4-[Bis(4-fluoro-phen-yl)meth-yl]-1-[(2E)-3-phenyl-prop-2-en-1-yl]piperazin-1-ium 3-carb-oxy-propano-ate.

In the title salt, C(26)H(27)F(2)N(2) (+)·C(4)H(5)O(4) (-), the piperazine N atom bearing the vinylic substituent is protonated. The piperazine ring adopts a chair conformation. In ther crystal, the succinate monoanions are connected via short O-H⋯O hydrogen bonds between the carb-oxy-lic acid and carboxyl-ate groups into undulating chains extending along [001] and the flunarizinium monocations are attached to these chains via N(+)-H⋯O(-) hydrogen bonds. C-H⋯O inter-actions connect these chains into a three-dimensional network. The shortest centroid-centroid distance of 3.7256 (10) Å was found between one of the fluorinated benzene rings and the non-fluorinated phenyl ring in the neighbouring mol-ecule related by a glide plane.

Related literature

For pharmaceutical properties of flunarizine, see: Holmes et al. (1984 ▶); Amery (1983 ▶) and of piperazine derivatives, see: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶); Elliott (2011 ▶). For related structures, see: Betz et al. (2011a ▶,b ▶); Dayananda et al. (2012a ▶,b ▶); Fillers & Hawkinson (1982 ▶); Vanier & Brisse (1983 ▶). For puckering analysis of six-membered rings, see: Cremer & Pople (1975 ▶); Boeyens (1978 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H27F2N2 +·C4H5O4 −

M = 522.58

Monoclinic,

a = 10.7824 (2) Å

b = 10.6270 (2) Å

c = 11.2364 (2) Å

β = 91.678 (1)°

V = 1286.97 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.56 × 0.29 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.947, T max = 0.985

16870 measured reflections

3619 independent reflections

3524 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.081

S = 1.03

3619 reflections

348 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000706/gk2534sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000706/gk2534Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000706/gk2534Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000706/gk2534Isup4.cml

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

C26H27F2N2+·C4H5O4−	F(000) = 552
Mr = 522.58	Dx = 1.349 Mg m−3
Monoclinic, Pc	Melting point = 383–378 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7824 (2) Å	Cell parameters from 9972 reflections
b = 10.6270 (2) Å	θ = 2.6–29.6°
c = 11.2364 (2) Å	µ = 0.10 mm−1
β = 91.678 (1)°	T = 200 K
V = 1286.97 (4) Å3	Rectangular, yellow
Z = 2	0.56 × 0.29 × 0.16 mm

Bruker APEXII CCD diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	3524 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 29.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.947, Tmax = 0.985	k = −14→14
16870 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.1548P] where P = (Fo2 + 2Fc2)/3
3619 reflections	(Δ/σ)max < 0.001
348 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (3016 pairs) have been merged and the item was removed from the CIF.

	x	y	z	Uiso*/Ueq
F1	0.60945 (15)	−0.00547 (14)	0.96672 (13)	0.0575 (3)
F2	0.76769 (12)	0.30206 (12)	0.22338 (10)	0.0453 (3)
N1	0.39495 (10)	0.42901 (11)	0.63218 (10)	0.0199 (2)
N2	0.16828 (10)	0.57409 (11)	0.64797 (10)	0.0205 (2)
H72	0.192 (2)	0.640 (2)	0.7023 (19)	0.028 (5)*
C1	0.52807 (12)	0.40104 (13)	0.65297 (11)	0.0204 (2)
H1	0.5681	0.4768	0.6903	0.024*
C2	0.32435 (13)	0.43027 (13)	0.74174 (12)	0.0223 (2)
H2A	0.3558	0.4980	0.7950	0.027*
H2B	0.3351	0.3490	0.7839	0.027*
C3	0.18784 (13)	0.45191 (13)	0.71164 (12)	0.0222 (2)
H3A	0.1560	0.3822	0.6609	0.027*
H3B	0.1406	0.4521	0.7859	0.027*
C4	0.24729 (12)	0.57850 (13)	0.54108 (11)	0.0214 (2)
H4A	0.2400	0.6623	0.5031	0.026*
H4B	0.2181	0.5146	0.4825	0.026*
C5	0.38119 (13)	0.55330 (13)	0.57621 (12)	0.0220 (2)
H5A	0.4325	0.5572	0.5047	0.026*
H5B	0.4111	0.6190	0.6325	0.026*
C6	0.03255 (13)	0.58877 (15)	0.61516 (13)	0.0268 (3)
H6A	0.0047	0.5155	0.5669	0.032*
H6B	−0.0159	0.5900	0.6886	0.032*
C7	0.00768 (14)	0.70704 (15)	0.54620 (14)	0.0282 (3)
H7	0.0228	0.7860	0.5836	0.034*
C8	−0.03506 (14)	0.70463 (14)	0.43376 (14)	0.0268 (3)
H8	−0.0467	0.6237	0.3993	0.032*
C11	0.54868 (12)	0.29049 (13)	0.73680 (12)	0.0216 (2)
C12	0.60202 (14)	0.31075 (15)	0.84953 (13)	0.0274 (3)
H12	0.6246	0.3936	0.8733	0.033*
C13	0.62266 (16)	0.21099 (19)	0.92779 (14)	0.0351 (3)
H13	0.6591	0.2248	1.0047	0.042*
C14	0.58933 (17)	0.09282 (18)	0.89143 (16)	0.0365 (4)
C15	0.53618 (18)	0.06793 (16)	0.78097 (16)	0.0364 (3)
H15	0.5139	−0.0154	0.7584	0.044*
C16	0.51610 (15)	0.16833 (14)	0.70341 (14)	0.0291 (3)
H16	0.4797	0.1534	0.6267	0.035*
C21	0.58957 (12)	0.37651 (12)	0.53494 (12)	0.0212 (2)
C22	0.52566 (13)	0.32091 (13)	0.43931 (13)	0.0243 (2)
H22	0.4402	0.3010	0.4460	0.029*
C23	0.58533 (15)	0.29394 (14)	0.33373 (13)	0.0279 (3)
H23	0.5418	0.2559	0.2684	0.033*
C24	0.70925 (15)	0.32415 (15)	0.32721 (14)	0.0301 (3)
C25	0.77684 (14)	0.37818 (16)	0.41996 (15)	0.0317 (3)
H25	0.8626	0.3964	0.4132	0.038*
C26	0.71468 (13)	0.40504 (15)	0.52386 (13)	0.0269 (3)
H26	0.7586	0.4437	0.5886	0.032*
C31	−0.06628 (13)	0.81225 (14)	0.35691 (13)	0.0257 (3)
C32	−0.05674 (15)	0.93704 (15)	0.39524 (15)	0.0310 (3)
H32	−0.0249	0.9550	0.4731	0.037*
C33	−0.09348 (17)	1.03489 (17)	0.32034 (17)	0.0369 (3)
H33	−0.0861	1.1194	0.3471	0.044*
C34	−0.14092 (17)	1.00983 (18)	0.20662 (17)	0.0379 (4)
H34	−0.1675	1.0769	0.1562	0.046*
C35	−0.14940 (18)	0.88675 (19)	0.16704 (15)	0.0378 (4)
H35	−0.1810	0.8693	0.0890	0.045*
C36	−0.11186 (16)	0.78902 (16)	0.24134 (14)	0.0326 (3)
H36	−0.1172	0.7048	0.2132	0.039*
O1	0.21803 (11)	0.76463 (10)	0.79808 (9)	0.0295 (2)
O2	0.09155 (11)	0.65696 (11)	0.91333 (10)	0.0310 (2)
O3	0.20616 (15)	1.03647 (13)	1.15502 (12)	0.0423 (3)
H3	0.2229	1.0913	1.2069	0.063*
O4	0.35531 (19)	1.13282 (17)	1.06159 (18)	0.0694 (6)
C41	0.16219 (13)	0.74667 (13)	0.89574 (12)	0.0226 (2)
C42	0.18904 (14)	0.83825 (13)	0.99780 (12)	0.0254 (3)
H42A	0.1093	0.8623	1.0328	0.030*
H42B	0.2387	0.7939	1.0602	0.030*
C43	0.25742 (15)	0.95766 (14)	0.96455 (13)	0.0279 (3)
H43A	0.3386	0.9337	0.9325	0.034*
H43B	0.2094	1.0003	0.8999	0.034*
C44	0.27975 (16)	1.05070 (14)	1.06472 (14)	0.0296 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0687 (8)	0.0515 (7)	0.0524 (7)	0.0115 (6)	0.0015 (6)	0.0322 (6)
F2	0.0511 (6)	0.0496 (6)	0.0364 (5)	0.0085 (5)	0.0228 (5)	0.0009 (5)
N1	0.0200 (5)	0.0214 (5)	0.0185 (5)	0.0035 (4)	0.0028 (4)	0.0027 (4)
N2	0.0216 (5)	0.0220 (5)	0.0178 (5)	0.0036 (4)	0.0005 (4)	−0.0015 (4)
C1	0.0204 (5)	0.0204 (5)	0.0203 (5)	0.0017 (4)	0.0001 (4)	0.0002 (4)
C2	0.0239 (6)	0.0246 (6)	0.0184 (5)	0.0038 (5)	0.0023 (4)	0.0026 (4)
C3	0.0246 (6)	0.0226 (6)	0.0197 (5)	0.0025 (5)	0.0035 (4)	0.0017 (4)
C4	0.0234 (6)	0.0248 (6)	0.0160 (5)	0.0035 (5)	0.0021 (4)	0.0011 (4)
C5	0.0228 (6)	0.0212 (6)	0.0221 (6)	0.0020 (5)	0.0017 (4)	0.0033 (4)
C6	0.0204 (6)	0.0346 (7)	0.0253 (6)	0.0044 (5)	0.0001 (5)	0.0004 (5)
C7	0.0267 (6)	0.0290 (7)	0.0288 (7)	0.0081 (5)	−0.0017 (5)	−0.0033 (5)
C8	0.0254 (6)	0.0271 (6)	0.0277 (6)	0.0009 (5)	−0.0005 (5)	−0.0010 (5)
C11	0.0207 (5)	0.0235 (6)	0.0205 (6)	0.0036 (5)	0.0010 (4)	0.0019 (5)
C12	0.0264 (6)	0.0332 (7)	0.0226 (6)	0.0017 (5)	−0.0002 (5)	0.0007 (5)
C13	0.0315 (7)	0.0496 (9)	0.0242 (7)	0.0048 (7)	−0.0009 (5)	0.0089 (6)
C14	0.0359 (8)	0.0392 (8)	0.0348 (8)	0.0085 (7)	0.0061 (6)	0.0178 (7)
C15	0.0461 (9)	0.0245 (7)	0.0388 (8)	0.0033 (6)	0.0047 (7)	0.0073 (6)
C16	0.0361 (7)	0.0233 (6)	0.0278 (7)	0.0015 (5)	−0.0005 (5)	0.0017 (5)
C21	0.0223 (6)	0.0198 (6)	0.0215 (5)	0.0031 (4)	0.0027 (4)	0.0029 (4)
C22	0.0238 (6)	0.0236 (6)	0.0257 (6)	0.0004 (5)	0.0018 (5)	0.0004 (5)
C23	0.0353 (7)	0.0244 (6)	0.0240 (6)	0.0043 (5)	0.0027 (5)	−0.0003 (5)
C24	0.0353 (8)	0.0272 (7)	0.0285 (7)	0.0082 (6)	0.0118 (6)	0.0054 (5)
C25	0.0251 (6)	0.0320 (8)	0.0383 (8)	0.0043 (5)	0.0082 (6)	0.0072 (6)
C26	0.0221 (6)	0.0281 (7)	0.0304 (7)	0.0012 (5)	0.0006 (5)	0.0041 (5)
C31	0.0217 (6)	0.0297 (7)	0.0258 (6)	−0.0004 (5)	0.0000 (5)	0.0006 (5)
C32	0.0303 (7)	0.0314 (7)	0.0311 (7)	−0.0006 (6)	−0.0012 (6)	−0.0020 (6)
C33	0.0388 (8)	0.0285 (7)	0.0434 (9)	0.0013 (6)	−0.0005 (7)	0.0014 (6)
C34	0.0354 (8)	0.0396 (9)	0.0387 (8)	0.0021 (7)	−0.0011 (6)	0.0096 (7)
C35	0.0412 (8)	0.0432 (9)	0.0286 (7)	−0.0014 (7)	−0.0055 (6)	0.0041 (6)
C36	0.0358 (8)	0.0339 (8)	0.0280 (7)	−0.0027 (6)	−0.0029 (6)	−0.0013 (6)
O1	0.0443 (6)	0.0237 (5)	0.0207 (4)	−0.0016 (4)	0.0052 (4)	−0.0010 (4)
O2	0.0343 (5)	0.0262 (5)	0.0328 (5)	−0.0049 (4)	0.0033 (4)	−0.0012 (4)
O3	0.0591 (8)	0.0372 (6)	0.0314 (6)	−0.0147 (6)	0.0143 (5)	−0.0140 (5)
O4	0.0814 (12)	0.0525 (9)	0.0770 (11)	−0.0382 (9)	0.0448 (10)	−0.0354 (9)
C41	0.0273 (6)	0.0185 (5)	0.0219 (5)	0.0044 (5)	−0.0009 (4)	0.0002 (4)
C42	0.0345 (7)	0.0219 (6)	0.0200 (5)	−0.0021 (5)	0.0049 (5)	−0.0017 (4)
C43	0.0377 (7)	0.0217 (6)	0.0248 (6)	−0.0033 (5)	0.0075 (5)	−0.0025 (5)
C44	0.0356 (7)	0.0221 (6)	0.0312 (7)	−0.0006 (5)	0.0061 (6)	−0.0041 (5)

F1—C14	1.3576 (18)	C15—C16	1.391 (2)
F2—C24	1.3625 (17)	C15—H15	0.9500
N1—C2	1.4663 (16)	C16—H16	0.9500
N1—C5	1.4686 (17)	C21—C22	1.3911 (19)
N1—C1	1.4776 (16)	C21—C26	1.3918 (19)
N2—C4	1.4934 (16)	C22—C23	1.3957 (19)
N2—C3	1.4944 (17)	C22—H22	0.9500
N2—C6	1.5069 (17)	C23—C24	1.378 (2)
N2—H72	0.96 (2)	C23—H23	0.9500
C1—C11	1.5181 (18)	C24—C25	1.379 (2)
C1—C21	1.5225 (18)	C25—C26	1.393 (2)
C1—H1	1.0000	C25—H25	0.9500
C2—C3	1.5182 (19)	C26—H26	0.9500
C2—H2A	0.9900	C31—C36	1.397 (2)
C2—H2B	0.9900	C31—C32	1.397 (2)
C3—H3A	0.9900	C32—C33	1.388 (2)
C3—H3B	0.9900	C32—H32	0.9500
C4—C5	1.5094 (19)	C33—C34	1.388 (3)
C4—H4A	0.9900	C33—H33	0.9500
C4—H4B	0.9900	C34—C35	1.384 (3)
C5—H5A	0.9900	C34—H34	0.9500
C5—H5B	0.9900	C35—C36	1.385 (2)
C6—C7	1.497 (2)	C35—H35	0.9500
C6—H6A	0.9900	C36—H36	0.9500
C6—H6B	0.9900	O1—C41	1.2813 (17)
C7—C8	1.332 (2)	O2—C41	1.2398 (19)
C7—H7	0.9500	O3—C44	1.3150 (19)
C8—C31	1.466 (2)	O3—H3	0.8400
C8—H8	0.9500	O4—C44	1.195 (2)
C11—C12	1.3924 (19)	C41—C42	1.5254 (19)
C11—C16	1.394 (2)	C42—C43	1.520 (2)
C12—C13	1.391 (2)	C42—H42A	0.9900
C12—H12	0.9500	C42—H42B	0.9900
C13—C14	1.366 (3)	C43—C44	1.512 (2)
C13—H13	0.9500	C43—H43A	0.9900
C14—C15	1.377 (3)	C43—H43B	0.9900
C2—N1—C5	107.63 (10)	C13—C14—C15	123.04 (14)
C2—N1—C1	113.26 (10)	C14—C15—C16	118.06 (16)
C5—N1—C1	109.52 (10)	C14—C15—H15	121.0
C4—N2—C3	109.66 (10)	C16—C15—H15	121.0
C4—N2—C6	111.89 (10)	C15—C16—C11	120.84 (15)
C3—N2—C6	109.24 (11)	C15—C16—H16	119.6
C4—N2—H72	110.2 (13)	C11—C16—H16	119.6
C3—N2—H72	107.3 (13)	C22—C21—C26	118.88 (12)
C6—N2—H72	108.5 (13)	C22—C21—C1	121.80 (12)
N1—C1—C11	112.18 (11)	C26—C21—C1	119.25 (12)
N1—C1—C21	110.04 (10)	C21—C22—C23	120.90 (13)
C11—C1—C21	110.39 (11)	C21—C22—H22	119.6
N1—C1—H1	108.0	C23—C22—H22	119.6
C11—C1—H1	108.0	C24—C23—C22	117.97 (14)
C21—C1—H1	108.0	C24—C23—H23	121.0
N1—C2—C3	109.77 (10)	C22—C23—H23	121.0
N1—C2—H2A	109.7	F2—C24—C23	118.61 (15)
C3—C2—H2A	109.7	F2—C24—C25	118.12 (14)
N1—C2—H2B	109.7	C23—C24—C25	123.26 (13)
C3—C2—H2B	109.7	C24—C25—C26	117.53 (14)
H2A—C2—H2B	108.2	C24—C25—H25	121.2
N2—C3—C2	111.13 (11)	C26—C25—H25	121.2
N2—C3—H3A	109.4	C21—C26—C25	121.46 (14)
C2—C3—H3A	109.4	C21—C26—H26	119.3
N2—C3—H3B	109.4	C25—C26—H26	119.3
C2—C3—H3B	109.4	C36—C31—C32	118.35 (14)
H3A—C3—H3B	108.0	C36—C31—C8	118.57 (14)
N2—C4—C5	110.36 (10)	C32—C31—C8	123.04 (13)
N2—C4—H4A	109.6	C33—C32—C31	120.47 (15)
C5—C4—H4A	109.6	C33—C32—H32	119.8
N2—C4—H4B	109.6	C31—C32—H32	119.8
C5—C4—H4B	109.6	C32—C33—C34	120.35 (17)
H4A—C4—H4B	108.1	C32—C33—H33	119.8
N1—C5—C4	110.82 (11)	C34—C33—H33	119.8
N1—C5—H5A	109.5	C35—C34—C33	119.75 (16)
C4—C5—H5A	109.5	C35—C34—H34	120.1
N1—C5—H5B	109.5	C33—C34—H34	120.1
C4—C5—H5B	109.5	C34—C35—C36	119.97 (16)
H5A—C5—H5B	108.1	C34—C35—H35	120.0
C7—C6—N2	111.81 (12)	C36—C35—H35	120.0
C7—C6—H6A	109.3	C35—C36—C31	121.09 (16)
N2—C6—H6A	109.3	C35—C36—H36	119.5
C7—C6—H6B	109.3	C31—C36—H36	119.5
N2—C6—H6B	109.3	C44—O3—H3	109.5
H6A—C6—H6B	107.9	O2—C41—O1	123.88 (13)
C8—C7—C6	121.77 (14)	O2—C41—C42	118.34 (12)
C8—C7—H7	119.1	O1—C41—C42	117.73 (12)
C6—C7—H7	119.1	C43—C42—C41	115.51 (11)
C7—C8—C31	127.63 (14)	C43—C42—H42A	108.4
C7—C8—H8	116.2	C41—C42—H42A	108.4
C31—C8—H8	116.2	C43—C42—H42B	108.4
C12—C11—C16	118.89 (13)	C41—C42—H42B	108.4
C12—C11—C1	119.60 (13)	H42A—C42—H42B	107.5
C16—C11—C1	121.51 (12)	C44—C43—C42	115.52 (12)
C13—C12—C11	120.76 (15)	C44—C43—H43A	108.4
C13—C12—H12	119.6	C42—C43—H43A	108.4
C11—C12—H12	119.6	C44—C43—H43B	108.4
C14—C13—C12	118.41 (15)	C42—C43—H43B	108.4
C14—C13—H13	120.8	H43A—C43—H43B	107.5
C12—C13—H13	120.8	O4—C44—O3	122.28 (15)
F1—C14—C13	119.03 (17)	O4—C44—C43	123.32 (15)
F1—C14—C15	117.93 (18)	O3—C44—C43	114.37 (13)
C2—N1—C1—C11	45.82 (15)	C1—C11—C16—C15	179.64 (15)
C5—N1—C1—C11	165.97 (11)	N1—C1—C21—C22	−32.40 (17)
C2—N1—C1—C21	169.14 (11)	C11—C1—C21—C22	91.95 (15)
C5—N1—C1—C21	−70.72 (13)	N1—C1—C21—C26	150.61 (12)
C5—N1—C2—C3	62.13 (13)	C11—C1—C21—C26	−85.03 (15)
C1—N1—C2—C3	−176.65 (11)	C26—C21—C22—C23	0.0 (2)
C4—N2—C3—C2	54.54 (14)	C1—C21—C22—C23	−177.01 (12)
C6—N2—C3—C2	177.49 (11)	C21—C22—C23—C24	−0.1 (2)
N1—C2—C3—N2	−59.43 (14)	C22—C23—C24—F2	−177.93 (13)
C3—N2—C4—C5	−54.17 (14)	C22—C23—C24—C25	0.7 (2)
C6—N2—C4—C5	−175.54 (11)	F2—C24—C25—C26	177.40 (13)
C2—N1—C5—C4	−62.90 (13)	C23—C24—C25—C26	−1.3 (2)
C1—N1—C5—C4	173.58 (10)	C22—C21—C26—C25	−0.5 (2)
N2—C4—C5—N1	59.60 (14)	C1—C21—C26—C25	176.52 (13)
C4—N2—C6—C7	−55.86 (15)	C24—C25—C26—C21	1.2 (2)
C3—N2—C6—C7	−177.48 (11)	C7—C8—C31—C36	−179.03 (16)
N2—C6—C7—C8	115.58 (16)	C7—C8—C31—C32	−1.4 (2)
C6—C7—C8—C31	178.37 (14)	C36—C31—C32—C33	0.9 (2)
N1—C1—C11—C12	−111.85 (14)	C8—C31—C32—C33	−176.78 (15)
C21—C1—C11—C12	125.03 (13)	C31—C32—C33—C34	0.4 (3)
N1—C1—C11—C16	68.57 (17)	C32—C33—C34—C35	−1.2 (3)
C21—C1—C11—C16	−54.55 (17)	C33—C34—C35—C36	0.7 (3)
C16—C11—C12—C13	0.0 (2)	C34—C35—C36—C31	0.6 (3)
C1—C11—C12—C13	−179.58 (13)	C32—C31—C36—C35	−1.4 (2)
C11—C12—C13—C14	0.0 (2)	C8—C31—C36—C35	176.36 (15)
C12—C13—C14—F1	179.71 (16)	O2—C41—C42—C43	−169.74 (14)
C12—C13—C14—C15	−0.1 (3)	O1—C41—C42—C43	12.88 (19)
F1—C14—C15—C16	−179.64 (16)	C41—C42—C43—C44	177.78 (13)
C13—C14—C15—C16	0.1 (3)	C42—C43—C44—O4	161.8 (2)
C14—C15—C16—C11	−0.1 (3)	C42—C43—C44—O3	−20.2 (2)
C12—C11—C16—C15	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H72···O1	0.96 (2)	1.73 (2)	2.6795 (16)	174 (2)
O3—H3···O1i	0.84	1.84	2.6564 (16)	162
C4—H4A···O4ii	0.99	2.58	3.287 (3)	128
C4—H4B···O2iii	0.99	2.39	3.3167 (19)	155
C25—H25···O2iv	0.95	2.53	3.4168 (19)	155
C12—H12···Cgv	0.95	2.81	3.7511 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H72⋯O1	0.96 (2)	1.73 (2)	2.6795 (16)	174 (2)
O3—H3⋯O1i	0.84	1.84	2.6564 (16)	162
C4—H4A⋯O4ii	0.99	2.58	3.287 (3)	128
C4—H4B⋯O2iii	0.99	2.39	3.3167 (19)	155
C25—H25⋯O2iv	0.95	2.53	3.4168 (19)	155
C12—H12⋯Cg v	0.95	2.81	3.7511 (17)	170

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