4-(4-Chloro-phen-yl)-1-[3-(4-fluoro-benzo-yl)prop-yl]-4-hydroxy-piperidin-1-ium 2,4,6-trinitro-phenolate (haloperidol picrate).

In the title salt, C(21)H(24)ClFNO(2) (+)·C(6)H(2)N(3)O(7) (-), the dihedral angle between the aromatic rings in the cation is 16.5 (1)°. The piperidium ring adopts a slightly distorted chair conformation. Strong hydrogen-bonding inter-actions occur between the N-H and O-H functions of the 4-hydroxy-piperidin-1-ium ring and the phenolate and p-NO(2) O atoms of the picrate anion. In addition, a variety of weak C-H⋯O and π-π ring inter-actions between cations and cation-anion neighbors [centroid-centroid distances = 3.597 (1) and 3.848 (10) Å] further consolidate the packing.

Related literature

For related structures, see: Casellato et al. (2003 ▶); Datta et al. (1979 ▶); Prasanna & Guru Row (2001 ▶); Reed & Schafer (1973 ▶). For general background, see: Kurzawa et al. (2004 ▶); Volavka & Cooper, (1987 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶) and for Mogul, see: Bruno et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H24ClFNO2 +·C6H2N3O7 −

M = 604.97

Orthorhombic,

a = 14.9089 (5) Å

b = 12.5934 (3) Å

c = 14.5074 (5) Å

V = 2723.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 110 K

0.53 × 0.47 × 0.34 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.889, T max = 0.931

19020 measured reflections

7472 independent reflections

5784 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.077

S = 0.92

7472 reflections

384 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 2287 Friedel pairs

Flack parameter: 0.03 (4)

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033261/im2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033261/im2134Isup2.hkl

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

C21H24ClFNO2+·C6H2N3O7−	F(000) = 1256
Mr = 604.97	Dx = 1.475 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8346 reflections
a = 14.9089 (5) Å	θ = 5.0–32.6°
b = 12.5934 (3) Å	µ = 0.21 mm−1
c = 14.5074 (5) Å	T = 110 K
V = 2723.8 (2) Å3	Chunk, pale yellow
Z = 4	0.53 × 0.47 × 0.34 mm

Oxford Diffraction Gemini R CCD diffractometer	7472 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5784 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 10.5081 pixels mm-1	θmax = 32.7°, θmin = 5.0°
φ and ω scans	h = −21→22
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −11→18
Tmin = 0.889, Tmax = 0.931	l = −15→21
19020 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.002
7472 reflections	Δρmax = 0.30 e Å−3
384 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 2287 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (4)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1A	1.34757 (3)	0.42144 (3)	0.45280 (3)	0.03220 (10)
F1A	0.37134 (7)	0.23216 (9)	1.20789 (10)	0.0486 (3)
O1AA	0.7069 (12)	0.3214 (11)	0.9777 (13)	0.0512 (15)	0.28 (2)
O1AB	0.7328 (7)	0.3329 (4)	0.9962 (6)	0.0512 (15)	0.72 (2)
O2A	1.06195 (7)	0.08904 (7)	0.66072 (9)	0.0258 (3)
H2O	1.1099	0.0624	0.6805	0.031*
N1A	0.90790 (8)	0.20672 (9)	0.80712 (9)	0.0186 (3)
H1N	0.9070	0.2798	0.8163	0.022*
C1A	0.61183 (12)	0.24014 (12)	1.07122 (12)	0.0276 (4)
C2A	0.57077 (13)	0.33404 (13)	1.10171 (13)	0.0310 (4)
H2AA	0.5990	0.4003	1.0900	0.037*
C3A	0.49075 (13)	0.33187 (13)	1.14801 (13)	0.0322 (4)
H3AA	0.4639	0.3956	1.1696	0.039*
C4A	0.45020 (12)	0.23523 (14)	1.16256 (13)	0.0321 (4)
C5A	0.48711 (12)	0.14068 (13)	1.13194 (13)	0.0316 (4)
H5AA	0.4568	0.0752	1.1413	0.038*
C6A	0.56849 (12)	0.14369 (12)	1.08783 (12)	0.0284 (4)
H6AA	0.5957	0.0793	1.0683	0.034*
C7A	0.70033 (13)	0.24665 (12)	1.02276 (14)	0.0337 (4)
C8A	0.75704 (12)	0.14780 (12)	1.01555 (12)	0.0282 (4)
H8AA	0.7222	0.0920	0.9836	0.034*
H8AB	0.7707	0.1218	1.0784	0.034*
C9A	0.84472 (12)	0.16547 (13)	0.96399 (13)	0.0292 (4)
H9AA	0.8695	0.2359	0.9806	0.035*
H9AB	0.8887	0.1108	0.9828	0.035*
C10A	0.83088 (10)	0.15999 (11)	0.86049 (11)	0.0207 (3)
H10A	0.8230	0.0849	0.8421	0.025*
H10B	0.7752	0.1986	0.8443	0.025*
C11A	0.89490 (10)	0.18710 (12)	0.70629 (11)	0.0206 (3)
H11A	0.8359	0.2155	0.6870	0.025*
H11B	0.8951	0.1097	0.6945	0.025*
C12A	0.96782 (10)	0.23902 (11)	0.64998 (12)	0.0219 (3)
H12A	0.9642	0.3170	0.6576	0.026*
H12B	0.9583	0.2226	0.5840	0.026*
C13A	1.06140 (10)	0.20075 (10)	0.67912 (12)	0.0206 (3)
C14A	1.07294 (10)	0.21878 (11)	0.78277 (12)	0.0220 (3)
H14A	1.1314	0.1894	0.8026	0.026*
H14B	1.0733	0.2960	0.7955	0.026*
C15A	0.99821 (10)	0.16667 (11)	0.83823 (12)	0.0218 (3)
H15A	1.0010	0.0887	0.8302	0.026*
H15B	1.0065	0.1826	0.9045	0.026*
C16A	1.13368 (10)	0.25698 (11)	0.62300 (12)	0.0216 (3)
C17A	1.18453 (11)	0.20234 (12)	0.55825 (12)	0.0240 (3)
H17A	1.1747	0.1285	0.5497	0.029*
C18A	1.24937 (11)	0.25346 (12)	0.50584 (12)	0.0254 (3)
H18A	1.2838	0.2148	0.4621	0.031*
C19A	1.26326 (10)	0.36054 (12)	0.51775 (12)	0.0240 (3)
C20A	1.21366 (11)	0.41814 (12)	0.58018 (13)	0.0272 (4)
H20A	1.2231	0.4924	0.5869	0.033*
C21A	1.14966 (11)	0.36643 (12)	0.63330 (12)	0.0257 (3)
H21A	1.1161	0.4056	0.6774	0.031*
O1B	0.94487 (8)	0.41234 (7)	0.84639 (9)	0.0295 (3)
O21B	1.11786 (8)	0.49095 (10)	0.85835 (11)	0.0404 (3)
O22B	1.09827 (10)	0.58450 (9)	0.98236 (10)	0.0400 (3)
O41B	0.93213 (9)	0.90496 (8)	0.86429 (10)	0.0362 (3)
O42B	0.80467 (8)	0.87709 (8)	0.79751 (11)	0.0382 (3)
O61B	0.70990 (7)	0.52946 (8)	0.72810 (9)	0.0295 (3)
O62B	0.78680 (7)	0.39063 (8)	0.76248 (10)	0.0334 (3)
N2B	1.07400 (10)	0.55211 (10)	0.90649 (11)	0.0289 (3)
N4B	0.87478 (9)	0.84545 (10)	0.83136 (10)	0.0262 (3)
N6B	0.77742 (8)	0.48709 (9)	0.76187 (10)	0.0200 (3)
C1B	0.92607 (10)	0.50846 (11)	0.83829 (11)	0.0198 (3)
C2B	0.98785 (10)	0.58939 (11)	0.87141 (11)	0.0208 (3)
C3B	0.97235 (11)	0.69557 (11)	0.87218 (11)	0.0222 (3)
H3BA	1.0146	0.7435	0.8981	0.027*
C4B	0.89221 (10)	0.73212 (11)	0.83366 (12)	0.0213 (3)
C5B	0.82938 (10)	0.66318 (11)	0.79824 (11)	0.0197 (3)
H5BA	0.7754	0.6896	0.7721	0.024*
C6B	0.84571 (9)	0.55469 (11)	0.80103 (11)	0.0185 (3)

	U11	U22	U33	U12	U13	U23
Cl1A	0.02537 (19)	0.0366 (2)	0.0347 (2)	−0.00290 (16)	0.00370 (19)	0.0040 (2)
F1A	0.0313 (6)	0.0495 (6)	0.0650 (9)	0.0082 (5)	0.0082 (6)	0.0025 (6)
O1AA	0.062 (3)	0.0202 (11)	0.071 (3)	−0.0155 (15)	0.032 (3)	−0.0022 (14)
O1AB	0.062 (3)	0.0202 (11)	0.071 (3)	−0.0155 (15)	0.032 (3)	−0.0022 (14)
O2A	0.0220 (6)	0.0150 (4)	0.0403 (7)	0.0024 (4)	−0.0042 (5)	−0.0022 (5)
N1A	0.0202 (6)	0.0127 (5)	0.0229 (7)	−0.0005 (4)	−0.0043 (5)	0.0007 (5)
C1A	0.0413 (10)	0.0230 (7)	0.0186 (8)	−0.0022 (7)	−0.0016 (7)	0.0006 (6)
C2A	0.0464 (11)	0.0218 (7)	0.0249 (9)	0.0001 (7)	−0.0048 (8)	0.0017 (7)
C3A	0.0417 (10)	0.0265 (8)	0.0284 (10)	0.0108 (7)	−0.0082 (8)	0.0001 (7)
C4A	0.0271 (9)	0.0389 (9)	0.0303 (10)	0.0047 (7)	−0.0040 (8)	0.0024 (8)
C5A	0.0352 (10)	0.0258 (8)	0.0340 (10)	−0.0050 (7)	−0.0048 (8)	0.0010 (7)
C6A	0.0405 (10)	0.0204 (7)	0.0243 (9)	0.0009 (6)	−0.0032 (8)	−0.0035 (7)
C7A	0.0509 (11)	0.0232 (8)	0.0270 (9)	−0.0062 (7)	0.0094 (9)	−0.0016 (7)
C8A	0.0354 (9)	0.0255 (7)	0.0236 (9)	−0.0061 (6)	−0.0024 (8)	0.0028 (7)
C9A	0.0297 (8)	0.0319 (8)	0.0260 (9)	−0.0084 (7)	−0.0050 (7)	0.0039 (7)
C10A	0.0197 (7)	0.0176 (6)	0.0247 (8)	−0.0032 (5)	−0.0025 (6)	0.0008 (6)
C11A	0.0190 (7)	0.0211 (6)	0.0217 (8)	0.0017 (5)	−0.0049 (6)	−0.0005 (6)
C12A	0.0209 (8)	0.0209 (7)	0.0239 (8)	0.0033 (5)	−0.0040 (6)	0.0022 (6)
C13A	0.0191 (7)	0.0135 (6)	0.0292 (9)	0.0026 (5)	−0.0022 (6)	0.0012 (6)
C14A	0.0187 (7)	0.0175 (6)	0.0298 (9)	−0.0003 (5)	−0.0046 (6)	0.0021 (6)
C15A	0.0186 (7)	0.0195 (7)	0.0271 (8)	−0.0013 (5)	−0.0080 (6)	0.0046 (6)
C16A	0.0188 (7)	0.0185 (7)	0.0276 (8)	0.0019 (5)	−0.0045 (6)	0.0031 (6)
C17A	0.0246 (8)	0.0186 (7)	0.0286 (9)	0.0024 (6)	−0.0058 (7)	−0.0020 (6)
C18A	0.0224 (8)	0.0298 (8)	0.0241 (9)	0.0063 (6)	−0.0025 (7)	−0.0024 (7)
C19A	0.0170 (7)	0.0299 (7)	0.0250 (9)	−0.0003 (6)	−0.0023 (6)	0.0052 (7)
C20A	0.0263 (8)	0.0185 (7)	0.0368 (10)	0.0010 (6)	0.0016 (8)	0.0025 (7)
C21A	0.0256 (8)	0.0184 (7)	0.0331 (10)	0.0037 (6)	0.0020 (7)	−0.0003 (7)
O1B	0.0305 (6)	0.0142 (5)	0.0438 (8)	−0.0018 (4)	−0.0126 (6)	−0.0010 (5)
O21B	0.0274 (7)	0.0356 (7)	0.0582 (9)	0.0055 (5)	−0.0121 (6)	−0.0040 (7)
O22B	0.0523 (8)	0.0237 (6)	0.0439 (8)	−0.0080 (5)	−0.0284 (7)	0.0023 (6)
O41B	0.0394 (7)	0.0167 (5)	0.0525 (9)	−0.0058 (5)	−0.0035 (6)	−0.0052 (6)
O42B	0.0315 (7)	0.0203 (5)	0.0628 (9)	0.0053 (5)	−0.0052 (7)	−0.0002 (6)
O61B	0.0273 (6)	0.0221 (5)	0.0392 (7)	−0.0005 (4)	−0.0148 (5)	0.0015 (5)
O62B	0.0259 (6)	0.0161 (5)	0.0582 (9)	−0.0023 (4)	−0.0096 (6)	−0.0047 (5)
N2B	0.0296 (8)	0.0170 (6)	0.0401 (9)	−0.0064 (5)	−0.0144 (7)	0.0048 (6)
N4B	0.0314 (7)	0.0139 (6)	0.0334 (8)	−0.0014 (5)	0.0032 (6)	−0.0011 (6)
N6B	0.0203 (6)	0.0178 (6)	0.0220 (7)	−0.0027 (4)	0.0002 (5)	−0.0013 (5)
C1B	0.0244 (7)	0.0163 (6)	0.0188 (7)	−0.0040 (5)	−0.0019 (6)	0.0006 (6)
C2B	0.0223 (7)	0.0183 (6)	0.0220 (8)	−0.0022 (5)	−0.0040 (6)	0.0016 (6)
C3B	0.0277 (8)	0.0181 (7)	0.0209 (8)	−0.0064 (5)	−0.0022 (7)	−0.0009 (6)
C4B	0.0250 (8)	0.0124 (6)	0.0263 (8)	−0.0013 (5)	0.0037 (7)	−0.0013 (6)
C5B	0.0220 (7)	0.0177 (7)	0.0195 (7)	−0.0004 (5)	0.0018 (6)	−0.0001 (6)
C6B	0.0207 (7)	0.0158 (6)	0.0189 (7)	−0.0043 (5)	0.0006 (6)	−0.0002 (6)

Cl1A—C19A	1.7482 (16)	C13A—C16A	1.525 (2)
F1A—C4A	1.348 (2)	C13A—C14A	1.530 (2)
O1AA—C7A	1.151 (15)	C14A—C15A	1.523 (2)
O1AB—C7A	1.250 (6)	C14A—H14A	0.9900
O2A—C13A	1.4320 (16)	C14A—H14B	0.9900
O2A—H2O	0.8400	C15A—H15A	0.9900
N1A—C11A	1.496 (2)	C15A—H15B	0.9900
N1A—C10A	1.5047 (19)	C16A—C17A	1.389 (2)
N1A—C15A	1.5070 (19)	C16A—C21A	1.407 (2)
N1A—H1N	0.9300	C17A—C18A	1.388 (2)
C1A—C6A	1.397 (2)	C17A—H17A	0.9500
C1A—C2A	1.403 (2)	C18A—C19A	1.375 (2)
C1A—C7A	1.497 (3)	C18A—H18A	0.9500
C2A—C3A	1.369 (3)	C19A—C20A	1.376 (2)
C2A—H2AA	0.9500	C20A—C21A	1.389 (2)
C3A—C4A	1.375 (2)	C20A—H20A	0.9500
C3A—H3AA	0.9500	C21A—H21A	0.9500
C4A—C5A	1.385 (2)	O1B—C1B	1.2481 (17)
C5A—C6A	1.372 (3)	O21B—N2B	1.228 (2)
C5A—H5AA	0.9500	O22B—N2B	1.2284 (19)
C6A—H6AA	0.9500	O41B—N4B	1.2333 (18)
C7A—C8A	1.508 (2)	O42B—N4B	1.2217 (18)
C8A—C9A	1.522 (2)	O61B—N6B	1.2403 (16)
C8A—H8AA	0.9900	O62B—N6B	1.2229 (15)
C8A—H8AB	0.9900	N2B—C2B	1.459 (2)
C9A—C10A	1.517 (2)	N4B—C4B	1.4511 (18)
C9A—H9AA	0.9900	N6B—C6B	1.4436 (18)
C9A—H9AB	0.9900	C1B—C6B	1.438 (2)
C10A—H10A	0.9900	C1B—C2B	1.455 (2)
C10A—H10B	0.9900	C2B—C3B	1.357 (2)
C11A—C12A	1.509 (2)	C3B—C4B	1.397 (2)
C11A—H11A	0.9900	C3B—H3BA	0.9500
C11A—H11B	0.9900	C4B—C5B	1.377 (2)
C12A—C13A	1.535 (2)	C5B—C6B	1.3883 (18)
C12A—H12A	0.9900	C5B—H5BA	0.9500
C12A—H12B	0.9900
C13A—O2A—H2O	109.5	O2A—C13A—C14A	109.17 (12)
C11A—N1A—C10A	109.86 (11)	C16A—C13A—C14A	112.10 (12)
C11A—N1A—C15A	110.68 (12)	O2A—C13A—C12A	105.20 (11)
C10A—N1A—C15A	113.38 (11)	C16A—C13A—C12A	110.45 (12)
C11A—N1A—H1N	107.6	C14A—C13A—C12A	109.03 (13)
C10A—N1A—H1N	107.6	C15A—C14A—C13A	111.90 (12)
C15A—N1A—H1N	107.6	C15A—C14A—H14A	109.2
C6A—C1A—C2A	118.48 (17)	C13A—C14A—H14A	109.2
C6A—C1A—C7A	122.43 (15)	C15A—C14A—H14B	109.2
C2A—C1A—C7A	119.09 (15)	C13A—C14A—H14B	109.2
C3A—C2A—C1A	121.19 (16)	H14A—C14A—H14B	107.9
C3A—C2A—H2AA	119.4	N1A—C15A—C14A	110.56 (12)
C1A—C2A—H2AA	119.4	N1A—C15A—H15A	109.5
C2A—C3A—C4A	118.42 (16)	C14A—C15A—H15A	109.5
C2A—C3A—H3AA	120.8	N1A—C15A—H15B	109.5
C4A—C3A—H3AA	120.8	C14A—C15A—H15B	109.5
F1A—C4A—C3A	118.94 (16)	H15A—C15A—H15B	108.1
F1A—C4A—C5A	118.58 (16)	C17A—C16A—C21A	117.69 (14)
C3A—C4A—C5A	122.48 (17)	C17A—C16A—C13A	121.10 (13)
C6A—C5A—C4A	118.50 (16)	C21A—C16A—C13A	121.20 (14)
C6A—C5A—H5AA	120.8	C18A—C17A—C16A	121.37 (13)
C4A—C5A—H5AA	120.8	C18A—C17A—H17A	119.3
C5A—C6A—C1A	120.89 (16)	C16A—C17A—H17A	119.3
C5A—C6A—H6AA	119.6	C19A—C18A—C17A	119.40 (15)
C1A—C6A—H6AA	119.6	C19A—C18A—H18A	120.3
O1AA—C7A—O1AB	23.2 (8)	C17A—C18A—H18A	120.3
O1AA—C7A—C1A	112.8 (8)	C18A—C19A—C20A	121.24 (14)
O1AB—C7A—C1A	122.2 (3)	C18A—C19A—Cl1A	118.08 (12)
O1AA—C7A—C8A	126.0 (8)	C20A—C19A—Cl1A	120.66 (11)
O1AB—C7A—C8A	118.6 (3)	C19A—C20A—C21A	119.17 (13)
C1A—C7A—C8A	118.76 (14)	C19A—C20A—H20A	120.4
C7A—C8A—C9A	113.24 (13)	C21A—C20A—H20A	120.4
C7A—C8A—H8AA	108.9	C20A—C21A—C16A	121.13 (15)
C9A—C8A—H8AA	108.9	C20A—C21A—H21A	119.4
C7A—C8A—H8AB	108.9	C16A—C21A—H21A	119.4
C9A—C8A—H8AB	108.9	O21B—N2B—O22B	124.12 (15)
H8AA—C8A—H8AB	107.7	O21B—N2B—C2B	118.17 (14)
C10A—C9A—C8A	111.27 (14)	O22B—N2B—C2B	117.71 (15)
C10A—C9A—H9AA	109.4	O42B—N4B—O41B	123.42 (12)
C8A—C9A—H9AA	109.4	O42B—N4B—C4B	118.90 (13)
C10A—C9A—H9AB	109.4	O41B—N4B—C4B	117.68 (13)
C8A—C9A—H9AB	109.4	O62B—N6B—O61B	121.54 (12)
H9AA—C9A—H9AB	108.0	O62B—N6B—C6B	120.16 (12)
N1A—C10A—C9A	112.81 (12)	O61B—N6B—C6B	118.31 (11)
N1A—C10A—H10A	109.0	O1B—C1B—C6B	127.98 (13)
C9A—C10A—H10A	109.0	O1B—C1B—C2B	120.40 (14)
N1A—C10A—H10B	109.0	C6B—C1B—C2B	111.59 (12)
C9A—C10A—H10B	109.0	C3B—C2B—C1B	125.81 (14)
H10A—C10A—H10B	107.8	C3B—C2B—N2B	117.65 (13)
N1A—C11A—C12A	111.37 (12)	C1B—C2B—N2B	116.54 (12)
N1A—C11A—H11A	109.4	C2B—C3B—C4B	117.84 (13)
C12A—C11A—H11A	109.4	C2B—C3B—H3BA	121.1
N1A—C11A—H11B	109.4	C4B—C3B—H3BA	121.1
C12A—C11A—H11B	109.4	C5B—C4B—C3B	121.56 (13)
H11A—C11A—H11B	108.0	C5B—C4B—N4B	119.33 (14)
C11A—C12A—C13A	111.70 (12)	C3B—C4B—N4B	119.11 (13)
C11A—C12A—H12A	109.3	C4B—C5B—C6B	119.37 (14)
C13A—C12A—H12A	109.3	C4B—C5B—H5BA	120.3
C11A—C12A—H12B	109.3	C6B—C5B—H5BA	120.3
C13A—C12A—H12B	109.3	C5B—C6B—C1B	123.76 (13)
H12A—C12A—H12B	107.9	C5B—C6B—N6B	116.43 (13)
O2A—C13A—C16A	110.65 (12)	C1B—C6B—N6B	119.79 (12)
C6A—C1A—C2A—C3A	1.0 (3)	C12A—C13A—C16A—C21A	67.61 (19)
C7A—C1A—C2A—C3A	−178.65 (17)	C21A—C16A—C17A—C18A	0.4 (2)
C1A—C2A—C3A—C4A	−1.3 (3)	C13A—C16A—C17A—C18A	178.89 (14)
C2A—C3A—C4A—F1A	−179.87 (17)	C16A—C17A—C18A—C19A	−0.4 (2)
C2A—C3A—C4A—C5A	−0.2 (3)	C17A—C18A—C19A—C20A	−0.5 (2)
F1A—C4A—C5A—C6A	−178.39 (17)	C17A—C18A—C19A—Cl1A	178.28 (12)
C3A—C4A—C5A—C6A	2.0 (3)	C18A—C19A—C20A—C21A	1.3 (3)
C4A—C5A—C6A—C1A	−2.2 (3)	Cl1A—C19A—C20A—C21A	−177.43 (13)
C2A—C1A—C6A—C5A	0.8 (3)	C19A—C20A—C21A—C16A	−1.2 (3)
C7A—C1A—C6A—C5A	−179.57 (17)	C17A—C16A—C21A—C20A	0.4 (2)
C6A—C1A—C7A—O1AA	145.5 (10)	C13A—C16A—C21A—C20A	−178.05 (15)
C2A—C1A—C7A—O1AA	−34.8 (10)	O1B—C1B—C2B—C3B	−175.26 (16)
C6A—C1A—C7A—O1AB	169.5 (6)	C6B—C1B—C2B—C3B	2.9 (2)
C2A—C1A—C7A—O1AB	−10.9 (7)	O1B—C1B—C2B—N2B	4.9 (2)
C6A—C1A—C7A—C8A	−17.8 (3)	C6B—C1B—C2B—N2B	−176.93 (14)
C2A—C1A—C7A—C8A	161.86 (17)	O21B—N2B—C2B—C3B	−129.26 (17)
O1AA—C7A—C8A—C9A	18.6 (12)	O22B—N2B—C2B—C3B	50.4 (2)
O1AB—C7A—C8A—C9A	−7.5 (6)	O21B—N2B—C2B—C1B	50.6 (2)
C1A—C7A—C8A—C9A	179.51 (15)	O22B—N2B—C2B—C1B	−129.80 (15)
C7A—C8A—C9A—C10A	−82.40 (18)	C1B—C2B—C3B—C4B	−3.5 (3)
C11A—N1A—C10A—C9A	173.30 (12)	N2B—C2B—C3B—C4B	176.28 (15)
C15A—N1A—C10A—C9A	48.88 (16)	C2B—C3B—C4B—C5B	1.8 (2)
C8A—C9A—C10A—N1A	163.71 (12)	C2B—C3B—C4B—N4B	−178.45 (15)
C10A—N1A—C11A—C12A	176.32 (11)	O42B—N4B—C4B—C5B	−0.4 (2)
C15A—N1A—C11A—C12A	−57.71 (14)	O41B—N4B—C4B—C5B	179.46 (16)
N1A—C11A—C12A—C13A	57.12 (16)	O42B—N4B—C4B—C3B	179.91 (16)
C11A—C12A—C13A—O2A	62.24 (16)	O41B—N4B—C4B—C3B	−0.3 (2)
C11A—C12A—C13A—C16A	−178.33 (13)	C3B—C4B—C5B—C6B	0.2 (2)
C11A—C12A—C13A—C14A	−54.73 (16)	N4B—C4B—C5B—C6B	−179.53 (13)
O2A—C13A—C14A—C15A	−59.63 (15)	C4B—C5B—C6B—C1B	−0.8 (2)
C16A—C13A—C14A—C15A	177.41 (11)	C4B—C5B—C6B—N6B	−179.40 (15)
C12A—C13A—C14A—C15A	54.80 (15)	O1B—C1B—C6B—C5B	177.33 (16)
C11A—N1A—C15A—C14A	57.19 (15)	C2B—C1B—C6B—C5B	−0.6 (2)
C10A—N1A—C15A—C14A	−178.85 (12)	O1B—C1B—C6B—N6B	−4.1 (3)
C13A—C14A—C15A—N1A	−56.78 (16)	C2B—C1B—C6B—N6B	177.97 (14)
O2A—C13A—C16A—C17A	5.3 (2)	O62B—N6B—C6B—C5B	−179.44 (14)
C14A—C13A—C16A—C17A	127.42 (15)	O61B—N6B—C6B—C5B	0.5 (2)
C12A—C13A—C16A—C17A	−110.78 (16)	O62B—N6B—C6B—C1B	1.9 (2)
O2A—C13A—C16A—C21A	−176.32 (14)	O61B—N6B—C6B—C1B	−178.16 (15)
C14A—C13A—C16A—C21A	−54.19 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2O···O61Bi	0.84	2.01	2.837 (2)	168
N1A—H1N···O1B	0.93	1.82	2.708 (1)	160
N1A—H1N···O62B	0.93	2.40	3.007 (2)	123
C3A—H3AA···O2Aii	0.95	2.47	3.338 (2)	152
C6A—H6AA···O22Biii	0.95	2.41	3.286 (2)	153
C8A—H8AA···O21Biii	0.99	2.61	3.544 (2)	158
C8A—H8AB···O61Biv	0.99	2.48	3.460 (2)	170
C14A—H14A···O62Bi	0.99	2.59	3.486 (2)	150
C15A—H15A···O41Bv	0.99	2.58	3.461 (2)	148
C18A—H18A···O22Bvi	0.95	2.42	3.131 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2O⋯O61Bi	0.84	2.01	2.837 (2)	168
N1A—H1N⋯O1B	0.93	1.82	2.708 (1)	160
N1A—H1N⋯O62B	0.93	2.40	3.007 (2)	123
C3A—H3AA⋯O2Aii	0.95	2.47	3.338 (2)	152
C6A—H6AA⋯O22Biii	0.95	2.41	3.286 (2)	153
C8A—H8AA⋯O21Biii	0.99	2.61	3.544 (2)	158
C8A—H8AB⋯O61Biv	0.99	2.48	3.460 (2)	170
C14A—H14A⋯O62Bi	0.99	2.59	3.486 (2)	150
C15A—H15A⋯O41Bv	0.99	2.58	3.461 (2)	148
C18A—H18A⋯O22Bvi	0.95	2.42	3.131 (2)	131

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