Crystallographic studies of piperazine derivatives of 5,5-di­methyl­hy­dan­toin in the search for structural features of α₁-adrenoreceptors antagonists

A number of piperazine derivatives of hy­dan­toin display high affinity for α₁-adrenoreceptors and antagonistic properties, which make them potent hypotensive agents. In order to study the correlations between affinity for α₁-adrenoreceptors and mol­ecular structures, the crystal structures of six piperazine derivatives of 5,5-di­methyl­hy­dan­toin were determined by X-ray diffraction, namely, 4-(3-{3-[(2,4-di­chloro­phen­yl)meth­yl]-5,5-dimethyl-2,4-dioxoimidaz­oli­din-1-yl}-2-hy­droxy­prop­yl)-1-phenyl­piperazine-1,4-diium dichloride monohy­drate ethyl acetate hemisolvate, C₂₅H₃₂Cl₂N₄O₃²⁺·2Cl⁻·H₂O·0.5C₄H₈O₂ (1), 4-(2-cyano­phen­yl)-1-(3-{3-[(2,4-di­chloro­phen­yl)meth­yl]-5,5-dimethyl-2,4-dioxo­imidazolidin-1-yl}-2-hy­droxy­prop­yl)piperazin-1-ium chloride aceto­nitrile monosolvate, C₂₆H₃₀Cl₂N₅O₃⁺·Cl⁻·C₂H₃N (2), 1-(3-{3-[(2,4-di­chloro­phen­yl)meth­yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hy­droxy­prop­yl)-4-(3,4-di­methyl­phen­yl)piperazin-1-ium chloride, C₂₇H₃₅Cl₂N₄O₃⁺·Cl⁻ (3), 1-(3-{3-[(2,4-di­chloro­phen­yl)meth­yl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hy­droxy­prop­yl)-4-(3-meth­oxy­phen­yl)piperazin-1-ium chloride, C₂₆H₃₃Cl₂N₄O₄⁺·Cl⁻ (4), 4-(2,3-di­chloro­phen­yl)-1-(3-{3-[(2,4-di­chloro­phen­yl)meth­yl]-5,5-dimethyl-2,4-dioxo­imidazolidin-1-yl}-2-hy­droxy­prop­yl)piperazin-1-ium chloride 0.2-hydrate, C₂₅H₂₉Cl₄N₄O₃⁺·Cl⁻·0.2H₂O (5), and 3-[(2,4-di­chloro­phen­yl)meth­yl]-1-{3-[4-(3,4-di­chloro­phen­yl)piperazin-1-yl]-2-hy­droxy­prop­yl}-5,5-di­methyl­imidazolidine-2,4-di­one, C₂₅H₂₈Cl₄N₄O₃ (6). The com­pounds crystallize in the centrosymmetric triclinic space group, except for 2, which crystallizes in the monoclinic space group P2₁/c. For all six com­pounds, one mol­ecule is ob­served in the asymmetric unit. The mol­ecule of 1 is doubly protonated at both N atoms of the piperazine ring, whereas 2, 3, 4 and 5 are only protonated at one ring N atom. The protonated N atoms are engaged in charge-assisted hy­dro­gen bonds with the chloride anions, and in 1 the N atom inter­acts with the chloride anion via the water mol­ecule. The crystal packing in the protonated mol­ecules (1–5) is in each case dominated by a network of N—H⁺⋯Cl⁻, O—H⋯Cl⁻ and C—H⋯Cl⁻ hy­dro­gen bonds, while in the base mol­ecule of 6, O—H⋯O hy­dro­gen bonds dominate.

Computing details

4-(3-{3-[(2,4-Dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-1-phenylpiperazine-1,4-diium dichloride monohydrate ethyl acetate hemisolvate (1)

Crystal data

C25H32Cl2N4O3^2+·2Cl^−·H2O·0.5C4H8O2	Z = 2
Mr = 640.41	F(000) = 672
Triclinic, P1	Dx = 1.389 Mg m^−3
a = 6.8758 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.5636 (1) Å	Cell parameters from 28554 reflections
c = 20.2149 (2) Å	θ = 4.0–80.2°
α = 88.668 (1)°	µ = 3.87 mm^−1
β = 82.257 (1)°	T = 100 K
γ = 74.113 (1)°	Irregular, clear colourless
V = 1531.62 (3) Å^3	0.64 × 0.27 × 0.10 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	6558 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	6292 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.057
Detector resolution: 10.0000 pixels mm^-1	θmax = 80.4°, θmin = 2.2°
ω scans	h = −8→8
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −14→14
Tmin = 0.090, Tmax = 1.000	l = −25→25
46587 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 1.0082P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.62 e Å^−3
6558 reflections	Δρmin = −0.49 e Å^−3
341 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0017 (2)
Primary atom site location: dual

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	−0.06273 (7)	0.54868 (5)	0.12610 (3)	0.04414 (14)
O1	0.78073 (17)	0.85717 (10)	0.39722 (6)	0.0230 (2)
H1	0.876370	0.796214	0.402951	0.034*
N1	0.50948 (19)	0.74669 (11)	0.27495 (6)	0.0164 (2)
Cl2	0.57263 (10)	0.29636 (4)	−0.04276 (2)	0.04619 (15)
O2	0.60819 (17)	0.54075 (9)	0.28950 (5)	0.0212 (2)
N2	0.50704 (18)	0.75785 (11)	0.49208 (6)	0.0169 (2)
H2	0.607294	0.797329	0.506422	0.020*
C2	0.4976 (2)	0.63222 (13)	0.26991 (7)	0.0166 (3)
N3	0.32924 (19)	0.63655 (11)	0.23592 (6)	0.0181 (3)
O4	0.08736 (18)	0.78177 (11)	0.18935 (6)	0.0266 (2)
N4	0.23854 (18)	0.75578 (10)	0.61686 (6)	0.0140 (2)
H4	0.143927	0.717143	0.598108	0.017*
C4	0.2361 (2)	0.75116 (13)	0.21828 (7)	0.0192 (3)
C5	0.3524 (2)	0.83334 (13)	0.24291 (7)	0.0181 (3)
C6	0.6743 (2)	0.77616 (13)	0.30320 (7)	0.0180 (3)
H6A	0.717192	0.839179	0.275782	0.022*
H6B	0.792449	0.703882	0.300452	0.022*
C7	0.6176 (2)	0.82054 (14)	0.37620 (7)	0.0192 (3)
H7	0.493842	0.890983	0.379515	0.023*
C8	0.5694 (2)	0.72128 (13)	0.41958 (7)	0.0177 (3)
H8A	0.457670	0.696385	0.402981	0.021*
H8B	0.690979	0.650924	0.415664	0.021*
C9	0.5157 (2)	0.64589 (13)	0.53120 (8)	0.0191 (3)
H9A	0.657040	0.592959	0.524366	0.023*
H9B	0.426440	0.602550	0.514156	0.023*
C10	0.4501 (2)	0.67058 (12)	0.60477 (7)	0.0180 (3)
H10A	0.547354	0.706167	0.623179	0.022*
H10B	0.451281	0.594142	0.628026	0.022*
C11	0.2966 (2)	0.84315 (13)	0.50536 (7)	0.0177 (3)
H11A	0.197576	0.807120	0.488370	0.021*
H11B	0.294084	0.918880	0.481179	0.021*
C12	0.2340 (2)	0.87071 (12)	0.57961 (7)	0.0155 (3)
H12A	0.328562	0.910497	0.596367	0.019*
H12B	0.094712	0.926159	0.587164	0.019*
C13	0.2504 (3)	0.53323 (14)	0.22790 (8)	0.0217 (3)
H13A	0.099369	0.559836	0.234586	0.026*
H13B	0.294559	0.473496	0.262553	0.026*
C14	0.3235 (2)	0.47425 (13)	0.15968 (7)	0.0200 (3)
C15	0.1967 (3)	0.47628 (15)	0.11126 (8)	0.0252 (3)
C16	0.2700 (3)	0.42103 (16)	0.04912 (8)	0.0307 (4)
H16	0.180734	0.422878	0.016845	0.037*
C17	0.4752 (3)	0.36349 (15)	0.03539 (8)	0.0306 (4)
C18	0.6078 (3)	0.35862 (16)	0.08207 (9)	0.0313 (4)
H18	0.748876	0.318433	0.072000	0.038*
C19	0.5293 (3)	0.41386 (14)	0.14374 (8)	0.0255 (3)
H19	0.618599	0.410443	0.176162	0.031*
C20	0.4449 (3)	0.89402 (15)	0.18356 (8)	0.0267 (3)
H20A	0.511530	0.950574	0.199811	0.040*
H20B	0.336720	0.937578	0.157978	0.040*
H20C	0.545634	0.832825	0.154829	0.040*
C21	0.2051 (2)	0.92510 (14)	0.29224 (8)	0.0233 (3)
H21A	0.154323	0.883100	0.330555	0.035*
H21B	0.090156	0.971098	0.270184	0.035*
H21C	0.276475	0.979966	0.307617	0.035*
C22	0.1669 (2)	0.77759 (13)	0.68866 (7)	0.0180 (3)
C23	−0.0040 (3)	0.74298 (14)	0.71535 (8)	0.0234 (3)
H23	−0.070799	0.704289	0.688268	0.028*
C24	−0.0760 (3)	0.76599 (15)	0.78262 (9)	0.0314 (4)
H24	−0.193492	0.743057	0.801913	0.038*
C25	0.0227 (3)	0.82218 (16)	0.82166 (8)	0.0355 (4)
H25	−0.028115	0.838291	0.867554	0.043*
C26	0.1947 (3)	0.85497 (16)	0.79426 (9)	0.0331 (4)
H26	0.262054	0.892958	0.821506	0.040*
C27	0.2699 (3)	0.83270 (15)	0.72691 (8)	0.0248 (3)
H27	0.388455	0.854639	0.707732	0.030*
O3	0.09321 (17)	0.58539 (10)	0.56177 (6)	0.0222 (2)
H3A	0.023261	0.535900	0.577080	0.033*
H3B	0.068303	0.597765	0.520749	0.033*
Cl5	0.74671 (5)	0.87028 (3)	0.57694 (2)	0.01913 (10)
Cl6	−0.12797 (5)	0.38563 (3)	0.59541 (2)	0.02050 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0274 (2)	0.0703 (3)	0.0402 (3)	−0.0189 (2)	−0.01128 (18)	−0.0058 (2)
O1	0.0191 (5)	0.0270 (6)	0.0266 (6)	−0.0118 (4)	−0.0045 (4)	−0.0025 (4)
N1	0.0182 (6)	0.0154 (6)	0.0154 (6)	−0.0043 (5)	−0.0021 (5)	−0.0025 (4)
Cl2	0.0810 (4)	0.0386 (3)	0.0202 (2)	−0.0205 (2)	−0.0005 (2)	−0.01133 (17)
O2	0.0247 (5)	0.0169 (5)	0.0200 (5)	−0.0029 (4)	−0.0023 (4)	−0.0006 (4)
N2	0.0167 (6)	0.0190 (6)	0.0173 (6)	−0.0088 (5)	−0.0020 (5)	−0.0026 (4)
C2	0.0192 (7)	0.0174 (7)	0.0126 (6)	−0.0053 (5)	0.0016 (5)	−0.0036 (5)
N3	0.0223 (6)	0.0185 (6)	0.0155 (6)	−0.0084 (5)	−0.0030 (5)	−0.0016 (4)
O4	0.0272 (6)	0.0289 (6)	0.0249 (6)	−0.0066 (5)	−0.0101 (5)	0.0008 (4)
N4	0.0149 (5)	0.0123 (5)	0.0156 (6)	−0.0049 (4)	−0.0019 (4)	−0.0011 (4)
C4	0.0229 (7)	0.0210 (7)	0.0133 (6)	−0.0062 (6)	0.0001 (5)	−0.0014 (5)
C5	0.0216 (7)	0.0166 (7)	0.0161 (7)	−0.0048 (6)	−0.0028 (5)	−0.0004 (5)
C6	0.0149 (6)	0.0199 (7)	0.0192 (7)	−0.0063 (5)	0.0016 (5)	−0.0041 (5)
C7	0.0161 (7)	0.0229 (7)	0.0205 (7)	−0.0086 (6)	−0.0020 (5)	−0.0026 (6)
C8	0.0157 (6)	0.0175 (7)	0.0202 (7)	−0.0047 (5)	−0.0019 (5)	−0.0038 (5)
C9	0.0178 (7)	0.0150 (6)	0.0243 (7)	−0.0047 (5)	−0.0005 (6)	−0.0048 (5)
C10	0.0167 (7)	0.0130 (6)	0.0231 (7)	−0.0011 (5)	−0.0039 (5)	−0.0011 (5)
C11	0.0165 (7)	0.0198 (7)	0.0196 (7)	−0.0080 (5)	−0.0059 (5)	0.0027 (5)
C12	0.0149 (6)	0.0124 (6)	0.0207 (7)	−0.0050 (5)	−0.0052 (5)	0.0026 (5)
C13	0.0286 (8)	0.0229 (7)	0.0178 (7)	−0.0143 (6)	−0.0021 (6)	−0.0011 (6)
C14	0.0286 (8)	0.0184 (7)	0.0173 (7)	−0.0133 (6)	−0.0041 (6)	0.0006 (5)
C15	0.0282 (8)	0.0286 (8)	0.0247 (8)	−0.0161 (7)	−0.0069 (6)	0.0009 (6)
C16	0.0471 (10)	0.0332 (9)	0.0214 (8)	−0.0233 (8)	−0.0129 (7)	0.0009 (6)
C17	0.0539 (11)	0.0240 (8)	0.0179 (7)	−0.0171 (8)	−0.0044 (7)	−0.0038 (6)
C18	0.0382 (10)	0.0261 (8)	0.0274 (9)	−0.0046 (7)	−0.0038 (7)	−0.0077 (7)
C19	0.0335 (9)	0.0226 (8)	0.0217 (8)	−0.0071 (6)	−0.0081 (6)	−0.0041 (6)
C20	0.0372 (9)	0.0255 (8)	0.0203 (7)	−0.0141 (7)	−0.0025 (7)	0.0043 (6)
C21	0.0249 (8)	0.0186 (7)	0.0229 (7)	0.0006 (6)	−0.0033 (6)	−0.0044 (6)
C22	0.0223 (7)	0.0151 (6)	0.0150 (7)	−0.0029 (5)	−0.0012 (5)	−0.0001 (5)
C23	0.0272 (8)	0.0183 (7)	0.0234 (8)	−0.0063 (6)	0.0010 (6)	0.0024 (6)
C24	0.0368 (9)	0.0251 (8)	0.0253 (8)	−0.0035 (7)	0.0085 (7)	0.0056 (6)
C25	0.0513 (11)	0.0290 (9)	0.0163 (7)	0.0023 (8)	0.0019 (7)	0.0008 (6)
C26	0.0453 (11)	0.0315 (9)	0.0204 (8)	−0.0038 (8)	−0.0096 (7)	−0.0051 (7)
C27	0.0287 (8)	0.0246 (8)	0.0211 (8)	−0.0057 (6)	−0.0062 (6)	−0.0030 (6)
O3	0.0254 (6)	0.0195 (5)	0.0257 (6)	−0.0119 (4)	−0.0056 (4)	−0.0015 (4)
Cl5	0.01611 (17)	0.01910 (17)	0.02486 (18)	−0.00731 (13)	−0.00620 (13)	−0.00400 (13)
Cl6	0.01769 (17)	0.02382 (18)	0.02318 (18)	−0.01017 (13)	−0.00442 (13)	0.00036 (13)

Geometric parameters (Å, º)

Cl1—C15	1.7384 (18)	C11—H11B	0.9900
O1—H1	0.8400	C11—C12	1.521 (2)
O1—C7	1.4192 (17)	C12—H12A	0.9900
N1—C2	1.3554 (19)	C12—H12B	0.9900
N1—C5	1.4683 (18)	C13—H13A	0.9900
N1—C6	1.4564 (18)	C13—H13B	0.9900
Cl2—C17	1.7419 (17)	C13—C14	1.513 (2)
O2—C2	1.2146 (18)	C14—C15	1.391 (2)
N2—H2	1.0000	C14—C19	1.393 (2)
N2—C8	1.5069 (18)	C15—C16	1.390 (2)
N2—C9	1.4926 (19)	C16—H16	0.9500
N2—C11	1.5050 (19)	C16—C17	1.379 (3)
C2—N3	1.4124 (19)	C17—C18	1.388 (3)
N3—C4	1.3670 (19)	C18—H18	0.9500
N3—C13	1.4613 (18)	C18—C19	1.386 (2)
O4—C4	1.2110 (19)	C19—H19	0.9500
N4—H4	1.0000	C20—H20A	0.9800
N4—C10	1.5089 (18)	C20—H20B	0.9800
N4—C12	1.5071 (17)	C20—H20C	0.9800
N4—C22	1.4728 (18)	C21—H21A	0.9800
C4—C5	1.528 (2)	C21—H21B	0.9800
C5—C20	1.528 (2)	C21—H21C	0.9800
C5—C21	1.528 (2)	C22—C23	1.382 (2)
C6—H6A	0.9900	C22—C27	1.387 (2)
C6—H6B	0.9900	C23—H23	0.9500
C6—C7	1.5375 (19)	C23—C24	1.389 (2)
C7—H7	1.0000	C24—H24	0.9500
C7—C8	1.510 (2)	C24—C25	1.384 (3)
C8—H8A	0.9900	C25—H25	0.9500
C8—H8B	0.9900	C25—C26	1.381 (3)
C9—H9A	0.9900	C26—H26	0.9500
C9—H9B	0.9900	C26—C27	1.393 (2)
C9—C10	1.505 (2)	C27—H27	0.9500
C10—H10A	0.9900	O3—H3A	0.8700
C10—H10B	0.9900	O3—H3B	0.8700
C11—H11A	0.9900
C7—O1—H1	109.5	H11A—C11—H11B	108.0
C2—N1—C5	112.56 (12)	C12—C11—H11A	109.4
C2—N1—C6	122.50 (12)	C12—C11—H11B	109.4
C6—N1—C5	124.66 (12)	N4—C12—C11	109.75 (11)
C8—N2—H2	108.8	N4—C12—H12A	109.7
C9—N2—H2	108.8	N4—C12—H12B	109.7
C9—N2—C8	107.45 (11)	C11—C12—H12A	109.7
C9—N2—C11	109.89 (11)	C11—C12—H12B	109.7
C11—N2—H2	108.8	H12A—C12—H12B	108.2
C11—N2—C8	112.90 (11)	N3—C13—H13A	109.2
N1—C2—N3	107.04 (12)	N3—C13—H13B	109.2
O2—C2—N1	128.33 (14)	N3—C13—C14	112.15 (12)
O2—C2—N3	124.62 (13)	H13A—C13—H13B	107.9
C2—N3—C13	123.69 (12)	C14—C13—H13A	109.2
C4—N3—C2	111.81 (12)	C14—C13—H13B	109.2
C4—N3—C13	124.13 (13)	C15—C14—C13	123.82 (15)
C10—N4—H4	107.6	C15—C14—C19	117.40 (14)
C12—N4—H4	107.6	C19—C14—C13	118.78 (14)
C12—N4—C10	109.80 (11)	C14—C15—Cl1	121.15 (13)
C22—N4—H4	107.6	C16—C15—Cl1	116.81 (13)
C22—N4—C10	111.67 (11)	C16—C15—C14	122.04 (16)
C22—N4—C12	112.22 (10)	C15—C16—H16	120.8
N3—C4—C5	107.25 (12)	C17—C16—C15	118.43 (15)
O4—C4—N3	126.21 (14)	C17—C16—H16	120.8
O4—C4—C5	126.53 (14)	C16—C17—Cl2	119.49 (13)
N1—C5—C4	101.32 (11)	C16—C17—C18	121.71 (16)
N1—C5—C20	112.00 (13)	C18—C17—Cl2	118.79 (15)
N1—C5—C21	112.82 (12)	C17—C18—H18	120.8
C4—C5—C20	109.82 (12)	C19—C18—C17	118.32 (17)
C21—C5—C4	108.43 (12)	C19—C18—H18	120.8
C21—C5—C20	111.87 (13)	C14—C19—H19	119.0
N1—C6—H6A	108.7	C18—C19—C14	122.08 (15)
N1—C6—H6B	108.7	C18—C19—H19	119.0
N1—C6—C7	114.07 (12)	C5—C20—H20A	109.5
H6A—C6—H6B	107.6	C5—C20—H20B	109.5
C7—C6—H6A	108.7	C5—C20—H20C	109.5
C7—C6—H6B	108.7	H20A—C20—H20B	109.5
O1—C7—C6	109.83 (12)	H20A—C20—H20C	109.5
O1—C7—H7	108.9	H20B—C20—H20C	109.5
O1—C7—C8	110.94 (12)	C5—C21—H21A	109.5
C6—C7—H7	108.9	C5—C21—H21B	109.5
C8—C7—C6	109.34 (12)	C5—C21—H21C	109.5
C8—C7—H7	108.9	H21A—C21—H21B	109.5
N2—C8—C7	113.06 (11)	H21A—C21—H21C	109.5
N2—C8—H8A	109.0	H21B—C21—H21C	109.5
N2—C8—H8B	109.0	C23—C22—N4	118.08 (13)
C7—C8—H8A	109.0	C23—C22—C27	122.27 (14)
C7—C8—H8B	109.0	C27—C22—N4	119.65 (14)
H8A—C8—H8B	107.8	C22—C23—H23	120.7
N2—C9—H9A	109.0	C22—C23—C24	118.56 (16)
N2—C9—H9B	109.0	C24—C23—H23	120.7
N2—C9—C10	112.74 (11)	C23—C24—H24	119.9
H9A—C9—H9B	107.8	C25—C24—C23	120.26 (17)
C10—C9—H9A	109.0	C25—C24—H24	119.9
C10—C9—H9B	109.0	C24—C25—H25	119.8
N4—C10—H10A	109.6	C26—C25—C24	120.36 (16)
N4—C10—H10B	109.6	C26—C25—H25	119.8
C9—C10—N4	110.50 (11)	C25—C26—H26	119.8
C9—C10—H10A	109.6	C25—C26—C27	120.42 (17)
C9—C10—H10B	109.6	C27—C26—H26	119.8
H10A—C10—H10B	108.1	C22—C27—C26	118.13 (17)
N2—C11—H11A	109.4	C22—C27—H27	120.9
N2—C11—H11B	109.4	C26—C27—H27	120.9
N2—C11—C12	111.16 (11)	H3A—O3—H3B	104.5
Cl1—C15—C16—C17	179.53 (13)	C6—N1—C5—C21	−68.96 (18)
O1—C7—C8—N2	60.09 (15)	C6—C7—C8—N2	−178.62 (11)
N1—C2—N3—C4	1.03 (16)	C8—N2—C9—C10	−178.20 (11)
N1—C2—N3—C13	−172.12 (13)	C8—N2—C11—C12	175.97 (11)
N1—C6—C7—O1	−174.72 (12)	C9—N2—C8—C7	−165.83 (12)
N1—C6—C7—C8	63.32 (16)	C9—N2—C11—C12	56.03 (14)
Cl2—C17—C18—C19	179.05 (13)	C10—N4—C12—C11	58.73 (14)
O2—C2—N3—C4	−178.30 (14)	C10—N4—C22—C23	−117.62 (14)
O2—C2—N3—C13	8.5 (2)	C10—N4—C22—C27	63.08 (17)
N2—C9—C10—N4	56.12 (15)	C11—N2—C8—C7	72.85 (15)
N2—C11—C12—N4	−58.74 (14)	C11—N2—C9—C10	−55.01 (15)
C2—N1—C5—C4	1.35 (15)	C12—N4—C10—C9	−57.24 (14)
C2—N1—C5—C20	−115.64 (14)	C12—N4—C22—C23	118.59 (14)
C2—N1—C5—C21	117.07 (14)	C12—N4—C22—C27	−60.70 (17)
C2—N1—C6—C7	−99.65 (15)	C13—N3—C4—O4	−6.1 (2)
C2—N3—C4—O4	−179.21 (14)	C13—N3—C4—C5	172.94 (13)
C2—N3—C4—C5	−0.18 (16)	C13—C14—C15—Cl1	−0.1 (2)
C2—N3—C13—C14	−99.98 (16)	C13—C14—C15—C16	179.94 (15)
N3—C4—C5—N1	−0.66 (15)	C13—C14—C19—C18	−179.40 (15)
N3—C4—C5—C20	117.91 (14)	C14—C15—C16—C17	−0.5 (3)
N3—C4—C5—C21	−119.59 (13)	C15—C14—C19—C18	0.7 (2)
N3—C13—C14—C15	−111.61 (17)	C15—C16—C17—Cl2	−178.54 (13)
N3—C13—C14—C19	68.52 (18)	C15—C16—C17—C18	0.7 (3)
O4—C4—C5—N1	178.37 (14)	C16—C17—C18—C19	−0.2 (3)
O4—C4—C5—C20	−63.1 (2)	C17—C18—C19—C14	−0.5 (3)
O4—C4—C5—C21	59.44 (19)	C19—C14—C15—Cl1	179.78 (12)
N4—C22—C23—C24	−178.33 (13)	C19—C14—C15—C16	−0.2 (2)
N4—C22—C27—C26	178.25 (14)	C22—N4—C10—C9	177.62 (11)
C4—N3—C13—C14	87.71 (17)	C22—N4—C12—C11	−176.45 (11)
C5—N1—C2—O2	177.80 (14)	C22—C23—C24—C25	−0.1 (2)
C5—N1—C2—N3	−1.51 (16)	C23—C22—C27—C26	−1.0 (2)
C5—N1—C6—C7	86.95 (17)	C23—C24—C25—C26	−0.6 (3)
C6—N1—C2—O2	3.7 (2)	C24—C25—C26—C27	0.5 (3)
C6—N1—C2—N3	−175.63 (12)	C25—C26—C27—C22	0.3 (3)
C6—N1—C5—C4	175.32 (12)	C27—C22—C23—C24	0.9 (2)
C6—N1—C5—C20	58.33 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl6^i	0.84	2.33	3.164 (1)	171
N2—H2···Cl5	1.00	2.13	3.064 (1)	155
N4—H4···O3	1.00	1.84	2.757 (2)	151
O3—H3A···Cl6	0.87	2.26	3.112 (1)	167
O3—H3B···Cl6^ii	0.87	2.34	3.171 (1)	160

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

4-(2-Cyanophenyl)-1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)piperazin-1-ium chloride acetonitrile monosolvate (2)

Crystal data

C26H30Cl2N5O3^+·Cl^−·C2H3N	F(000) = 1272
Mr = 607.95	Dx = 1.331 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.3245 (3) Å	Cell parameters from 5669 reflections
b = 19.7187 (4) Å	θ = 3.2–28.1°
c = 10.2687 (2) Å	µ = 0.34 mm^−1
β = 102.051 (2)°	T = 130 K
V = 3034.60 (11) Å^3	Block, colourless
Z = 4	0.35 × 0.31 × 0.18 mm

Data collection

Rigaku SuperNova Dual Source diffractometer with an Atlas detector	7004 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	5088 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.6°, θmin = 2.7°
ω scans	h = −20→18
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	k = −23→24
Tmin = 0.375, Tmax = 1.000	l = −13→13
16402 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0708P)^2 + 1.7909P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
7004 reflections	Δρmax = 0.95 e Å^−3
365 parameters	Δρmin = −0.41 e Å^−3
0 restraints

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	0.35331 (5)	0.06111 (4)	0.34029 (8)	0.0474 (2)
O1	−0.08181 (12)	−0.11771 (11)	0.76062 (19)	0.0401 (5)
H1	−0.073114	−0.132300	0.839127	0.060*
N1	0.15501 (13)	−0.10637 (10)	0.72658 (19)	0.0247 (4)
Cl2	0.61468 (6)	0.14674 (5)	0.73809 (11)	0.0700 (3)
O2	0.13904 (12)	−0.00709 (8)	0.60495 (17)	0.0299 (4)
N2	−0.09791 (13)	−0.15995 (10)	0.47104 (19)	0.0241 (4)
H2	−0.081061	−0.208495	0.489994	0.029*
C2	0.18039 (16)	−0.05726 (11)	0.6507 (2)	0.0234 (5)
N3	0.26576 (13)	−0.07457 (10)	0.6302 (2)	0.0268 (4)
O4	0.36220 (13)	−0.16428 (10)	0.6794 (2)	0.0421 (5)
N4	−0.25851 (13)	−0.16592 (10)	0.26901 (19)	0.0260 (4)
C4	0.29347 (17)	−0.13552 (13)	0.6872 (3)	0.0308 (6)
C5	0.22273 (17)	−0.15971 (13)	0.7620 (3)	0.0327 (6)
C6	0.07431 (15)	−0.09904 (13)	0.7796 (2)	0.0271 (5)
H6A	0.060142	−0.050139	0.782167	0.033*
H6B	0.087155	−0.115733	0.872612	0.033*
C7	−0.00885 (16)	−0.13610 (13)	0.7028 (2)	0.0271 (5)
H7	0.000883	−0.186196	0.711227	0.033*
C8	−0.02770 (16)	−0.11649 (12)	0.5572 (2)	0.0263 (5)
H8A	−0.047388	−0.068587	0.548672	0.032*
H8B	0.028319	−0.119878	0.523957	0.032*
C9	−0.09753 (16)	−0.14654 (12)	0.3271 (2)	0.0253 (5)
H9A	−0.039747	−0.161253	0.307908	0.030*
H9B	−0.103845	−0.097230	0.309546	0.030*
C10	−0.17256 (16)	−0.18375 (13)	0.2363 (2)	0.0278 (5)
H10A	−0.173316	−0.171584	0.142506	0.033*
H10B	−0.162786	−0.233274	0.246319	0.033*
C11	−0.18926 (16)	−0.14952 (13)	0.4997 (2)	0.0270 (5)
H11A	−0.204257	−0.100635	0.492823	0.032*
H11B	−0.189105	−0.164251	0.591943	0.032*
C12	−0.25966 (16)	−0.18904 (13)	0.4037 (2)	0.0270 (5)
H12A	−0.246558	−0.238199	0.411841	0.032*
H12B	−0.319214	−0.181110	0.423935	0.032*
C13	0.30481 (17)	−0.03967 (13)	0.5322 (2)	0.0305 (5)
H13A	0.257203	−0.014262	0.471695	0.037*
H13B	0.328568	−0.073886	0.478163	0.037*
C14	0.37877 (16)	0.00898 (12)	0.5899 (3)	0.0296 (5)
C15	0.40858 (18)	0.05543 (13)	0.5063 (3)	0.0346 (6)
C16	0.4811 (2)	0.09747 (14)	0.5509 (3)	0.0430 (7)
H16	0.501356	0.127569	0.491335	0.052*
C17	0.5228 (2)	0.09485 (15)	0.6821 (3)	0.0453 (8)
C18	0.4944 (2)	0.05117 (16)	0.7706 (3)	0.0474 (8)
H18	0.523268	0.050437	0.861954	0.057*
C19	0.42244 (18)	0.00833 (15)	0.7225 (3)	0.0381 (6)
H19	0.402858	−0.022091	0.782201	0.046*
C20	0.2609 (2)	−0.1611 (2)	0.9112 (3)	0.0588 (10)
H20A	0.282184	−0.115665	0.941231	0.088*
H20B	0.310744	−0.193190	0.930415	0.088*
H20C	0.214419	−0.175187	0.958102	0.088*
C21	0.1874 (2)	−0.22874 (15)	0.7074 (4)	0.0572 (9)
H21A	0.141326	−0.244126	0.754039	0.086*
H21B	0.236442	−0.261590	0.721283	0.086*
H21C	0.161713	−0.224784	0.611989	0.086*
C22	−0.33498 (16)	−0.17707 (12)	0.1689 (2)	0.0257 (5)
C23	−0.34811 (17)	−0.13634 (13)	0.0540 (2)	0.0308 (6)
C24	−0.42380 (19)	−0.14572 (16)	−0.0487 (3)	0.0396 (7)
H24	−0.431203	−0.119149	−0.127424	0.048*
C25	−0.48706 (18)	−0.19317 (17)	−0.0355 (3)	0.0424 (7)
H25	−0.537689	−0.199873	−0.105411	0.051*
C26	−0.47679 (18)	−0.23108 (15)	0.0798 (3)	0.0382 (6)
H26	−0.521869	−0.262440	0.090321	0.046*
C27	−0.40120 (17)	−0.22386 (13)	0.1807 (3)	0.0307 (5)
H27	−0.394575	−0.251095	0.258425	0.037*
C28	−0.2891 (2)	−0.08067 (15)	0.0453 (3)	0.0387 (6)
N29	−0.2449 (2)	−0.03464 (15)	0.0384 (3)	0.0591 (8)
Cl5	−0.02731 (5)	−0.30460 (3)	0.52092 (6)	0.03570 (18)
N31	0.14166 (19)	−0.12635 (16)	0.3688 (3)	0.0545 (7)
C32	0.1309 (2)	−0.09311 (17)	0.2768 (3)	0.0452 (8)
C33	0.1161 (3)	−0.04961 (18)	0.1598 (4)	0.0655 (10)
H33A	0.063396	−0.065348	0.095604	0.098*
H33B	0.168368	−0.051303	0.118864	0.098*
H33C	0.106493	−0.002872	0.186095	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0441 (4)	0.0517 (4)	0.0500 (4)	0.0021 (4)	0.0186 (3)	0.0183 (3)
O1	0.0295 (10)	0.0586 (13)	0.0337 (10)	0.0029 (9)	0.0100 (8)	−0.0022 (9)
N1	0.0190 (9)	0.0264 (10)	0.0287 (10)	0.0003 (8)	0.0052 (8)	0.0019 (8)
Cl2	0.0489 (5)	0.0724 (6)	0.0992 (7)	−0.0335 (5)	0.0394 (5)	−0.0482 (5)
O2	0.0304 (9)	0.0245 (9)	0.0347 (9)	0.0022 (8)	0.0066 (7)	0.0033 (7)
N2	0.0220 (10)	0.0255 (10)	0.0252 (10)	−0.0004 (8)	0.0057 (8)	0.0010 (8)
C2	0.0220 (11)	0.0233 (11)	0.0246 (11)	−0.0013 (10)	0.0040 (9)	−0.0035 (9)
N3	0.0223 (10)	0.0294 (11)	0.0289 (10)	−0.0015 (9)	0.0060 (8)	0.0029 (8)
O4	0.0298 (10)	0.0474 (12)	0.0504 (12)	0.0135 (9)	0.0117 (9)	0.0067 (9)
N4	0.0228 (10)	0.0309 (11)	0.0254 (10)	−0.0019 (9)	0.0073 (8)	0.0007 (8)
C4	0.0245 (12)	0.0339 (13)	0.0327 (13)	0.0020 (11)	0.0029 (10)	0.0024 (10)
C5	0.0235 (12)	0.0315 (13)	0.0428 (15)	0.0055 (11)	0.0064 (11)	0.0099 (11)
C6	0.0232 (12)	0.0334 (13)	0.0255 (12)	0.0023 (11)	0.0068 (9)	−0.0032 (10)
C7	0.0235 (12)	0.0328 (13)	0.0259 (12)	0.0022 (11)	0.0069 (9)	−0.0006 (10)
C8	0.0244 (12)	0.0290 (12)	0.0247 (12)	0.0007 (10)	0.0033 (9)	−0.0013 (9)
C9	0.0251 (12)	0.0280 (12)	0.0244 (11)	0.0003 (10)	0.0090 (9)	−0.0001 (9)
C10	0.0247 (12)	0.0320 (13)	0.0275 (12)	−0.0014 (11)	0.0075 (10)	−0.0030 (10)
C11	0.0241 (12)	0.0311 (13)	0.0273 (12)	0.0007 (10)	0.0088 (9)	0.0001 (10)
C12	0.0228 (12)	0.0312 (13)	0.0283 (12)	−0.0010 (10)	0.0086 (9)	0.0015 (10)
C13	0.0281 (13)	0.0344 (14)	0.0320 (13)	−0.0036 (11)	0.0131 (10)	0.0016 (10)
C14	0.0232 (12)	0.0290 (13)	0.0399 (14)	0.0007 (11)	0.0139 (11)	−0.0029 (10)
C15	0.0294 (13)	0.0310 (13)	0.0487 (16)	0.0024 (11)	0.0201 (12)	−0.0009 (11)
C16	0.0380 (16)	0.0273 (14)	0.072 (2)	−0.0030 (12)	0.0295 (15)	−0.0058 (13)
C17	0.0324 (15)	0.0402 (16)	0.070 (2)	−0.0111 (13)	0.0250 (14)	−0.0241 (15)
C18	0.0363 (16)	0.060 (2)	0.0491 (18)	−0.0111 (15)	0.0168 (13)	−0.0217 (15)
C19	0.0322 (14)	0.0470 (16)	0.0384 (15)	−0.0079 (13)	0.0148 (12)	−0.0090 (12)
C20	0.0336 (16)	0.096 (3)	0.0461 (18)	0.0170 (18)	0.0075 (13)	0.0372 (18)
C21	0.0357 (16)	0.0262 (14)	0.112 (3)	0.0051 (13)	0.0206 (18)	0.0057 (16)
C22	0.0238 (12)	0.0280 (12)	0.0261 (12)	0.0006 (10)	0.0069 (9)	−0.0040 (9)
C23	0.0276 (13)	0.0369 (14)	0.0286 (12)	0.0026 (11)	0.0078 (10)	−0.0012 (10)
C24	0.0347 (15)	0.0553 (18)	0.0292 (13)	0.0089 (14)	0.0073 (11)	−0.0027 (12)
C25	0.0251 (13)	0.066 (2)	0.0348 (15)	0.0029 (14)	0.0041 (11)	−0.0140 (13)
C26	0.0266 (13)	0.0431 (16)	0.0470 (16)	−0.0065 (12)	0.0121 (12)	−0.0149 (13)
C27	0.0268 (13)	0.0328 (13)	0.0344 (13)	−0.0024 (11)	0.0105 (10)	−0.0029 (10)
C28	0.0421 (16)	0.0449 (16)	0.0299 (14)	0.0014 (14)	0.0092 (12)	0.0093 (11)
N29	0.067 (2)	0.0551 (17)	0.0580 (18)	−0.0104 (16)	0.0185 (15)	0.0161 (14)
Cl5	0.0421 (4)	0.0333 (3)	0.0342 (3)	0.0099 (3)	0.0139 (3)	0.0028 (2)
N31	0.0489 (16)	0.0684 (19)	0.0486 (17)	−0.0147 (15)	0.0156 (13)	−0.0207 (14)
C32	0.0416 (17)	0.0489 (18)	0.0508 (19)	−0.0167 (15)	0.0231 (14)	−0.0248 (15)
C33	0.084 (3)	0.052 (2)	0.067 (2)	−0.017 (2)	0.030 (2)	−0.0154 (17)

Geometric parameters (Å, º)

Cl1—C15	1.742 (3)	C12—H12A	0.9900
O1—H1	0.8400	C12—H12B	0.9900
O1—C7	1.418 (3)	C13—H13A	0.9900
N1—C2	1.350 (3)	C13—H13B	0.9900
N1—C5	1.469 (3)	C13—C14	1.509 (3)
N1—C6	1.459 (3)	C14—C15	1.396 (4)
Cl2—C17	1.738 (3)	C14—C19	1.386 (4)
O2—C2	1.215 (3)	C15—C16	1.385 (4)
N2—H2	1.0000	C16—H16	0.9500
N2—C8	1.509 (3)	C16—C17	1.367 (5)
N2—C9	1.503 (3)	C17—C18	1.387 (5)
N2—C11	1.504 (3)	C18—H18	0.9500
C2—N3	1.409 (3)	C18—C19	1.395 (4)
N3—C4	1.365 (3)	C19—H19	0.9500
N3—C13	1.448 (3)	C20—H20A	0.9800
O4—C4	1.213 (3)	C20—H20B	0.9800
N4—C10	1.469 (3)	C20—H20C	0.9800
N4—C12	1.459 (3)	C21—H21A	0.9800
N4—C22	1.405 (3)	C21—H21B	0.9800
C4—C5	1.530 (4)	C21—H21C	0.9800
C5—C20	1.523 (4)	C22—C23	1.407 (3)
C5—C21	1.527 (4)	C22—C27	1.395 (4)
C6—H6A	0.9900	C23—C24	1.407 (4)
C6—H6B	0.9900	C23—C28	1.437 (4)
C6—C7	1.537 (3)	C24—H24	0.9500
C7—H7	1.0000	C24—C25	1.374 (4)
C7—C8	1.512 (3)	C25—H25	0.9500
C8—H8A	0.9900	C25—C26	1.381 (4)
C8—H8B	0.9900	C26—H26	0.9500
C9—H9A	0.9900	C26—C27	1.391 (4)
C9—H9B	0.9900	C27—H27	0.9500
C9—C10	1.511 (3)	C28—N29	1.144 (4)
C10—H10A	0.9900	N31—C32	1.133 (4)
C10—H10B	0.9900	C32—C33	1.455 (5)
C11—H11A	0.9900	C33—H33A	0.9800
C11—H11B	0.9900	C33—H33B	0.9800
C11—C12	1.517 (3)	C33—H33C	0.9800
C7—O1—H1	109.5	N4—C12—H12B	110.1
C2—N1—C5	112.5 (2)	C11—C12—H12A	110.1
C2—N1—C6	120.9 (2)	C11—C12—H12B	110.1
C6—N1—C5	126.1 (2)	H12A—C12—H12B	108.4
C8—N2—H2	107.8	N3—C13—H13A	108.6
C9—N2—H2	107.8	N3—C13—H13B	108.6
C9—N2—C8	109.15 (18)	N3—C13—C14	114.5 (2)
C9—N2—C11	111.32 (17)	H13A—C13—H13B	107.6
C11—N2—H2	107.8	C14—C13—H13A	108.6
C11—N2—C8	112.74 (18)	C14—C13—H13B	108.6
N1—C2—N3	107.48 (19)	C15—C14—C13	119.4 (2)
O2—C2—N1	128.1 (2)	C19—C14—C13	123.3 (2)
O2—C2—N3	124.4 (2)	C19—C14—C15	117.2 (2)
C2—N3—C13	121.3 (2)	C14—C15—Cl1	119.3 (2)
C4—N3—C2	111.4 (2)	C16—C15—Cl1	118.5 (2)
C4—N3—C13	125.4 (2)	C16—C15—C14	122.2 (3)
C12—N4—C10	109.32 (18)	C15—C16—H16	120.6
C22—N4—C10	116.48 (19)	C17—C16—C15	118.8 (3)
C22—N4—C12	118.09 (19)	C17—C16—H16	120.6
N3—C4—C5	107.5 (2)	C16—C17—Cl2	119.0 (2)
O4—C4—N3	125.4 (2)	C16—C17—C18	121.5 (3)
O4—C4—C5	127.1 (2)	C18—C17—Cl2	119.5 (3)
N1—C5—C4	100.99 (19)	C17—C18—H18	120.7
N1—C5—C20	111.4 (2)	C17—C18—C19	118.5 (3)
N1—C5—C21	111.7 (2)	C19—C18—H18	120.7
C20—C5—C4	110.3 (2)	C14—C19—C18	121.7 (3)
C20—C5—C21	112.7 (3)	C14—C19—H19	119.1
C21—C5—C4	109.2 (2)	C18—C19—H19	119.1
N1—C6—H6A	108.3	C5—C20—H20A	109.5
N1—C6—H6B	108.3	C5—C20—H20B	109.5
N1—C6—C7	115.97 (19)	C5—C20—H20C	109.5
H6A—C6—H6B	107.4	H20A—C20—H20B	109.5
C7—C6—H6A	108.3	H20A—C20—H20C	109.5
C7—C6—H6B	108.3	H20B—C20—H20C	109.5
O1—C7—C6	107.76 (19)	C5—C21—H21A	109.5
O1—C7—H7	109.4	C5—C21—H21B	109.5
O1—C7—C8	110.1 (2)	C5—C21—H21C	109.5
C6—C7—H7	109.4	H21A—C21—H21B	109.5
C8—C7—C6	110.7 (2)	H21A—C21—H21C	109.5
C8—C7—H7	109.4	H21B—C21—H21C	109.5
N2—C8—C7	113.6 (2)	N4—C22—C23	118.4 (2)
N2—C8—H8A	108.9	C27—C22—N4	123.4 (2)
N2—C8—H8B	108.9	C27—C22—C23	118.1 (2)
C7—C8—H8A	108.9	C22—C23—C28	120.4 (2)
C7—C8—H8B	108.9	C24—C23—C22	120.3 (2)
H8A—C8—H8B	107.7	C24—C23—C28	119.0 (2)
N2—C9—H9A	109.4	C23—C24—H24	119.9
N2—C9—H9B	109.4	C25—C24—C23	120.2 (3)
N2—C9—C10	111.29 (19)	C25—C24—H24	119.9
H9A—C9—H9B	108.0	C24—C25—H25	120.1
C10—C9—H9A	109.4	C24—C25—C26	119.8 (3)
C10—C9—H9B	109.4	C26—C25—H25	120.1
N4—C10—C9	110.22 (19)	C25—C26—H26	119.6
N4—C10—H10A	109.6	C25—C26—C27	120.7 (3)
N4—C10—H10B	109.6	C27—C26—H26	119.6
C9—C10—H10A	109.6	C22—C27—H27	119.6
C9—C10—H10B	109.6	C26—C27—C22	120.7 (2)
H10A—C10—H10B	108.1	C26—C27—H27	119.6
N2—C11—H11A	109.3	N29—C28—C23	177.3 (3)
N2—C11—H11B	109.3	N31—C32—C33	178.9 (4)
N2—C11—C12	111.54 (19)	C32—C33—H33A	109.5
H11A—C11—H11B	108.0	C32—C33—H33B	109.5
C12—C11—H11A	109.3	C32—C33—H33C	109.5
C12—C11—H11B	109.3	H33A—C33—H33B	109.5
N4—C12—C11	107.95 (19)	H33A—C33—H33C	109.5
N4—C12—H12A	110.1	H33B—C33—H33C	109.5
Cl1—C15—C16—C17	177.8 (2)	C6—N1—C5—C21	70.1 (3)
O1—C7—C8—N2	−71.4 (3)	C6—C7—C8—N2	169.59 (19)
N1—C2—N3—C4	2.7 (3)	C8—N2—C9—C10	−174.54 (19)
N1—C2—N3—C13	167.9 (2)	C8—N2—C11—C12	174.95 (19)
N1—C6—C7—O1	−174.3 (2)	C9—N2—C8—C7	−167.98 (19)
N1—C6—C7—C8	−53.8 (3)	C9—N2—C11—C12	51.9 (3)
Cl2—C17—C18—C19	−177.8 (2)	C10—N4—C12—C11	64.9 (2)
O2—C2—N3—C4	−176.5 (2)	C10—N4—C22—C23	−68.4 (3)
O2—C2—N3—C13	−11.3 (3)	C10—N4—C22—C27	115.3 (3)
N2—C9—C10—N4	55.4 (3)	C11—N2—C8—C7	67.8 (3)
N2—C11—C12—N4	−59.3 (3)	C11—N2—C9—C10	−49.5 (3)
C2—N1—C5—C4	−2.5 (3)	C12—N4—C10—C9	−63.9 (3)
C2—N1—C5—C20	114.6 (3)	C12—N4—C22—C23	158.3 (2)
C2—N1—C5—C21	−118.5 (3)	C12—N4—C22—C27	−17.9 (3)
C2—N1—C6—C7	99.5 (3)	C13—N3—C4—O4	11.6 (4)
C2—N3—C4—O4	176.1 (2)	C13—N3—C4—C5	−168.7 (2)
C2—N3—C4—C5	−4.3 (3)	C13—C14—C15—Cl1	5.5 (3)
C2—N3—C13—C14	106.2 (3)	C13—C14—C15—C16	−174.5 (2)
N3—C4—C5—N1	4.0 (3)	C13—C14—C19—C18	175.8 (3)
N3—C4—C5—C20	−113.9 (3)	C14—C15—C16—C17	−2.2 (4)
N3—C4—C5—C21	121.8 (2)	C15—C14—C19—C18	−1.3 (4)
N3—C13—C14—C15	−166.8 (2)	C15—C16—C17—Cl2	179.2 (2)
N3—C13—C14—C19	16.2 (4)	C15—C16—C17—C18	0.1 (4)
O4—C4—C5—N1	−176.4 (3)	C16—C17—C18—C19	1.2 (4)
O4—C4—C5—C20	65.7 (4)	C17—C18—C19—C14	−0.6 (4)
O4—C4—C5—C21	−58.6 (4)	C19—C14—C15—Cl1	−177.3 (2)
N4—C22—C23—C24	−179.9 (2)	C19—C14—C15—C16	2.7 (4)
N4—C22—C23—C28	−5.8 (4)	C22—N4—C10—C9	159.0 (2)
N4—C22—C27—C26	177.9 (2)	C22—N4—C12—C11	−158.8 (2)
C4—N3—C13—C14	−90.8 (3)	C22—C23—C24—C25	2.2 (4)
C5—N1—C2—O2	179.3 (2)	C23—C22—C27—C26	1.6 (4)
C5—N1—C2—N3	0.2 (3)	C23—C24—C25—C26	0.9 (4)
C5—N1—C6—C7	−89.7 (3)	C24—C25—C26—C27	−2.7 (4)
C6—N1—C2—O2	−8.7 (4)	C25—C26—C27—C22	1.4 (4)
C6—N1—C2—N3	172.15 (19)	C27—C22—C23—C24	−3.5 (4)
C6—N1—C5—C4	−174.0 (2)	C27—C22—C23—C28	170.7 (2)
C6—N1—C5—C20	−56.9 (3)	C28—C23—C24—C25	−172.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5^i	0.84	2.23	3.043 (2)	162
N2—H2···Cl5	1.00	2.06	3.056 (2)	171

Symmetry code: (i) x, −y−1/2, z+1/2.

1-(3-{3-[(2,4-Dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-4-(3,4-dimethylphenyl)piperazin-1-ium chloride (3)

Crystal data

C27H35Cl2N4O3^+·Cl^−	Z = 2
Mr = 569.94	F(000) = 600
Triclinic, P1	Dx = 1.357 Mg m^−3
a = 7.8861 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.2000 (1) Å	Cell parameters from 27288 reflections
c = 15.0567 (1) Å	θ = 3.3–80.1°
α = 64.519 (1)°	µ = 3.27 mm^−1
β = 80.332 (1)°	T = 100 K
γ = 85.943 (1)°	Prism, clear colourless
V = 1394.79 (3) Å^3	0.31 × 0.23 × 0.09 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	5980 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5677 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 10.0000 pixels mm^-1	θmax = 80.6°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −16→16
Tmin = 0.290, Tmax = 1.000	l = −19→19
45993 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 0.7012P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.59 e Å^−3
5980 reflections	Δρmin = −0.51 e Å^−3
439 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
17 restraints	Extinction coefficient: 0.0022 (2)
Primary atom site location: dual

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	Occ. (<1)
Cl1	0.34657 (5)	0.48820 (4)	0.29821 (3)	0.03600 (11)
O1	0.81166 (14)	0.91068 (9)	−0.02799 (8)	0.0251 (3)	0.874 (3)
H1	0.780321	0.965867	−0.076726	0.038*	0.874 (3)
O1A	0.6147 (10)	0.9140 (6)	0.0139 (6)	0.025 (2)	0.126 (3)
H1A	0.622076	0.963724	−0.044840	0.037*	0.126 (3)
N1	0.48696 (14)	0.71096 (9)	−0.01341 (8)	0.0195 (2)
Cl2	−0.30629 (5)	0.41241 (3)	0.47755 (3)	0.04056 (12)
O2	0.58404 (12)	0.53461 (8)	0.08533 (7)	0.0224 (2)
N2	0.71209 (15)	0.78971 (9)	0.19507 (8)	0.0231 (2)
H2	0.621053	0.848696	0.184736	0.028*	0.9578 (16)
C2	0.47189 (16)	0.60003 (11)	0.04837 (9)	0.0191 (2)
N3	0.29680 (14)	0.57181 (9)	0.06320 (8)	0.0195 (2)
O4	0.05647 (13)	0.65432 (8)	−0.00667 (8)	0.0289 (2)
N4	0.83768 (16)	0.78691 (10)	0.36562 (9)	0.0261 (3)
H4	0.922214	0.726572	0.366139	0.031*	0.0422 (16)
C4	0.20583 (17)	0.65804 (11)	0.00234 (10)	0.0217 (3)
C5	0.32649 (17)	0.75907 (11)	−0.05254 (10)	0.0228 (3)
C6	0.64881 (17)	0.77242 (11)	−0.04571 (10)	0.0214 (3)
H6AA	0.652217	0.829208	−0.115396	0.026*	0.874 (3)
H6AB	0.745225	0.719669	−0.044051	0.026*	0.874 (3)
H6BC	0.643385	0.833424	−0.112787	0.026*	0.126 (3)
H6BD	0.740860	0.720613	−0.053678	0.026*	0.126 (3)
C7	0.6735 (3)	0.8318 (2)	0.02028 (18)	0.0215 (5)	0.874 (3)
H7	0.565328	0.872028	0.030986	0.026*	0.874 (3)
C7A	0.706 (3)	0.8237 (16)	0.0151 (13)	0.0215 (5)	0.126 (3)
H7A	0.826359	0.850343	−0.015291	0.026*	0.126 (3)
C8	0.7127 (2)	0.74385 (12)	0.11949 (11)	0.0279 (3)
H8AA	0.626291	0.682975	0.145744	0.033*	0.874 (3)
H8AB	0.826987	0.710890	0.109354	0.033*	0.874 (3)
H8BC	0.817983	0.698075	0.120413	0.033*	0.126 (3)
H8BD	0.613317	0.692310	0.141935	0.033*	0.126 (3)
C9	0.6684 (2)	0.69823 (12)	0.29790 (10)	0.0295 (3)
H9A	0.752783	0.636552	0.307804	0.035*
H9B	0.553054	0.667747	0.305437	0.035*
C10	0.66978 (19)	0.74122 (12)	0.37610 (10)	0.0282 (3)
H10A	0.581249	0.800181	0.368664	0.034*
H10B	0.641883	0.679136	0.443244	0.034*
C11	0.88076 (19)	0.84183 (12)	0.18587 (11)	0.0275 (3)
H11A	0.904578	0.906565	0.119999	0.033*
H11B	0.974058	0.786335	0.190419	0.033*
C12	0.87827 (19)	0.88091 (12)	0.26727 (11)	0.0272 (3)
H12A	0.991970	0.912609	0.261189	0.033*
H12B	0.791060	0.940652	0.259679	0.033*
C13	0.22665 (17)	0.45927 (11)	0.12411 (10)	0.0215 (3)
H13A	0.321890	0.407119	0.149362	0.026*
H13B	0.173337	0.434135	0.081955	0.026*
C14	0.09405 (17)	0.45308 (10)	0.21135 (10)	0.0211 (3)
C15	0.13564 (17)	0.46145 (11)	0.29435 (10)	0.0241 (3)
C16	0.01463 (19)	0.44892 (12)	0.37665 (10)	0.0274 (3)
H16	0.046159	0.454910	0.432392	0.033*
C17	−0.15330 (19)	0.42742 (11)	0.37482 (11)	0.0277 (3)
C18	−0.20213 (18)	0.42042 (12)	0.29362 (11)	0.0283 (3)
H18	−0.318682	0.406686	0.293441	0.034*
C19	−0.07779 (18)	0.43382 (11)	0.21250 (10)	0.0240 (3)
H19	−0.110661	0.429751	0.156237	0.029*
C20	0.3459 (2)	0.79350 (14)	−0.16445 (11)	0.0334 (3)
H20A	0.425874	0.856938	−0.199751	0.050*
H20B	0.233551	0.815563	−0.186599	0.050*
H20C	0.390792	0.730101	−0.178806	0.050*
C21	0.25710 (19)	0.85487 (12)	−0.02564 (13)	0.0312 (3)
H21A	0.254006	0.831422	0.045845	0.047*
H21B	0.140633	0.874103	−0.042273	0.047*
H21C	0.332130	0.920576	−0.063216	0.047*
C22	0.8590 (6)	0.8090 (4)	0.4502 (4)	0.0206 (9)	0.823 (5)
C22A	0.899 (4)	0.815 (2)	0.4253 (17)	0.030 (5)	0.177 (5)
C23	0.7253 (4)	0.8006 (3)	0.5266 (3)	0.0254 (6)	0.823 (5)
H23	0.612237	0.782033	0.524437	0.031*	0.823 (5)
C23A	1.075 (2)	0.8342 (14)	0.4275 (12)	0.032 (3)	0.177 (5)
H23A	1.161313	0.832543	0.375815	0.038*	0.177 (5)
C24	0.7588 (4)	0.8195 (2)	0.6053 (2)	0.0282 (6)	0.823 (5)
H24	0.667097	0.813202	0.657137	0.034*	0.823 (5)
C24A	1.124 (2)	0.8553 (11)	0.5037 (13)	0.038 (4)	0.177 (5)
H24A	1.240324	0.869885	0.502916	0.046*	0.177 (5)
C25	0.9211 (5)	0.8472 (2)	0.6116 (2)	0.0251 (5)	0.823 (5)
C25A	0.998 (3)	0.8542 (9)	0.5789 (15)	0.032 (3)	0.177 (5)
C26	1.0560 (5)	0.8549 (2)	0.5349 (2)	0.0236 (6)	0.823 (5)
C26A	0.836 (3)	0.8372 (9)	0.5849 (10)	0.034 (3)	0.177 (5)
C27	1.0224 (4)	0.8362 (3)	0.4553 (2)	0.0232 (6)	0.823 (5)
H27	1.113639	0.842266	0.403312	0.028*	0.823 (5)
C27A	0.783 (3)	0.8163 (16)	0.5025 (13)	0.032 (4)	0.177 (5)
H27A	0.664748	0.803615	0.504757	0.039*	0.177 (5)
C28	0.9488 (3)	0.86678 (19)	0.69973 (17)	0.0340 (5)	0.823 (5)
H28A	0.981572	0.796082	0.752081	0.051*	0.823 (5)
H28B	0.842197	0.894737	0.725273	0.051*	0.823 (5)
H28C	1.040597	0.922248	0.679092	0.051*	0.823 (5)
C28A	1.063 (3)	0.8759 (10)	0.6617 (12)	0.077 (6)	0.177 (5)
H28D	0.987104	0.930163	0.677084	0.116*	0.177 (5)
H28E	1.180411	0.905792	0.638342	0.116*	0.177 (5)
H28F	1.061871	0.805227	0.721814	0.116*	0.177 (5)
C29	1.2371 (2)	0.88143 (16)	0.53844 (14)	0.0317 (5)	0.823 (5)
H29A	1.313122	0.883561	0.479059	0.048*	0.823 (5)
H29B	1.276738	0.823371	0.598116	0.048*	0.823 (5)
H29C	1.238990	0.954552	0.540464	0.048*	0.823 (5)
C29A	0.699 (2)	0.8415 (11)	0.6644 (8)	0.066 (4)	0.177 (5)
H29D	0.585847	0.844397	0.644426	0.098*	0.177 (5)
H29E	0.714723	0.908467	0.674573	0.098*	0.177 (5)
H29F	0.705627	0.774289	0.726530	0.098*	0.177 (5)
Cl5	0.37553 (5)	0.92052 (3)	0.19984 (3)	0.03521 (13)	0.9578 (16)
Cl6	1.212 (2)	0.7073 (11)	0.2679 (15)	0.079 (5)	0.0422 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02250 (18)	0.0587 (2)	0.03340 (19)	−0.00616 (15)	−0.00347 (13)	−0.02513 (17)
O1	0.0233 (6)	0.0222 (6)	0.0285 (6)	−0.0029 (4)	−0.0062 (4)	−0.0083 (4)
O1A	0.029 (4)	0.021 (4)	0.028 (4)	0.008 (3)	−0.004 (3)	−0.015 (3)
N1	0.0168 (5)	0.0200 (5)	0.0229 (5)	0.0009 (4)	−0.0040 (4)	−0.0100 (4)
Cl2	0.0322 (2)	0.0420 (2)	0.0350 (2)	0.00108 (15)	0.01162 (15)	−0.01083 (16)
O2	0.0195 (5)	0.0234 (4)	0.0245 (5)	0.0041 (3)	−0.0039 (4)	−0.0107 (4)
N2	0.0278 (6)	0.0210 (5)	0.0231 (5)	0.0010 (4)	−0.0063 (4)	−0.0109 (4)
C2	0.0188 (6)	0.0228 (6)	0.0191 (6)	0.0012 (5)	−0.0016 (5)	−0.0127 (5)
N3	0.0176 (5)	0.0197 (5)	0.0222 (5)	0.0004 (4)	−0.0029 (4)	−0.0101 (4)
O4	0.0205 (5)	0.0282 (5)	0.0386 (6)	0.0005 (4)	−0.0095 (4)	−0.0130 (4)
N4	0.0291 (6)	0.0246 (6)	0.0265 (6)	−0.0006 (5)	−0.0101 (5)	−0.0105 (5)
C4	0.0204 (6)	0.0226 (6)	0.0252 (6)	0.0018 (5)	−0.0046 (5)	−0.0128 (5)
C5	0.0184 (6)	0.0218 (6)	0.0280 (7)	0.0014 (5)	−0.0065 (5)	−0.0095 (5)
C6	0.0183 (6)	0.0253 (6)	0.0224 (6)	−0.0018 (5)	−0.0008 (5)	−0.0124 (5)
C7	0.0186 (14)	0.0248 (8)	0.0231 (7)	−0.0029 (7)	−0.0002 (8)	−0.0126 (6)
C7A	0.0186 (14)	0.0248 (8)	0.0231 (7)	−0.0029 (7)	−0.0002 (8)	−0.0126 (6)
C8	0.0385 (8)	0.0235 (7)	0.0282 (7)	0.0061 (6)	−0.0117 (6)	−0.0157 (6)
C9	0.0384 (8)	0.0241 (7)	0.0256 (7)	−0.0063 (6)	−0.0085 (6)	−0.0079 (6)
C10	0.0302 (8)	0.0309 (7)	0.0238 (6)	−0.0037 (6)	−0.0066 (5)	−0.0104 (6)
C11	0.0260 (7)	0.0289 (7)	0.0279 (7)	−0.0007 (5)	−0.0040 (5)	−0.0122 (6)
C12	0.0288 (7)	0.0251 (7)	0.0286 (7)	−0.0021 (5)	−0.0080 (6)	−0.0105 (6)
C13	0.0218 (6)	0.0193 (6)	0.0247 (6)	0.0002 (5)	−0.0016 (5)	−0.0113 (5)
C14	0.0205 (6)	0.0172 (6)	0.0242 (6)	0.0010 (5)	−0.0022 (5)	−0.0082 (5)
C15	0.0194 (6)	0.0267 (7)	0.0267 (6)	−0.0005 (5)	−0.0032 (5)	−0.0118 (5)
C16	0.0278 (7)	0.0286 (7)	0.0249 (7)	0.0015 (5)	−0.0018 (5)	−0.0115 (6)
C17	0.0251 (7)	0.0223 (6)	0.0278 (7)	0.0021 (5)	0.0041 (5)	−0.0064 (5)
C18	0.0191 (7)	0.0242 (7)	0.0366 (8)	−0.0001 (5)	−0.0020 (6)	−0.0091 (6)
C19	0.0227 (7)	0.0201 (6)	0.0283 (7)	0.0009 (5)	−0.0049 (5)	−0.0093 (5)
C20	0.0305 (8)	0.0368 (8)	0.0278 (7)	−0.0027 (6)	−0.0105 (6)	−0.0065 (6)
C21	0.0213 (7)	0.0225 (7)	0.0503 (9)	0.0034 (5)	−0.0068 (6)	−0.0160 (6)
C22	0.027 (2)	0.0204 (12)	0.014 (3)	0.0008 (12)	−0.0051 (19)	−0.0063 (17)
C22A	0.052 (14)	0.022 (5)	0.005 (8)	0.002 (7)	0.006 (7)	−0.001 (6)
C23	0.0248 (15)	0.0286 (14)	0.0211 (18)	0.0000 (10)	−0.0020 (12)	−0.0094 (12)
C23A	0.029 (8)	0.027 (5)	0.033 (8)	−0.009 (5)	−0.018 (6)	0.000 (5)
C24	0.0284 (14)	0.0323 (12)	0.0221 (13)	0.0014 (10)	−0.0029 (10)	−0.0104 (10)
C24A	0.032 (8)	0.023 (5)	0.049 (9)	−0.001 (6)	−0.025 (6)	0.002 (5)
C25	0.0312 (17)	0.0232 (9)	0.0210 (12)	0.0036 (11)	−0.0083 (12)	−0.0084 (9)
C25A	0.036 (10)	0.026 (5)	0.039 (11)	0.001 (7)	−0.016 (7)	−0.014 (7)
C26	0.0217 (17)	0.0200 (9)	0.0271 (18)	0.0020 (12)	−0.0055 (11)	−0.0078 (12)
C26A	0.057 (11)	0.022 (5)	0.025 (7)	−0.005 (6)	−0.008 (7)	−0.009 (4)
C27	0.0230 (16)	0.0212 (9)	0.0234 (14)	0.0017 (10)	−0.0043 (10)	−0.0075 (10)
C27A	0.046 (12)	0.037 (7)	0.007 (8)	−0.005 (8)	−0.004 (8)	−0.003 (6)
C28	0.0466 (13)	0.0327 (10)	0.0258 (10)	0.0018 (9)	−0.0123 (9)	−0.0132 (8)
C28A	0.161 (19)	0.032 (6)	0.052 (8)	0.001 (9)	−0.068 (11)	−0.012 (6)
C29	0.0325 (11)	0.0304 (9)	0.0339 (10)	−0.0020 (7)	−0.0136 (8)	−0.0117 (8)
C29A	0.117 (12)	0.051 (7)	0.030 (5)	0.019 (7)	−0.008 (6)	−0.023 (5)
Cl5	0.0278 (2)	0.0330 (2)	0.0347 (2)	0.00763 (14)	−0.00655 (15)	−0.00553 (15)
Cl6	0.079 (10)	0.046 (7)	0.122 (14)	0.012 (6)	−0.051 (9)	−0.035 (8)

Geometric parameters (Å, º)

Cl1—C15	1.7402 (14)	C13—H13B	0.9900
O1—H1	0.8400	C13—C14	1.5114 (18)
O1—C7	1.429 (3)	C14—C15	1.3939 (19)
O1A—H1A	0.8400	C14—C19	1.3923 (19)
O1A—C7A	1.342 (16)	C15—C16	1.3865 (19)
N1—C2	1.3560 (17)	C16—H16	0.9500
N1—C5	1.4719 (16)	C16—C17	1.381 (2)
N1—C6	1.4568 (16)	C17—C18	1.383 (2)
Cl2—C17	1.7408 (14)	C18—H18	0.9500
O2—C2	1.2172 (16)	C18—C19	1.386 (2)
N2—H2	1.0000	C19—H19	0.9500
N2—C8	1.5007 (17)	C20—H20A	0.9800
N2—C9	1.4983 (18)	C20—H20B	0.9800
N2—C11	1.4991 (18)	C20—H20C	0.9800
C2—N3	1.4117 (16)	C21—H21A	0.9800
N3—C4	1.3630 (17)	C21—H21B	0.9800
N3—C13	1.4587 (16)	C21—H21C	0.9800
O4—C4	1.2148 (17)	C22—C23	1.395 (4)
N4—H4	1.0000	C22—C27	1.385 (7)
N4—C10	1.4500 (19)	C22A—C23A	1.44 (4)
N4—C12	1.4667 (18)	C22A—C27A	1.358 (18)
N4—C22	1.461 (5)	C23—H23	0.9500
N4—C22A	1.28 (3)	C23—C24	1.381 (5)
C4—C5	1.5278 (18)	C23A—H23A	0.9500
C5—C20	1.528 (2)	C23A—C24A	1.41 (3)
C5—C21	1.5267 (19)	C24—H24	0.9500
C6—H6AA	0.9900	C24—C25	1.385 (4)
C6—H6AB	0.9900	C24A—H24A	0.9500
C6—H6BC	0.9900	C24A—C25A	1.37 (2)
C6—H6BD	0.9900	C25—C26	1.406 (4)
C6—C7	1.548 (3)	C25—C28	1.508 (4)
C6—C7A	1.488 (18)	C25A—C26A	1.30 (2)
C7—H7	1.0000	C25A—C28A	1.561 (18)
C7—C8	1.512 (3)	C26—C27	1.391 (5)
C7A—H7A	1.0000	C26—C29	1.509 (4)
C7A—C8	1.476 (17)	C26A—C27A	1.51 (2)
C8—H8AA	0.9900	C26A—C29A	1.49 (2)
C8—H8AB	0.9900	C27—H27	0.9500
C8—H8BC	0.9900	C27A—H27A	0.9500
C8—H8BD	0.9900	C28—H28A	0.9800
C9—H9A	0.9900	C28—H28B	0.9800
C9—H9B	0.9900	C28—H28C	0.9800
C9—C10	1.513 (2)	C28A—H28D	0.9800
C10—H10A	0.9900	C28A—H28E	0.9800
C10—H10B	0.9900	C28A—H28F	0.9800
C11—H11A	0.9900	C29—H29A	0.9800
C11—H11B	0.9900	C29—H29B	0.9800
C11—C12	1.518 (2)	C29—H29C	0.9800
C12—H12A	0.9900	C29A—H29D	0.9800
C12—H12B	0.9900	C29A—H29E	0.9800
C13—H13A	0.9900	C29A—H29F	0.9800
C7—O1—H1	109.5	N3—C13—H13B	109.0
C7A—O1A—H1A	109.5	N3—C13—C14	113.03 (10)
C2—N1—C5	112.46 (10)	H13A—C13—H13B	107.8
C2—N1—C6	123.52 (11)	C14—C13—H13A	109.0
C6—N1—C5	123.71 (11)	C14—C13—H13B	109.0
C8—N2—H2	108.3	C15—C14—C13	123.12 (12)
C9—N2—H2	108.3	C19—C14—C13	119.64 (12)
C9—N2—C8	109.84 (10)	C19—C14—C15	117.19 (12)
C9—N2—C11	109.50 (11)	C14—C15—Cl1	120.28 (10)
C11—N2—H2	108.3	C16—C15—Cl1	117.02 (11)
C11—N2—C8	112.59 (11)	C16—C15—C14	122.69 (13)
N1—C2—N3	106.81 (11)	C15—C16—H16	121.1
O2—C2—N1	128.33 (12)	C17—C16—C15	117.72 (13)
O2—C2—N3	124.87 (12)	C17—C16—H16	121.1
C2—N3—C13	124.24 (11)	C16—C17—Cl2	118.02 (12)
C4—N3—C2	111.70 (11)	C16—C17—C18	121.94 (13)
C4—N3—C13	123.39 (11)	C18—C17—Cl2	120.02 (11)
C10—N4—H4	105.8	C17—C18—H18	120.6
C10—N4—C12	110.06 (11)	C17—C18—C19	118.74 (13)
C10—N4—C22	112.8 (2)	C19—C18—H18	120.6
C12—N4—H4	105.8	C14—C19—H19	119.2
C22—N4—H4	105.8	C18—C19—C14	121.69 (13)
C22—N4—C12	115.7 (2)	C18—C19—H19	119.2
C22A—N4—C10	129.1 (11)	C5—C20—H20A	109.5
C22A—N4—C12	105.3 (11)	C5—C20—H20B	109.5
N3—C4—C5	107.44 (11)	C5—C20—H20C	109.5
O4—C4—N3	125.93 (12)	H20A—C20—H20B	109.5
O4—C4—C5	126.63 (12)	H20A—C20—H20C	109.5
N1—C5—C4	101.01 (10)	H20B—C20—H20C	109.5
N1—C5—C20	111.42 (11)	C5—C21—H21A	109.5
N1—C5—C21	112.98 (11)	C5—C21—H21B	109.5
C20—C5—C4	109.27 (11)	C5—C21—H21C	109.5
C21—C5—C4	109.75 (11)	H21A—C21—H21B	109.5
C21—C5—C20	111.84 (12)	H21A—C21—H21C	109.5
N1—C6—H6AA	109.1	H21B—C21—H21C	109.5
N1—C6—H6AB	109.1	C23—C22—N4	123.4 (4)
N1—C6—H6BC	107.2	C27—C22—N4	117.5 (3)
N1—C6—H6BD	107.2	C27—C22—C23	119.0 (4)
N1—C6—C7	112.51 (13)	N4—C22A—C23A	128.8 (17)
N1—C6—C7A	120.6 (10)	N4—C22A—C27A	115 (3)
H6AA—C6—H6AB	107.8	C27A—C22A—C23A	116 (3)
H6BC—C6—H6BD	106.8	C22—C23—H23	120.3
C7—C6—H6AA	109.1	C24—C23—C22	119.3 (3)
C7—C6—H6AB	109.1	C24—C23—H23	120.3
C7A—C6—H6BC	107.2	C22A—C23A—H23A	119.0
C7A—C6—H6BD	107.2	C24A—C23A—C22A	122.0 (17)
O1—C7—C6	109.52 (16)	C24A—C23A—H23A	119.0
O1—C7—H7	109.4	C23—C24—H24	118.7
O1—C7—C8	110.50 (17)	C23—C24—C25	122.5 (2)
C6—C7—H7	109.4	C25—C24—H24	118.7
C8—C7—C6	108.55 (17)	C23A—C24A—H24A	120.9
C8—C7—H7	109.4	C25A—C24A—C23A	118.2 (13)
O1A—C7A—C6	114.4 (13)	C25A—C24A—H24A	120.9
O1A—C7A—H7A	106.4	C24—C25—C26	118.0 (2)
O1A—C7A—C8	108.9 (12)	C24—C25—C28	119.8 (3)
C6—C7A—H7A	106.4	C26—C25—C28	122.2 (3)
C8—C7A—C6	113.9 (14)	C24A—C25A—C28A	115.2 (16)
C8—C7A—H7A	106.4	C26A—C25A—C24A	125.0 (14)
N2—C8—C7	113.04 (13)	C26A—C25A—C28A	120 (2)
N2—C8—H8AA	109.0	C25—C26—C29	120.9 (3)
N2—C8—H8AB	109.0	C27—C26—C25	119.5 (3)
N2—C8—H8BC	107.7	C27—C26—C29	119.6 (3)
N2—C8—H8BD	107.7	C25A—C26A—C27A	117.0 (14)
C7—C8—H8AA	109.0	C25A—C26A—C29A	124.9 (17)
C7—C8—H8AB	109.0	C29A—C26A—C27A	118.1 (17)
C7A—C8—N2	118.4 (7)	C22—C27—C26	121.5 (3)
C7A—C8—H8BC	107.7	C22—C27—H27	119.2
C7A—C8—H8BD	107.7	C26—C27—H27	119.2
H8AA—C8—H8AB	107.8	C22A—C27A—C26A	122 (2)
H8BC—C8—H8BD	107.1	C22A—C27A—H27A	119.0
N2—C9—H9A	109.4	C26A—C27A—H27A	119.0
N2—C9—H9B	109.4	C25—C28—H28A	109.5
N2—C9—C10	111.21 (11)	C25—C28—H28B	109.5
H9A—C9—H9B	108.0	C25—C28—H28C	109.5
C10—C9—H9A	109.4	H28A—C28—H28B	109.5
C10—C9—H9B	109.4	H28A—C28—H28C	109.5
N4—C10—C9	110.08 (12)	H28B—C28—H28C	109.5
N4—C10—H10A	109.6	C25A—C28A—H28D	109.5
N4—C10—H10B	109.6	C25A—C28A—H28E	109.5
C9—C10—H10A	109.6	C25A—C28A—H28F	109.5
C9—C10—H10B	109.6	H28D—C28A—H28E	109.5
H10A—C10—H10B	108.2	H28D—C28A—H28F	109.5
N2—C11—H11A	109.5	H28E—C28A—H28F	109.5
N2—C11—H11B	109.5	C26—C29—H29A	109.5
N2—C11—C12	110.93 (11)	C26—C29—H29B	109.5
H11A—C11—H11B	108.0	C26—C29—H29C	109.5
C12—C11—H11A	109.5	H29A—C29—H29B	109.5
C12—C11—H11B	109.5	H29A—C29—H29C	109.5
N4—C12—C11	110.37 (11)	H29B—C29—H29C	109.5
N4—C12—H12A	109.6	C26A—C29A—H29D	109.5
N4—C12—H12B	109.6	C26A—C29A—H29E	109.5
C11—C12—H12A	109.6	C26A—C29A—H29F	109.5
C11—C12—H12B	109.6	H29D—C29A—H29E	109.5
H12A—C12—H12B	108.1	H29D—C29A—H29F	109.5
N3—C13—H13A	109.0	H29E—C29A—H29F	109.5
Cl1—C15—C16—C17	−179.87 (11)	C10—N4—C22—C23	−7.7 (5)
O1—C7—C8—N2	68.82 (18)	C10—N4—C22—C27	170.3 (3)
O1A—C7A—C8—N2	−32 (2)	C10—N4—C22A—C23A	163.3 (16)
N1—C2—N3—C4	8.08 (14)	C10—N4—C22A—C27A	−10 (3)
N1—C2—N3—C13	178.97 (11)	C11—N2—C8—C7	−84.29 (17)
N1—C6—C7—O1	−166.45 (13)	C11—N2—C8—C7A	−74.0 (11)
N1—C6—C7—C8	72.82 (18)	C11—N2—C9—C10	54.86 (15)
N1—C6—C7A—O1A	−71.6 (17)	C12—N4—C10—C9	60.77 (15)
N1—C6—C7A—C8	54.5 (16)	C12—N4—C22—C23	120.3 (4)
Cl2—C17—C18—C19	179.37 (10)	C12—N4—C22—C27	−61.7 (4)
O2—C2—N3—C4	−171.83 (12)	C12—N4—C22A—C23A	−64 (3)
O2—C2—N3—C13	−0.94 (19)	C12—N4—C22A—C27A	123.2 (19)
N2—C9—C10—N4	−58.67 (16)	C13—N3—C4—O4	2.7 (2)
N2—C11—C12—N4	57.31 (15)	C13—N3—C4—C5	−176.84 (11)
C2—N1—C5—C4	3.48 (13)	C13—C14—C15—Cl1	3.80 (18)
C2—N1—C5—C20	−112.47 (13)	C13—C14—C15—C16	−175.99 (12)
C2—N1—C5—C21	120.63 (12)	C13—C14—C19—C18	175.86 (12)
C2—N1—C6—C7	−94.64 (16)	C14—C15—C16—C17	−0.1 (2)
C2—N1—C6—C7A	−87.3 (8)	C15—C14—C19—C18	−1.70 (19)
C2—N3—C4—O4	173.70 (13)	C15—C16—C17—Cl2	−179.62 (11)
C2—N3—C4—C5	−5.86 (14)	C15—C16—C17—C18	−1.2 (2)
C2—N3—C13—C14	118.37 (13)	C16—C17—C18—C19	1.0 (2)
N3—C4—C5—N1	1.52 (13)	C17—C18—C19—C14	0.5 (2)
N3—C4—C5—C20	119.04 (12)	C19—C14—C15—Cl1	−178.74 (10)
N3—C4—C5—C21	−117.99 (12)	C19—C14—C15—C16	1.5 (2)
N3—C13—C14—C15	−71.63 (16)	C22—N4—C10—C9	−168.4 (2)
N3—C13—C14—C19	110.96 (13)	C22—N4—C12—C11	170.3 (2)
O4—C4—C5—N1	−178.04 (13)	C22—C23—C24—C25	0.3 (5)
O4—C4—C5—C20	−60.52 (18)	C22A—N4—C10—C9	−168.1 (17)
O4—C4—C5—C21	62.45 (18)	C22A—N4—C12—C11	156.9 (14)
N4—C22—C23—C24	177.9 (3)	C22A—C23A—C24A—C25A	2 (2)
N4—C22—C27—C26	−177.8 (3)	C23—C22—C27—C26	0.2 (6)
N4—C22A—C23A—C24A	−174 (2)	C23—C24—C25—C26	−0.7 (4)
N4—C22A—C27A—C26A	174.3 (16)	C23—C24—C25—C28	180.0 (3)
C4—N3—C13—C14	−71.78 (15)	C23A—C22A—C27A—C26A	0 (3)
C5—N1—C2—O2	172.91 (12)	C23A—C24A—C25A—C26A	−1 (2)
C5—N1—C2—N3	−7.00 (14)	C23A—C24A—C25A—C28A	178.8 (11)
C5—N1—C6—C7	92.27 (16)	C24—C25—C26—C27	0.8 (4)
C5—N1—C6—C7A	99.6 (8)	C24—C25—C26—C29	−178.2 (2)
C6—N1—C2—O2	−0.9 (2)	C24A—C25A—C26A—C27A	0 (2)
C6—N1—C2—N3	179.22 (10)	C24A—C25A—C26A—C29A	−176.9 (12)
C6—N1—C5—C4	177.24 (11)	C25—C26—C27—C22	−0.6 (5)
C6—N1—C5—C20	61.30 (16)	C25A—C26A—C27A—C22A	0 (3)
C6—N1—C5—C21	−65.60 (16)	C27—C22—C23—C24	−0.1 (6)
C6—C7—C8—N2	−171.06 (13)	C27A—C22A—C23A—C24A	−1 (3)
C6—C7A—C8—N2	−160.6 (9)	C28—C25—C26—C27	−179.8 (2)
C8—N2—C9—C10	178.98 (12)	C28—C25—C26—C29	1.1 (4)
C8—N2—C11—C12	−176.65 (11)	C28A—C25A—C26A—C27A	−179.7 (11)
C9—N2—C8—C7	153.40 (15)	C28A—C25A—C26A—C29A	2.9 (18)
C9—N2—C8—C7A	163.6 (11)	C29—C26—C27—C22	178.4 (3)
C9—N2—C11—C12	−54.15 (15)	C29A—C26A—C27A—C22A	177.6 (18)
C10—N4—C12—C11	−60.37 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5^i	0.84	2.30	3.114 (1)	162
O1A—H1A···Cl5^i	0.84	2.17	3.005 (8)	174
N2—H2···Cl5	1.00	2.12	3.070 (1)	159
N4—H4···Cl6	1.00	2.56	3.378 (19)	138

Symmetry code: (i) −x+1, −y+2, −z.

1-(3-{3-[(2,4-Dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-4-(3-methoxyphenyl)piperazin-1-ium chloride (4)

Crystal data

C26H33Cl2N4O4^+·Cl^−	Z = 2
Mr = 571.91	F(000) = 600
Triclinic, P1	Dx = 1.405 Mg m^−3
a = 7.9118 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.4409 (2) Å	Cell parameters from 27017 reflections
c = 14.3160 (2) Å	θ = 3.5–79.6°
α = 63.760 (2)°	µ = 3.40 mm^−1
β = 82.393 (2)°	T = 100 K
γ = 89.401 (2)°	Needle, clear light orange
V = 1351.51 (5) Å^3	0.52 × 0.1 × 0.04 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	5785 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5278 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.063
Detector resolution: 10.0000 pixels mm^-1	θmax = 79.9°, θmin = 3.5°
ω scans	h = −10→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022)	k = −17→17
Tmin = 0.250, Tmax = 1.000	l = −18→18
46291 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.1157P)^2 + 0.516P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
5785 reflections	Δρmax = 0.76 e Å^−3
388 parameters	Δρmin = −1.03 e Å^−3
12 restraints

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	Occ. (<1)
Cl1	0.65738 (6)	0.50379 (5)	0.20117 (4)	0.03534 (17)
O1	0.18283 (18)	0.07812 (12)	0.54444 (13)	0.0322 (3)
H1	0.217536	0.022818	0.593445	0.048*
N1	0.51756 (19)	0.27805 (12)	0.52969 (12)	0.0222 (3)
Cl2	1.30395 (6)	0.59448 (5)	0.01072 (4)	0.03735 (17)
O2	0.42568 (16)	0.45156 (10)	0.42505 (10)	0.0232 (3)
C2	0.5355 (2)	0.38871 (14)	0.46436 (14)	0.0204 (3)
N3	0.71070 (19)	0.41988 (12)	0.44851 (12)	0.0204 (3)
O4	0.95258 (17)	0.33847 (11)	0.51551 (11)	0.0268 (3)
C4	0.8010 (2)	0.33386 (14)	0.50912 (14)	0.0215 (3)
C5	0.6785 (2)	0.23209 (15)	0.56743 (15)	0.0233 (4)
C6	0.3547 (2)	0.21429 (15)	0.56374 (15)	0.0247 (4)
H6A	0.262045	0.263849	0.565266	0.030*
H6B	0.353737	0.155084	0.636334	0.030*
C7	0.3179 (2)	0.16087 (15)	0.49269 (15)	0.0253 (4)
H7	0.422835	0.125398	0.477452	0.030*
C8	0.2723 (3)	0.24898 (16)	0.39031 (17)	0.0296 (4)
H8A	0.157741	0.274416	0.403718	0.035*
H8B	0.355115	0.313482	0.363647	0.035*
C9	0.3017 (3)	0.30617 (17)	0.19965 (17)	0.0363 (5)
H9A	0.411954	0.345849	0.190543	0.044*
H9B	0.210080	0.358678	0.192705	0.044*
C10	0.3048 (3)	0.2675 (2)	0.11496 (17)	0.0386 (5)
H10A	0.324805	0.332278	0.044783	0.046*
H10B	0.399296	0.217316	0.119914	0.046*
C11	0.1089 (2)	0.14691 (16)	0.31793 (17)	0.0285 (4)
H11A	0.011330	0.194190	0.315887	0.034*
H11B	0.092254	0.080018	0.386687	0.034*
C12	0.1136 (3)	0.11249 (17)	0.23020 (17)	0.0324 (4)
H12A	0.205287	0.060322	0.235747	0.039*
H12B	0.003544	0.073586	0.237335	0.039*
C13	0.7846 (2)	0.53226 (14)	0.38305 (14)	0.0209 (3)
H13A	0.839973	0.557950	0.427208	0.025*
H13B	0.691843	0.582292	0.355170	0.025*
C14	0.9143 (2)	0.54090 (14)	0.29219 (14)	0.0212 (3)
C15	0.8697 (2)	0.53272 (16)	0.20522 (15)	0.0252 (4)
C16	0.9873 (3)	0.54972 (17)	0.11803 (15)	0.0285 (4)
H16	0.952959	0.545007	0.058918	0.034*
C17	1.1556 (3)	0.57369 (16)	0.11962 (15)	0.0273 (4)
C18	1.2083 (2)	0.57922 (16)	0.20595 (16)	0.0270 (4)
H18	1.325190	0.594194	0.206488	0.032*
C19	1.0868 (2)	0.56240 (15)	0.29135 (15)	0.0242 (4)
H19	1.121814	0.565606	0.350965	0.029*
C20	0.6685 (3)	0.19318 (19)	0.68574 (17)	0.0356 (5)
H20A	0.630245	0.253422	0.703002	0.053*
H20B	0.781572	0.172375	0.706753	0.053*
H20C	0.587305	0.128755	0.723424	0.053*
N2	0.2715 (2)	0.20964 (13)	0.30707 (13)	0.0255 (3)
H2	0.367416	0.159044	0.313124	0.031*
C21	0.7378 (3)	0.14094 (16)	0.53596 (18)	0.0302 (4)
H21A	0.660210	0.074792	0.574910	0.045*
H21B	0.853651	0.122189	0.552563	0.045*
H21C	0.737395	0.167486	0.460272	0.045*
C22	0.0956 (6)	0.1813 (4)	0.0491 (3)	0.0293 (12)	0.570 (10)
C27	0.2141 (7)	0.2001 (4)	−0.0386 (3)	0.0363 (13)	0.570 (10)
H27	0.327325	0.226703	−0.043519	0.044*	0.570 (10)
C26	0.1671 (8)	0.1800 (3)	−0.1191 (3)	0.0412 (14)	0.570 (10)
H26	0.248061	0.192797	−0.179049	0.049*	0.570 (10)
C25	0.0014 (9)	0.1410 (3)	−0.1119 (4)	0.0408 (14)	0.570 (10)
H25	−0.030733	0.127281	−0.166960	0.049*	0.570 (10)
C24	−0.1171 (7)	0.1223 (3)	−0.0242 (4)	0.0338 (12)	0.570 (10)
C23	−0.0700 (6)	0.1424 (4)	0.0563 (4)	0.0292 (11)	0.570 (10)
H23	−0.151003	0.129576	0.116191	0.035*	0.570 (10)
C22A	0.1419 (8)	0.1967 (6)	0.0313 (4)	0.0282 (16)	0.430 (10)
C27A	0.2779 (9)	0.2164 (5)	−0.0479 (4)	0.0326 (16)	0.430 (10)
H27A	0.386878	0.240835	−0.042524	0.039*	0.430 (10)
C26A	0.2546 (11)	0.2004 (5)	−0.1349 (3)	0.0462 (19)	0.430 (10)
H26A	0.347552	0.213854	−0.189038	0.055*	0.430 (10)
C25A	0.0951 (13)	0.1646 (5)	−0.1427 (4)	0.045 (2)	0.430 (10)
H25A	0.079164	0.153669	−0.202202	0.054*	0.430 (10)
C24A	−0.0409 (10)	0.1449 (5)	−0.0635 (5)	0.0355 (18)	0.430 (10)
C23A	−0.0176 (8)	0.1609 (5)	0.0235 (4)	0.0276 (15)	0.430 (10)
H23A	−0.110576	0.147442	0.077663	0.033*	0.430 (10)
N4	0.1442 (2)	0.20960 (14)	0.12710 (14)	0.0330 (4)
O28	−0.2757 (7)	0.0870 (4)	−0.0257 (5)	0.0375 (14)	0.570 (10)
O28A	−0.1915 (10)	0.1132 (4)	−0.0798 (6)	0.0422 (18)	0.430 (10)
C29	−0.3931 (6)	0.0586 (5)	0.0690 (6)	0.0442 (17)	0.570 (10)
H29A	−0.501824	0.029605	0.062543	0.066*	0.570 (10)
H29B	−0.412170	0.124900	0.080226	0.066*	0.570 (10)
H29C	−0.345384	0.001827	0.128874	0.066*	0.570 (10)
C29A	−0.3363 (12)	0.1039 (9)	−0.0059 (10)	0.042 (2)	0.430 (10)
H29D	−0.439712	0.091066	−0.030726	0.063*	0.430 (10)
H29E	−0.344090	0.172713	0.001969	0.063*	0.430 (10)
H29F	−0.325071	0.041491	0.062249	0.063*	0.430 (10)
Cl5	0.61265 (7)	0.10023 (4)	0.29610 (5)	0.04123 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0197 (3)	0.0592 (3)	0.0359 (3)	−0.0009 (2)	−0.00522 (19)	−0.0287 (2)
O1	0.0241 (7)	0.0235 (6)	0.0462 (8)	−0.0026 (5)	−0.0109 (6)	−0.0113 (6)
N1	0.0172 (7)	0.0194 (7)	0.0309 (8)	0.0003 (5)	−0.0038 (6)	−0.0119 (6)
Cl2	0.0295 (3)	0.0438 (3)	0.0352 (3)	0.0013 (2)	0.0078 (2)	−0.0176 (2)
O2	0.0178 (6)	0.0226 (6)	0.0326 (7)	0.0034 (5)	−0.0044 (5)	−0.0152 (5)
C2	0.0182 (8)	0.0209 (8)	0.0259 (8)	0.0008 (6)	−0.0019 (6)	−0.0142 (7)
N3	0.0172 (7)	0.0201 (7)	0.0270 (7)	0.0014 (5)	−0.0037 (5)	−0.0129 (6)
O4	0.0192 (6)	0.0267 (6)	0.0376 (7)	0.0011 (5)	−0.0098 (5)	−0.0157 (6)
C4	0.0201 (8)	0.0219 (8)	0.0272 (8)	0.0018 (6)	−0.0052 (6)	−0.0148 (7)
C5	0.0201 (8)	0.0207 (8)	0.0312 (9)	0.0005 (6)	−0.0082 (7)	−0.0123 (7)
C6	0.0169 (8)	0.0247 (8)	0.0339 (9)	−0.0027 (7)	−0.0017 (7)	−0.0147 (7)
C7	0.0217 (9)	0.0209 (8)	0.0355 (10)	−0.0014 (7)	−0.0057 (7)	−0.0139 (7)
C8	0.0306 (10)	0.0224 (8)	0.0418 (11)	0.0035 (7)	−0.0156 (8)	−0.0169 (8)
C9	0.0350 (11)	0.0263 (9)	0.0387 (11)	−0.0070 (8)	−0.0158 (9)	−0.0033 (8)
C10	0.0301 (11)	0.0429 (12)	0.0321 (10)	0.0018 (9)	−0.0110 (8)	−0.0052 (9)
C11	0.0225 (9)	0.0251 (9)	0.0394 (10)	−0.0014 (7)	−0.0077 (8)	−0.0149 (8)
C12	0.0355 (11)	0.0252 (9)	0.0398 (11)	0.0027 (8)	−0.0139 (9)	−0.0151 (8)
C13	0.0192 (8)	0.0192 (8)	0.0270 (8)	0.0001 (6)	−0.0022 (6)	−0.0130 (7)
C14	0.0190 (8)	0.0186 (7)	0.0270 (8)	0.0016 (6)	−0.0033 (6)	−0.0110 (6)
C15	0.0182 (8)	0.0292 (9)	0.0293 (9)	0.0023 (7)	−0.0045 (7)	−0.0138 (7)
C16	0.0266 (10)	0.0335 (10)	0.0275 (9)	0.0050 (8)	−0.0045 (7)	−0.0153 (8)
C17	0.0247 (9)	0.0260 (9)	0.0283 (9)	0.0038 (7)	0.0024 (7)	−0.0112 (7)
C18	0.0175 (8)	0.0264 (9)	0.0380 (10)	0.0005 (7)	−0.0025 (7)	−0.0155 (8)
C19	0.0204 (9)	0.0227 (8)	0.0316 (9)	0.0011 (7)	−0.0046 (7)	−0.0138 (7)
C20	0.0362 (11)	0.0357 (11)	0.0311 (10)	−0.0049 (9)	−0.0093 (8)	−0.0101 (8)
N2	0.0222 (8)	0.0204 (7)	0.0329 (8)	0.0003 (6)	−0.0101 (6)	−0.0093 (6)
C21	0.0228 (9)	0.0224 (8)	0.0503 (12)	0.0050 (7)	−0.0112 (8)	−0.0192 (8)
C22	0.033 (3)	0.021 (2)	0.031 (2)	0.0043 (19)	−0.015 (2)	−0.0063 (17)
C27	0.030 (3)	0.037 (2)	0.034 (3)	−0.003 (2)	−0.012 (2)	−0.0059 (18)
C26	0.046 (4)	0.042 (2)	0.027 (2)	0.002 (2)	−0.010 (2)	−0.0052 (18)
C25	0.050 (4)	0.038 (2)	0.033 (3)	0.002 (2)	−0.022 (3)	−0.010 (2)
C24	0.044 (3)	0.0237 (18)	0.034 (3)	0.0056 (18)	−0.020 (2)	−0.0088 (17)
C23	0.030 (3)	0.025 (2)	0.032 (2)	0.0016 (17)	−0.012 (2)	−0.010 (2)
C22A	0.028 (3)	0.023 (3)	0.031 (3)	0.007 (2)	−0.008 (3)	−0.009 (2)
C27A	0.031 (4)	0.028 (3)	0.028 (3)	0.009 (3)	−0.003 (2)	−0.004 (2)
C26A	0.049 (5)	0.046 (4)	0.029 (3)	0.015 (3)	0.002 (3)	−0.007 (2)
C25A	0.066 (6)	0.038 (4)	0.031 (4)	0.022 (4)	−0.015 (4)	−0.012 (3)
C24A	0.056 (5)	0.026 (3)	0.028 (4)	0.013 (3)	−0.018 (4)	−0.012 (3)
C23A	0.035 (4)	0.022 (3)	0.024 (3)	0.007 (2)	−0.005 (3)	−0.008 (2)
N4	0.0365 (10)	0.0281 (8)	0.0381 (9)	0.0066 (7)	−0.0187 (8)	−0.0146 (7)
O28	0.034 (3)	0.042 (2)	0.044 (3)	0.002 (2)	−0.017 (3)	−0.023 (2)
O28A	0.054 (4)	0.040 (2)	0.044 (3)	0.012 (2)	−0.024 (3)	−0.024 (2)
C29	0.026 (2)	0.061 (3)	0.074 (4)	0.009 (2)	−0.016 (2)	−0.054 (3)
C29A	0.034 (5)	0.042 (4)	0.061 (6)	0.003 (3)	−0.016 (5)	−0.030 (4)
Cl5	0.0278 (3)	0.0341 (3)	0.0510 (3)	0.0074 (2)	−0.0114 (2)	−0.0077 (2)

Geometric parameters (Å, º)

Cl1—C15	1.7422 (19)	C16—C17	1.379 (3)
O1—H1	0.8400	C17—C18	1.388 (3)
O1—C7	1.419 (2)	C18—H18	0.9500
N1—C2	1.359 (2)	C18—C19	1.386 (3)
N1—C5	1.472 (2)	C19—H19	0.9500
N1—C6	1.456 (2)	C20—H20A	0.9800
Cl2—C17	1.7388 (19)	C20—H20B	0.9800
O2—C2	1.216 (2)	C20—H20C	0.9800
C2—N3	1.412 (2)	N2—H2	1.0000
N3—C4	1.364 (2)	C21—H21A	0.9800
N3—C13	1.457 (2)	C21—H21B	0.9800
O4—C4	1.219 (2)	C21—H21C	0.9800
C4—C5	1.520 (2)	C22—C27	1.3900
C5—C20	1.527 (3)	C22—C23	1.3900
C5—C21	1.531 (3)	C22—N4	1.426 (3)
C6—H6A	0.9900	C27—H27	0.9500
C6—H6B	0.9900	C27—C26	1.3900
C6—C7	1.537 (2)	C26—H26	0.9500
C7—H7	1.0000	C26—C25	1.3900
C7—C8	1.509 (3)	C25—H25	0.9500
C8—H8A	0.9900	C25—C24	1.3900
C8—H8B	0.9900	C24—C23	1.3900
C8—N2	1.503 (2)	C24—O28	1.352 (5)
C9—H9A	0.9900	C23—H23	0.9500
C9—H9B	0.9900	C22A—C27A	1.3900
C9—C10	1.513 (3)	C22A—C23A	1.3900
C9—N2	1.500 (3)	C22A—N4	1.459 (4)
C10—H10A	0.9900	C27A—H27A	0.9500
C10—H10B	0.9900	C27A—C26A	1.3900
C10—N4	1.446 (3)	C26A—H26A	0.9500
C11—H11A	0.9900	C26A—C25A	1.3900
C11—H11B	0.9900	C25A—H25A	0.9500
C11—C12	1.515 (3)	C25A—C24A	1.3900
C11—N2	1.498 (2)	C24A—C23A	1.3900
C12—H12A	0.9900	C24A—O28A	1.352 (6)
C12—H12B	0.9900	C23A—H23A	0.9500
C12—N4	1.466 (3)	O28—C29	1.436 (6)
C13—H13A	0.9900	O28A—C29A	1.419 (10)
C13—H13B	0.9900	C29—H29A	0.9800
C13—C14	1.508 (2)	C29—H29B	0.9800
C14—C15	1.387 (3)	C29—H29C	0.9800
C14—C19	1.395 (3)	C29A—H29D	0.9800
C15—C16	1.386 (3)	C29A—H29E	0.9800
C16—H16	0.9500	C29A—H29F	0.9800
C7—O1—H1	109.5	C17—C18—H18	120.7
C2—N1—C5	112.37 (14)	C19—C18—C17	118.52 (17)
C2—N1—C6	123.48 (15)	C19—C18—H18	120.7
C6—N1—C5	124.03 (15)	C14—C19—H19	119.1
N1—C2—N3	106.86 (14)	C18—C19—C14	121.81 (17)
O2—C2—N1	128.32 (16)	C18—C19—H19	119.1
O2—C2—N3	124.83 (16)	C5—C20—H20A	109.5
C2—N3—C13	124.52 (14)	C5—C20—H20B	109.5
C4—N3—C2	111.63 (14)	C5—C20—H20C	109.5
C4—N3—C13	123.63 (15)	H20A—C20—H20B	109.5
N3—C4—C5	107.72 (15)	H20A—C20—H20C	109.5
O4—C4—N3	125.86 (17)	H20B—C20—H20C	109.5
O4—C4—C5	126.41 (16)	C8—N2—H2	108.1
N1—C5—C4	101.17 (14)	C9—N2—C8	110.33 (15)
N1—C5—C20	111.50 (16)	C9—N2—H2	108.1
N1—C5—C21	112.97 (15)	C11—N2—C8	113.17 (16)
C4—C5—C20	109.35 (15)	C11—N2—C9	108.97 (15)
C4—C5—C21	109.61 (16)	C11—N2—H2	108.1
C20—C5—C21	111.70 (16)	C5—C21—H21A	109.5
N1—C6—H6A	108.9	C5—C21—H21B	109.5
N1—C6—H6B	108.9	C5—C21—H21C	109.5
N1—C6—C7	113.50 (15)	H21A—C21—H21B	109.5
H6A—C6—H6B	107.7	H21A—C21—H21C	109.5
C7—C6—H6A	108.9	H21B—C21—H21C	109.5
C7—C6—H6B	108.9	C27—C22—C23	120.0
O1—C7—C6	110.04 (16)	C27—C22—N4	118.7 (3)
O1—C7—H7	108.9	C23—C22—N4	121.1 (3)
O1—C7—C8	110.38 (15)	C22—C27—H27	120.0
C6—C7—H7	108.9	C26—C27—C22	120.0
C8—C7—C6	109.71 (15)	C26—C27—H27	120.0
C8—C7—H7	108.9	C27—C26—H26	120.0
C7—C8—H8A	108.9	C25—C26—C27	120.0
C7—C8—H8B	108.9	C25—C26—H26	120.0
H8A—C8—H8B	107.7	C26—C25—H25	120.0
N2—C8—C7	113.41 (15)	C24—C25—C26	120.0
N2—C8—H8A	108.9	C24—C25—H25	120.0
N2—C8—H8B	108.9	C25—C24—C23	120.0
H9A—C9—H9B	108.0	O28—C24—C25	115.6 (3)
C10—C9—H9A	109.5	O28—C24—C23	124.4 (3)
C10—C9—H9B	109.5	C22—C23—H23	120.0
N2—C9—H9A	109.5	C24—C23—C22	120.0
N2—C9—H9B	109.5	C24—C23—H23	120.0
N2—C9—C10	110.89 (17)	C27A—C22A—C23A	120.0
C9—C10—H10A	109.6	C27A—C22A—N4	127.0 (3)
C9—C10—H10B	109.6	C23A—C22A—N4	113.0 (3)
H10A—C10—H10B	108.2	C22A—C27A—H27A	120.0
N4—C10—C9	110.08 (18)	C26A—C27A—C22A	120.0
N4—C10—H10A	109.6	C26A—C27A—H27A	120.0
N4—C10—H10B	109.6	C27A—C26A—H26A	120.0
H11A—C11—H11B	108.1	C27A—C26A—C25A	120.0
C12—C11—H11A	109.5	C25A—C26A—H26A	120.0
C12—C11—H11B	109.5	C26A—C25A—H25A	120.0
N2—C11—H11A	109.5	C26A—C25A—C24A	120.0
N2—C11—H11B	109.5	C24A—C25A—H25A	120.0
N2—C11—C12	110.77 (17)	C23A—C24A—C25A	120.0
C11—C12—H12A	109.5	O28A—C24A—C25A	115.5 (4)
C11—C12—H12B	109.5	O28A—C24A—C23A	124.5 (4)
H12A—C12—H12B	108.1	C22A—C23A—H23A	120.0
N4—C12—C11	110.78 (16)	C24A—C23A—C22A	120.0
N4—C12—H12A	109.5	C24A—C23A—H23A	120.0
N4—C12—H12B	109.5	C10—N4—C12	110.36 (16)
N3—C13—H13A	108.9	C10—N4—C22A	106.8 (3)
N3—C13—H13B	108.9	C22—N4—C10	123.3 (3)
N3—C13—C14	113.22 (14)	C22—N4—C12	109.4 (2)
H13A—C13—H13B	107.7	C22A—N4—C12	120.1 (3)
C14—C13—H13A	108.9	C24—O28—C29	115.2 (4)
C14—C13—H13B	108.9	C24A—O28A—C29A	116.6 (5)
C15—C14—C13	122.84 (16)	O28—C29—H29A	109.5
C15—C14—C19	117.16 (16)	O28—C29—H29B	109.5
C19—C14—C13	119.95 (16)	O28—C29—H29C	109.5
C14—C15—Cl1	119.96 (14)	H29A—C29—H29B	109.5
C16—C15—Cl1	117.32 (15)	H29A—C29—H29C	109.5
C16—C15—C14	122.70 (17)	H29B—C29—H29C	109.5
C15—C16—H16	121.0	O28A—C29A—H29D	109.5
C17—C16—C15	118.02 (18)	O28A—C29A—H29E	109.5
C17—C16—H16	121.0	O28A—C29A—H29F	109.5
C16—C17—Cl2	118.25 (15)	H29D—C29A—H29E	109.5
C16—C17—C18	121.73 (17)	H29D—C29A—H29F	109.5
C18—C17—Cl2	120.01 (15)	H29E—C29A—H29F	109.5
Cl1—C15—C16—C17	179.43 (15)	C13—N3—C4—C5	178.39 (15)
O1—C7—C8—N2	−71.1 (2)	C13—C14—C15—Cl1	−3.6 (2)
N1—C2—N3—C4	−5.19 (19)	C13—C14—C15—C16	174.56 (17)
N1—C2—N3—C13	−179.96 (15)	C13—C14—C19—C18	−175.09 (16)
N1—C6—C7—O1	164.75 (15)	C14—C15—C16—C17	1.2 (3)
N1—C6—C7—C8	−73.6 (2)	C15—C14—C19—C18	2.4 (3)
Cl2—C17—C18—C19	179.91 (14)	C15—C16—C17—Cl2	179.71 (14)
O2—C2—N3—C4	175.14 (16)	C15—C16—C17—C18	1.0 (3)
O2—C2—N3—C13	0.4 (3)	C16—C17—C18—C19	−1.4 (3)
C2—N1—C5—C4	−2.57 (19)	C17—C18—C19—C14	−0.4 (3)
C2—N1—C5—C20	113.58 (17)	C19—C14—C15—Cl1	178.97 (13)
C2—N1—C5—C21	−119.65 (17)	C19—C14—C15—C16	−2.9 (3)
C2—N1—C6—C7	92.1 (2)	N2—C9—C10—N4	59.3 (2)
C2—N3—C4—O4	−176.05 (16)	N2—C11—C12—N4	−57.1 (2)
C2—N3—C4—C5	3.57 (19)	C22—C27—C26—C25	0.0
C2—N3—C13—C14	−118.71 (17)	C27—C22—C23—C24	0.0
N3—C4—C5—N1	−0.66 (18)	C27—C22—N4—C10	6.6 (4)
N3—C4—C5—C20	−118.39 (17)	C27—C22—N4—C12	−125.7 (2)
N3—C4—C5—C21	118.85 (16)	C27—C26—C25—C24	0.0
N3—C13—C14—C15	72.0 (2)	C26—C25—C24—C23	0.0
N3—C13—C14—C19	−110.65 (18)	C26—C25—C24—O28	178.5 (3)
O4—C4—C5—N1	178.95 (17)	C25—C24—C23—C22	0.0
O4—C4—C5—C20	61.2 (2)	C25—C24—O28—C29	174.8 (3)
O4—C4—C5—C21	−61.5 (2)	C23—C22—C27—C26	0.0
C4—N3—C13—C14	67.1 (2)	C23—C22—N4—C10	−169.3 (2)
C5—N1—C2—O2	−175.62 (17)	C23—C22—N4—C12	58.4 (3)
C5—N1—C2—N3	4.73 (19)	C23—C24—O28—C29	−6.8 (5)
C5—N1—C6—C7	−92.2 (2)	C22A—C27A—C26A—C25A	0.0
C6—N1—C2—O2	0.5 (3)	C27A—C22A—C23A—C24A	0.0
C6—N1—C2—N3	−179.15 (15)	C27A—C22A—N4—C10	11.1 (5)
C6—N1—C5—C4	−178.67 (15)	C27A—C22A—N4—C12	−115.5 (4)
C6—N1—C5—C20	−62.5 (2)	C27A—C26A—C25A—C24A	0.0
C6—N1—C5—C21	64.2 (2)	C26A—C25A—C24A—C23A	0.0
C6—C7—C8—N2	167.43 (15)	C26A—C25A—C24A—O28A	178.3 (4)
C7—C8—N2—C9	−155.39 (17)	C25A—C24A—C23A—C22A	0.0
C7—C8—N2—C11	82.2 (2)	C25A—C24A—O28A—C29A	−173.5 (5)
C9—C10—N4—C12	−60.0 (2)	C23A—C22A—C27A—C26A	0.0
C9—C10—N4—C22	168.0 (3)	C23A—C22A—N4—C10	−168.7 (2)
C9—C10—N4—C22A	167.8 (3)	C23A—C22A—N4—C12	64.7 (4)
C10—C9—N2—C8	178.89 (17)	C23A—C24A—O28A—C29A	4.7 (7)
C10—C9—N2—C11	−56.3 (2)	N4—C22—C27—C26	−175.9 (4)
C11—C12—N4—C10	59.3 (2)	N4—C22—C23—C24	175.8 (4)
C11—C12—N4—C22	−161.9 (3)	N4—C22A—C27A—C26A	−179.8 (6)
C11—C12—N4—C22A	−175.7 (3)	N4—C22A—C23A—C24A	179.8 (5)
C12—C11—N2—C8	178.28 (15)	O28—C24—C23—C22	−178.3 (4)
C12—C11—N2—C9	55.1 (2)	O28A—C24A—C23A—C22A	−178.2 (4)
C13—N3—C4—O4	−1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5^i	0.84	2.29	3.104 (2)	163
N2—H2···Cl5	1.00	2.11	3.079 (2)	162

Symmetry code: (i) −x+1, −y, −z+1.

4-(2,3-Dichlorophenyl)-1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)piperazin-1-ium chloride 0.2-hydrate (5)

Crystal data

C25H29Cl4N4O3^+·Cl^−·0.2H2O	Z = 2
Mr = 614.37	F(000) = 636
Triclinic, P1	Dx = 1.463 Mg m^−3
a = 7.8666 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.9316 (1) Å	Cell parameters from 29271 reflections
c = 14.7308 (1) Å	θ = 3.2–76.6°
α = 70.208 (1)°	µ = 5.04 mm^−1
β = 81.435 (1)°	T = 100 K
γ = 87.759 (1)°	Irregular, clear colourless
V = 1394.18 (2) Å^3	0.38 × 0.23 × 0.04 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	5819 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5573 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.045
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.9°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −16→16
Tmin = 0.161, Tmax = 1.000	l = −18→18
47487 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.033	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.8642P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.089	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.59 e Å^−3
5819 reflections	Δρmin = −0.51 e Å^−3
352 parameters	Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
5 restraints	Extinction coefficient: 0.00077 (19)
Primary atom site location: dual

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	Occ. (<1)
Cl1	0.34762 (5)	0.40948 (4)	0.82415 (3)	0.02839 (11)
O1	0.80143 (17)	0.89853 (11)	0.49881 (10)	0.0219 (4)	0.840 (4)
H1	0.783009	0.947274	0.446712	0.033*	0.840 (4)
O1A	0.6030 (10)	0.9163 (5)	0.5277 (5)	0.022 (2)	0.160 (4)
H1A	0.508238	0.904068	0.564514	0.033*	0.160 (4)
N1	0.47237 (16)	0.69872 (10)	0.50132 (9)	0.0166 (2)
Cl2	−0.30106 (5)	0.46126 (3)	0.97230 (3)	0.02625 (11)
O2	0.56519 (14)	0.53182 (9)	0.59899 (8)	0.0196 (2)
C2	0.45522 (19)	0.59249 (12)	0.56013 (10)	0.0159 (3)
Cl3	1.17419 (6)	0.84212 (4)	1.12188 (3)	0.03706 (13)
O3	0.04266 (14)	0.63899 (9)	0.50086 (9)	0.0237 (2)
N3	0.28143 (16)	0.56212 (10)	0.57001 (9)	0.0161 (2)
Cl4	1.11644 (5)	0.80478 (3)	0.92952 (3)	0.02718 (11)
C4	0.1921 (2)	0.64377 (12)	0.51104 (11)	0.0179 (3)
C5	0.31441 (19)	0.74106 (12)	0.45933 (11)	0.0183 (3)
C6	0.63581 (19)	0.75840 (13)	0.47447 (11)	0.0189 (3)
H6AA	0.645877	0.806986	0.405535	0.023*	0.840 (4)
H6AB	0.731051	0.705250	0.480283	0.023*	0.840 (4)
H6BC	0.636396	0.812350	0.408078	0.023*	0.160 (4)
H6BD	0.727655	0.705078	0.469891	0.023*	0.160 (4)
C7	0.6533 (4)	0.8283 (2)	0.5392 (2)	0.0185 (6)	0.840 (4)
H7	0.548391	0.874053	0.541525	0.022*	0.840 (4)
C7A	0.687 (3)	0.8202 (13)	0.5384 (11)	0.0185 (6)	0.160 (4)
H7A	0.812149	0.839387	0.516600	0.022*	0.160 (4)
C8	0.6704 (2)	0.75218 (13)	0.64079 (12)	0.0271 (4)
H8A	0.577754	0.695785	0.662191	0.033*
H8B	0.781710	0.713897	0.639173	0.033*
C9	0.5933 (3)	0.73405 (14)	0.81385 (12)	0.0301 (4)
H9A	0.668748	0.669348	0.831487	0.036*
H9B	0.476814	0.707817	0.813636	0.036*
C10	0.5852 (2)	0.79099 (15)	0.88910 (12)	0.0272 (4)
H10A	0.507560	0.854725	0.873001	0.033*
H10B	0.540154	0.739494	0.954528	0.033*
C11	0.8315 (2)	0.85826 (14)	0.71458 (12)	0.0232 (3)
H11A	0.868753	0.914594	0.650293	0.028*
H11B	0.918527	0.799558	0.725832	0.028*
C12	0.8201 (2)	0.90994 (13)	0.79361 (11)	0.0221 (3)
H12A	0.934780	0.937907	0.794867	0.026*
H12B	0.740298	0.972671	0.779665	0.026*
C13	0.21101 (19)	0.45193 (12)	0.62626 (11)	0.0178 (3)
H13A	0.306502	0.401519	0.647385	0.021*
H13B	0.151897	0.424418	0.583973	0.021*
C14	0.08576 (19)	0.45119 (12)	0.71485 (11)	0.0173 (3)
C15	0.13405 (19)	0.43485 (13)	0.80598 (12)	0.0195 (3)
C16	0.0177 (2)	0.43696 (13)	0.88592 (11)	0.0207 (3)
H16	0.054148	0.425836	0.947167	0.025*
C17	−0.1530 (2)	0.45578 (13)	0.87360 (12)	0.0207 (3)
C18	−0.2082 (2)	0.47069 (13)	0.78509 (12)	0.0223 (3)
H18	−0.326127	0.482705	0.778067	0.027*
C19	−0.0882 (2)	0.46777 (13)	0.70697 (12)	0.0203 (3)
H19	−0.125653	0.477368	0.646263	0.024*
C20	0.3385 (2)	0.76112 (15)	0.34982 (12)	0.0271 (4)
H20A	0.420151	0.822081	0.316023	0.041*
H20B	0.227726	0.779571	0.325770	0.041*
H20C	0.383097	0.694576	0.337445	0.041*
N21	0.66104 (19)	0.81064 (11)	0.71405 (10)	0.0223 (3)
H21	0.578389	0.872482	0.695913	0.027*
C21	0.2445 (2)	0.84248 (13)	0.48285 (14)	0.0264 (4)
H21A	0.233879	0.827477	0.553284	0.040*
H21B	0.131274	0.860155	0.461718	0.040*
H21C	0.323400	0.904824	0.448612	0.040*
C22	0.7832 (2)	0.85386 (12)	0.97197 (11)	0.0210 (3)
C23	0.6485 (2)	0.88468 (14)	1.03014 (12)	0.0264 (3)
H23	0.536127	0.892243	1.012507	0.032*
N24	0.75810 (18)	0.82763 (11)	0.88872 (9)	0.0215 (3)
C24	0.6773 (3)	0.90449 (15)	1.11397 (13)	0.0311 (4)
H24	0.584522	0.926454	1.152354	0.037*
C25	0.8383 (3)	0.89265 (14)	1.14184 (12)	0.0312 (4)
H25	0.856964	0.905635	1.199340	0.037*
C26	0.9728 (2)	0.86148 (13)	1.08468 (12)	0.0264 (4)
C27	0.9475 (2)	0.84335 (13)	0.99948 (11)	0.0220 (3)
Cl5	0.34439 (6)	0.95711 (4)	0.68940 (3)	0.03302 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01492 (19)	0.0458 (2)	0.02247 (19)	0.00232 (16)	−0.00483 (14)	−0.00822 (17)
O1	0.0218 (7)	0.0200 (7)	0.0245 (7)	−0.0041 (5)	−0.0055 (5)	−0.0067 (5)
O1A	0.031 (4)	0.017 (4)	0.017 (3)	0.004 (3)	−0.002 (3)	−0.007 (3)
N1	0.0150 (6)	0.0177 (6)	0.0189 (6)	−0.0004 (5)	−0.0041 (5)	−0.0075 (5)
Cl2	0.0212 (2)	0.0294 (2)	0.0245 (2)	0.00331 (15)	0.00347 (15)	−0.00739 (15)
O2	0.0167 (5)	0.0213 (5)	0.0220 (5)	0.0033 (4)	−0.0058 (4)	−0.0082 (4)
C2	0.0156 (7)	0.0204 (7)	0.0147 (7)	0.0010 (5)	−0.0029 (5)	−0.0097 (6)
Cl3	0.0443 (3)	0.0380 (2)	0.0312 (2)	−0.00815 (19)	−0.0200 (2)	−0.00759 (18)
O3	0.0178 (6)	0.0253 (6)	0.0305 (6)	0.0014 (4)	−0.0103 (5)	−0.0099 (5)
N3	0.0150 (6)	0.0173 (6)	0.0175 (6)	0.0001 (5)	−0.0035 (5)	−0.0073 (5)
Cl4	0.0249 (2)	0.0315 (2)	0.0253 (2)	0.00226 (16)	−0.00429 (15)	−0.00967 (16)
C4	0.0188 (7)	0.0202 (7)	0.0180 (7)	0.0019 (6)	−0.0052 (6)	−0.0099 (6)
C5	0.0166 (7)	0.0191 (7)	0.0210 (7)	0.0015 (6)	−0.0061 (6)	−0.0077 (6)
C6	0.0173 (7)	0.0220 (7)	0.0198 (7)	−0.0033 (6)	−0.0019 (6)	−0.0103 (6)
C7	0.0149 (18)	0.0224 (9)	0.0209 (8)	−0.0026 (9)	−0.0001 (9)	−0.0114 (7)
C7A	0.0149 (18)	0.0224 (9)	0.0209 (8)	−0.0026 (9)	−0.0001 (9)	−0.0114 (7)
C8	0.0419 (10)	0.0197 (8)	0.0258 (8)	0.0033 (7)	−0.0157 (8)	−0.0114 (7)
C9	0.0436 (11)	0.0252 (8)	0.0204 (8)	−0.0117 (7)	−0.0085 (7)	−0.0033 (7)
C10	0.0300 (9)	0.0316 (9)	0.0191 (8)	−0.0084 (7)	−0.0049 (7)	−0.0058 (7)
C11	0.0292 (9)	0.0237 (8)	0.0188 (7)	−0.0012 (6)	−0.0052 (6)	−0.0088 (6)
C12	0.0297 (8)	0.0205 (7)	0.0167 (7)	−0.0027 (6)	−0.0042 (6)	−0.0064 (6)
C13	0.0176 (7)	0.0166 (7)	0.0209 (7)	−0.0002 (5)	−0.0035 (6)	−0.0080 (6)
C14	0.0167 (7)	0.0149 (6)	0.0211 (7)	−0.0008 (5)	−0.0025 (6)	−0.0071 (6)
C15	0.0144 (7)	0.0212 (7)	0.0226 (7)	−0.0002 (6)	−0.0039 (6)	−0.0065 (6)
C16	0.0202 (8)	0.0221 (7)	0.0198 (7)	−0.0015 (6)	−0.0033 (6)	−0.0069 (6)
C17	0.0184 (7)	0.0187 (7)	0.0227 (8)	−0.0002 (6)	0.0011 (6)	−0.0056 (6)
C18	0.0153 (7)	0.0221 (7)	0.0277 (8)	0.0002 (6)	−0.0040 (6)	−0.0059 (6)
C19	0.0188 (8)	0.0211 (7)	0.0222 (7)	−0.0005 (6)	−0.0050 (6)	−0.0077 (6)
C20	0.0281 (9)	0.0319 (9)	0.0192 (8)	−0.0016 (7)	−0.0073 (7)	−0.0040 (7)
N21	0.0319 (8)	0.0189 (6)	0.0180 (6)	−0.0019 (5)	−0.0081 (6)	−0.0066 (5)
C21	0.0209 (8)	0.0213 (8)	0.0408 (10)	0.0050 (6)	−0.0094 (7)	−0.0138 (7)
C22	0.0295 (8)	0.0172 (7)	0.0164 (7)	−0.0009 (6)	−0.0046 (6)	−0.0052 (6)
C23	0.0308 (9)	0.0245 (8)	0.0229 (8)	0.0031 (7)	−0.0031 (7)	−0.0073 (6)
N24	0.0269 (7)	0.0227 (6)	0.0159 (6)	−0.0025 (5)	−0.0058 (5)	−0.0065 (5)
C24	0.0444 (11)	0.0265 (8)	0.0218 (8)	0.0022 (8)	0.0022 (7)	−0.0108 (7)
C25	0.0539 (12)	0.0241 (8)	0.0173 (8)	−0.0066 (8)	−0.0041 (8)	−0.0087 (6)
C26	0.0382 (10)	0.0208 (8)	0.0208 (8)	−0.0057 (7)	−0.0103 (7)	−0.0047 (6)
C27	0.0290 (8)	0.0184 (7)	0.0179 (7)	−0.0016 (6)	−0.0043 (6)	−0.0048 (6)
Cl5	0.0430 (3)	0.0311 (2)	0.0246 (2)	0.00798 (18)	−0.00984 (18)	−0.00764 (16)

Geometric parameters (Å, º)

Cl1—C15	1.7416 (15)	C10—N24	1.456 (2)
O1—H1	0.8400	C11—H11A	0.9900
O1—C7	1.431 (4)	C11—H11B	0.9900
O1A—H1A	0.8400	C11—C12	1.517 (2)
O1A—C7A	1.358 (15)	C11—N21	1.500 (2)
N1—C2	1.353 (2)	C12—H12A	0.9900
N1—C5	1.4741 (18)	C12—H12B	0.9900
N1—C6	1.4575 (19)	C12—N24	1.470 (2)
Cl2—C17	1.7421 (16)	C13—H13A	0.9900
O2—C2	1.2174 (18)	C13—H13B	0.9900
C2—N3	1.4101 (19)	C13—C14	1.511 (2)
Cl3—C26	1.7343 (18)	C14—C15	1.394 (2)
O3—C4	1.2134 (19)	C14—C19	1.393 (2)
N3—C4	1.3662 (19)	C15—C16	1.387 (2)
N3—C13	1.4660 (19)	C16—H16	0.9500
Cl4—C27	1.7222 (17)	C16—C17	1.383 (2)
C4—C5	1.522 (2)	C17—C18	1.385 (2)
C5—C20	1.528 (2)	C18—H18	0.9500
C5—C21	1.529 (2)	C18—C19	1.386 (2)
C6—H6AA	0.9900	C19—H19	0.9500
C6—H6AB	0.9900	C20—H20A	0.9800
C6—H6BC	0.9900	C20—H20B	0.9800
C6—H6BD	0.9900	C20—H20C	0.9800
C6—C7	1.542 (3)	N21—H21	1.0000
C6—C7A	1.529 (15)	C21—H21A	0.9800
C7—H7	1.0000	C21—H21B	0.9800
C7—C8	1.509 (3)	C21—H21C	0.9800
C7A—H7A	1.0000	C22—C23	1.395 (2)
C7A—C8	1.455 (16)	C22—N24	1.4203 (19)
C8—H8A	0.9900	C22—C27	1.399 (2)
C8—H8B	0.9900	C23—H23	0.9500
C8—N21	1.505 (2)	C23—C24	1.394 (2)
C9—H9A	0.9900	C24—H24	0.9500
C9—H9B	0.9900	C24—C25	1.376 (3)
C9—C10	1.518 (2)	C25—H25	0.9500
C9—N21	1.499 (2)	C25—C26	1.387 (3)
C10—H10A	0.9900	C26—C27	1.395 (2)
C10—H10B	0.9900
C7—O1—H1	109.5	C11—C12—H12A	109.7
C7A—O1A—H1A	109.5	C11—C12—H12B	109.7
C2—N1—C5	112.28 (12)	H12A—C12—H12B	108.2
C2—N1—C6	122.71 (13)	N24—C12—C11	109.62 (13)
C6—N1—C5	124.62 (12)	N24—C12—H12A	109.7
N1—C2—N3	107.18 (12)	N24—C12—H12B	109.7
O2—C2—N1	128.20 (14)	N3—C13—H13A	109.2
O2—C2—N3	124.62 (14)	N3—C13—H13B	109.2
C2—N3—C13	124.17 (12)	N3—C13—C14	112.12 (12)
C4—N3—C2	111.42 (12)	H13A—C13—H13B	107.9
C4—N3—C13	123.94 (12)	C14—C13—H13A	109.2
O3—C4—N3	126.10 (15)	C14—C13—H13B	109.2
O3—C4—C5	126.21 (14)	C15—C14—C13	123.62 (14)
N3—C4—C5	107.68 (12)	C19—C14—C13	119.40 (13)
N1—C5—C4	101.02 (12)	C19—C14—C15	116.98 (14)
N1—C5—C20	111.45 (13)	C14—C15—Cl1	120.45 (12)
N1—C5—C21	113.20 (12)	C16—C15—Cl1	116.76 (12)
C4—C5—C20	108.81 (12)	C16—C15—C14	122.79 (14)
C4—C5—C21	110.11 (13)	C15—C16—H16	121.1
C20—C5—C21	111.67 (14)	C17—C16—C15	117.85 (14)
N1—C6—H6AA	109.2	C17—C16—H16	121.1
N1—C6—H6AB	109.2	C16—C17—Cl2	118.76 (12)
N1—C6—H6BC	107.3	C16—C17—C18	121.68 (15)
N1—C6—H6BD	107.3	C18—C17—Cl2	119.56 (12)
N1—C6—C7	112.21 (16)	C17—C18—H18	120.6
N1—C6—C7A	120.0 (9)	C17—C18—C19	118.78 (15)
H6AA—C6—H6AB	107.9	C19—C18—H18	120.6
H6BC—C6—H6BD	106.9	C14—C19—H19	119.0
C7—C6—H6AA	109.2	C18—C19—C14	121.91 (14)
C7—C6—H6AB	109.2	C18—C19—H19	119.0
C7A—C6—H6BC	107.3	C5—C20—H20A	109.5
C7A—C6—H6BD	107.3	C5—C20—H20B	109.5
O1—C7—C6	109.2 (2)	C5—C20—H20C	109.5
O1—C7—H7	109.4	H20A—C20—H20B	109.5
O1—C7—C8	110.6 (2)	H20A—C20—H20C	109.5
C6—C7—H7	109.4	H20B—C20—H20C	109.5
C8—C7—C6	108.7 (2)	C8—N21—H21	108.0
C8—C7—H7	109.4	C9—N21—C8	110.13 (13)
O1A—C7A—C6	113.4 (12)	C9—N21—C11	110.34 (12)
O1A—C7A—H7A	106.7	C9—N21—H21	108.0
O1A—C7A—C8	110.5 (12)	C11—N21—C8	112.27 (13)
C6—C7A—H7A	106.7	C11—N21—H21	108.0
C8—C7A—C6	112.3 (11)	C5—C21—H21A	109.5
C8—C7A—H7A	106.7	C5—C21—H21B	109.5
C7—C8—H8A	108.9	C5—C21—H21C	109.5
C7—C8—H8B	108.9	H21A—C21—H21B	109.5
C7A—C8—N21	117.1 (6)	H21A—C21—H21C	109.5
H8A—C8—H8B	107.7	H21B—C21—H21C	109.5
N21—C8—C7	113.25 (15)	C23—C22—N24	122.38 (15)
N21—C8—H8A	108.9	C23—C22—C27	118.63 (15)
N21—C8—H8B	108.9	C27—C22—N24	118.92 (15)
H9A—C9—H9B	108.0	C22—C23—H23	119.7
C10—C9—H9A	109.4	C24—C23—C22	120.53 (17)
C10—C9—H9B	109.4	C24—C23—H23	119.7
N21—C9—H9A	109.4	C10—N24—C12	109.94 (13)
N21—C9—H9B	109.4	C22—N24—C10	115.45 (14)
N21—C9—C10	110.96 (14)	C22—N24—C12	116.06 (13)
C9—C10—H10A	110.0	C23—C24—H24	119.6
C9—C10—H10B	110.0	C25—C24—C23	120.88 (17)
H10A—C10—H10B	108.4	C25—C24—H24	119.6
N24—C10—C9	108.35 (15)	C24—C25—H25	120.5
N24—C10—H10A	110.0	C24—C25—C26	118.95 (15)
N24—C10—H10B	110.0	C26—C25—H25	120.5
H11A—C11—H11B	108.1	C25—C26—Cl3	118.98 (13)
C12—C11—H11A	109.5	C25—C26—C27	121.10 (17)
C12—C11—H11B	109.5	C27—C26—Cl3	119.90 (14)
N21—C11—H11A	109.5	C22—C27—Cl4	119.76 (12)
N21—C11—H11B	109.5	C26—C27—Cl4	120.33 (14)
N21—C11—C12	110.85 (14)	C26—C27—C22	119.89 (16)
Cl1—C15—C16—C17	−179.32 (12)	C7—C8—N21—C11	−84.3 (2)
O1—C7—C8—N21	69.0 (2)	C7A—C8—N21—C9	163.5 (10)
O1A—C7A—C8—N21	−33.0 (18)	C7A—C8—N21—C11	−73.2 (10)
N1—C2—N3—C4	5.93 (16)	C9—C10—N24—C12	63.62 (17)
N1—C2—N3—C13	178.32 (12)	C9—C10—N24—C22	−162.73 (14)
N1—C6—C7—O1	−170.14 (15)	C10—C9—N21—C8	179.18 (15)
N1—C6—C7—C8	69.1 (2)	C10—C9—N21—C11	54.70 (19)
N1—C6—C7A—O1A	−76.0 (14)	C11—C12—N24—C10	−62.73 (17)
N1—C6—C7A—C8	50.2 (15)	C11—C12—N24—C22	163.93 (14)
Cl2—C17—C18—C19	179.00 (12)	C12—C11—N21—C8	−176.28 (13)
O2—C2—N3—C4	−174.36 (14)	C12—C11—N21—C9	−53.03 (17)
O2—C2—N3—C13	−2.0 (2)	C13—N3—C4—O3	4.0 (2)
C2—N1—C5—C4	5.01 (15)	C13—N3—C4—C5	−175.13 (12)
C2—N1—C5—C20	−110.42 (15)	C13—C14—C15—Cl1	−2.0 (2)
C2—N1—C5—C21	122.70 (14)	C13—C14—C15—C16	178.47 (14)
C2—N1—C6—C7	−97.07 (18)	C13—C14—C19—C18	−178.34 (14)
C2—N1—C6—C7A	−89.0 (7)	C14—C15—C16—C17	0.2 (2)
C2—N3—C4—O3	176.44 (14)	C15—C14—C19—C18	1.5 (2)
C2—N3—C4—C5	−2.72 (16)	C15—C16—C17—Cl2	−178.87 (12)
C2—N3—C13—C14	113.25 (15)	C15—C16—C17—C18	0.9 (2)
Cl3—C26—C27—Cl4	−1.5 (2)	C16—C17—C18—C19	−0.7 (2)
Cl3—C26—C27—C22	176.94 (12)	C17—C18—C19—C14	−0.5 (2)
O3—C4—C5—N1	179.61 (14)	C19—C14—C15—Cl1	178.15 (11)
O3—C4—C5—C20	−63.0 (2)	C19—C14—C15—C16	−1.4 (2)
O3—C4—C5—C21	59.7 (2)	N21—C9—C10—N24	−59.74 (19)
N3—C4—C5—N1	−1.23 (15)	N21—C11—C12—N24	56.85 (17)
N3—C4—C5—C20	116.15 (14)	C22—C23—C24—C25	−0.9 (3)
N3—C4—C5—C21	−121.15 (14)	C23—C22—N24—C10	−24.2 (2)
N3—C13—C14—C15	−89.60 (17)	C23—C22—N24—C12	106.60 (18)
N3—C13—C14—C19	90.25 (16)	C23—C22—C27—Cl4	179.69 (12)
C4—N3—C13—C14	−75.30 (17)	C23—C22—C27—C26	1.3 (2)
C5—N1—C2—O2	173.48 (14)	C23—C24—C25—C26	0.6 (3)
C5—N1—C2—N3	−6.82 (16)	N24—C22—C23—C24	176.81 (15)
C5—N1—C6—C7	90.70 (19)	N24—C22—C27—Cl4	2.7 (2)
C5—N1—C6—C7A	98.7 (7)	N24—C22—C27—C26	−175.68 (14)
C6—N1—C2—O2	0.4 (2)	C24—C25—C26—Cl3	−177.89 (14)
C6—N1—C2—N3	−179.92 (12)	C24—C25—C26—C27	0.7 (3)
C6—N1—C5—C4	177.96 (12)	C25—C26—C27—Cl4	179.95 (13)
C6—N1—C5—C20	62.52 (18)	C25—C26—C27—C22	−1.7 (2)
C6—N1—C5—C21	−64.35 (19)	C27—C22—C23—C24	0.0 (2)
C6—C7—C8—N21	−171.13 (16)	C27—C22—N24—C10	152.66 (15)
C6—C7A—C8—N21	−160.8 (8)	C27—C22—N24—C12	−76.56 (19)
C7—C8—N21—C9	152.36 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl5^i	0.84	2.32	3.124 (1)	161
O1A—H1A···Cl5	0.84	2.37	3.068 (7)	142
N21—H21···Cl5	1.00	2.10	3.059 (2)	160

Symmetry code: (i) −x+1, −y+2, −z+1.

3-[(2,4-Dichlorophenyl)methyl]-1-{3-[4-(3,4-dichlorophenyl)piperazin-1-yl]-2-hydroxypropyl}-5,5-dimethylimidazolidine-2,4-dione (6)

Crystal data

C25H28Cl4N4O3	Z = 2
Mr = 574.31	F(000) = 596
Triclinic, P1	Dx = 1.451 Mg m^−3
a = 8.0564 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5668 (5) Å	Cell parameters from 6148 reflections
c = 15.0297 (7) Å	θ = 2.9–28.3°
α = 75.730 (4)°	µ = 0.49 mm^−1
β = 85.666 (3)°	T = 130 K
γ = 75.595 (4)°	Irregular, clear colourless
V = 1314.53 (10) Å^3	0.52 × 0.45 × 0.19 mm

Data collection

Rigaku SuperNova Dual Source diffractometer with an Atlas detector	6207 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4342 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.6°, θmin = 2.8°
ω scans	h = −10→10
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2020)	k = −15→15
Tmin = 0.312, Tmax = 1.000	l = −20→20
18279 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 1.5026P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
6207 reflections	Δρmax = 0.75 e Å^−3
428 parameters	Δρmin = −0.44 e Å^−3
39 restraints

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	Occ. (<1)
Cl1	0.34466 (9)	0.48841 (8)	0.80036 (5)	0.0442 (2)
O1	0.7266 (4)	0.8773 (3)	0.5768 (2)	0.0383 (10)	0.603 (6)
H1	0.813297	0.831650	0.561436	0.057*	0.603 (6)
O1A	0.5198 (8)	0.9258 (5)	0.6089 (4)	0.0513 (19)	0.397 (6)
H1A	0.492760	0.933223	0.661225	0.077*	0.397 (6)
N1	0.4155 (3)	0.7045 (2)	0.54942 (16)	0.0314 (5)
Cl2	−0.24650 (12)	0.40311 (11)	0.95320 (7)	0.0748 (3)
O2	0.5609 (2)	0.50172 (18)	0.60083 (13)	0.0361 (5)
N2	0.6659 (7)	0.7410 (5)	0.7803 (3)	0.0566 (14)	0.711 (3)
N2A	0.5882 (18)	0.7966 (16)	0.7764 (9)	0.0566 (14)	0.289 (3)
C2	0.4320 (3)	0.5823 (3)	0.58011 (18)	0.0300 (6)
Cl3	1.05348 (17)	0.91788 (12)	1.16561 (7)	0.0515 (4)	0.711 (3)
Cl3A	0.4888 (6)	0.8520 (4)	1.2500 (3)	0.0873 (15)	0.289 (3)
N3	0.2649 (3)	0.5620 (2)	0.58567 (15)	0.0291 (5)
Cl4	0.7667 (3)	0.8865 (3)	1.32034 (14)	0.0525 (5)	0.711 (3)
Cl4A	0.8202 (12)	0.9130 (8)	1.2935 (5)	0.118 (3)	0.289 (3)
O4	−0.0036 (2)	0.67468 (19)	0.53811 (16)	0.0448 (5)
N4	0.6898 (9)	0.8358 (5)	0.9350 (4)	0.0593 (19)	0.711 (3)
N4A	0.672 (2)	0.7974 (16)	0.9618 (12)	0.0593 (19)	0.289 (3)
C4	0.1482 (3)	0.6660 (3)	0.54824 (19)	0.0327 (6)
C5	0.2397 (4)	0.7706 (3)	0.5218 (2)	0.0349 (6)
C6	0.5618 (4)	0.7598 (3)	0.5332 (2)	0.0397 (7)
H6A	0.540667	0.826376	0.478524	0.048*
H6B	0.661690	0.698767	0.520612	0.048*
C7	0.6038 (4)	0.8099 (3)	0.6114 (2)	0.0411 (7)
H7A	0.499870	0.870999	0.621117	0.049*	0.603 (6)
H7B	0.721071	0.818389	0.595330	0.049*	0.397 (6)
C8	0.6288 (7)	0.7157 (4)	0.6983 (3)	0.0719 (13)
H8AA	0.525628	0.685095	0.709823	0.086*	0.711 (3)
H8AB	0.720695	0.648148	0.687565	0.086*	0.711 (3)
H8BC	0.745370	0.665726	0.702793	0.086*	0.289 (3)
H8BD	0.550130	0.662865	0.704177	0.086*	0.289 (3)
C9	0.8098 (7)	0.7900 (6)	0.7879 (4)	0.0445 (12)	0.711 (3)
H9A	0.789092	0.874733	0.753070	0.053*	0.711 (3)
H9B	0.911607	0.743458	0.762562	0.053*	0.711 (3)
C9A	0.7598 (18)	0.7702 (15)	0.8132 (10)	0.0445 (12)	0.289 (3)
H9AA	0.841617	0.781644	0.762952	0.053*	0.289 (3)
H9AB	0.791607	0.685232	0.847392	0.053*	0.289 (3)
C10	0.8381 (8)	0.7833 (7)	0.8885 (4)	0.0644 (15)	0.711 (3)
H10A	0.878691	0.697814	0.920051	0.077*	0.711 (3)
H10B	0.927198	0.825043	0.891705	0.077*	0.711 (3)
C10A	0.767 (2)	0.8550 (15)	0.8765 (10)	0.0644 (15)	0.289 (3)
H10C	0.883578	0.852163	0.890000	0.077*	0.289 (3)
H10D	0.707298	0.939322	0.850356	0.077*	0.289 (3)
C11	0.5247 (8)	0.8010 (6)	0.8151 (4)	0.0618 (15)	0.711 (3)
H11A	0.431122	0.765057	0.808229	0.074*	0.711 (3)
H11B	0.497230	0.885580	0.779899	0.074*	0.711 (3)
C11A	0.5043 (18)	0.7367 (14)	0.8639 (9)	0.0618 (15)	0.289 (3)
H11C	0.572203	0.653956	0.887179	0.074*	0.289 (3)
H11D	0.391423	0.730942	0.849839	0.074*	0.289 (3)
C12	0.5366 (8)	0.8001 (9)	0.9194 (5)	0.0488 (16)	0.711 (3)
H12A	0.436403	0.856493	0.937277	0.059*	0.711 (3)
H12B	0.538695	0.718405	0.956886	0.059*	0.711 (3)
C12A	0.487 (2)	0.810 (3)	0.9387 (15)	0.0488 (16)	0.289 (3)
H12C	0.429367	0.895594	0.915378	0.059*	0.289 (3)
H12D	0.424472	0.775284	0.992104	0.059*	0.289 (3)
C13	0.2258 (3)	0.4428 (2)	0.62180 (19)	0.0331 (6)
H13A	0.331950	0.381395	0.638457	0.040*
H13B	0.173700	0.421408	0.573858	0.040*
C14	0.1071 (3)	0.4387 (2)	0.70441 (19)	0.0314 (6)
C15	0.1502 (3)	0.4549 (3)	0.7880 (2)	0.0342 (6)
C16	0.0425 (4)	0.4448 (3)	0.8643 (2)	0.0399 (7)
H16	0.073888	0.456059	0.919333	0.048*
C17	−0.1127 (4)	0.4178 (3)	0.8568 (2)	0.0457 (8)
C18	−0.1618 (4)	0.4023 (3)	0.7757 (2)	0.0454 (8)
H18	−0.267173	0.384825	0.771512	0.055*
C19	−0.0517 (4)	0.4132 (3)	0.7004 (2)	0.0384 (7)
H19	−0.084983	0.403225	0.645419	0.046*
C20	0.2268 (5)	0.8246 (3)	0.4185 (2)	0.0512 (8)
H20A	0.110276	0.866886	0.403297	0.077*
H20B	0.299196	0.881229	0.400279	0.077*
H20C	0.262868	0.759679	0.386793	0.077*
C21	0.1629 (4)	0.8670 (3)	0.5766 (2)	0.0467 (8)
H21A	0.048392	0.907845	0.556405	0.070*
H21B	0.160495	0.827654	0.640689	0.070*
H21C	0.231750	0.925979	0.566992	0.070*
C22	0.6884 (12)	0.8427 (11)	1.0361 (7)	0.041 (2)	0.711 (3)
C22A	0.739 (2)	0.851 (3)	1.0147 (13)	0.029 (4)	0.289 (3)
C23	0.8423 (15)	0.8687 (12)	1.0575 (6)	0.0435 (19)	0.711 (3)
H23	0.929089	0.874693	1.013396	0.052*	0.711 (3)
C23A	0.610 (3)	0.845 (3)	1.0846 (14)	0.037 (5)	0.289 (3)
H23A	0.505541	0.830371	1.074589	0.045*	0.289 (3)
C24	0.8635 (12)	0.8849 (11)	1.1436 (6)	0.0371 (17)	0.711 (3)
C24A	0.649 (2)	0.8603 (19)	1.1674 (11)	0.063 (6)	0.289 (3)
C25	0.7384 (15)	0.8727 (10)	1.2106 (5)	0.040 (2)	0.711 (3)
C25A	0.790 (3)	0.894 (3)	1.1855 (12)	0.064 (10)	0.289 (3)
C26	0.5892 (7)	0.8507 (6)	1.1889 (4)	0.0407 (14)	0.711 (3)
H26	0.502035	0.846991	1.233009	0.049*	0.711 (3)
C26A	0.917 (3)	0.895 (3)	1.1197 (14)	0.075 (9)	0.289 (3)
H26A	1.023960	0.904126	1.132290	0.090*	0.289 (3)
C27	0.5637 (15)	0.8337 (15)	1.1034 (8)	0.055 (3)	0.711 (3)
H27	0.462155	0.816303	1.091429	0.066*	0.711 (3)
C27A	0.884 (3)	0.882 (3)	1.0332 (15)	0.053 (6)	0.289 (3)
H27A	0.963970	0.894656	0.986141	0.064*	0.289 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0368 (4)	0.0621 (5)	0.0418 (4)	−0.0217 (3)	0.0008 (3)	−0.0175 (4)
O1	0.0324 (18)	0.037 (2)	0.049 (2)	−0.0176 (14)	0.0003 (15)	−0.0078 (16)
O1A	0.058 (4)	0.040 (3)	0.056 (4)	−0.016 (3)	−0.005 (3)	−0.009 (3)
N1	0.0250 (11)	0.0357 (13)	0.0356 (12)	−0.0075 (9)	0.0000 (9)	−0.0121 (10)
Cl2	0.0453 (5)	0.1067 (9)	0.0615 (6)	−0.0219 (5)	0.0171 (4)	−0.0011 (6)
O2	0.0243 (9)	0.0420 (11)	0.0417 (11)	0.0002 (8)	−0.0027 (8)	−0.0170 (9)
N2	0.062 (4)	0.080 (4)	0.0431 (19)	−0.039 (3)	0.000 (3)	−0.021 (3)
N2A	0.062 (4)	0.080 (4)	0.0431 (19)	−0.039 (3)	0.000 (3)	−0.021 (3)
C2	0.0256 (13)	0.0382 (15)	0.0282 (13)	−0.0053 (11)	0.0006 (10)	−0.0140 (11)
Cl3	0.0722 (8)	0.0638 (8)	0.0353 (6)	−0.0473 (6)	−0.0041 (5)	−0.0101 (5)
Cl3A	0.114 (4)	0.074 (3)	0.060 (2)	0.001 (2)	−0.005 (2)	−0.0113 (19)
N3	0.0232 (11)	0.0311 (12)	0.0327 (11)	−0.0040 (9)	−0.0020 (9)	−0.0088 (9)
Cl4	0.0639 (10)	0.0538 (9)	0.0351 (7)	−0.0097 (7)	−0.0044 (6)	−0.0050 (6)
Cl4A	0.145 (7)	0.102 (6)	0.102 (5)	0.041 (5)	−0.087 (5)	−0.062 (5)
O4	0.0255 (10)	0.0445 (12)	0.0616 (14)	−0.0051 (9)	−0.0100 (9)	−0.0076 (10)
N4	0.065 (3)	0.042 (4)	0.077 (5)	0.004 (3)	−0.043 (3)	−0.029 (3)
N4A	0.065 (3)	0.042 (4)	0.077 (5)	0.004 (3)	−0.043 (3)	−0.029 (3)
C4	0.0271 (13)	0.0360 (15)	0.0341 (14)	−0.0041 (11)	−0.0033 (11)	−0.0096 (12)
C5	0.0304 (14)	0.0345 (15)	0.0395 (15)	−0.0062 (11)	−0.0061 (12)	−0.0079 (12)
C6	0.0346 (15)	0.0518 (18)	0.0393 (16)	−0.0182 (13)	0.0075 (12)	−0.0177 (14)
C7	0.0360 (16)	0.0462 (18)	0.0493 (18)	−0.0184 (13)	0.0069 (13)	−0.0199 (15)
C8	0.118 (4)	0.055 (2)	0.056 (2)	−0.043 (2)	−0.038 (2)	−0.0042 (18)
C9	0.040 (3)	0.047 (3)	0.052 (3)	−0.015 (2)	−0.006 (2)	−0.017 (2)
C9A	0.040 (3)	0.047 (3)	0.052 (3)	−0.015 (2)	−0.006 (2)	−0.017 (2)
C10	0.067 (4)	0.079 (4)	0.055 (3)	−0.028 (3)	−0.015 (3)	−0.018 (3)
C10A	0.067 (4)	0.079 (4)	0.055 (3)	−0.028 (3)	−0.015 (3)	−0.018 (3)
C11	0.074 (3)	0.063 (4)	0.056 (4)	−0.021 (3)	−0.036 (3)	−0.012 (3)
C11A	0.074 (3)	0.063 (4)	0.056 (4)	−0.021 (3)	−0.036 (3)	−0.012 (3)
C12	0.048 (4)	0.050 (3)	0.054 (4)	−0.010 (4)	−0.012 (3)	−0.021 (3)
C12A	0.048 (4)	0.050 (3)	0.054 (4)	−0.010 (4)	−0.012 (3)	−0.021 (3)
C13	0.0308 (14)	0.0301 (14)	0.0400 (15)	−0.0055 (11)	−0.0012 (11)	−0.0130 (12)
C14	0.0277 (13)	0.0245 (13)	0.0402 (15)	−0.0027 (10)	−0.0026 (11)	−0.0070 (11)
C15	0.0262 (13)	0.0312 (14)	0.0428 (16)	−0.0041 (11)	−0.0010 (11)	−0.0072 (12)
C16	0.0354 (15)	0.0390 (16)	0.0408 (16)	−0.0047 (12)	0.0019 (13)	−0.0059 (13)
C17	0.0316 (15)	0.0462 (18)	0.0501 (18)	−0.0056 (13)	0.0069 (13)	−0.0003 (15)
C18	0.0254 (14)	0.0431 (17)	0.063 (2)	−0.0095 (12)	−0.0051 (14)	−0.0004 (15)
C19	0.0293 (14)	0.0340 (15)	0.0495 (17)	−0.0057 (12)	−0.0078 (12)	−0.0049 (13)
C20	0.061 (2)	0.0475 (19)	0.0430 (18)	−0.0187 (16)	−0.0145 (16)	0.0030 (15)
C21	0.0360 (16)	0.0416 (18)	0.063 (2)	−0.0013 (13)	−0.0036 (15)	−0.0199 (16)
C22	0.034 (6)	0.033 (3)	0.059 (6)	0.000 (4)	−0.013 (4)	−0.018 (5)
C22A	0.024 (10)	0.029 (6)	0.035 (8)	−0.004 (7)	−0.005 (6)	−0.008 (6)
C23	0.062 (5)	0.033 (4)	0.039 (4)	−0.018 (3)	−0.006 (3)	−0.008 (3)
C23A	0.035 (15)	0.047 (8)	0.031 (8)	−0.012 (11)	−0.006 (8)	−0.009 (7)
C24	0.044 (5)	0.029 (3)	0.041 (4)	−0.012 (4)	−0.008 (3)	−0.007 (3)
C24A	0.053 (13)	0.057 (9)	0.056 (10)	0.009 (9)	0.040 (10)	−0.006 (8)
C25	0.047 (6)	0.030 (3)	0.041 (3)	−0.008 (3)	−0.016 (3)	−0.004 (2)
C25A	0.06 (2)	0.042 (14)	0.10 (3)	0.012 (12)	−0.039 (17)	−0.041 (18)
C26	0.027 (3)	0.045 (3)	0.044 (4)	0.002 (3)	0.005 (2)	−0.013 (3)
C26A	0.09 (2)	0.049 (15)	0.09 (2)	0.013 (13)	−0.055 (15)	−0.031 (15)
C27	0.035 (5)	0.048 (6)	0.083 (7)	0.001 (4)	−0.017 (4)	−0.024 (6)
C27A	0.072 (15)	0.036 (9)	0.057 (13)	−0.022 (10)	−0.040 (11)	0.002 (11)

Geometric parameters (Å, º)

Cl1—C15	1.738 (3)	C10—H10B	0.9700
O1—H1	0.8200	C10A—H10C	0.9700
O1—C7	1.401 (4)	C10A—H10D	0.9700
O1A—H1A	0.8200	C11—H11A	0.9700
O1A—C7	1.336 (6)	C11—H11B	0.9700
N1—C2	1.349 (4)	C11—C12	1.575 (8)
N1—C5	1.468 (3)	C11A—H11C	0.9700
N1—C6	1.454 (3)	C11A—H11D	0.9700
Cl2—C17	1.738 (3)	C11A—C12A	1.548 (16)
O2—C2	1.211 (3)	C12—H12A	0.9700
N2—C8	1.405 (6)	C12—H12B	0.9700
N2—C9	1.434 (6)	C12A—H12C	0.9700
N2—C11	1.322 (7)	C12A—H12D	0.9700
N2A—C8	1.641 (16)	C13—H13A	0.9700
N2A—C9A	1.460 (15)	C13—H13B	0.9700
N2A—C11A	1.521 (15)	C13—C14	1.507 (4)
C2—N3	1.417 (3)	C14—C15	1.396 (4)
Cl3—C24	1.739 (8)	C14—C19	1.391 (4)
Cl3A—C24A	1.725 (12)	C15—C16	1.384 (4)
N3—C4	1.353 (3)	C16—H16	0.9300
N3—C13	1.455 (3)	C16—C17	1.381 (4)
Cl4—C25	1.732 (7)	C17—C18	1.375 (5)
Cl4A—C25A	1.732 (13)	C18—H18	0.9300
O4—C4	1.220 (3)	C18—C19	1.385 (4)
N4—C10	1.417 (9)	C19—H19	0.9300
N4—C12	1.447 (8)	C20—H20A	0.9600
N4—C22	1.540 (11)	C20—H20B	0.9600
N4A—C10A	1.532 (16)	C20—H20C	0.9600
N4A—C12A	1.521 (17)	C21—H21A	0.9600
N4A—C22A	1.34 (3)	C21—H21B	0.9600
C4—C5	1.525 (4)	C21—H21C	0.9600
C5—C20	1.526 (4)	C22—C23	1.423 (11)
C5—C21	1.528 (4)	C22—C27	1.375 (10)
C6—H6A	0.9700	C22A—C23A	1.421 (16)
C6—H6B	0.9700	C22A—C27A	1.368 (18)
C6—C7	1.525 (4)	C23—H23	0.9300
C7—H7A	0.9800	C23—C24	1.381 (12)
C7—H7B	0.9800	C23A—H23A	0.9300
C7—C8	1.470 (5)	C23A—C24A	1.37 (2)
C8—H8AA	0.9700	C24—C25	1.378 (11)
C8—H8AB	0.9700	C24A—C25A	1.357 (19)
C8—H8BC	0.9700	C25—C26	1.367 (10)
C8—H8BD	0.9700	C25A—C26A	1.370 (18)
C9—H9A	0.9700	C26—H26	0.9300
C9—H9B	0.9700	C26—C27	1.385 (13)
C9—C10	1.526 (7)	C26A—H26A	0.9300
C9A—H9AA	0.9700	C26A—C27A	1.40 (2)
C9A—H9AB	0.9700	C27—H27	0.9300
C9A—C10A	1.539 (15)	C27A—H27A	0.9300
C10—H10A	0.9700
C7—O1—H1	109.5	N2A—C11A—H11C	109.2
C7—O1A—H1A	109.5	N2A—C11A—H11D	109.2
C2—N1—C5	112.5 (2)	N2A—C11A—C12A	111.8 (14)
C2—N1—C6	122.6 (2)	H11C—C11A—H11D	107.9
C6—N1—C5	124.3 (2)	C12A—C11A—H11C	109.2
C8—N2—C9	122.1 (4)	C12A—C11A—H11D	109.2
C11—N2—C8	109.9 (5)	N4—C12—C11	110.4 (6)
C11—N2—C9	111.7 (5)	N4—C12—H12A	109.6
C9A—N2A—C8	99.8 (11)	N4—C12—H12B	109.6
C9A—N2A—C11A	96.9 (11)	C11—C12—H12A	109.6
C11A—N2A—C8	114.3 (11)	C11—C12—H12B	109.6
N1—C2—N3	106.9 (2)	H12A—C12—H12B	108.1
O2—C2—N1	129.0 (3)	N4A—C12A—C11A	103.1 (12)
O2—C2—N3	124.1 (3)	N4A—C12A—H12C	111.1
C2—N3—C13	124.2 (2)	N4A—C12A—H12D	111.1
C4—N3—C2	111.3 (2)	C11A—C12A—H12C	111.1
C4—N3—C13	124.5 (2)	C11A—C12A—H12D	111.1
C10—N4—C12	114.4 (5)	H12C—C12A—H12D	109.1
C10—N4—C22	123.4 (6)	N3—C13—H13A	108.9
C12—N4—C22	108.3 (6)	N3—C13—H13B	108.9
C12A—N4A—C10A	109.8 (16)	N3—C13—C14	113.5 (2)
C22A—N4A—C10A	91.7 (14)	H13A—C13—H13B	107.7
C22A—N4A—C12A	130.7 (19)	C14—C13—H13A	108.9
N3—C4—C5	107.9 (2)	C14—C13—H13B	108.9
O4—C4—N3	126.0 (3)	C15—C14—C13	123.3 (2)
O4—C4—C5	126.1 (3)	C19—C14—C13	119.8 (3)
N1—C5—C4	100.8 (2)	C19—C14—C15	116.8 (3)
N1—C5—C20	112.1 (2)	C14—C15—Cl1	120.7 (2)
N1—C5—C21	112.2 (2)	C16—C15—Cl1	117.0 (2)
C4—C5—C20	109.4 (2)	C16—C15—C14	122.3 (3)
C4—C5—C21	109.7 (2)	C15—C16—H16	120.8
C20—C5—C21	112.1 (3)	C17—C16—C15	118.4 (3)
N1—C6—H6A	108.4	C17—C16—H16	120.8
N1—C6—H6B	108.4	C16—C17—Cl2	118.3 (3)
N1—C6—C7	115.5 (2)	C18—C17—Cl2	120.1 (2)
H6A—C6—H6B	107.5	C18—C17—C16	121.5 (3)
C7—C6—H6A	108.4	C17—C18—H18	120.6
C7—C6—H6B	108.4	C17—C18—C19	118.8 (3)
O1—C7—C6	106.6 (3)	C19—C18—H18	120.6
O1—C7—H7A	105.2	C14—C19—H19	118.9
O1—C7—C8	121.5 (3)	C18—C19—C14	122.1 (3)
O1A—C7—C6	114.4 (4)	C18—C19—H19	118.9
O1A—C7—H7B	101.9	C5—C20—H20A	109.5
O1A—C7—C8	121.3 (4)	C5—C20—H20B	109.5
C6—C7—H7A	105.2	C5—C20—H20C	109.5
C6—C7—H7B	101.9	H20A—C20—H20B	109.5
C8—C7—C6	111.8 (3)	H20A—C20—H20C	109.5
C8—C7—H7A	105.2	H20B—C20—H20C	109.5
C8—C7—H7B	101.9	C5—C21—H21A	109.5
N2—C8—C7	122.1 (4)	C5—C21—H21B	109.5
N2—C8—H8AA	106.8	C5—C21—H21C	109.5
N2—C8—H8AB	106.8	H21A—C21—H21B	109.5
N2A—C8—H8BC	111.1	H21A—C21—H21C	109.5
N2A—C8—H8BD	111.1	H21B—C21—H21C	109.5
C7—C8—N2A	103.3 (6)	C23—C22—N4	111.0 (7)
C7—C8—H8AA	106.8	C27—C22—N4	130.9 (8)
C7—C8—H8AB	106.8	C27—C22—C23	118.0 (7)
C7—C8—H8BC	111.1	N4A—C22A—C23A	95.6 (16)
C7—C8—H8BD	111.1	N4A—C22A—C27A	145 (2)
H8AA—C8—H8AB	106.7	C27A—C22A—C23A	117.6 (15)
H8BC—C8—H8BD	109.1	C22—C23—H23	119.8
N2—C9—H9A	109.7	C24—C23—C22	120.3 (8)
N2—C9—H9B	109.7	C24—C23—H23	119.8
N2—C9—C10	109.9 (4)	C22A—C23A—H23A	121.7
H9A—C9—H9B	108.2	C24A—C23A—C22A	116.6 (16)
C10—C9—H9A	109.7	C24A—C23A—H23A	121.7
C10—C9—H9B	109.7	C23—C24—Cl3	118.3 (6)
N2A—C9A—H9AA	109.5	C25—C24—Cl3	121.1 (7)
N2A—C9A—H9AB	109.5	C25—C24—C23	120.6 (8)
N2A—C9A—C10A	110.8 (13)	C23A—C24A—Cl3A	114.9 (13)
H9AA—C9A—H9AB	108.1	C25A—C24A—Cl3A	118.7 (13)
C10A—C9A—H9AA	109.5	C25A—C24A—C23A	125.9 (13)
C10A—C9A—H9AB	109.5	C24—C25—Cl4	121.2 (7)
N4—C10—C9	114.1 (5)	C26—C25—Cl4	120.1 (6)
N4—C10—H10A	108.7	C26—C25—C24	118.8 (7)
N4—C10—H10B	108.7	C24A—C25A—Cl4A	120.8 (14)
C9—C10—H10A	108.7	C24A—C25A—C26A	117.0 (14)
C9—C10—H10B	108.7	C26A—C25A—Cl4A	121.5 (14)
H10A—C10—H10B	107.6	C25—C26—H26	118.9
N4A—C10A—C9A	100.6 (12)	C25—C26—C27	122.1 (7)
N4A—C10A—H10C	111.6	C27—C26—H26	118.9
N4A—C10A—H10D	111.6	C25A—C26A—H26A	120.6
C9A—C10A—H10C	111.6	C25A—C26A—C27A	118.8 (18)
C9A—C10A—H10D	111.6	C27A—C26A—H26A	120.6
H10C—C10A—H10D	109.4	C22—C27—C26	120.1 (9)
N2—C11—H11A	108.7	C22—C27—H27	120.0
N2—C11—H11B	108.7	C26—C27—H27	120.0
N2—C11—C12	114.4 (5)	C22A—C27A—C26A	123.0 (17)
H11A—C11—H11B	107.6	C22A—C27A—H27A	118.5
C12—C11—H11A	108.7	C26A—C27A—H27A	118.5
C12—C11—H11B	108.7
Cl1—C15—C16—C17	−179.8 (2)	C9—N2—C8—C7	−55.9 (8)
N1—C2—N3—C4	7.9 (3)	C9—N2—C11—C12	−58.7 (8)
N1—C2—N3—C13	−175.7 (2)	C9A—N2A—C8—C7	−111.6 (9)
N1—C6—C7—O1	−169.9 (3)	C9A—N2A—C11A—C12A	69.8 (16)
N1—C6—C7—O1A	−87.6 (4)	C10—N4—C12—C11	−42.3 (9)
N1—C6—C7—C8	55.2 (4)	C10—N4—C22—C23	38.1 (13)
Cl2—C17—C18—C19	−179.3 (2)	C10—N4—C22—C27	−145.3 (13)
O2—C2—N3—C4	−172.8 (3)	C10A—N4A—C12A—C11A	62 (2)
O2—C2—N3—C13	3.6 (4)	C10A—N4A—C22A—C23A	158 (2)
N2—C9—C10—N4	−52.1 (8)	C10A—N4A—C22A—C27A	−41 (5)
N2—C11—C12—N4	49.9 (9)	C11—N2—C8—C7	77.7 (7)
N2A—C9A—C10A—N4A	74.7 (16)	C11—N2—C9—C10	58.6 (8)
N2A—C11A—C12A—N4A	−66 (2)	C11A—N2A—C8—C7	146.2 (10)
C2—N1—C5—C4	4.0 (3)	C11A—N2A—C9A—C10A	−74.7 (15)
C2—N1—C5—C20	−112.2 (3)	C12—N4—C10—C9	46.3 (8)
C2—N1—C5—C21	120.6 (3)	C12—N4—C22—C23	175.7 (9)
C2—N1—C6—C7	−96.4 (3)	C12—N4—C22—C27	−7.7 (16)
C2—N3—C4—O4	175.2 (3)	C12A—N4A—C10A—C9A	−64.5 (18)
C2—N3—C4—C5	−5.3 (3)	C12A—N4A—C22A—C23A	40 (3)
C2—N3—C13—C14	119.2 (3)	C12A—N4A—C22A—C27A	−159 (4)
Cl3—C24—C25—Cl4	−1.3 (15)	C13—N3—C4—O4	−1.2 (4)
Cl3—C24—C25—C26	177.9 (8)	C13—N3—C4—C5	178.3 (2)
Cl3A—C24A—C25A—Cl4A	7 (3)	C13—C14—C15—Cl1	3.0 (4)
Cl3A—C24A—C25A—C26A	178 (2)	C13—C14—C15—C16	−176.8 (3)
N3—C4—C5—N1	0.9 (3)	C13—C14—C19—C18	176.7 (3)
N3—C4—C5—C20	119.2 (3)	C14—C15—C16—C17	0.0 (4)
N3—C4—C5—C21	−117.6 (3)	C15—C14—C19—C18	−1.0 (4)
N3—C13—C14—C15	−64.0 (3)	C15—C16—C17—Cl2	179.1 (2)
N3—C13—C14—C19	118.4 (3)	C15—C16—C17—C18	−0.7 (5)
Cl4—C25—C26—C27	−177.2 (10)	C16—C17—C18—C19	0.6 (5)
Cl4A—C25A—C26A—C27A	−179 (3)	C17—C18—C19—C14	0.3 (5)
O4—C4—C5—N1	−179.6 (3)	C19—C14—C15—Cl1	−179.4 (2)
O4—C4—C5—C20	−61.4 (4)	C19—C14—C15—C16	0.8 (4)
O4—C4—C5—C21	61.9 (4)	C22—N4—C10—C9	−178.4 (6)
N4—C22—C23—C24	176.7 (11)	C22—N4—C12—C11	175.9 (7)
N4—C22—C27—C26	−175.9 (11)	C22—C23—C24—Cl3	−179.4 (10)
N4A—C22A—C23A—C24A	163 (3)	C22—C23—C24—C25	2 (2)
N4A—C22A—C27A—C26A	−152 (4)	C22A—N4A—C10A—C9A	160.7 (17)
C4—N3—C13—C14	−64.8 (3)	C22A—N4A—C12A—C11A	172 (2)
C5—N1—C2—O2	173.5 (3)	C22A—C23A—C24A—Cl3A	180 (2)
C5—N1—C2—N3	−7.2 (3)	C22A—C23A—C24A—C25A	7 (5)
C5—N1—C6—C7	93.2 (3)	C23—C22—C27—C26	0 (2)
C6—N1—C2—O2	2.1 (4)	C23—C24—C25—Cl4	177.3 (10)
C6—N1—C2—N3	−178.6 (2)	C23—C24—C25—C26	−3.4 (18)
C6—N1—C5—C4	175.2 (2)	C23A—C22A—C27A—C26A	6 (5)
C6—N1—C5—C20	59.0 (3)	C23A—C24A—C25A—Cl4A	179 (2)
C6—N1—C5—C21	−68.1 (3)	C23A—C24A—C25A—C26A	−10 (5)
C6—C7—C8—N2	−178.9 (4)	C24—C25—C26—C27	3.6 (16)
C6—C7—C8—N2A	−156.2 (5)	C24A—C25A—C26A—C27A	11 (5)
C8—N2—C9—C10	−168.6 (5)	C25—C26—C27—C22	−2.1 (19)
C8—N2—C11—C12	162.6 (5)	C25A—C26A—C27A—C22A	−9 (5)
C8—N2A—C9A—C10A	169.1 (11)	C27—C22—C23—C24	0 (2)
C8—N2A—C11A—C12A	173.8 (12)	C27A—C22A—C23A—C24A	−5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4^i	0.82	2.12	2.916 (4)	163

Symmetry code: (i) x+1, y, z.