Crystallographic studies of piperazine derivatives of 3-methyl-5-spiro­fluorenehydantoin in search of structural features of P-gp inhibitors

5-Spiro­fluorenehydantoin derivatives show efflux modulating, cytotoxic and anti­proliferative effects in sensitive and resistant mouse T-lymphoma cells. In order to extend the knowledge available about the pharmacophoric features responsible for the glycoprotein P (P-gp) inhibitory properties of aryl­piperazine derivatives of 3-methyl-5-spiro­fluorenehydantoin, we have performed crystal structure analyses for 1-[3-(3′-methyl-2′,4′-dioxo­spiro­[fluorene-9,5′-imidazolidin]-1′-yl)prop­yl]-4-phenyl­piperazine-1,4-diium dichloride monohydrate, C₂₉H₃₂N₄O₂²⁺·2Cl⁻·H₂O (1), 3′-methyl-1′-{3-[4-(4-nitro­phen­yl)piperazin-1-yl]prop­yl}spiro­[fluorene-9,5′-imidazolidine]-2′,4′-dione, C₂₉H₂₉N₅O₄·H₂O (2), 3′-methyl-1′-{5-[4-(4-nitro­phen­yl)piperazin-1-yl]pent­yl}spiro­[fluorene-9,5′-imidazolidine]-2′,4′-dione, C₃₁H₃₃N₅O₄ (3), and 1-benzyl-4-[5-(3′-methyl-2′,4′-dioxo­spiro­[fluorene-9,5′-imidazolidin]-1′-yl)pent­yl]­piperazine-1,4-diium dichloride 0.613-hydrate, C₃₂H₃₈N₄O₂²⁺·2Cl⁻·0.613H₂O (4). Structure 3 is anhydrous but the other three structures crystallize with water present. The investigated com­pounds crystallize in the monoclinic crystal system, with the space group P2₁/n for 1 and 3, and P2₁/c for 2 and 4. The cations of salts 1 and 4 are doubly protonated, with the protons located on the N atoms of the piperazine rings. The packing of 1 and 4 in the crystals is dominated by inter­molecular N—H...Cl and O—H...Cl hydrogen bonds. In the crystal structure of 2, the inter­molecular inter­actions are dominated by O—H...O and O—H...N hydrogen bonds, while in 3, which is lacking in classic hydrogen-bond donors, it is C—H...O contacts that dominate. Additionally, we have performed induced-fit docking studies for the investigated com­pounds docked to the P-gp human homology model.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018) for (1), (4); CrysAlis PRO (Rigaku OD, 2015) for (2), (3). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (1), (4); CrysAlis PRO (Rigaku OD, 2015) for (2), (3). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (1), (4); CrysAlis PRO (Rigaku OD, 2015) for (2), (3). For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SIR2014 (Burla et al., 2015) and SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

1-[3-(3'-Methyl-2',4'-dioxospiro[fluorene-9,5'-imidazolidin]-1'-yl)propyl]-4-phenylpiperazine-1,4-diium dichloride monohydrate (1)

Crystal data

C29H32N4O2^2+·2Cl^−·H2O	F(000) = 1176
Mr = 557.5	Dx = 1.34 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 52853 reflections
a = 8.9645 (1) Å	θ = 2.6–76.2°
b = 33.8111 (1) Å	µ = 2.42 mm^−1
c = 9.2237 (1) Å	T = 100 K
β = 98.698 (1)°	Block, colourless
V = 2763.55 (4) Å^3	0.18 × 0.12 × 0.06 mm
Z = 4

Data collection

XtaLAB Synergy Dualflex HyPix diffractometer	5743 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5436 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
ω scans	θmax = 76.8°, θmin = 2.6°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −11→10
Tmin = 0.538, Tmax = 1	k = −42→42
82562 measured reflections	l = −11→11

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 1.4194P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
5743 reflections	Δρmax = 0.69 e Å^−3
352 parameters	Δρmin = −0.37 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C14	0.92416 (15)	0.16437 (4)	0.96487 (14)	0.0181 (3)
C15	0.84624 (15)	0.13821 (4)	1.04108 (15)	0.0208 (3)
H15	0.76369	0.123361	0.992094	0.025*
C16	0.89216 (17)	0.13418 (4)	1.19219 (16)	0.0235 (3)
H16	0.840179	0.116416	1.246804	0.028*
C17	1.01333 (17)	0.15596 (4)	1.26315 (15)	0.0247 (3)
H17	1.043028	0.152807	1.365804	0.03*
C18	1.09202 (16)	0.18234 (4)	1.18634 (15)	0.0225 (3)
H18	1.174393	0.197232	1.235382	0.027*
C19	1.04661 (15)	0.18625 (4)	1.03593 (15)	0.0191 (3)
C20	1.10968 (15)	0.21003 (4)	0.92608 (15)	0.0188 (3)
C21	1.23306 (16)	0.23540 (4)	0.94024 (16)	0.0223 (3)
H21	1.289624	0.240788	1.033786	0.027*
C22	1.27186 (16)	0.25276 (4)	0.81409 (17)	0.0245 (3)
H22	1.354979	0.270477	0.822336	0.029*
C23	1.19126 (16)	0.24465 (4)	0.67639 (16)	0.0233 (3)
H23	1.220821	0.256409	0.591607	0.028*
C24	1.06689 (16)	0.21927 (4)	0.66229 (15)	0.0203 (3)
H24	1.011147	0.21355	0.56865	0.024*
C25	1.02691 (15)	0.20265 (4)	0.78810 (15)	0.0182 (3)
C5	0.89401 (15)	0.17550 (4)	0.80305 (14)	0.0177 (3)
C4	0.74489 (15)	0.19889 (4)	0.76523 (14)	0.0185 (3)
N3	0.66566 (13)	0.18135 (3)	0.64444 (13)	0.0202 (2)
C2	0.74346 (15)	0.14874 (4)	0.59755 (15)	0.0194 (3)
N1	0.86996 (13)	0.14342 (3)	0.69669 (12)	0.0187 (2)
O4	0.70709 (11)	0.22761 (3)	0.82960 (11)	0.0235 (2)
C26	0.51580 (16)	0.19307 (4)	0.57351 (17)	0.0259 (3)
H26A	0.480176	0.215425	0.626584	0.039*
H26B	0.446078	0.170771	0.574288	0.039*
H26C	0.520378	0.200882	0.471965	0.039*
O2	0.70114 (11)	0.12952 (3)	0.48774 (11)	0.0242 (2)
C6	0.98429 (15)	0.11395 (4)	0.67694 (15)	0.0200 (3)
H6A	1.084605	0.123997	0.721269	0.024*
H6B	0.98577	0.110218	0.570709	0.024*
C7	0.95679 (15)	0.07389 (4)	0.74586 (15)	0.0206 (3)
H7A	1.042754	0.056039	0.738032	0.025*
H7B	0.950398	0.077575	0.851224	0.025*
C8	0.81165 (16)	0.05510 (4)	0.66982 (15)	0.0220 (3)
H8A	0.728114	0.074371	0.666956	0.026*
H8B	0.823019	0.048608	0.567403	0.026*
N2	0.77203 (13)	0.01816 (3)	0.74610 (13)	0.0194 (2)
C10	0.61729 (15)	0.00425 (4)	0.68391 (16)	0.0213 (3)
H10A	0.615485	−0.00368	0.580346	0.026*
H10B	0.544313	0.026127	0.686421	0.026*
C11	0.57137 (15)	−0.03058 (4)	0.77098 (16)	0.0219 (3)
H11A	0.564581	−0.021967	0.872365	0.026*
H11B	0.470446	−0.040036	0.725862	0.026*
N4	0.68333 (13)	−0.06389 (3)	0.77508 (13)	0.0192 (2)
C13	0.84061 (15)	−0.04964 (4)	0.82970 (16)	0.0208 (3)
H13A	0.913079	−0.071476	0.824124	0.025*
H13B	0.847725	−0.041546	0.933672	0.025*
C12	0.88168 (15)	−0.01493 (4)	0.73938 (16)	0.0210 (3)
H12A	0.985032	−0.005792	0.777774	0.025*
H12B	0.879759	−0.023281	0.636244	0.025*
C27	0.63582 (15)	−0.09757 (4)	0.85999 (15)	0.0199 (3)
C28	0.56547 (17)	−0.12877 (4)	0.78161 (16)	0.0251 (3)
H28	0.551822	−0.128805	0.677443	0.03*
C29	0.51484 (18)	−0.16021 (5)	0.85816 (18)	0.0299 (3)
H29	0.46628	−0.182038	0.805974	0.036*
C30	0.53466 (17)	−0.15993 (4)	1.00974 (17)	0.0277 (3)
H30	0.50114	−0.181735	1.06124	0.033*
C31	0.60319 (18)	−0.12799 (5)	1.08673 (17)	0.0293 (3)
H31	0.615575	−0.127776	1.190854	0.035*
C32	0.65391 (18)	−0.09620 (5)	1.01184 (16)	0.0272 (3)
H32	0.700006	−0.074011	1.063674	0.033*
O1W	0.77434 (15)	−0.00116 (4)	0.37870 (13)	0.0389 (3)
H2W	0.767082	0.007945	0.280568	0.058*
H1W	0.742038	−0.027502	0.391083	0.058*
Cl1	0.75787 (4)	0.03266 (2)	1.06444 (4)	0.02518 (10)
Cl2	0.67675 (4)	−0.08565 (2)	0.45311 (4)	0.02638 (10)
H2N	0.773 (2)	0.0243 (5)	0.847 (2)	0.031 (5)*
H4N	0.680 (2)	−0.0728 (6)	0.673 (2)	0.033 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.0195 (6)	0.0159 (6)	0.0192 (6)	0.0032 (5)	0.0036 (5)	0.0001 (5)
C15	0.0200 (6)	0.0184 (6)	0.0246 (7)	0.0014 (5)	0.0051 (5)	0.0007 (5)
C16	0.0277 (7)	0.0195 (6)	0.0250 (7)	0.0035 (5)	0.0100 (6)	0.0041 (5)
C17	0.0331 (8)	0.0230 (7)	0.0182 (6)	0.0052 (6)	0.0051 (6)	0.0014 (5)
C18	0.0251 (7)	0.0210 (6)	0.0206 (7)	0.0018 (5)	0.0011 (5)	−0.0020 (5)
C19	0.0213 (6)	0.0153 (6)	0.0208 (6)	0.0021 (5)	0.0038 (5)	−0.0003 (5)
C20	0.0204 (6)	0.0155 (6)	0.0205 (6)	0.0022 (5)	0.0034 (5)	0.0000 (5)
C21	0.0224 (7)	0.0193 (6)	0.0246 (7)	−0.0012 (5)	0.0019 (5)	−0.0020 (5)
C22	0.0224 (7)	0.0192 (6)	0.0325 (8)	−0.0027 (5)	0.0064 (6)	0.0013 (5)
C23	0.0236 (7)	0.0207 (6)	0.0269 (7)	0.0029 (5)	0.0082 (5)	0.0053 (5)
C24	0.0210 (6)	0.0197 (6)	0.0203 (6)	0.0036 (5)	0.0032 (5)	0.0021 (5)
C25	0.0177 (6)	0.0147 (6)	0.0222 (6)	0.0026 (5)	0.0035 (5)	0.0004 (5)
C5	0.0186 (6)	0.0153 (6)	0.0191 (6)	0.0008 (5)	0.0023 (5)	0.0000 (5)
C4	0.0192 (6)	0.0172 (6)	0.0196 (6)	−0.0006 (5)	0.0042 (5)	0.0031 (5)
N3	0.0179 (6)	0.0201 (5)	0.0220 (6)	0.0023 (4)	0.0008 (4)	0.0003 (4)
C2	0.0201 (6)	0.0187 (6)	0.0196 (6)	−0.0006 (5)	0.0038 (5)	0.0023 (5)
N1	0.0191 (5)	0.0158 (5)	0.0207 (5)	0.0008 (4)	0.0008 (4)	−0.0016 (4)
O4	0.0265 (5)	0.0197 (5)	0.0246 (5)	0.0047 (4)	0.0050 (4)	−0.0004 (4)
C26	0.0190 (7)	0.0268 (7)	0.0305 (8)	0.0038 (5)	−0.0007 (6)	0.0014 (6)
O2	0.0258 (5)	0.0245 (5)	0.0212 (5)	−0.0006 (4)	−0.0005 (4)	−0.0026 (4)
C6	0.0182 (6)	0.0171 (6)	0.0252 (7)	0.0013 (5)	0.0050 (5)	−0.0006 (5)
C7	0.0191 (6)	0.0181 (6)	0.0244 (7)	0.0017 (5)	0.0023 (5)	0.0008 (5)
C8	0.0229 (7)	0.0182 (6)	0.0242 (7)	−0.0007 (5)	0.0012 (5)	0.0039 (5)
N2	0.0170 (6)	0.0176 (5)	0.0230 (6)	0.0004 (4)	0.0011 (4)	0.0018 (4)
C10	0.0151 (6)	0.0201 (6)	0.0275 (7)	0.0014 (5)	−0.0003 (5)	0.0021 (5)
C11	0.0166 (6)	0.0197 (6)	0.0290 (7)	0.0016 (5)	0.0025 (5)	0.0016 (5)
N4	0.0176 (5)	0.0178 (5)	0.0219 (6)	−0.0002 (4)	0.0019 (4)	0.0007 (4)
C13	0.0161 (6)	0.0192 (6)	0.0263 (7)	0.0008 (5)	0.0004 (5)	0.0022 (5)
C12	0.0159 (6)	0.0191 (6)	0.0278 (7)	0.0011 (5)	0.0028 (5)	0.0017 (5)
C27	0.0175 (6)	0.0187 (6)	0.0231 (7)	0.0004 (5)	0.0018 (5)	0.0030 (5)
C28	0.0248 (7)	0.0247 (7)	0.0252 (7)	−0.0036 (5)	0.0023 (6)	−0.0012 (6)
C29	0.0306 (8)	0.0237 (7)	0.0358 (8)	−0.0070 (6)	0.0060 (6)	−0.0016 (6)
C30	0.0232 (7)	0.0248 (7)	0.0359 (8)	0.0010 (6)	0.0075 (6)	0.0079 (6)
C31	0.0271 (8)	0.0362 (8)	0.0243 (7)	−0.0017 (6)	0.0025 (6)	0.0062 (6)
C32	0.0287 (8)	0.0280 (7)	0.0241 (7)	−0.0055 (6)	0.0010 (6)	−0.0011 (6)
O1W	0.0441 (7)	0.0406 (7)	0.0321 (6)	−0.0012 (5)	0.0062 (5)	0.0050 (5)
Cl1	0.02299 (18)	0.02942 (18)	0.02331 (17)	−0.00030 (12)	0.00411 (13)	0.00027 (12)
Cl2	0.03159 (19)	0.02725 (18)	0.02142 (17)	0.00011 (13)	0.00765 (13)	−0.00322 (12)

Geometric parameters (Å, º)

C14—C15	1.3832 (19)	C6—H6B	0.99
C14—C19	1.4015 (19)	C7—C8	1.5207 (19)
C14—C5	1.5233 (18)	C7—H7A	0.99
C15—C16	1.399 (2)	C7—H7B	0.99
C15—H15	0.95	C8—N2	1.5023 (17)
C16—C17	1.391 (2)	C8—H8A	0.99
C16—H16	0.95	C8—H8B	0.99
C17—C18	1.395 (2)	N2—C10	1.4945 (17)
C17—H17	0.95	N2—C12	1.4966 (17)
C18—C19	1.3918 (19)	N2—H2N	0.95 (2)
C18—H18	0.95	C10—C11	1.5169 (19)
C19—C20	1.4718 (18)	C10—H10A	0.99
C20—C21	1.3902 (19)	C10—H10B	0.99
C20—C25	1.3953 (19)	C11—N4	1.5054 (17)
C21—C22	1.393 (2)	C11—H11A	0.99
C21—H21	0.95	C11—H11B	0.99
C22—C23	1.390 (2)	N4—C27	1.4808 (17)
C22—H22	0.95	N4—C13	1.5031 (17)
C23—C24	1.397 (2)	N4—H4N	0.98 (2)
C23—H23	0.95	C13—C12	1.5163 (18)
C24—C25	1.3844 (19)	C13—H13A	0.99
C24—H24	0.95	C13—H13B	0.99
C25—C5	1.5266 (18)	C12—H12A	0.99
C5—N1	1.4566 (16)	C12—H12B	0.99
C5—C4	1.5470 (18)	C27—C28	1.377 (2)
C4—O4	1.2129 (16)	C27—C32	1.386 (2)
C4—N3	1.3632 (18)	C28—C29	1.390 (2)
N3—C2	1.4072 (17)	C28—H28	0.95
N3—C26	1.4573 (17)	C29—C30	1.383 (2)
C2—O2	1.2148 (17)	C29—H29	0.95
C2—N1	1.3568 (18)	C30—C31	1.384 (2)
N1—C6	1.4605 (16)	C30—H30	0.95
C26—H26A	0.98	C31—C32	1.391 (2)
C26—H26B	0.98	C31—H31	0.95
C26—H26C	0.98	C32—H32	0.95
C6—C7	1.5320 (18)	O1W—H2W	0.9489
C6—H6A	0.99	O1W—H1W	0.9488
C15—C14—C19	121.33 (12)	C8—C7—H7A	109.4
C15—C14—C5	128.87 (12)	C6—C7—H7A	109.4
C19—C14—C5	109.77 (11)	C8—C7—H7B	109.4
C14—C15—C16	118.26 (13)	C6—C7—H7B	109.4
C14—C15—H15	120.9	H7A—C7—H7B	108
C16—C15—H15	120.9	N2—C8—C7	112.19 (11)
C17—C16—C15	120.55 (13)	N2—C8—H8A	109.2
C17—C16—H16	119.7	C7—C8—H8A	109.2
C15—C16—H16	119.7	N2—C8—H8B	109.2
C16—C17—C18	121.22 (13)	C7—C8—H8B	109.2
C16—C17—H17	119.4	H8A—C8—H8B	107.9
C18—C17—H17	119.4	C10—N2—C12	109.04 (10)
C19—C18—C17	118.22 (13)	C10—N2—C8	110.68 (10)
C19—C18—H18	120.9	C12—N2—C8	113.51 (11)
C17—C18—H18	120.9	C10—N2—H2N	108.3 (12)
C18—C19—C14	120.42 (13)	C12—N2—H2N	107.1 (11)
C18—C19—C20	130.79 (13)	C8—N2—H2N	108.0 (11)
C14—C19—C20	108.76 (12)	N2—C10—C11	110.58 (11)
C21—C20—C25	120.12 (12)	N2—C10—H10A	109.5
C21—C20—C19	130.96 (13)	C11—C10—H10A	109.5
C25—C20—C19	108.88 (12)	N2—C10—H10B	109.5
C20—C21—C22	118.49 (13)	C11—C10—H10B	109.5
C20—C21—H21	120.8	H10A—C10—H10B	108.1
C22—C21—H21	120.8	N4—C11—C10	111.15 (11)
C23—C22—C21	121.25 (13)	N4—C11—H11A	109.4
C23—C22—H22	119.4	C10—C11—H11A	109.4
C21—C22—H22	119.4	N4—C11—H11B	109.4
C22—C23—C24	120.22 (13)	C10—C11—H11B	109.4
C22—C23—H23	119.9	H11A—C11—H11B	108
C24—C23—H23	119.9	C27—N4—C13	113.55 (10)
C25—C24—C23	118.38 (13)	C27—N4—C11	110.17 (10)
C25—C24—H24	120.8	C13—N4—C11	110.89 (10)
C23—C24—H24	120.8	C27—N4—H4N	107.5 (11)
C24—C25—C20	121.51 (13)	C13—N4—H4N	108.2 (11)
C24—C25—C5	128.62 (12)	C11—N4—H4N	106.3 (11)
C20—C25—C5	109.86 (11)	N4—C13—C12	110.94 (11)
N1—C5—C14	117.53 (11)	N4—C13—H13A	109.5
N1—C5—C25	115.15 (11)	C12—C13—H13A	109.5
C14—C5—C25	102.23 (10)	N4—C13—H13B	109.5
N1—C5—C4	101.19 (10)	C12—C13—H13B	109.5
C14—C5—C4	111.50 (10)	H13A—C13—H13B	108
C25—C5—C4	109.38 (10)	N2—C12—C13	109.89 (11)
O4—C4—N3	126.79 (13)	N2—C12—H12A	109.7
O4—C4—C5	126.49 (12)	C13—C12—H12A	109.7
N3—C4—C5	106.71 (11)	N2—C12—H12B	109.7
C4—N3—C2	111.77 (11)	C13—C12—H12B	109.7
C4—N3—C26	125.43 (12)	H12A—C12—H12B	108.2
C2—N3—C26	122.75 (11)	C28—C27—C32	122.05 (13)
O2—C2—N1	127.93 (13)	C28—C27—N4	117.20 (12)
O2—C2—N3	124.65 (13)	C32—C27—N4	120.64 (12)
N1—C2—N3	107.42 (11)	C27—C28—C29	118.56 (14)
C2—N1—C5	112.25 (11)	C27—C28—H28	120.7
C2—N1—C6	122.49 (11)	C29—C28—H28	120.7
C5—N1—C6	123.85 (11)	C30—C29—C28	120.45 (14)
N3—C26—H26A	109.5	C30—C29—H29	119.8
N3—C26—H26B	109.5	C28—C29—H29	119.8
H26A—C26—H26B	109.5	C29—C30—C31	120.21 (14)
N3—C26—H26C	109.5	C29—C30—H30	119.9
H26A—C26—H26C	109.5	C31—C30—H30	119.9
H26B—C26—H26C	109.5	C30—C31—C32	120.08 (14)
N1—C6—C7	113.05 (11)	C30—C31—H31	120
N1—C6—H6A	109	C32—C31—H31	120
C7—C6—H6A	109	C27—C32—C31	118.62 (14)
N1—C6—H6B	109	C27—C32—H32	120.7
C7—C6—H6B	109	C31—C32—H32	120.7
H6A—C6—H6B	107.8	H2W—O1W—H1W	116.2
C8—C7—C6	110.98 (11)
C19—C14—C15—C16	0.35 (19)	C5—C4—N3—C2	0.52 (14)
C5—C14—C15—C16	−177.28 (12)	O4—C4—N3—C26	−2.9 (2)
C14—C15—C16—C17	−0.1 (2)	C5—C4—N3—C26	178.02 (12)
C15—C16—C17—C18	0.1 (2)	C4—N3—C2—O2	−175.58 (13)
C16—C17—C18—C19	−0.3 (2)	C26—N3—C2—O2	6.8 (2)
C17—C18—C19—C14	0.5 (2)	C4—N3—C2—N1	4.60 (15)
C17—C18—C19—C20	−177.31 (13)	C26—N3—C2—N1	−172.97 (12)
C15—C14—C19—C18	−0.6 (2)	O2—C2—N1—C5	171.99 (13)
C5—C14—C19—C18	177.48 (12)	N3—C2—N1—C5	−8.20 (15)
C15—C14—C19—C20	177.70 (12)	O2—C2—N1—C6	5.1 (2)
C5—C14—C19—C20	−4.26 (14)	N3—C2—N1—C6	−175.11 (11)
C18—C19—C20—C21	0.2 (2)	C14—C5—N1—C2	129.72 (12)
C14—C19—C20—C21	−177.82 (14)	C25—C5—N1—C2	−109.72 (13)
C18—C19—C20—C25	177.72 (14)	C4—C5—N1—C2	8.09 (14)
C14—C19—C20—C25	−0.29 (15)	C14—C5—N1—C6	−63.58 (16)
C25—C20—C21—C22	−0.5 (2)	C25—C5—N1—C6	56.99 (16)
C19—C20—C21—C22	176.77 (13)	C4—C5—N1—C6	174.79 (11)
C20—C21—C22—C23	−1.0 (2)	C2—N1—C6—C7	−91.18 (15)
C21—C22—C23—C24	1.2 (2)	C5—N1—C6—C7	103.44 (14)
C22—C23—C24—C25	0.0 (2)	N1—C6—C7—C8	64.84 (15)
C23—C24—C25—C20	−1.50 (19)	C6—C7—C8—N2	−173.22 (11)
C23—C24—C25—C5	177.56 (12)	C7—C8—N2—C10	170.67 (11)
C21—C20—C25—C24	1.8 (2)	C7—C8—N2—C12	−66.34 (15)
C19—C20—C25—C24	−176.06 (12)	C12—N2—C10—C11	60.15 (14)
C21—C20—C25—C5	−177.44 (12)	C8—N2—C10—C11	−174.31 (11)
C19—C20—C25—C5	4.72 (14)	N2—C10—C11—N4	−56.83 (15)
C15—C14—C5—N1	−48.36 (19)	C10—C11—N4—C27	−179.75 (11)
C19—C14—C5—N1	133.79 (12)	C10—C11—N4—C13	53.68 (15)
C15—C14—C5—C25	−175.47 (13)	C27—N4—C13—C12	−179.40 (11)
C19—C14—C5—C25	6.68 (13)	C11—N4—C13—C12	−54.72 (14)
C15—C14—C5—C4	67.77 (17)	C10—N2—C12—C13	−60.93 (14)
C19—C14—C5—C4	−110.08 (12)	C8—N2—C12—C13	175.18 (11)
C24—C25—C5—N1	45.36 (18)	N4—C13—C12—N2	58.67 (14)
C20—C25—C5—N1	−135.50 (12)	C13—N4—C27—C28	−134.47 (13)
C24—C25—C5—C14	173.98 (13)	C11—N4—C27—C28	100.48 (14)
C20—C25—C5—C14	−6.88 (13)	C13—N4—C27—C32	49.37 (17)
C24—C25—C5—C4	−67.74 (17)	C11—N4—C27—C32	−75.69 (16)
C20—C25—C5—C4	111.40 (12)	C32—C27—C28—C29	−1.7 (2)
N1—C5—C4—O4	175.98 (13)	N4—C27—C28—C29	−177.79 (13)
C14—C5—C4—O4	50.23 (17)	C27—C28—C29—C30	0.2 (2)
C25—C5—C4—O4	−62.10 (17)	C28—C29—C30—C31	1.0 (2)
N1—C5—C4—N3	−4.96 (13)	C29—C30—C31—C32	−0.7 (2)
C14—C5—C4—N3	−130.71 (11)	C28—C27—C32—C31	2.0 (2)
C25—C5—C4—N3	116.96 (12)	N4—C27—C32—C31	177.94 (13)
O4—C4—N3—C2	179.58 (13)	C30—C31—C32—C27	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cl1	0.95 (2)	2.05 (2)	2.999 (1)	174 (2)
N4—H4N···Cl2	0.98 (2)	2.07 (2)	3.051 (1)	174 (2)
C8—H8A···O2	0.99	2.48	3.103 (2)	121
C8—H8B···O1W	0.99	2.41	3.266 (2)	144
C10—H10A···O1W	0.99	2.51	3.338 (2)	141
C10—H10B···Cl2^i	0.99	2.98	3.887 (1)	153
C11—H11A···Cl1	0.99	2.94	3.650 (2)	130
C11—H11B···O1W^i	0.99	2.65	3.372 (2)	130
C12—H12A···Cl1^ii	0.99	2.69	3.508 (1)	140
C12—H12B···O1W	0.99	2.53	3.353 (2)	140
C13—H13B···Cl1	0.99	2.95	3.670 (1)	131
C28—H28···O2^i	0.95	2.53	3.176 (2)	125
C28—H28···Cl2	0.95	2.89	3.635 (2)	136
O1W—H2W···Cl1^iii	0.95	2.15	3.099 (1)	176
O1W—H1W···Cl2	0.95	2.15	3.095 (1)	172

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

3'-Methyl-1'-{3-[4-(4-nitrophenyl)piperazin-1-yl]propyl}spiro[fluorene-9,5'-\ imidazolidine]-2',4'-dione monohydrate (2)

Crystal data

C29H29N5O4·H2O	F(000) = 1120
Mr = 529.59	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12039 reflections
a = 21.7033 (5) Å	θ = 3.4–28.4°
b = 7.2190 (2) Å	µ = 0.10 mm^−1
c = 16.8210 (4) Å	T = 130 K
β = 103.464 (2)°	Plate, light yellow
V = 2563.02 (11) Å^3	0.66 × 0.39 × 0.02 mm
Z = 4

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	6229 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4715 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.6°, θmin = 2.9°
ω scans	h = −29→28
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −9→9
Tmin = 0.963, Tmax = 0.997	l = −22→22
34285 measured reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0474P)^2 + 1.8477P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6229 reflections	Δρmax = 0.31 e Å^−3
361 parameters	Δρmin = −0.31 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C25	0.93922 (8)	0.2454 (2)	0.58121 (10)	0.0222 (3)
C24	0.97090 (8)	0.3240 (3)	0.65422 (11)	0.0289 (4)
H24	0.951232	0.333553	0.698945	0.035*
C23	1.03215 (9)	0.3887 (3)	0.66075 (11)	0.0304 (4)
H23	1.054347	0.445481	0.710074	0.036*
C22	1.06124 (8)	0.3711 (3)	0.59579 (11)	0.0268 (4)
H22	1.103413	0.414244	0.601688	0.032*
C21	1.02982 (8)	0.2917 (2)	0.52252 (10)	0.0232 (3)
H21	1.049967	0.279697	0.478333	0.028*
C20	0.96816 (8)	0.2300 (2)	0.51535 (10)	0.0204 (3)
C19	0.92261 (8)	0.1466 (2)	0.44602 (10)	0.0204 (3)
C18	0.92729 (8)	0.1094 (2)	0.36665 (10)	0.0244 (4)
H18	0.965075	0.136307	0.349557	0.029*
C17	0.87522 (9)	0.0318 (3)	0.31284 (10)	0.0269 (4)
H17	0.877473	0.006958	0.258129	0.032*
C16	0.82003 (8)	−0.0100 (2)	0.33738 (10)	0.0257 (4)
H16	0.785076	−0.062769	0.29944	0.031*
C15	0.81561 (8)	0.0248 (2)	0.41715 (10)	0.0232 (3)
H15	0.778305	−0.005999	0.434644	0.028*
C14	0.86668 (8)	0.1053 (2)	0.47032 (9)	0.0206 (3)
C5	0.87269 (8)	0.1639 (2)	0.55889 (10)	0.0217 (3)
C4	0.86604 (8)	0.0014 (3)	0.61513 (10)	0.0238 (4)
C2	0.79243 (8)	0.2217 (3)	0.62804 (10)	0.0255 (4)
C26	0.79915 (9)	−0.0657 (3)	0.71382 (12)	0.0363 (5)
H26A	0.826015	−0.176105	0.725206	0.054*
H26B	0.754941	−0.103205	0.692943	0.054*
H26C	0.802918	0.005829	0.764257	0.054*
C6	0.81251 (8)	0.4756 (2)	0.53823 (11)	0.0258 (4)
H6A	0.854141	0.531785	0.538354	0.031*
H6B	0.792546	0.551197	0.574479	0.031*
C7	0.77102 (8)	0.4839 (2)	0.45158 (11)	0.0263 (4)
H7A	0.769807	0.612941	0.431339	0.032*
H7B	0.790069	0.405595	0.415316	0.032*
C8	0.70356 (8)	0.4183 (3)	0.44736 (11)	0.0266 (4)
H8A	0.704802	0.287771	0.465767	0.032*
H8B	0.685245	0.493428	0.485394	0.032*
C12	0.67480 (8)	0.2845 (3)	0.31055 (11)	0.0265 (4)
H12A	0.665945	0.162743	0.332544	0.032*
H12B	0.720112	0.287393	0.309004	0.032*
C13	0.63437 (8)	0.3069 (3)	0.22466 (11)	0.0285 (4)
H13A	0.648262	0.418745	0.1996	0.034*
H13B	0.640915	0.198575	0.191462	0.034*
C11	0.55172 (8)	0.4423 (3)	0.28655 (11)	0.0282 (4)
H11A	0.507667	0.418329	0.290717	0.034*
H11B	0.554529	0.573674	0.270877	0.034*
C10	0.59606 (8)	0.4097 (3)	0.36884 (11)	0.0265 (4)
H10A	0.5862	0.498555	0.408975	0.032*
H10B	0.589557	0.282977	0.387829	0.032*
C27	0.52397 (8)	0.3218 (2)	0.14778 (11)	0.0255 (4)
C32	0.54045 (9)	0.2488 (3)	0.07752 (11)	0.0310 (4)
H32	0.582479	0.206845	0.081016	0.037*
C31	0.49647 (10)	0.2377 (3)	0.00427 (12)	0.0331 (4)
H31	0.508206	0.187346	−0.04226	0.04*
C30	0.43560 (9)	0.2991 (3)	−0.00199 (11)	0.0313 (4)
C29	0.41760 (9)	0.3761 (3)	0.06469 (12)	0.0331 (4)
H29	0.37554	0.419488	0.05968	0.04*
C28	0.46140 (9)	0.3889 (3)	0.13823 (11)	0.0291 (4)
H28	0.449353	0.443992	0.183619	0.035*
N3	0.81923 (7)	0.0475 (2)	0.65325 (9)	0.0259 (3)
N1	0.82275 (6)	0.2884 (2)	0.57175 (8)	0.0229 (3)
N2	0.66220 (7)	0.4319 (2)	0.36474 (9)	0.0242 (3)
N4	0.56639 (7)	0.3236 (2)	0.22272 (9)	0.0257 (3)
N5	0.38947 (9)	0.2818 (3)	−0.07882 (11)	0.0412 (4)
O4	0.89677 (6)	−0.14016 (18)	0.62492 (8)	0.0308 (3)
O2	0.75032 (6)	0.2941 (2)	0.65303 (8)	0.0333 (3)
O3	0.40684 (8)	0.2162 (3)	−0.13807 (9)	0.0545 (4)
O1	0.33503 (8)	0.3325 (3)	−0.08277 (10)	0.0614 (5)
OW	0.67803 (8)	0.8013 (2)	0.30476 (10)	0.0461 (4)
H2W	0.6695 (15)	0.673 (2)	0.3251 (18)	0.092 (11)*
H1W	0.6549 (14)	0.798 (5)	0.2445 (8)	0.100 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C25	0.0184 (8)	0.0265 (9)	0.0218 (8)	0.0013 (6)	0.0047 (6)	0.0004 (7)
C24	0.0263 (9)	0.0393 (10)	0.0217 (8)	0.0016 (8)	0.0065 (7)	−0.0055 (7)
C23	0.0263 (9)	0.0360 (10)	0.0257 (9)	0.0002 (8)	−0.0005 (7)	−0.0065 (8)
C22	0.0184 (8)	0.0292 (9)	0.0312 (9)	−0.0003 (7)	0.0026 (7)	0.0014 (7)
C21	0.0217 (8)	0.0246 (8)	0.0245 (8)	0.0014 (7)	0.0078 (7)	0.0033 (7)
C20	0.0216 (8)	0.0206 (8)	0.0188 (8)	0.0016 (6)	0.0046 (6)	0.0015 (6)
C19	0.0222 (8)	0.0197 (8)	0.0197 (8)	−0.0003 (6)	0.0053 (6)	0.0019 (6)
C18	0.0265 (9)	0.0274 (9)	0.0207 (8)	−0.0010 (7)	0.0081 (7)	0.0016 (7)
C17	0.0330 (9)	0.0298 (9)	0.0179 (8)	−0.0002 (7)	0.0060 (7)	−0.0008 (7)
C16	0.0257 (9)	0.0251 (9)	0.0239 (8)	−0.0009 (7)	0.0007 (7)	−0.0035 (7)
C15	0.0213 (8)	0.0233 (8)	0.0253 (8)	−0.0007 (7)	0.0060 (6)	−0.0003 (7)
C14	0.0226 (8)	0.0221 (8)	0.0179 (7)	0.0016 (6)	0.0060 (6)	0.0012 (6)
C5	0.0196 (8)	0.0279 (9)	0.0182 (8)	0.0012 (6)	0.0055 (6)	−0.0007 (6)
C4	0.0218 (8)	0.0317 (9)	0.0176 (8)	−0.0012 (7)	0.0037 (6)	−0.0003 (7)
C2	0.0192 (8)	0.0374 (10)	0.0194 (8)	−0.0013 (7)	0.0032 (6)	−0.0029 (7)
C26	0.0287 (10)	0.0532 (13)	0.0295 (10)	0.0024 (9)	0.0118 (8)	0.0136 (9)
C6	0.0239 (9)	0.0239 (9)	0.0296 (9)	−0.0018 (7)	0.0062 (7)	−0.0031 (7)
C7	0.0251 (9)	0.0248 (9)	0.0287 (9)	−0.0011 (7)	0.0058 (7)	0.0030 (7)
C8	0.0248 (9)	0.0278 (9)	0.0276 (9)	−0.0001 (7)	0.0069 (7)	0.0006 (7)
C12	0.0206 (8)	0.0285 (9)	0.0309 (9)	0.0024 (7)	0.0075 (7)	0.0002 (7)
C13	0.0228 (9)	0.0347 (10)	0.0295 (9)	0.0019 (7)	0.0090 (7)	−0.0022 (8)
C11	0.0210 (9)	0.0329 (10)	0.0315 (9)	0.0023 (7)	0.0079 (7)	−0.0052 (8)
C10	0.0238 (9)	0.0271 (9)	0.0307 (9)	−0.0002 (7)	0.0102 (7)	−0.0027 (7)
C27	0.0263 (9)	0.0215 (8)	0.0299 (9)	−0.0032 (7)	0.0091 (7)	0.0020 (7)
C32	0.0265 (9)	0.0353 (10)	0.0325 (10)	−0.0003 (8)	0.0096 (8)	0.0001 (8)
C31	0.0396 (11)	0.0329 (10)	0.0290 (9)	−0.0038 (8)	0.0126 (8)	0.0013 (8)
C30	0.0350 (10)	0.0283 (9)	0.0284 (9)	−0.0022 (8)	0.0028 (8)	0.0066 (8)
C29	0.0279 (10)	0.0311 (10)	0.0388 (11)	0.0032 (8)	0.0047 (8)	0.0069 (8)
C28	0.0276 (9)	0.0286 (9)	0.0318 (9)	0.0019 (7)	0.0084 (7)	0.0011 (8)
N3	0.0211 (7)	0.0363 (8)	0.0217 (7)	0.0009 (6)	0.0075 (6)	0.0039 (6)
N1	0.0201 (7)	0.0274 (7)	0.0228 (7)	0.0012 (6)	0.0077 (5)	−0.0007 (6)
N2	0.0211 (7)	0.0259 (7)	0.0262 (7)	0.0014 (6)	0.0066 (6)	0.0001 (6)
N4	0.0212 (7)	0.0288 (8)	0.0282 (8)	0.0014 (6)	0.0078 (6)	−0.0032 (6)
N5	0.0436 (11)	0.0428 (10)	0.0338 (9)	−0.0016 (8)	0.0019 (8)	0.0096 (8)
O4	0.0339 (7)	0.0317 (7)	0.0277 (7)	0.0066 (6)	0.0092 (5)	0.0048 (5)
O2	0.0251 (7)	0.0458 (8)	0.0328 (7)	0.0053 (6)	0.0143 (5)	−0.0008 (6)
O3	0.0618 (11)	0.0663 (11)	0.0311 (8)	0.0026 (9)	0.0021 (7)	−0.0008 (8)
O1	0.0432 (10)	0.0851 (14)	0.0484 (10)	0.0067 (9)	−0.0048 (8)	0.0085 (9)
OW	0.0462 (9)	0.0401 (9)	0.0508 (10)	−0.0097 (7)	0.0085 (7)	0.0026 (7)

Geometric parameters (Å, º)

C25—C24	1.382 (2)	C6—H6B	0.99
C25—C20	1.399 (2)	C7—C8	1.525 (2)
C25—C5	1.523 (2)	C7—H7A	0.99
C24—C23	1.389 (3)	C7—H7B	0.99
C24—H24	0.95	C8—N2	1.472 (2)
C23—C22	1.389 (3)	C8—H8A	0.99
C23—H23	0.95	C8—H8B	0.99
C22—C21	1.386 (2)	C12—N2	1.467 (2)
C22—H22	0.95	C12—C13	1.514 (2)
C21—C20	1.389 (2)	C12—H12A	0.99
C21—H21	0.95	C12—H12B	0.99
C20—C19	1.471 (2)	C13—N4	1.473 (2)
C19—C18	1.389 (2)	C13—H13A	0.99
C19—C14	1.400 (2)	C13—H13B	0.99
C18—C17	1.391 (2)	C11—N4	1.466 (2)
C18—H18	0.95	C11—C10	1.509 (2)
C17—C16	1.388 (2)	C11—H11A	0.99
C17—H17	0.95	C11—H11B	0.99
C16—C15	1.390 (2)	C10—N2	1.462 (2)
C16—H16	0.95	C10—H10A	0.99
C15—C14	1.380 (2)	C10—H10B	0.99
C15—H15	0.95	C27—N4	1.377 (2)
C14—C5	1.525 (2)	C27—C32	1.414 (2)
C5—N1	1.462 (2)	C27—C28	1.415 (2)
C5—C4	1.535 (2)	C32—C31	1.374 (3)
C4—O4	1.210 (2)	C32—H32	0.95
C4—N3	1.363 (2)	C31—C30	1.374 (3)
C2—O2	1.210 (2)	C31—H31	0.95
C2—N1	1.361 (2)	C30—C29	1.387 (3)
C2—N3	1.408 (2)	C30—N5	1.444 (2)
C26—N3	1.450 (2)	C29—C28	1.377 (3)
C26—H26A	0.98	C29—H29	0.95
C26—H26B	0.98	C28—H28	0.95
C26—H26C	0.98	N5—O1	1.224 (2)
C6—N1	1.461 (2)	N5—O3	1.239 (2)
C6—C7	1.526 (2)	OW—H2W	1.019 (10)
C6—H6A	0.99	OW—H1W	1.021 (10)
C24—C25—C20	120.93 (16)	H7A—C7—H7B	107.9
C24—C25—C5	128.65 (15)	N2—C8—C7	113.02 (14)
C20—C25—C5	110.41 (14)	N2—C8—H8A	109
C25—C24—C23	118.50 (16)	C7—C8—H8A	109
C25—C24—H24	120.7	N2—C8—H8B	109
C23—C24—H24	120.7	C7—C8—H8B	109
C24—C23—C22	120.59 (16)	H8A—C8—H8B	107.8
C24—C23—H23	119.7	N2—C12—C13	111.41 (14)
C22—C23—H23	119.7	N2—C12—H12A	109.3
C21—C22—C23	121.18 (16)	C13—C12—H12A	109.3
C21—C22—H22	119.4	N2—C12—H12B	109.3
C23—C22—H22	119.4	C13—C12—H12B	109.3
C22—C21—C20	118.32 (15)	H12A—C12—H12B	108
C22—C21—H21	120.8	N4—C13—C12	112.63 (14)
C20—C21—H21	120.8	N4—C13—H13A	109.1
C21—C20—C25	120.46 (15)	C12—C13—H13A	109.1
C21—C20—C19	131.03 (15)	N4—C13—H13B	109.1
C25—C20—C19	108.50 (14)	C12—C13—H13B	109.1
C18—C19—C14	120.14 (15)	H13A—C13—H13B	107.8
C18—C19—C20	130.94 (15)	N4—C11—C10	112.32 (14)
C14—C19—C20	108.92 (14)	N4—C11—H11A	109.1
C19—C18—C17	118.25 (15)	C10—C11—H11A	109.1
C19—C18—H18	120.9	N4—C11—H11B	109.1
C17—C18—H18	120.9	C10—C11—H11B	109.1
C16—C17—C18	121.39 (15)	H11A—C11—H11B	107.9
C16—C17—H17	119.3	N2—C10—C11	111.29 (14)
C18—C17—H17	119.3	N2—C10—H10A	109.4
C17—C16—C15	120.39 (16)	C11—C10—H10A	109.4
C17—C16—H16	119.8	N2—C10—H10B	109.4
C15—C16—H16	119.8	C11—C10—H10B	109.4
C14—C15—C16	118.43 (15)	H10A—C10—H10B	108
C14—C15—H15	120.8	N4—C27—C32	121.54 (16)
C16—C15—H15	120.8	N4—C27—C28	121.34 (16)
C15—C14—C19	121.37 (15)	C32—C27—C28	117.09 (17)
C15—C14—C5	128.54 (15)	C31—C32—C27	120.88 (18)
C19—C14—C5	110.09 (14)	C31—C32—H32	119.6
N1—C5—C25	114.76 (14)	C27—C32—H32	119.6
N1—C5—C14	114.66 (13)	C32—C31—C30	120.30 (18)
C25—C5—C14	102.03 (12)	C32—C31—H31	119.8
N1—C5—C4	101.50 (12)	C30—C31—H31	119.8
C25—C5—C4	111.30 (13)	C31—C30—C29	120.94 (18)
C14—C5—C4	113.03 (14)	C31—C30—N5	119.64 (18)
O4—C4—N3	126.14 (16)	C29—C30—N5	119.42 (18)
O4—C4—C5	126.97 (15)	C28—C29—C30	119.21 (18)
N3—C4—C5	106.88 (14)	C28—C29—H29	120.4
O2—C2—N1	127.99 (18)	C30—C29—H29	120.4
O2—C2—N3	124.98 (16)	C29—C28—C27	121.52 (17)
N1—C2—N3	107.03 (14)	C29—C28—H28	119.2
N3—C26—H26A	109.5	C27—C28—H28	119.2
N3—C26—H26B	109.5	C4—N3—C2	112.17 (14)
H26A—C26—H26B	109.5	C4—N3—C26	124.86 (16)
N3—C26—H26C	109.5	C2—N3—C26	122.96 (15)
H26A—C26—H26C	109.5	C2—N1—C6	122.76 (14)
H26B—C26—H26C	109.5	C2—N1—C5	112.36 (14)
N1—C6—C7	114.07 (14)	C6—N1—C5	124.25 (13)
N1—C6—H6A	108.7	C10—N2—C12	106.08 (13)
C7—C6—H6A	108.7	C10—N2—C8	109.75 (13)
N1—C6—H6B	108.7	C12—N2—C8	112.16 (14)
C7—C6—H6B	108.7	C27—N4—C11	117.57 (14)
H6A—C6—H6B	107.6	C27—N4—C13	118.18 (14)
C8—C7—C6	112.27 (14)	C11—N4—C13	114.77 (14)
C8—C7—H7A	109.2	O1—N5—O3	122.78 (18)
C6—C7—H7A	109.2	O1—N5—C30	118.83 (18)
C8—C7—H7B	109.2	O3—N5—C30	118.39 (18)
C6—C7—H7B	109.2	H2W—OW—H1W	103 (3)
C20—C25—C24—C23	0.4 (3)	N4—C27—C32—C31	176.01 (17)
C5—C25—C24—C23	179.56 (17)	C28—C27—C32—C31	−2.4 (3)
C25—C24—C23—C22	−1.3 (3)	C27—C32—C31—C30	0.5 (3)
C24—C23—C22—C21	1.1 (3)	C32—C31—C30—C29	1.1 (3)
C23—C22—C21—C20	0.1 (3)	C32—C31—C30—N5	−178.29 (17)
C22—C21—C20—C25	−1.1 (2)	C31—C30—C29—C28	−0.7 (3)
C22—C21—C20—C19	177.90 (17)	N5—C30—C29—C28	178.70 (17)
C24—C25—C20—C21	0.8 (3)	C30—C29—C28—C27	−1.3 (3)
C5—C25—C20—C21	−178.50 (15)	N4—C27—C28—C29	−175.60 (17)
C24—C25—C20—C19	−178.38 (16)	C32—C27—C28—C29	2.8 (3)
C5—C25—C20—C19	2.33 (19)	O4—C4—N3—C2	−179.64 (17)
C21—C20—C19—C18	−2.0 (3)	C5—C4—N3—C2	1.17 (19)
C25—C20—C19—C18	177.09 (17)	O4—C4—N3—C26	1.3 (3)
C21—C20—C19—C14	178.96 (17)	C5—C4—N3—C26	−177.93 (16)
C25—C20—C19—C14	−1.99 (19)	O2—C2—N3—C4	−179.69 (17)
C14—C19—C18—C17	0.3 (3)	N1—C2—N3—C4	0.37 (19)
C20—C19—C18—C17	−178.68 (17)	O2—C2—N3—C26	−0.6 (3)
C19—C18—C17—C16	−0.8 (3)	N1—C2—N3—C26	179.48 (16)
C18—C17—C16—C15	−0.1 (3)	O2—C2—N1—C6	7.0 (3)
C17—C16—C15—C14	1.4 (3)	N3—C2—N1—C6	−173.10 (14)
C16—C15—C14—C19	−1.9 (3)	O2—C2—N1—C5	178.19 (17)
C16—C15—C14—C5	177.38 (16)	N3—C2—N1—C5	−1.87 (19)
C18—C19—C14—C15	1.0 (3)	C7—C6—N1—C2	−103.91 (18)
C20—C19—C14—C15	−179.80 (15)	C7—C6—N1—C5	85.91 (19)
C18—C19—C14—C5	−178.35 (15)	C25—C5—N1—C2	−117.69 (16)
C20—C19—C14—C5	0.85 (19)	C14—C5—N1—C2	124.64 (15)
C24—C25—C5—N1	54.4 (2)	C4—C5—N1—C2	2.44 (17)
C20—C25—C5—N1	−126.36 (15)	C25—C5—N1—C6	53.4 (2)
C24—C25—C5—C14	179.03 (18)	C14—C5—N1—C6	−64.3 (2)
C20—C25—C5—C14	−1.75 (18)	C4—C5—N1—C6	173.52 (14)
C24—C25—C5—C4	−60.1 (2)	C11—C10—N2—C12	−64.45 (18)
C20—C25—C5—C4	119.08 (15)	C11—C10—N2—C8	174.18 (15)
C15—C14—C5—N1	−54.1 (2)	C13—C12—N2—C10	63.31 (18)
C19—C14—C5—N1	125.18 (15)	C13—C12—N2—C8	−176.88 (14)
C15—C14—C5—C25	−178.80 (17)	C7—C8—N2—C10	−166.56 (15)
C19—C14—C5—C25	0.50 (18)	C7—C8—N2—C12	75.80 (18)
C15—C14—C5—C4	61.6 (2)	C32—C27—N4—C11	164.67 (16)
C19—C14—C5—C4	−119.12 (15)	C28—C27—N4—C11	−17.0 (2)
N1—C5—C4—O4	178.72 (17)	C32—C27—N4—C13	20.0 (2)
C25—C5—C4—O4	−58.7 (2)	C28—C27—N4—C13	−161.65 (16)
C14—C5—C4—O4	55.4 (2)	C10—C11—N4—C27	171.09 (15)
N1—C5—C4—N3	−2.10 (17)	C10—C11—N4—C13	−43.1 (2)
C25—C5—C4—N3	120.45 (15)	C12—C13—N4—C27	−172.22 (15)
C14—C5—C4—N3	−125.41 (15)	C12—C13—N4—C11	42.1 (2)
N1—C6—C7—C8	64.34 (19)	C31—C30—N5—O1	178.00 (19)
C6—C7—C8—N2	177.84 (14)	C29—C30—N5—O1	−1.4 (3)
N2—C12—C13—N4	−53.0 (2)	C31—C30—N5—O3	−2.1 (3)
N4—C11—C10—N2	55.2 (2)	C29—C30—N5—O3	178.54 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2^i	0.99	2.6	3.119 (2)	113
C26—H26B···O1^ii	0.98	2.4	3.300 (3)	152
OW—H2W···N2	1.02 (1)	1.88 (1)	2.900 (2)	175 (3)
OW—H1W···O3^iii	1.02 (1)	1.97 (1)	2.978 (2)	167 (3)

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

3'-Methyl-1'-{5-[4-(4-nitrophenyl)piperazin-1-yl]pentyl}spiro[fluorene-9,5'-imidazolidine]-2',4'-dione (3)

Crystal data

C31H33N5O4	F(000) = 1144
Mr = 539.62	Dx = 1.31 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6350 reflections
a = 8.8799 (2) Å	θ = 2.9–28.6°
b = 23.5550 (5) Å	µ = 0.09 mm^−1
c = 13.2498 (3) Å	T = 130 K
β = 99.072 (3)°	Irregular, orange
V = 2736.74 (11) Å^3	0.34 × 0.18 × 0.13 mm
Z = 4

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	6418 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	4351 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.050
Detector resolution: 10.3756 pixels mm^-1	θmax = 28.6°, θmin = 2.9°
ω scans	h = −11→11
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −30→27
Tmin = 0.982, Tmax = 0.991	l = −17→17
22381 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.7052P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
6418 reflections	Δρmax = 0.26 e Å^−3
362 parameters	Δρmin = −0.24 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C14	0.3359 (2)	0.34448 (7)	0.11271 (14)	0.0291 (4)
C15	0.2007 (2)	0.37384 (8)	0.11229 (15)	0.0362 (5)
H15	0.112576	0.355266	0.128413	0.043*
C16	0.1975 (3)	0.43136 (9)	0.08758 (16)	0.0444 (6)
H16	0.105508	0.452252	0.085468	0.053*
C17	0.3268 (3)	0.45819 (9)	0.06618 (17)	0.0501 (6)
H17	0.322784	0.497525	0.050181	0.06*
C18	0.4635 (3)	0.42871 (9)	0.06756 (17)	0.0470 (6)
H18	0.552047	0.447544	0.052788	0.056*
C19	0.4669 (2)	0.37136 (8)	0.09094 (15)	0.0355 (5)
C20	0.5924 (2)	0.32949 (8)	0.10053 (15)	0.0356 (5)
C21	0.7439 (3)	0.33353 (10)	0.08571 (18)	0.0473 (6)
H21	0.785157	0.368807	0.068512	0.057*
C22	0.8332 (3)	0.28502 (11)	0.09660 (19)	0.0511 (6)
H22	0.935639	0.287241	0.084369	0.061*
C23	0.7781 (2)	0.23360 (10)	0.12465 (17)	0.0447 (6)
H23	0.842138	0.201078	0.131893	0.054*
C24	0.6287 (2)	0.22963 (9)	0.14220 (16)	0.0361 (5)
H24	0.590044	0.194727	0.163342	0.043*
C25	0.5369 (2)	0.27727 (8)	0.12846 (15)	0.0303 (4)
C5	0.3695 (2)	0.28268 (7)	0.14026 (14)	0.0273 (4)
C4	0.3473 (2)	0.26910 (8)	0.25074 (15)	0.0307 (4)
C2	0.1975 (2)	0.20788 (8)	0.14417 (15)	0.0282 (4)
C26	0.1948 (3)	0.19863 (10)	0.33286 (17)	0.0460 (6)
H26A	0.241698	0.161026	0.34414	0.069*
H26B	0.083614	0.194682	0.319526	0.069*
H26C	0.224377	0.22215	0.393775	0.069*
C6	0.2264 (2)	0.24001 (8)	−0.02878 (14)	0.0288 (4)
H6A	0.205184	0.279231	−0.053914	0.035*
H6B	0.131622	0.217681	−0.047133	0.035*
C7	0.3495 (2)	0.21463 (8)	−0.08269 (15)	0.0320 (4)
H7A	0.441401	0.238923	−0.069119	0.038*
H7B	0.313298	0.215139	−0.157292	0.038*
C8	0.3938 (2)	0.15419 (7)	−0.05045 (15)	0.0307 (4)
H8A	0.305201	0.128882	−0.070896	0.037*
H8B	0.420345	0.152649	0.024921	0.037*
C9	0.5286 (2)	0.13262 (8)	−0.09812 (16)	0.0354 (5)
H9A	0.497898	0.13043	−0.173161	0.043*
H9B	0.613111	0.160331	−0.084023	0.043*
C9A	0.5859 (2)	0.07477 (8)	−0.05863 (15)	0.0310 (4)
H9AA	0.626742	0.077644	0.015159	0.037*
H9AB	0.499666	0.047666	−0.066738	0.037*
C10	0.8515 (2)	0.08126 (8)	−0.08112 (15)	0.0299 (4)
H10A	0.89198	0.07059	−0.009716	0.036*
H10B	0.836704	0.122926	−0.08361	0.036*
C11	0.9652 (2)	0.06473 (7)	−0.14973 (15)	0.0299 (4)
H11A	0.932516	0.081107	−0.218509	0.036*
H11B	1.065933	0.081084	−0.122028	0.036*
C13	0.8383 (2)	−0.02983 (8)	−0.16599 (16)	0.0311 (4)
H13A	0.863576	−0.069887	−0.14804	0.037*
H13B	0.785146	−0.028975	−0.2375	0.037*
C12	0.7322 (2)	−0.00752 (7)	−0.09674 (15)	0.0305 (4)
H12A	0.633925	−0.028124	−0.110531	0.037*
H12B	0.777387	−0.014327	−0.024572	0.037*
C27	1.0962 (2)	−0.01862 (7)	−0.20550 (14)	0.0262 (4)
C28	1.2204 (2)	0.01525 (8)	−0.22479 (15)	0.0303 (4)
H28	1.222437	0.054398	−0.207391	0.036*
C29	1.3384 (2)	−0.00736 (8)	−0.26829 (15)	0.0317 (4)
H29	1.420848	0.016095	−0.280203	0.038*
C30	1.3364 (2)	−0.06437 (8)	−0.29459 (15)	0.0297 (4)
C31	1.2158 (2)	−0.09866 (8)	−0.27797 (15)	0.0333 (5)
H31	1.214626	−0.137611	−0.296675	0.04*
C32	1.0977 (2)	−0.07651 (8)	−0.23449 (15)	0.0326 (4)
H32	1.015701	−0.100479	−0.2237	0.039*
N5	1.45954 (19)	−0.08869 (7)	−0.34018 (13)	0.0352 (4)
N3	0.24674 (19)	0.22548 (7)	0.24519 (12)	0.0320 (4)
N1	0.26660 (17)	0.24137 (6)	0.08259 (11)	0.0249 (3)
N2	0.70529 (17)	0.05309 (6)	−0.11303 (12)	0.0282 (4)
N4	0.98048 (17)	0.00288 (6)	−0.15902 (12)	0.0269 (3)
O4	0.40858 (17)	0.29298 (6)	0.32722 (11)	0.0410 (4)
O2	0.10659 (15)	0.16980 (5)	0.12005 (11)	0.0375 (4)
O1	1.55536 (16)	−0.05671 (6)	−0.36781 (12)	0.0433 (4)
O3	1.46347 (17)	−0.14080 (6)	−0.35078 (13)	0.0496 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.0330 (11)	0.0246 (9)	0.0288 (10)	−0.0022 (8)	0.0018 (9)	−0.0040 (7)
C15	0.0382 (12)	0.0298 (10)	0.0391 (12)	0.0006 (9)	0.0017 (10)	−0.0024 (8)
C16	0.0606 (15)	0.0320 (11)	0.0389 (12)	0.0128 (10)	0.0028 (11)	−0.0011 (9)
C17	0.0842 (19)	0.0262 (10)	0.0428 (13)	0.0008 (12)	0.0193 (13)	0.0043 (9)
C18	0.0687 (16)	0.0344 (11)	0.0420 (12)	−0.0147 (11)	0.0216 (12)	0.0009 (9)
C19	0.0456 (13)	0.0316 (10)	0.0306 (11)	−0.0083 (9)	0.0100 (10)	−0.0064 (8)
C20	0.0337 (11)	0.0396 (11)	0.0340 (11)	−0.0096 (9)	0.0072 (9)	−0.0099 (8)
C21	0.0394 (13)	0.0554 (14)	0.0501 (14)	−0.0199 (11)	0.0165 (11)	−0.0125 (11)
C22	0.0268 (11)	0.0731 (17)	0.0550 (15)	−0.0095 (12)	0.0119 (11)	−0.0186 (12)
C23	0.0262 (11)	0.0611 (14)	0.0451 (13)	0.0022 (10)	0.0006 (10)	−0.0139 (11)
C24	0.0245 (10)	0.0431 (11)	0.0383 (11)	0.0004 (9)	−0.0025 (9)	−0.0084 (9)
C25	0.0243 (10)	0.0342 (10)	0.0313 (10)	−0.0037 (8)	0.0011 (8)	−0.0075 (8)
C5	0.0239 (9)	0.0257 (9)	0.0310 (10)	−0.0011 (7)	0.0007 (8)	−0.0029 (7)
C4	0.0286 (10)	0.0303 (10)	0.0319 (10)	0.0082 (8)	0.0005 (9)	−0.0029 (8)
C2	0.0215 (9)	0.0265 (9)	0.0370 (11)	0.0058 (8)	0.0059 (8)	0.0000 (8)
C26	0.0473 (13)	0.0533 (13)	0.0418 (13)	0.0052 (11)	0.0207 (11)	0.0102 (10)
C6	0.0253 (10)	0.0280 (9)	0.0306 (10)	0.0023 (8)	−0.0032 (8)	−0.0029 (7)
C7	0.0345 (11)	0.0320 (10)	0.0293 (10)	0.0019 (9)	0.0041 (9)	−0.0014 (8)
C8	0.0281 (10)	0.0289 (10)	0.0354 (11)	−0.0003 (8)	0.0061 (9)	−0.0057 (8)
C9	0.0360 (11)	0.0361 (11)	0.0358 (11)	0.0043 (9)	0.0105 (10)	0.0005 (8)
C9A	0.0283 (10)	0.0336 (10)	0.0325 (10)	−0.0004 (8)	0.0093 (9)	−0.0012 (8)
C10	0.0319 (10)	0.0262 (9)	0.0320 (10)	−0.0009 (8)	0.0068 (9)	−0.0001 (7)
C11	0.0288 (10)	0.0246 (9)	0.0371 (11)	−0.0006 (8)	0.0080 (9)	0.0017 (7)
C13	0.0257 (10)	0.0256 (9)	0.0421 (11)	−0.0014 (8)	0.0061 (9)	−0.0005 (8)
C12	0.0258 (10)	0.0285 (10)	0.0378 (11)	−0.0019 (8)	0.0071 (9)	0.0039 (8)
C27	0.0238 (9)	0.0277 (9)	0.0261 (9)	0.0019 (7)	0.0011 (8)	0.0022 (7)
C28	0.0312 (10)	0.0247 (9)	0.0350 (10)	−0.0034 (8)	0.0052 (9)	−0.0013 (8)
C29	0.0273 (10)	0.0324 (10)	0.0358 (11)	−0.0049 (8)	0.0063 (9)	−0.0006 (8)
C30	0.0243 (9)	0.0327 (10)	0.0315 (10)	0.0013 (8)	0.0028 (8)	−0.0017 (8)
C31	0.0324 (11)	0.0253 (9)	0.0422 (12)	−0.0006 (8)	0.0058 (9)	−0.0031 (8)
C32	0.0268 (10)	0.0282 (10)	0.0432 (12)	−0.0033 (8)	0.0065 (9)	−0.0005 (8)
N5	0.0285 (9)	0.0352 (9)	0.0420 (10)	0.0000 (8)	0.0056 (8)	−0.0060 (7)
N3	0.0302 (9)	0.0344 (9)	0.0330 (9)	0.0025 (7)	0.0095 (7)	0.0027 (7)
N1	0.0217 (8)	0.0232 (7)	0.0291 (8)	−0.0016 (6)	0.0022 (7)	−0.0025 (6)
N2	0.0256 (8)	0.0268 (8)	0.0330 (9)	0.0020 (6)	0.0069 (7)	−0.0002 (6)
N4	0.0256 (8)	0.0224 (7)	0.0329 (8)	−0.0004 (6)	0.0048 (7)	0.0018 (6)
O4	0.0446 (9)	0.0410 (8)	0.0342 (8)	0.0083 (7)	−0.0039 (7)	−0.0066 (6)
O2	0.0267 (7)	0.0301 (7)	0.0560 (10)	−0.0053 (6)	0.0069 (7)	0.0011 (6)
O1	0.0326 (8)	0.0435 (8)	0.0568 (10)	−0.0093 (7)	0.0164 (7)	−0.0086 (7)
O3	0.0399 (9)	0.0353 (8)	0.0770 (12)	0.0010 (7)	0.0192 (9)	−0.0101 (7)

Geometric parameters (Å, º)

C14—C15	1.385 (3)	C7—H7A	0.99
C14—C19	1.394 (3)	C7—H7B	0.99
C14—C5	1.519 (2)	C8—C9	1.526 (3)
C15—C16	1.393 (3)	C8—H8A	0.99
C15—H15	0.95	C8—H8B	0.99
C16—C17	1.379 (3)	C9—C9A	1.519 (3)
C16—H16	0.95	C9—H9A	0.99
C17—C18	1.396 (3)	C9—H9B	0.99
C17—H17	0.95	C9A—N2	1.464 (2)
C18—C19	1.385 (3)	C9A—H9AA	0.99
C18—H18	0.95	C9A—H9AB	0.99
C19—C20	1.478 (3)	C10—N2	1.460 (2)
C20—C21	1.394 (3)	C10—C11	1.512 (2)
C20—C25	1.397 (3)	C10—H10A	0.99
C21—C22	1.385 (3)	C10—H10B	0.99
C21—H21	0.95	C11—N4	1.470 (2)
C22—C23	1.380 (3)	C11—H11A	0.99
C22—H22	0.95	C11—H11B	0.99
C23—C24	1.385 (3)	C13—N4	1.469 (2)
C23—H23	0.95	C13—C12	1.510 (3)
C24—C25	1.382 (3)	C13—H13A	0.99
C24—H24	0.95	C13—H13B	0.99
C25—C5	1.524 (3)	C12—N2	1.458 (2)
C5—N1	1.464 (2)	C12—H12A	0.99
C5—C4	1.541 (3)	C12—H12B	0.99
C4—O4	1.211 (2)	C27—N4	1.375 (2)
C4—N3	1.356 (2)	C27—C28	1.417 (2)
C2—O2	1.215 (2)	C27—C32	1.417 (3)
C2—N1	1.350 (2)	C28—C29	1.380 (3)
C2—N3	1.404 (2)	C28—H28	0.95
C26—N3	1.460 (2)	C29—C30	1.387 (3)
C26—H26A	0.98	C29—H29	0.95
C26—H26B	0.98	C30—C31	1.387 (3)
C26—H26C	0.98	C30—N5	1.448 (2)
C6—N1	1.463 (2)	C31—C32	1.376 (3)
C6—C7	1.519 (3)	C31—H31	0.95
C6—H6A	0.99	C32—H32	0.95
C6—H6B	0.99	N5—O1	1.234 (2)
C7—C8	1.520 (3)	N5—O3	1.236 (2)
C15—C14—C19	121.58 (18)	H8A—C8—H8B	107.9
C15—C14—C5	128.09 (17)	C9A—C9—C8	113.49 (16)
C19—C14—C5	110.26 (17)	C9A—C9—H9A	108.9
C14—C15—C16	118.2 (2)	C8—C9—H9A	108.9
C14—C15—H15	120.9	C9A—C9—H9B	108.9
C16—C15—H15	120.9	C8—C9—H9B	108.9
C17—C16—C15	120.5 (2)	H9A—C9—H9B	107.7
C17—C16—H16	119.8	N2—C9A—C9	111.89 (15)
C15—C16—H16	119.8	N2—C9A—H9AA	109.2
C16—C17—C18	121.33 (19)	C9—C9A—H9AA	109.2
C16—C17—H17	119.3	N2—C9A—H9AB	109.2
C18—C17—H17	119.3	C9—C9A—H9AB	109.2
C19—C18—C17	118.5 (2)	H9AA—C9A—H9AB	107.9
C19—C18—H18	120.8	N2—C10—C11	110.86 (15)
C17—C18—H18	120.8	N2—C10—H10A	109.5
C18—C19—C14	119.9 (2)	C11—C10—H10A	109.5
C18—C19—C20	131.3 (2)	N2—C10—H10B	109.5
C14—C19—C20	108.74 (16)	C11—C10—H10B	109.5
C21—C20—C25	119.1 (2)	H10A—C10—H10B	108.1
C21—C20—C19	132.35 (19)	N4—C11—C10	112.64 (15)
C25—C20—C19	108.54 (17)	N4—C11—H11A	109.1
C22—C21—C20	118.6 (2)	C10—C11—H11A	109.1
C22—C21—H21	120.7	N4—C11—H11B	109.1
C20—C21—H21	120.7	C10—C11—H11B	109.1
C23—C22—C21	122.1 (2)	H11A—C11—H11B	107.8
C23—C22—H22	119	N4—C13—C12	113.06 (15)
C21—C22—H22	119	N4—C13—H13A	109
C22—C23—C24	119.6 (2)	C12—C13—H13A	109
C22—C23—H23	120.2	N4—C13—H13B	109
C24—C23—H23	120.2	C12—C13—H13B	109
C25—C24—C23	118.9 (2)	H13A—C13—H13B	107.8
C25—C24—H24	120.5	N2—C12—C13	110.75 (15)
C23—C24—H24	120.5	N2—C12—H12A	109.5
C24—C25—C20	121.63 (18)	C13—C12—H12A	109.5
C24—C25—C5	128.24 (17)	N2—C12—H12B	109.5
C20—C25—C5	110.13 (16)	C13—C12—H12B	109.5
N1—C5—C14	115.38 (15)	H12A—C12—H12B	108.1
N1—C5—C25	115.41 (14)	N4—C27—C28	122.09 (16)
C14—C5—C25	102.30 (15)	N4—C27—C32	121.04 (16)
N1—C5—C4	101.26 (14)	C28—C27—C32	116.86 (16)
C14—C5—C4	112.18 (14)	C29—C28—C27	121.47 (17)
C25—C5—C4	110.66 (16)	C29—C28—H28	119.3
O4—C4—N3	127.08 (19)	C27—C28—H28	119.3
O4—C4—C5	126.22 (18)	C28—C29—C30	119.88 (17)
N3—C4—C5	106.70 (16)	C28—C29—H29	120.1
O2—C2—N1	128.22 (18)	C30—C29—H29	120.1
O2—C2—N3	124.26 (17)	C29—C30—C31	120.24 (17)
N1—C2—N3	107.50 (16)	C29—C30—N5	120.50 (17)
N3—C26—H26A	109.5	C31—C30—N5	119.26 (16)
N3—C26—H26B	109.5	C32—C31—C30	120.28 (17)
H26A—C26—H26B	109.5	C32—C31—H31	119.9
N3—C26—H26C	109.5	C30—C31—H31	119.9
H26A—C26—H26C	109.5	C31—C32—C27	121.26 (17)
H26B—C26—H26C	109.5	C31—C32—H32	119.4
N1—C6—C7	113.83 (15)	C27—C32—H32	119.4
N1—C6—H6A	108.8	O1—N5—O3	122.61 (16)
C7—C6—H6A	108.8	O1—N5—C30	118.90 (15)
N1—C6—H6B	108.8	O3—N5—C30	118.48 (16)
C7—C6—H6B	108.8	C4—N3—C2	112.28 (16)
H6A—C6—H6B	107.7	C4—N3—C26	124.97 (18)
C6—C7—C8	114.20 (16)	C2—N3—C26	122.74 (17)
C6—C7—H7A	108.7	C2—N1—C6	122.35 (15)
C8—C7—H7A	108.7	C2—N1—C5	112.24 (15)
C6—C7—H7B	108.7	C6—N1—C5	125.01 (14)
C8—C7—H7B	108.7	C12—N2—C10	106.54 (14)
H7A—C7—H7B	107.6	C12—N2—C9A	112.52 (14)
C7—C8—C9	112.38 (16)	C10—N2—C9A	112.24 (14)
C7—C8—H8A	109.1	C27—N4—C13	118.29 (14)
C9—C8—H8A	109.1	C27—N4—C11	119.20 (14)
C7—C8—H8B	109.1	C13—N4—C11	115.80 (14)
C9—C8—H8B	109.1
C19—C14—C15—C16	1.1 (3)	N4—C13—C12—N2	52.5 (2)
C5—C14—C15—C16	177.78 (18)	N4—C27—C28—C29	177.73 (17)
C14—C15—C16—C17	−1.2 (3)	C32—C27—C28—C29	−1.0 (3)
C15—C16—C17—C18	0.7 (3)	C27—C28—C29—C30	0.4 (3)
C16—C17—C18—C19	0.1 (3)	C28—C29—C30—C31	0.4 (3)
C17—C18—C19—C14	−0.2 (3)	C28—C29—C30—N5	−179.93 (17)
C17—C18—C19—C20	−178.6 (2)	C29—C30—C31—C32	−0.5 (3)
C15—C14—C19—C18	−0.4 (3)	N5—C30—C31—C32	179.82 (18)
C5—C14—C19—C18	−177.61 (18)	C30—C31—C32—C27	−0.2 (3)
C15—C14—C19—C20	178.30 (18)	N4—C27—C32—C31	−177.85 (18)
C5—C14—C19—C20	1.1 (2)	C28—C27—C32—C31	0.9 (3)
C18—C19—C20—C21	−2.7 (4)	C29—C30—N5—O1	−9.6 (3)
C14—C19—C20—C21	178.7 (2)	C31—C30—N5—O1	170.04 (18)
C18—C19—C20—C25	178.3 (2)	C29—C30—N5—O3	171.11 (19)
C14—C19—C20—C25	−0.2 (2)	C31—C30—N5—O3	−9.2 (3)
C25—C20—C21—C22	1.7 (3)	O4—C4—N3—C2	179.91 (18)
C19—C20—C21—C22	−177.1 (2)	C5—C4—N3—C2	−0.2 (2)
C20—C21—C22—C23	−2.1 (4)	O4—C4—N3—C26	−0.7 (3)
C21—C22—C23—C24	0.4 (4)	C5—C4—N3—C26	179.16 (17)
C22—C23—C24—C25	1.7 (3)	O2—C2—N3—C4	−179.46 (17)
C23—C24—C25—C20	−2.0 (3)	N1—C2—N3—C4	−0.7 (2)
C23—C24—C25—C5	178.22 (19)	O2—C2—N3—C26	1.2 (3)
C21—C20—C25—C24	0.3 (3)	N1—C2—N3—C26	179.94 (17)
C19—C20—C25—C24	179.40 (18)	O2—C2—N1—C6	7.0 (3)
C21—C20—C25—C5	−179.91 (18)	N3—C2—N1—C6	−171.71 (15)
C19—C20—C25—C5	−0.8 (2)	O2—C2—N1—C5	−179.95 (17)
C15—C14—C5—N1	55.4 (3)	N3—C2—N1—C5	1.34 (19)
C19—C14—C5—N1	−127.64 (17)	C7—C6—N1—C2	−110.23 (19)
C15—C14—C5—C25	−178.47 (19)	C7—C6—N1—C5	77.6 (2)
C19—C14—C5—C25	−1.5 (2)	C14—C5—N1—C2	−122.75 (17)
C15—C14—C5—C4	−59.9 (3)	C25—C5—N1—C2	118.14 (17)
C19—C14—C5—C4	117.10 (18)	C4—C5—N1—C2	−1.38 (18)
C24—C25—C5—N1	−52.7 (3)	C14—C5—N1—C6	50.1 (2)
C20—C25—C5—N1	127.51 (17)	C25—C5—N1—C6	−69.0 (2)
C24—C25—C5—C14	−178.84 (19)	C4—C5—N1—C6	171.46 (15)
C20—C25—C5—C14	1.4 (2)	C13—C12—N2—C10	−65.02 (19)
C24—C25—C5—C4	61.5 (2)	C13—C12—N2—C9A	171.57 (15)
C20—C25—C5—C4	−118.28 (17)	C11—C10—N2—C12	65.33 (19)
N1—C5—C4—O4	−179.19 (18)	C11—C10—N2—C9A	−171.09 (15)
C14—C5—C4—O4	−55.6 (3)	C9—C9A—N2—C12	−164.30 (16)
C25—C5—C4—O4	57.9 (2)	C9—C9A—N2—C10	75.5 (2)
N1—C5—C4—N3	0.90 (18)	C28—C27—N4—C13	164.17 (17)
C14—C5—C4—N3	124.48 (16)	C32—C27—N4—C13	−17.2 (3)
C25—C5—C4—N3	−121.96 (16)	C28—C27—N4—C11	14.1 (3)
N1—C6—C7—C8	58.2 (2)	C32—C27—N4—C11	−167.26 (17)
C6—C7—C8—C9	−174.09 (16)	C12—C13—N4—C27	169.61 (16)
C7—C8—C9—C9A	173.93 (17)	C12—C13—N4—C11	−39.3 (2)
C8—C9—C9A—N2	174.51 (16)	C10—C11—N4—C27	−169.86 (16)
N2—C10—C11—N4	−52.7 (2)	C10—C11—N4—C13	39.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O3^i	0.99	2.61	3.525 (2)	154
C6—H6B···O4^ii	0.99	2.39	3.242 (2)	144
C10—H10B···O4^iii	0.99	2.44	3.271 (2)	141
C13—H13A···O2^iv	0.99	2.39	3.374 (2)	172
C13—H13B···O1^v	0.99	2.54	3.427 (3)	149
C26—H26A···O3^vi	0.98	2.65	3.300 (3)	124
C32—H32···O2^iv	0.95	2.49	3.360 (2)	152

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

1-Benzyl-4-[5-(3'-methyl-2',4'-dioxospiro[fluorene-9,5'-imidazolidin]-1'-yl)pentyl]piperazine-1,4-diium dichloride 0.613-hydrate (4)

Crystal data

C32H38N4O2^2+·2Cl^−·0.613H2O	F(000) = 1257
Mr = 592.6	Dx = 1.31 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 10750 reflections
a = 11.8717 (1) Å	θ = 3.8–76.2°
b = 33.6944 (3) Å	µ = 2.25 mm^−1
c = 7.6888 (1) Å	T = 100 K
β = 102.259 (1)°	Needle, colourless
V = 3005.46 (5) Å^3	0.37 × 0.07 × 0.02 mm
Z = 4

Data collection

XtaLAB Synergy Dualflex HyPix diffractometer	6065 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	5306 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
ω scans	θmax = 76.5°, θmin = 2.6°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −14→14
Tmin = 0.377, Tmax = 1	k = −42→31
20267 measured reflections	l = −9→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 1.1028P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.004
6065 reflections	Δρmax = 0.28 e Å^−3
380 parameters	Δρmin = −0.45 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C33	0.32892 (14)	1.16097 (5)	0.2875 (2)	0.0271 (3)
H33	0.350878	1.142484	0.20747	0.033*
C32	0.38903 (15)	1.19638 (5)	0.3254 (2)	0.0298 (3)
H32	0.452833	1.201918	0.272737	0.036*
C31	0.35592 (15)	1.22364 (5)	0.4400 (2)	0.0289 (3)
H31	0.397661	1.247707	0.466835	0.035*
C30	0.26230 (15)	1.21591 (5)	0.5156 (2)	0.0283 (3)
H30	0.238921	1.234874	0.592291	0.034*
C29	0.20249 (13)	1.18035 (4)	0.4791 (2)	0.0250 (3)
H29	0.138286	1.175023	0.531139	0.03*
C28	0.23640 (13)	1.15256 (4)	0.36670 (19)	0.0222 (3)
C27	0.17423 (13)	1.11341 (4)	0.3343 (2)	0.0229 (3)
H27A	0.185739	1.101996	0.220687	0.027*
H27B	0.090575	1.117762	0.323697	0.027*
N4	0.21764 (10)	1.08445 (3)	0.48393 (16)	0.0184 (2)
C11	0.14856 (12)	1.04698 (4)	0.45654 (19)	0.0197 (3)
H11A	0.155595	1.03465	0.342458	0.024*
H11B	0.066253	1.05328	0.449442	0.024*
C10	0.18924 (12)	1.01792 (4)	0.6069 (2)	0.0205 (3)
H10A	0.178505	1.029675	0.720257	0.025*
H10B	0.142388	0.993405	0.585091	0.025*
N2	0.31387 (10)	1.00784 (3)	0.62160 (16)	0.0188 (2)
C12	0.38353 (13)	1.04543 (4)	0.6483 (2)	0.0219 (3)
H12A	0.465516	1.039031	0.653092	0.026*
H12B	0.378024	1.057498	0.763638	0.026*
C13	0.34240 (12)	1.07503 (4)	0.5006 (2)	0.0206 (3)
H13A	0.38822	1.099717	0.525531	0.025*
H13B	0.354577	1.063997	0.386703	0.025*
C9A	0.35951 (14)	0.98015 (4)	0.77499 (19)	0.0244 (3)
H9AA	0.342972	0.991816	0.885076	0.029*
H9AB	0.444302	0.978366	0.790573	0.029*
C9	0.30963 (14)	0.93838 (4)	0.75303 (19)	0.0225 (3)
H9A	0.225433	0.940259	0.706153	0.027*
H9B	0.321874	0.925672	0.871656	0.027*
C8	0.36150 (13)	0.91179 (4)	0.62934 (19)	0.0218 (3)
H8A	0.446378	0.911465	0.670473	0.026*
H8B	0.343651	0.923209	0.507949	0.026*
C7	0.31662 (13)	0.86917 (4)	0.62149 (19)	0.0226 (3)
H7A	0.361955	0.852761	0.554317	0.027*
H7B	0.329441	0.858501	0.744092	0.027*
C6	0.18887 (13)	0.86515 (4)	0.53464 (18)	0.0199 (3)
H6A	0.166362	0.836911	0.537998	0.024*
H6B	0.143213	0.880441	0.605346	0.024*
N1	0.15991 (10)	0.87894 (3)	0.35088 (14)	0.0163 (2)
C2	0.10642 (11)	0.91367 (4)	0.30108 (18)	0.0166 (3)
N3	0.08313 (10)	0.91519 (3)	0.11459 (15)	0.0177 (2)
C4	0.11035 (11)	0.88067 (4)	0.04195 (18)	0.0166 (3)
C5	0.17287 (12)	0.85478 (4)	0.19769 (17)	0.0159 (3)
O2	0.08047 (9)	0.93980 (3)	0.39552 (13)	0.0213 (2)
C26	0.02922 (13)	0.94931 (4)	0.0161 (2)	0.0239 (3)
H26A	−0.053229	0.949492	0.016805	0.036*
H26B	0.039394	0.947845	−0.106903	0.036*
H26C	0.065035	0.973659	0.071878	0.036*
O4	0.09308 (9)	0.87246 (3)	−0.11499 (13)	0.0219 (2)
C25	0.12762 (12)	0.81250 (4)	0.20123 (17)	0.0170 (3)
C24	0.01922 (13)	0.80023 (4)	0.21727 (19)	0.0213 (3)
H24	−0.040878	0.818838	0.217436	0.026*
C23	0.00094 (14)	0.75961 (4)	0.2332 (2)	0.0250 (3)
H23	−0.072607	0.750438	0.245666	0.03*
C22	0.08858 (14)	0.73230 (4)	0.2312 (2)	0.0246 (3)
H22	0.074593	0.704824	0.244612	0.029*
C21	0.19640 (13)	0.74482 (4)	0.2099 (2)	0.0229 (3)
H21	0.255712	0.726138	0.205769	0.027*
C20	0.21564 (12)	0.78529 (4)	0.19469 (18)	0.0183 (3)
C19	0.31943 (12)	0.80720 (4)	0.17535 (18)	0.0184 (3)
C18	0.42659 (13)	0.79417 (4)	0.1537 (2)	0.0255 (3)
H18	0.442753	0.766606	0.15006	0.031*
C17	0.50998 (13)	0.82220 (5)	0.1374 (2)	0.0261 (3)
H17	0.58342	0.813573	0.12201	0.031*
C16	0.48735 (13)	0.86259 (4)	0.14337 (19)	0.0214 (3)
H16	0.545169	0.88126	0.131337	0.026*
C15	0.38025 (12)	0.87591 (4)	0.16691 (18)	0.0180 (3)
H15	0.364688	0.903472	0.173054	0.022*
C14	0.29741 (12)	0.84796 (4)	0.18104 (17)	0.0160 (3)
O1W	0.37714 (16)	1.06536 (5)	0.0761 (2)	0.0266 (6)	0.613 (4)
H1B	0.316506	1.078778	0.009816	0.04*	0.613 (4)
H1A	0.351891	1.041625	0.094576	0.04*	0.613 (4)
Cl1	0.32050 (3)	0.98513 (2)	0.23450 (4)	0.02132 (9)
Cl2	0.18713 (3)	1.11279 (2)	0.84368 (5)	0.02660 (10)
H4N	0.2053 (16)	1.0972 (5)	0.596 (3)	0.026 (4)*
H2N	0.3219 (16)	0.9961 (5)	0.512 (3)	0.027 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C33	0.0317 (8)	0.0231 (7)	0.0286 (8)	−0.0003 (6)	0.0107 (6)	0.0004 (6)
C32	0.0311 (8)	0.0257 (8)	0.0345 (8)	−0.0037 (6)	0.0116 (7)	0.0040 (6)
C31	0.0345 (9)	0.0193 (7)	0.0320 (8)	−0.0042 (6)	0.0052 (7)	0.0031 (6)
C30	0.0340 (9)	0.0202 (7)	0.0305 (8)	0.0033 (6)	0.0061 (7)	−0.0014 (6)
C29	0.0234 (7)	0.0224 (7)	0.0296 (8)	0.0025 (6)	0.0062 (6)	0.0027 (6)
C28	0.0222 (7)	0.0196 (7)	0.0230 (7)	0.0014 (5)	0.0006 (6)	0.0038 (5)
C27	0.0223 (7)	0.0215 (7)	0.0235 (7)	0.0001 (6)	0.0018 (6)	0.0016 (6)
N4	0.0170 (6)	0.0158 (5)	0.0224 (6)	−0.0011 (4)	0.0040 (5)	−0.0020 (5)
C11	0.0162 (6)	0.0170 (6)	0.0259 (7)	−0.0020 (5)	0.0042 (5)	−0.0047 (5)
C10	0.0202 (7)	0.0175 (6)	0.0250 (7)	−0.0033 (5)	0.0073 (6)	−0.0036 (5)
N2	0.0208 (6)	0.0152 (5)	0.0199 (6)	−0.0013 (4)	0.0029 (5)	−0.0009 (4)
C12	0.0199 (7)	0.0170 (7)	0.0269 (7)	−0.0041 (5)	0.0008 (6)	−0.0013 (5)
C13	0.0164 (7)	0.0181 (7)	0.0271 (7)	−0.0019 (5)	0.0045 (5)	0.0000 (5)
C9A	0.0325 (8)	0.0195 (7)	0.0186 (7)	−0.0021 (6)	−0.0005 (6)	0.0007 (5)
C9	0.0316 (8)	0.0170 (7)	0.0185 (7)	−0.0015 (6)	0.0043 (6)	0.0015 (5)
C8	0.0224 (7)	0.0212 (7)	0.0210 (7)	0.0000 (5)	0.0025 (6)	−0.0001 (5)
C7	0.0307 (8)	0.0176 (7)	0.0178 (7)	0.0043 (6)	0.0016 (6)	0.0012 (5)
C6	0.0306 (8)	0.0146 (6)	0.0152 (6)	−0.0022 (5)	0.0065 (6)	0.0004 (5)
N1	0.0222 (6)	0.0128 (5)	0.0141 (5)	0.0018 (4)	0.0045 (4)	−0.0008 (4)
C2	0.0151 (6)	0.0144 (6)	0.0206 (6)	−0.0015 (5)	0.0044 (5)	−0.0010 (5)
N3	0.0191 (6)	0.0142 (5)	0.0188 (6)	0.0022 (4)	0.0017 (4)	0.0016 (4)
C4	0.0150 (6)	0.0163 (6)	0.0186 (6)	−0.0006 (5)	0.0042 (5)	0.0014 (5)
C5	0.0196 (6)	0.0130 (6)	0.0150 (6)	0.0007 (5)	0.0034 (5)	−0.0007 (5)
O2	0.0221 (5)	0.0168 (5)	0.0256 (5)	0.0020 (4)	0.0061 (4)	−0.0060 (4)
C26	0.0254 (7)	0.0164 (6)	0.0270 (7)	0.0050 (6)	−0.0008 (6)	0.0038 (6)
O4	0.0240 (5)	0.0250 (5)	0.0161 (5)	0.0026 (4)	0.0029 (4)	0.0002 (4)
C25	0.0218 (7)	0.0134 (6)	0.0158 (6)	−0.0008 (5)	0.0043 (5)	−0.0013 (5)
C24	0.0222 (7)	0.0199 (7)	0.0227 (7)	0.0003 (5)	0.0067 (6)	−0.0036 (5)
C23	0.0266 (8)	0.0237 (7)	0.0266 (8)	−0.0082 (6)	0.0097 (6)	−0.0054 (6)
C22	0.0338 (8)	0.0151 (6)	0.0257 (8)	−0.0060 (6)	0.0084 (6)	−0.0032 (5)
C21	0.0287 (8)	0.0138 (6)	0.0263 (7)	0.0007 (5)	0.0062 (6)	−0.0013 (5)
C20	0.0212 (7)	0.0149 (6)	0.0186 (6)	0.0004 (5)	0.0036 (5)	−0.0004 (5)
C19	0.0207 (7)	0.0151 (6)	0.0190 (6)	0.0008 (5)	0.0032 (5)	−0.0002 (5)
C18	0.0230 (7)	0.0159 (7)	0.0378 (9)	0.0046 (5)	0.0072 (6)	−0.0009 (6)
C17	0.0185 (7)	0.0251 (7)	0.0352 (8)	0.0027 (6)	0.0070 (6)	−0.0034 (6)
C16	0.0202 (7)	0.0215 (7)	0.0223 (7)	−0.0041 (5)	0.0042 (5)	−0.0021 (5)
C15	0.0231 (7)	0.0148 (6)	0.0158 (6)	−0.0005 (5)	0.0032 (5)	−0.0009 (5)
C14	0.0185 (6)	0.0145 (6)	0.0146 (6)	0.0014 (5)	0.0024 (5)	−0.0002 (5)
O1W	0.0281 (10)	0.0238 (10)	0.0265 (10)	−0.0019 (7)	0.0028 (7)	0.0029 (7)
Cl1	0.02535 (17)	0.01952 (16)	0.01900 (16)	0.00307 (12)	0.00451 (13)	−0.00233 (12)
Cl2	0.0322 (2)	0.02407 (18)	0.02554 (18)	−0.00226 (14)	0.01062 (14)	−0.00571 (13)

Geometric parameters (Å, º)

C33—C32	1.389 (2)	C7—H7A	0.99
C33—C28	1.394 (2)	C7—H7B	0.99
C33—H33	0.95	C6—N1	1.4575 (17)
C32—C31	1.387 (2)	C6—H6A	0.99
C32—H32	0.95	C6—H6B	0.99
C31—C30	1.384 (2)	N1—C2	1.3474 (17)
C31—H31	0.95	N1—C5	1.4664 (16)
C30—C29	1.391 (2)	C2—O2	1.2218 (17)
C30—H30	0.95	C2—N3	1.4025 (18)
C29—C28	1.391 (2)	N3—C4	1.3587 (17)
C29—H29	0.95	N3—C26	1.4484 (17)
C28—C27	1.506 (2)	C4—O4	1.2123 (17)
C27—N4	1.5132 (18)	C4—C5	1.5389 (18)
C27—H27A	0.99	C5—C25	1.5249 (18)
C27—H27B	0.99	C5—C14	1.5283 (19)
N4—C13	1.4934 (18)	C26—H26A	0.98
N4—C11	1.4960 (17)	C26—H26B	0.98
N4—H4N	1.004 (19)	C26—H26C	0.98
C11—C10	1.514 (2)	C25—C24	1.382 (2)
C11—H11A	0.99	C25—C20	1.3990 (19)
C11—H11B	0.99	C24—C23	1.395 (2)
C10—N2	1.4988 (18)	C24—H24	0.95
C10—H10A	0.99	C23—C22	1.391 (2)
C10—H10B	0.99	C23—H23	0.95
N2—C12	1.5029 (17)	C22—C21	1.390 (2)
N2—C9A	1.5111 (18)	C22—H22	0.95
N2—H2N	0.95 (2)	C21—C20	1.3915 (19)
C12—C13	1.512 (2)	C21—H21	0.95
C12—H12A	0.99	C20—C19	1.4707 (19)
C12—H12B	0.99	C19—C18	1.389 (2)
C13—H13A	0.99	C19—C14	1.4007 (19)
C13—H13B	0.99	C18—C17	1.393 (2)
C9A—C9	1.5223 (19)	C18—H18	0.95
C9A—H9AA	0.99	C17—C16	1.390 (2)
C9A—H9AB	0.99	C17—H17	0.95
C9—C8	1.528 (2)	C16—C15	1.396 (2)
C9—H9A	0.99	C16—H16	0.95
C9—H9B	0.99	C15—C14	1.3824 (19)
C8—C7	1.528 (2)	C15—H15	0.95
C8—H8A	0.99	O1W—H1B	0.909
C8—H8B	0.99	O1W—H1A	0.8762
C7—C6	1.528 (2)
C32—C33—C28	120.04 (15)	C7—C8—H8B	109
C32—C33—H33	120	H8A—C8—H8B	107.8
C28—C33—H33	120	C6—C7—C8	113.95 (12)
C31—C32—C33	119.99 (15)	C6—C7—H7A	108.8
C31—C32—H32	120	C8—C7—H7A	108.8
C33—C32—H32	120	C6—C7—H7B	108.8
C30—C31—C32	120.25 (15)	C8—C7—H7B	108.8
C30—C31—H31	119.9	H7A—C7—H7B	107.7
C32—C31—H31	119.9	N1—C6—C7	113.79 (12)
C31—C30—C29	119.91 (15)	N1—C6—H6A	108.8
C31—C30—H30	120	C7—C6—H6A	108.8
C29—C30—H30	120	N1—C6—H6B	108.8
C28—C29—C30	120.18 (15)	C7—C6—H6B	108.8
C28—C29—H29	119.9	H6A—C6—H6B	107.7
C30—C29—H29	119.9	C2—N1—C6	123.53 (11)
C29—C28—C33	119.60 (14)	C2—N1—C5	112.16 (11)
C29—C28—C27	119.74 (14)	C6—N1—C5	123.93 (11)
C33—C28—C27	120.65 (14)	O2—C2—N1	128.33 (13)
C28—C27—N4	111.29 (12)	O2—C2—N3	124.15 (12)
C28—C27—H27A	109.4	N1—C2—N3	107.52 (11)
N4—C27—H27A	109.4	C4—N3—C2	112.11 (11)
C28—C27—H27B	109.4	C4—N3—C26	125.58 (12)
N4—C27—H27B	109.4	C2—N3—C26	122.20 (12)
H27A—C27—H27B	108	O4—C4—N3	126.86 (12)
C13—N4—C11	109.68 (10)	O4—C4—C5	126.64 (12)
C13—N4—C27	111.95 (11)	N3—C4—C5	106.43 (11)
C11—N4—C27	110.44 (11)	N1—C5—C25	114.01 (11)
C13—N4—H4N	109.9 (11)	N1—C5—C14	114.78 (11)
C11—N4—H4N	107.8 (11)	C25—C5—C14	102.22 (10)
C27—N4—H4N	106.9 (10)	N1—C5—C4	101.24 (10)
N4—C11—C10	111.22 (11)	C25—C5—C4	115.47 (11)
N4—C11—H11A	109.4	C14—C5—C4	109.60 (11)
C10—C11—H11A	109.4	N3—C26—H26A	109.5
N4—C11—H11B	109.4	N3—C26—H26B	109.5
C10—C11—H11B	109.4	H26A—C26—H26B	109.5
H11A—C11—H11B	108	N3—C26—H26C	109.5
N2—C10—C11	110.74 (11)	H26A—C26—H26C	109.5
N2—C10—H10A	109.5	H26B—C26—H26C	109.5
C11—C10—H10A	109.5	C24—C25—C20	121.60 (12)
N2—C10—H10B	109.5	C24—C25—C5	128.27 (12)
C11—C10—H10B	109.5	C20—C25—C5	110.07 (12)
H10A—C10—H10B	108.1	C25—C24—C23	117.80 (13)
C10—N2—C12	108.97 (11)	C25—C24—H24	121.1
C10—N2—C9A	112.55 (11)	C23—C24—H24	121.1
C12—N2—C9A	108.54 (11)	C22—C23—C24	121.14 (14)
C10—N2—H2N	108.1 (12)	C22—C23—H23	119.4
C12—N2—H2N	108.4 (11)	C24—C23—H23	119.4
C9A—N2—H2N	110.3 (11)	C21—C22—C23	120.66 (13)
N2—C12—C13	111.88 (11)	C21—C22—H22	119.7
N2—C12—H12A	109.2	C23—C22—H22	119.7
C13—C12—H12A	109.2	C22—C21—C20	118.61 (14)
N2—C12—H12B	109.2	C22—C21—H21	120.7
C13—C12—H12B	109.2	C20—C21—H21	120.7
H12A—C12—H12B	107.9	C21—C20—C25	120.13 (13)
N4—C13—C12	111.15 (11)	C21—C20—C19	131.02 (13)
N4—C13—H13A	109.4	C25—C20—C19	108.83 (12)
C12—C13—H13A	109.4	C18—C19—C14	119.70 (13)
N4—C13—H13B	109.4	C18—C19—C20	131.45 (13)
C12—C13—H13B	109.4	C14—C19—C20	108.85 (12)
H13A—C13—H13B	108	C19—C18—C17	118.89 (13)
N2—C9A—C9	114.69 (12)	C19—C18—H18	120.6
N2—C9A—H9AA	108.6	C17—C18—H18	120.6
C9—C9A—H9AA	108.6	C16—C17—C18	120.99 (14)
N2—C9A—H9AB	108.6	C16—C17—H17	119.5
C9—C9A—H9AB	108.6	C18—C17—H17	119.5
H9AA—C9A—H9AB	107.6	C17—C16—C15	120.46 (13)
C9A—C9—C8	114.36 (13)	C17—C16—H16	119.8
C9A—C9—H9A	108.7	C15—C16—H16	119.8
C8—C9—H9A	108.7	C14—C15—C16	118.29 (13)
C9A—C9—H9B	108.7	C14—C15—H15	120.9
C8—C9—H9B	108.7	C16—C15—H15	120.9
H9A—C9—H9B	107.6	C15—C14—C19	121.67 (13)
C9—C8—C7	113.10 (12)	C15—C14—C5	128.40 (12)
C9—C8—H8A	109	C19—C14—C5	109.90 (11)
C7—C8—H8A	109	H1B—O1W—H1A	106.7
C9—C8—H8B	109
C28—C33—C32—C31	−1.0 (2)	C2—N1—C5—C4	−2.98 (14)
C33—C32—C31—C30	−0.7 (3)	C6—N1—C5—C4	170.18 (12)
C32—C31—C30—C29	1.2 (2)	O4—C4—C5—N1	−176.45 (13)
C31—C30—C29—C28	−0.1 (2)	N3—C4—C5—N1	6.26 (13)
C30—C29—C28—C33	−1.5 (2)	O4—C4—C5—C25	−52.81 (19)
C30—C29—C28—C27	177.39 (14)	N3—C4—C5—C25	129.90 (12)
C32—C33—C28—C29	2.1 (2)	O4—C4—C5—C14	61.93 (17)
C32—C33—C28—C27	−176.85 (14)	N3—C4—C5—C14	−115.36 (12)
C29—C28—C27—N4	−81.34 (16)	N1—C5—C25—C24	54.53 (19)
C33—C28—C27—N4	97.58 (16)	C14—C5—C25—C24	179.00 (14)
C28—C27—N4—C13	−61.98 (15)	C4—C5—C25—C24	−62.10 (18)
C28—C27—N4—C11	175.49 (12)	N1—C5—C25—C20	−122.38 (12)
C13—N4—C11—C10	57.25 (15)	C14—C5—C25—C20	2.08 (14)
C27—N4—C11—C10	−178.90 (11)	C4—C5—C25—C20	120.98 (13)
N4—C11—C10—N2	−58.89 (15)	C20—C25—C24—C23	2.2 (2)
C11—C10—N2—C12	57.22 (14)	C5—C25—C24—C23	−174.37 (13)
C11—C10—N2—C9A	177.67 (11)	C25—C24—C23—C22	−0.6 (2)
C10—N2—C12—C13	−56.58 (15)	C24—C23—C22—C21	−1.2 (2)
C9A—N2—C12—C13	−179.46 (12)	C23—C22—C21—C20	1.5 (2)
C11—N4—C13—C12	−55.89 (15)	C22—C21—C20—C25	0.1 (2)
C27—N4—C13—C12	−178.85 (11)	C22—C21—C20—C19	178.44 (14)
N2—C12—C13—N4	56.79 (16)	C24—C25—C20—C21	−2.0 (2)
C10—N2—C9A—C9	68.07 (16)	C5—C25—C20—C21	175.18 (12)
C12—N2—C9A—C9	−171.24 (12)	C24—C25—C20—C19	179.33 (13)
N2—C9A—C9—C8	78.08 (17)	C5—C25—C20—C19	−3.51 (15)
C9A—C9—C8—C7	175.47 (12)	C21—C20—C19—C18	5.3 (3)
C9—C8—C7—C6	66.96 (16)	C25—C20—C19—C18	−176.22 (15)
C8—C7—C6—N1	60.12 (16)	C21—C20—C19—C14	−174.88 (15)
C7—C6—N1—C2	−104.31 (15)	C25—C20—C19—C14	3.61 (16)
C7—C6—N1—C5	83.30 (15)	C14—C19—C18—C17	−0.2 (2)
C6—N1—C2—O2	5.1 (2)	C20—C19—C18—C17	179.58 (15)
C5—N1—C2—O2	178.26 (13)	C19—C18—C17—C16	0.3 (2)
C6—N1—C2—N3	−174.50 (12)	C18—C17—C16—C15	0.4 (2)
C5—N1—C2—N3	−1.31 (15)	C17—C16—C15—C14	−1.0 (2)
O2—C2—N3—C4	−173.71 (13)	C16—C15—C14—C19	1.1 (2)
N1—C2—N3—C4	5.88 (15)	C16—C15—C14—C5	−176.60 (13)
O2—C2—N3—C26	2.5 (2)	C18—C19—C14—C15	−0.5 (2)
N1—C2—N3—C26	−177.87 (12)	C20—C19—C14—C15	179.67 (12)
C2—N3—C4—O4	175.06 (13)	C18—C19—C14—C5	177.62 (13)
C26—N3—C4—O4	−1.0 (2)	C20—C19—C14—C5	−2.24 (15)
C2—N3—C4—C5	−7.66 (15)	N1—C5—C14—C15	−57.95 (18)
C26—N3—C4—C5	176.25 (13)	C25—C5—C14—C15	178.10 (13)
C2—N1—C5—C25	−127.62 (12)	C4—C5—C14—C15	55.14 (17)
C6—N1—C5—C25	45.54 (17)	N1—C5—C14—C19	124.12 (12)
C2—N1—C5—C14	114.94 (13)	C25—C5—C14—C19	0.17 (14)
C6—N1—C5—C14	−71.90 (16)	C4—C5—C14—C19	−122.79 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···Cl2	1.00 (2)	2.03 (2)	3.020 (1)	169 (2)
N2—H2N···Cl1	0.95 (2)	2.16 (2)	3.090 (1)	164 (2)
C6—H6B···O4^i	0.99	2.37	3.148 (2)	136
C9—H9A···O2	0.99	2.63	3.433 (2)	138
C9A—H9AA···Cl1^i	0.99	2.76	3.663 (2)	151
C9A—H9AB···O1W^ii	0.99	2.61	3.452 (2)	143
C10—H10A···Cl2	0.99	2.95	3.681 (1)	131
C10—H10B···O2	0.99	2.34	3.216 (2)	147
C11—H11A···Cl1	0.99	2.83	3.592 (1)	135
C11—H11B···O2^iii	0.99	2.32	3.194 (2)	146
C12—H12A···Cl1^ii	0.99	2.63	3.588 (2)	162
C12—H12B···O1W^i	0.99	2.42	3.373 (2)	162
C13—H13B···O1W	0.99	2.46	3.392 (2)	157
C13—H13B···Cl1	0.99	2.9	3.634 (2)	132
C26—H26A···Cl2^iii	0.98	2.97	3.649 (2)	128
C27—H27A···Cl2^iv	0.99	2.93	3.808 (2)	149
C27—H27B···O4^v	0.99	2.44	3.297 (2)	145
O1W—H1B···Cl2^iv	0.91	2.11	3.020 (2)	174
O1W—H1A···Cl1	0.88	2.26	3.097 (2)	161

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