H4N	0.93 (3)	C11C—H11C	0.93
N2C—C10C	1.362 (3)	C15B—H15A	0.96
N2C—C13C	1.459 (3)	C15B—H15B	0.96
N2C—C14C	1.467 (3)	C15B—H15C	0.96
C11B—C12B	1.510 (3)	C9C—H9C	0.93
C11B—H11A	0.97	C10B—C9B	1.384 (4)
C11B—H11B	0.97	C10B—H10B	0.93
C12B—H12A	0.97	C18C—H18C	0.96
C12B—H12B	0.97	C18C—H18D	0.96
C5B—C10B	1.391 (3)	C18C—H18E	0.96
C5B—C6B	1.394 (3)	C13B—H13A	0.97
C5B—C4B	1.460 (3)	C13B—H13B	0.97
C4B—C3B	1.344 (3)	C19C—H19C	0.96
C4B—H4B	0.93	C19C—H19D	0.96
C2B—C3B	1.489 (3)	C19C—H19E	0.96
C6B—C7B	1.385 (3)	C9B—H9B	0.93
C6B—H6B	0.93
C2C—S1C—C5C	92.64 (11)	O1C—C4C—C5C	127.5 (2)
C2C—N3C—C4C	116.79 (19)	N3C—C4C—C5C	110.1 (2)
C2C—N3C—C15C	122.3 (2)	C6C—C5C—C4C	121.3 (2)
C4C—N3C—C15C	120.71 (19)	C6C—C5C—S1C	128.32 (18)
C1B—N1B—C3B	104.95 (18)	C4C—C5C—S1C	109.90 (17)
C2B—N2B—C1B	107.25 (18)	N4B—C14B—C13B	109.61 (19)
C2B—N2B—H2N	123.9 (19)	N4B—C14B—H14A	109.7
C1B—N2B—H2N	128.0 (19)	C13B—C14B—H14A	109.7
C1B—N3B—C11B	123.36 (18)	N4B—C14B—H14B	109.7
C1B—N3B—C13B	118.36 (18)	C13B—C14B—H14B	109.7
C11B—N3B—C13B	112.26 (17)	H14A—C14B—H14B	108.2
C17C—C16C—C15C	111.23 (18)	N3C—C15C—C16C	112.02 (18)
C17C—C16C—H16C	109.4	N3C—C15C—H25C	109.2
C15C—C16C—H16C	109.4	C16C—C15C—H25C	109.2
C17C—C16C—H16D	109.4	N3C—C15C—H25D	109.2
C15C—C16C—H16D	109.4	C16C—C15C—H25D	109.2
H16C—C16C—H16D	108	H25C—C15C—H25D	107.9
C15B—N4B—C14B	112.21 (19)	C8B—C7B—C6B	119.1 (2)
C15B—N4B—C12B	111.77 (19)	C8B—C7B—H7B	120.4
C14B—N4B—C12B	110.53 (17)	C6B—C7B—H7B	120.4
C15B—N4B—H4N	103.5 (19)	C9C—C8C—C7C	122.5 (2)
C14B—N4B—H4N	107.8 (19)	C9C—C8C—H8C	118.7
C12B—N4B—H4N	110.7 (19)	C7C—C8C—H8C	118.7
N1B—C1B—N3B	123.6 (2)	C9B—C8B—C7B	121.3 (2)
N1B—C1B—N2B	115.14 (19)	C9B—C8B—Cl1B	119.3 (2)
N3B—C1B—N2B	121.19 (19)	C7B—C8B—Cl1B	119.3 (2)
C10C—N2C—C13C	121.9 (2)	N2C—C13C—C19C	112.4 (2)
C10C—N2C—C14C	121.1 (2)	N2C—C13C—H13C	109.1
C13C—N2C—C14C	115.8 (2)	C19C—C13C—H13C	109.1
O3C—C17C—O2C	124.1 (2)	N2C—C13C—H13D	109.1
O3C—C17C—C16C	118.59 (18)	C19C—C13C—H13D	109.1
O2C—C17C—C16C	117.27 (18)	H13C—C13C—H13D	107.8
N3B—C11B—C12B	110.99 (19)	N2C—C14C—C18C	113.4 (2)
N3B—C11B—H11A	109.4	N2C—C14C—H14C	108.9
C12B—C11B—H11A	109.4	C18C—C14C—H14C	108.9
N3B—C11B—H11B	109.4	N2C—C14C—H14D	108.9
C12B—C11B—H11B	109.4	C18C—C14C—H14D	108.9
H11A—C11B—H11B	108	H14C—C14C—H14D	107.7
N3C—C2C—S2C	126.71 (18)	C12C—C11C—C10C	121.7 (2)
N3C—C2C—S1C	110.51 (17)	C12C—C11C—H11C	119.2
S2C—C2C—S1C	122.77 (14)	C10C—C11C—H11C	119.2
N4B—C12B—C11B	109.88 (19)	N4B—C15B—H15A	109.5
N4B—C12B—H12A	109.7	N4B—C15B—H15B	109.5
C11B—C12B—H12A	109.7	H15A—C15B—H15B	109.5
N4B—C12B—H12B	109.7	N4B—C15B—H15C	109.5
C11B—C12B—H12B	109.7	H15A—C15B—H15C	109.5
H12A—C12B—H12B	108.2	H15B—C15B—H15C	109.5
C10B—C5B—C6B	117.8 (2)	C8C—C9C—C10C	121.2 (2)
C10B—C5B—C4B	118.7 (2)	C8C—C9C—H9C	119.4
C6B—C5B—C4B	123.4 (2)	C10C—C9C—H9C	119.4
C3B—C4B—C5B	128.1 (2)	C9B—C10B—C5B	121.5 (2)
C3B—C4B—H4B	116	C9B—C10B—H10B	119.2
C5B—C4B—H4B	116	C5B—C10B—H10B	119.2
O1B—C2B—N2B	125.9 (2)	C14C—C18C—H18C	109.5
O1B—C2B—C3B	130.0 (2)	C14C—C18C—H18D	109.5
N2B—C2B—C3B	104.05 (18)	H18C—C18C—H18D	109.5
C7B—C6B—C5B	121.2 (2)	C14C—C18C—H18E	109.5
C7B—C6B—H6B	119.4	H18C—C18C—H18E	109.5
C5B—C6B—H6B	119.4	H18D—C18C—H18E	109.5
C8C—C7C—C12C	116.5 (2)	N3B—C13B—C14B	110.7 (2)
C8C—C7C—C6C	119.2 (2)	N3B—C13B—H13A	109.5
C12C—C7C—C6C	124.4 (2)	C14B—C13B—H13A	109.5
C11C—C12C—C7C	121.4 (2)	N3B—C13B—H13B	109.5
C11C—C12C—H12C	119.3	C14B—C13B—H13B	109.5
C7C—C12C—H12C	119.3	H13A—C13B—H13B	108.1
C4B—C3B—N1B	128.9 (2)	C13C—C19C—H19C	109.5
C4B—C3B—C2B	122.4 (2)	C13C—C19C—H19D	109.5
N1B—C3B—C2B	108.56 (19)	H19C—C19C—H19D	109.5
N2C—C10C—C9C	121.5 (2)	C13C—C19C—H19E	109.5
N2C—C10C—C11C	122.0 (2)	H19C—C19C—H19E	109.5
C9C—C10C—C11C	116.5 (2)	H19D—C19C—H19E	109.5
C5C—C6C—C7C	130.9 (2)	C8B—C9B—C10B	118.9 (2)
C5C—C6C—H6C	114.5	C8B—C9B—H9B	120.5
C7C—C6C—H6C	114.5	C10B—C9B—H9B	120.5
O1C—C4C—N3C	122.4 (2)
C3B—N1B—C1B—N3B	176.1 (2)	C12C—C7C—C6C—C5C	17.1 (4)
C3B—N1B—C1B—N2B	−1.7 (3)	C2C—N3C—C4C—O1C	−178.3 (2)
C11B—N3B—C1B—N1B	164.1 (2)	C15C—N3C—C4C—O1C	−3.0 (3)
C13B—N3B—C1B—N1B	13.6 (4)	C2C—N3C—C4C—C5C	1.2 (3)
C11B—N3B—C1B—N2B	−18.2 (4)	C15C—N3C—C4C—C5C	176.57 (19)
C13B—N3B—C1B—N2B	−168.8 (2)	C7C—C6C—C5C—C4C	174.6 (2)
C2B—N2B—C1B—N1B	0.7 (3)	C7C—C6C—C5C—S1C	2.8 (4)
C2B—N2B—C1B—N3B	−177.2 (2)	O1C—C4C—C5C—C6C	7.3 (4)
C15C—C16C—C17C—O3C	83.4 (2)	N3C—C4C—C5C—C6C	−172.2 (2)
C15C—C16C—C17C—O2C	−95.2 (2)	O1C—C4C—C5C—S1C	−179.6 (2)
C1B—N3B—C11B—C12B	−96.0 (3)	N3C—C4C—C5C—S1C	0.9 (2)
C13B—N3B—C11B—C12B	56.2 (3)	C2C—S1C—C5C—C6C	170.4 (2)
C4C—N3C—C2C—S2C	177.02 (17)	C2C—S1C—C5C—C4C	−2.07 (18)
C15C—N3C—C2C—S2C	1.8 (3)	C15B—N4B—C14B—C13B	176.34 (19)
C4C—N3C—C2C—S1C	−2.8 (2)	C12B—N4B—C14B—C13B	−58.2 (2)
C15C—N3C—C2C—S1C	−178.06 (16)	C2C—N3C—C15C—C16C	80.6 (3)
C5C—S1C—C2C—N3C	2.75 (18)	C4C—N3C—C15C—C16C	−94.5 (2)
C5C—S1C—C2C—S2C	−177.08 (16)	C17C—C16C—C15C—N3C	59.7 (2)
C15B—N4B—C12B—C11B	−176.65 (19)	C5B—C6B—C7B—C8B	−1.7 (4)
C14B—N4B—C12B—C11B	57.6 (2)	C12C—C7C—C8C—C9C	−4.1 (4)
N3B—C11B—C12B—N4B	−55.9 (2)	C6C—C7C—C8C—C9C	174.1 (2)
C10B—C5B—C4B—C3B	167.1 (3)	C6B—C7B—C8B—C9B	0.5 (4)
C6B—C5B—C4B—C3B	−13.8 (4)	C6B—C7B—C8B—Cl1B	−178.7 (2)
C1B—N2B—C2B—O1B	−179.0 (2)	C10C—N2C—C13C—C19C	−85.3 (3)
C1B—N2B—C2B—C3B	0.6 (3)	C14C—N2C—C13C—C19C	82.8 (3)
C10B—C5B—C6B—C7B	1.3 (4)	C10C—N2C—C14C—C18C	−91.0 (3)
C4B—C5B—C6B—C7B	−177.9 (2)	C13C—N2C—C14C—C18C	100.8 (3)
C8C—C7C—C12C—C11C	3.0 (4)	C7C—C12C—C11C—C10C	1.4 (4)
C6C—C7C—C12C—C11C	−175.1 (2)	N2C—C10C—C11C—C12C	175.5 (2)
C5B—C4B—C3B—N1B	−1.1 (5)	C9C—C10C—C11C—C12C	−4.7 (4)
C5B—C4B—C3B—C2B	−176.9 (2)	C7C—C8C—C9C—C10C	0.8 (4)
C1B—N1B—C3B—C4B	−174.3 (3)	N2C—C10C—C9C—C8C	−176.5 (2)
C1B—N1B—C3B—C2B	2.0 (3)	C11C—C10C—C9C—C8C	3.6 (4)
O1B—C2B—C3B—C4B	−5.4 (4)	C6B—C5B—C10B—C9B	0.4 (4)
N2B—C2B—C3B—C4B	174.9 (2)	C4B—C5B—C10B—C9B	179.6 (3)
O1B—C2B—C3B—N1B	178.0 (3)	C1B—N3B—C13B—C14B	97.0 (3)
N2B—C2B—C3B—N1B	−1.6 (3)	C11B—N3B—C13B—C14B	−56.7 (3)
C13C—N2C—C10C—C9C	178.2 (2)	N4B—C14B—C13B—N3B	57.1 (2)
C14C—N2C—C10C—C9C	10.7 (3)	C7B—C8B—C9B—C10B	1.1 (5)
C13C—N2C—C10C—C11C	−2.0 (4)	Cl1B—C8B—C9B—C10B	−179.7 (2)
C14C—N2C—C10C—C11C	−169.4 (2)	C5B—C10B—C9B—C8B	−1.5 (5)
C8C—C7C—C6C—C5C	−160.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H2N···O3C^i	0.84 (3)	1.95 (3)	2.779 (3)	169 (3)
N4B—H4N···O2C	0.93 (3)	1.71 (3)	2.642 (3)	173 (3)
N4B—H4N···O3C	0.93 (3)	2.55 (3)	3.207 (3)	128 (2)
C16C—H16C···O1B^i	0.97	2.63	3.533 (3)	155
C11B—H11A···O1C	0.97	2.44	3.364 (3)	160
C11B—H11B···O3C^i	0.97	2.31	3.261 (3)	166
C12B—H12A···S2C^ii	0.97	2.91	3.718 (3)	142
C14B—H14A···O2C^iii	0.97	2.46	3.380 (3)	159
C13C—H13D···O1B^iv	0.97	2.58	3.366 (3)	139
C15B—H15C···S2C^iii	0.96	3.02	3.735 (3)	132
C18C—H18C···O3C^v	0.96	2.49	3.425 (3)	166
C9B—H9B···S2C^vi	0.93	3.03	3.899 (3)	156
C6B—H6B···N1B	0.93	2.41	3.049 (3)	125
C13B—H13A···N1B	0.97	2.38	2.796 (3)	105

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