Literature DB >> 22606110

Cinnarizinium 3,5-dinitro-salicylate.

Alaloor S Dayananda, Hemmige S Yathirajan, Thomas Gerber, Eric Hosten, Richard Betz.

Abstract

THE TITLE COMPOUND [SYSTEMATIC NAME: 4-diphenyl-methyl-1-(3-phenylprop-2-en-1-yl)-piperazin-1-ium 2-carb-oxy-4,6-dinitro-pheno-late], C(26)H(29)N(2) (+)·C(7)H(3)N(2)O(7) (-), is the dinitro-salicylate salt of a tertiary amine. Deprotonation of the carb-oxy-lic acid group occurred on the phenolic hy-droxy group. The diaza-cyclo-hexane ring adopts a chair conformation. Intra-molecular O-H⋯O and inter-molecular C-H⋯O and N-H⋯O hydrogen bonds are observed. The N-H⋯O hydrogen bonds are bifurcated at the H atom and connect the cinnarizinium and 3,5-dinitro-salicylate ions together. Inter-molecular C-H⋯O hydrogen bonds connect the components into layers perpendicular to the crystallographic a axis.

Entities: Chemical Disease Species

Year: 2012 PMID： 22606110 PMCID： PMC3344107 DOI： 10.1107/S1600536812011518

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For pharmaceutical background to cinnarizine, see: Barrett & Zolov (1960 ▶). For related structures, see: Bertolasi et al. (1980 ▶); Smith et al. (2001 ▶); Jasinski et al. (2011 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H29N2 +·C7H3N2O7 − M = 596.63 Monoclinic, a = 14.5648 (3) Å b = 12.9374 (3) Å c = 16.1619 (3) Å β = 103.900 (1)° V = 2956.22 (11) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 200 K 0.51 × 0.26 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.932, T max = 1.000 29552 measured reflections 7344 independent reflections 6023 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.148 S = 1.03 7344 reflections 401 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.85 e Å−3 Δρmin = −0.35 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, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011518/rn2101sup1.cif Supplementary material file. DOI: 10.1107/S1600536812011518/rn2101Isup2.cdx Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011518/rn2101Isup3.hkl Supplementary material file. DOI: 10.1107/S1600536812011518/rn2101Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₆H₂₉N₂⁺·C₇H₃N₂O₇⁻	F(000) = 1256
M_r = 596.63	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.5648 (3) Å	Cell parameters from 9909 reflections
b = 12.9374 (3) Å	θ = 2.3–28.3°
c = 16.1619 (3) Å	µ = 0.10 mm⁻¹
β = 103.900 (1)°	T = 200 K
V = 2956.22 (11) Å³	Block, yellow
Z = 4	0.51 × 0.26 × 0.17 mm

Bruker APEXII CCD diffractometer	7344 independent reflections
Radiation source: fine-focus sealed tube	6023 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→19
T_min = 0.932, T_max = 1.000	k = −17→17
29552 measured reflections	l = −21→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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.070P)² + 1.6929P] where P = (F_o² + 2F_c²)/3
7344 reflections	(Δ/σ)_max < 0.001
401 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

	x	y	z	U_iso*/U_eq
N1	0.25623 (8)	0.71175 (10)	0.31330 (8)	0.0251 (2)
H71	0.2998 (14)	0.6749 (15)	0.3494 (13)	0.034 (5)*
N2	0.10014 (8)	0.56688 (9)	0.26578 (7)	0.0238 (2)
C1	0.29863 (11)	0.95171 (13)	0.41663 (10)	0.0338 (3)
H1A	0.2459	0.9812	0.3774	0.041*
C2	0.33475 (11)	0.86690 (12)	0.39167 (10)	0.0326 (3)
H2	0.3869	0.8355	0.4301	0.039*
C3	0.29836 (12)	0.81760 (12)	0.30658 (10)	0.0341 (3)
H3A	0.3508	0.8110	0.2777	0.041*
H3B	0.2495	0.8628	0.2711	0.041*
C4	0.17100 (10)	0.71680 (12)	0.34936 (10)	0.0287 (3)
H4A	0.1231	0.7629	0.3138	0.034*
H4B	0.1889	0.7459	0.4077	0.034*
C5	0.12940 (10)	0.61023 (12)	0.35209 (9)	0.0279 (3)
H5A	0.1770	0.5644	0.3883	0.034*
H5B	0.0741	0.6143	0.3775	0.034*
C6	0.18554 (10)	0.55568 (12)	0.23334 (9)	0.0267 (3)
H6A	0.1686	0.5236	0.1761	0.032*
H6B	0.2310	0.5095	0.2716	0.032*
C7	0.23147 (11)	0.65942 (12)	0.22794 (9)	0.0285 (3)
H7A	0.2895	0.6497	0.2072	0.034*
H7B	0.1877	0.7039	0.1866	0.034*
C8	0.05330 (9)	0.46543 (11)	0.26749 (9)	0.0234 (3)
H8	0.0999	0.4178	0.3043	0.028*
C11	0.33137 (12)	1.00538 (12)	0.49873 (10)	0.0328 (3)
C12	0.41578 (13)	0.97939 (14)	0.55689 (11)	0.0393 (4)
H12	0.4549	0.9265	0.5432	0.047*
C13	0.44279 (15)	1.03042 (18)	0.63443 (12)	0.0502 (5)
H13	0.4998	1.0115	0.6739	0.060*
C14	0.38744 (17)	1.10827 (18)	0.65452 (13)	0.0555 (5)
H14	0.4068	1.1435	0.7074	0.067*
C15	0.30396 (16)	1.13519 (17)	0.59790 (14)	0.0521 (5)
H15	0.2657	1.1887	0.6119	0.062*
C16	0.27599 (13)	1.08397 (14)	0.52044 (12)	0.0407 (4)
H16	0.2184	1.1027	0.4817	0.049*
C21	−0.03163 (10)	0.47510 (11)	0.30648 (9)	0.0246 (3)
C22	−0.04283 (11)	0.40380 (12)	0.36751 (10)	0.0323 (3)
H22	0.0030	0.3509	0.3849	0.039*
C23	−0.12068 (13)	0.40914 (14)	0.40346 (11)	0.0397 (4)
H23	−0.1275	0.3601	0.4454	0.048*
C24	−0.18792 (12)	0.48540 (14)	0.37840 (12)	0.0388 (4)
H24	−0.2414	0.4885	0.4024	0.047*
C25	−0.17702 (11)	0.55719 (13)	0.31830 (11)	0.0352 (3)
H25	−0.2231	0.6099	0.3011	0.042*
C26	−0.09910 (10)	0.55295 (12)	0.28272 (10)	0.0294 (3)
H26	−0.0918	0.6033	0.2420	0.035*
C31	0.02530 (10)	0.41884 (11)	0.17808 (9)	0.0251 (3)
C32	0.06680 (12)	0.32722 (12)	0.16047 (11)	0.0337 (3)
H32	0.1122	0.2937	0.2044	0.040*
C33	0.04250 (13)	0.28413 (13)	0.07907 (12)	0.0394 (4)
H33	0.0719	0.2220	0.0676	0.047*
C34	−0.02374 (13)	0.33119 (14)	0.01544 (11)	0.0386 (4)
H34	−0.0400	0.3019	−0.0401	0.046*
C35	−0.06687 (13)	0.42141 (15)	0.03242 (10)	0.0390 (4)
H35	−0.1138	0.4532	−0.0112	0.047*
C36	−0.04164 (11)	0.46560 (13)	0.11309 (10)	0.0322 (3)
H36	−0.0705	0.5284	0.1239	0.039*
O1	0.63343 (8)	0.37345 (10)	0.53526 (8)	0.0398 (3)
O2	0.58174 (10)	0.44031 (15)	0.67150 (9)	0.0619 (4)
O3	0.43582 (10)	0.48104 (13)	0.65686 (9)	0.0557 (4)
O4	0.19460 (9)	0.32142 (13)	0.44738 (11)	0.0578 (4)
O5	0.22771 (11)	0.24235 (14)	0.34093 (10)	0.0635 (4)
O6	0.54743 (11)	0.23538 (12)	0.30218 (9)	0.0525 (4)
O7	0.66612 (10)	0.28953 (12)	0.40548 (10)	0.0517 (4)
H7	0.6736	0.3061	0.4569	0.078*
N3	0.49860 (10)	0.43821 (12)	0.63196 (9)	0.0388 (3)
N4	0.25126 (10)	0.29137 (13)	0.40744 (10)	0.0436 (4)
C9	0.57578 (13)	0.27360 (14)	0.37134 (12)	0.0402 (4)
C41	0.54463 (10)	0.35631 (12)	0.50730 (10)	0.0305 (3)
C42	0.50991 (11)	0.30575 (12)	0.42633 (10)	0.0321 (3)
C43	0.41582 (12)	0.28489 (13)	0.39505 (10)	0.0332 (3)
H43	0.3951	0.2501	0.3421	0.040*
C44	0.35102 (11)	0.31446 (12)	0.44044 (10)	0.0318 (3)
C45	0.37853 (11)	0.36483 (12)	0.51759 (10)	0.0310 (3)
H45	0.3329	0.3856	0.5476	0.037*
C46	0.47329 (11)	0.38454 (12)	0.55055 (10)	0.0297 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0223 (6)	0.0289 (6)	0.0240 (6)	−0.0037 (5)	0.0053 (5)	−0.0023 (5)
N2	0.0211 (5)	0.0270 (6)	0.0237 (5)	−0.0032 (4)	0.0064 (4)	−0.0032 (4)
C1	0.0304 (7)	0.0359 (8)	0.0317 (8)	−0.0039 (6)	0.0011 (6)	−0.0002 (6)
C2	0.0314 (7)	0.0309 (7)	0.0331 (8)	−0.0073 (6)	0.0030 (6)	0.0005 (6)
C3	0.0400 (8)	0.0311 (8)	0.0322 (8)	−0.0112 (6)	0.0105 (6)	−0.0016 (6)
C4	0.0231 (6)	0.0334 (7)	0.0307 (7)	−0.0026 (5)	0.0087 (6)	−0.0078 (6)
C5	0.0251 (7)	0.0345 (7)	0.0254 (7)	−0.0053 (6)	0.0083 (5)	−0.0053 (6)
C6	0.0240 (6)	0.0307 (7)	0.0272 (7)	−0.0035 (5)	0.0095 (5)	−0.0048 (5)
C7	0.0287 (7)	0.0342 (7)	0.0235 (6)	−0.0061 (6)	0.0080 (5)	−0.0042 (6)
C8	0.0205 (6)	0.0252 (6)	0.0246 (6)	0.0003 (5)	0.0058 (5)	0.0008 (5)
C11	0.0354 (8)	0.0313 (7)	0.0310 (7)	−0.0078 (6)	0.0064 (6)	−0.0001 (6)
C12	0.0396 (9)	0.0414 (9)	0.0344 (8)	−0.0059 (7)	0.0040 (7)	0.0005 (7)
C13	0.0517 (11)	0.0614 (12)	0.0325 (9)	−0.0141 (9)	0.0000 (8)	0.0007 (8)
C14	0.0685 (14)	0.0629 (13)	0.0365 (9)	−0.0230 (11)	0.0154 (9)	−0.0156 (9)
C15	0.0600 (12)	0.0464 (11)	0.0552 (12)	−0.0103 (9)	0.0244 (10)	−0.0147 (9)
C16	0.0402 (9)	0.0359 (8)	0.0456 (9)	−0.0052 (7)	0.0095 (7)	−0.0041 (7)
C21	0.0217 (6)	0.0264 (6)	0.0253 (6)	−0.0019 (5)	0.0052 (5)	−0.0023 (5)
C22	0.0320 (7)	0.0331 (8)	0.0340 (8)	0.0033 (6)	0.0120 (6)	0.0052 (6)
C23	0.0436 (9)	0.0399 (9)	0.0423 (9)	0.0008 (7)	0.0236 (8)	0.0059 (7)
C24	0.0347 (8)	0.0390 (9)	0.0497 (10)	−0.0022 (7)	0.0241 (7)	−0.0077 (7)
C25	0.0279 (7)	0.0339 (8)	0.0446 (9)	0.0044 (6)	0.0105 (6)	−0.0057 (7)
C26	0.0281 (7)	0.0280 (7)	0.0325 (7)	0.0014 (6)	0.0084 (6)	0.0003 (6)
C31	0.0231 (6)	0.0258 (6)	0.0279 (7)	−0.0047 (5)	0.0089 (5)	−0.0018 (5)
C32	0.0337 (8)	0.0301 (7)	0.0373 (8)	0.0019 (6)	0.0084 (6)	−0.0025 (6)
C33	0.0452 (9)	0.0304 (8)	0.0451 (9)	−0.0014 (7)	0.0156 (8)	−0.0096 (7)
C34	0.0467 (9)	0.0383 (9)	0.0322 (8)	−0.0107 (7)	0.0122 (7)	−0.0100 (7)
C35	0.0401 (9)	0.0457 (9)	0.0285 (8)	−0.0005 (7)	0.0031 (7)	−0.0022 (7)
C36	0.0321 (7)	0.0341 (8)	0.0300 (7)	0.0026 (6)	0.0066 (6)	−0.0019 (6)
O1	0.0252 (5)	0.0475 (7)	0.0449 (7)	−0.0019 (5)	0.0047 (5)	0.0070 (5)
O2	0.0369 (7)	0.0965 (13)	0.0456 (8)	0.0019 (7)	−0.0034 (6)	−0.0231 (8)
O3	0.0473 (8)	0.0700 (10)	0.0462 (8)	0.0148 (7)	0.0041 (6)	−0.0177 (7)
O4	0.0247 (6)	0.0743 (10)	0.0719 (10)	0.0057 (6)	0.0065 (6)	0.0004 (8)
O5	0.0467 (8)	0.0779 (11)	0.0535 (9)	−0.0096 (8)	−0.0122 (7)	−0.0138 (8)
O6	0.0609 (9)	0.0615 (9)	0.0405 (7)	0.0067 (7)	0.0230 (7)	−0.0021 (6)
O7	0.0400 (7)	0.0633 (9)	0.0579 (8)	0.0010 (6)	0.0236 (6)	−0.0020 (7)
N3	0.0367 (7)	0.0409 (8)	0.0361 (7)	0.0042 (6)	0.0037 (6)	−0.0025 (6)
N4	0.0309 (7)	0.0474 (9)	0.0452 (8)	−0.0006 (6)	−0.0051 (6)	0.0038 (7)
C9	0.0398 (9)	0.0360 (8)	0.0489 (10)	0.0046 (7)	0.0188 (8)	0.0090 (7)
C41	0.0246 (7)	0.0280 (7)	0.0373 (8)	0.0023 (5)	0.0045 (6)	0.0099 (6)
C42	0.0336 (8)	0.0300 (7)	0.0354 (8)	0.0049 (6)	0.0135 (6)	0.0076 (6)
C43	0.0378 (8)	0.0321 (8)	0.0287 (7)	0.0010 (6)	0.0059 (6)	0.0027 (6)
C44	0.0245 (7)	0.0338 (8)	0.0338 (8)	0.0008 (6)	0.0003 (6)	0.0030 (6)
C45	0.0261 (7)	0.0327 (7)	0.0341 (8)	0.0058 (6)	0.0069 (6)	0.0022 (6)
C46	0.0292 (7)	0.0287 (7)	0.0286 (7)	0.0025 (6)	0.0018 (6)	0.0018 (6)

N1—C4	1.4940 (18)	C22—C23	1.395 (2)
N1—C7	1.5009 (18)	C22—H22	0.9500
N1—C3	1.5151 (19)	C23—C24	1.381 (3)
N1—H71	0.89 (2)	C23—H23	0.9500
N2—C6	1.4683 (17)	C24—C25	1.380 (3)
N2—C5	1.4685 (17)	C24—H24	0.9500
N2—C8	1.4826 (17)	C25—C26	1.391 (2)
C1—C2	1.321 (2)	C25—H25	0.9500
C1—C11	1.472 (2)	C26—H26	0.9500
C1—H1A	0.9500	C31—C36	1.388 (2)
C2—C3	1.493 (2)	C31—C32	1.391 (2)
C2—H2	0.9500	C32—C33	1.394 (2)
C3—H3A	0.9900	C32—H32	0.9500
C3—H3B	0.9900	C33—C34	1.372 (3)
C4—C5	1.511 (2)	C33—H33	0.9500
C4—H4A	0.9900	C34—C35	1.384 (3)
C4—H4B	0.9900	C34—H34	0.9500
C5—H5A	0.9900	C35—C36	1.390 (2)
C5—H5B	0.9900	C35—H35	0.9500
C6—C7	1.511 (2)	C36—H36	0.9500
C6—H6A	0.9900	O1—C41	1.2826 (19)
C6—H6B	0.9900	O2—N3	1.226 (2)
C7—H7A	0.9900	O3—N3	1.217 (2)
C7—H7B	0.9900	O4—N4	1.227 (2)
C8—C21	1.5224 (18)	O5—N4	1.224 (2)
C8—C31	1.5279 (19)	O6—C9	1.201 (2)
C8—H8	1.0000	O7—C9	1.315 (2)
C11—C16	1.394 (2)	O7—H7	0.8399
C11—C12	1.397 (2)	N3—C46	1.455 (2)
C12—C13	1.387 (3)	N4—C44	1.453 (2)
C12—H12	0.9500	C9—C42	1.514 (2)
C13—C14	1.377 (3)	C41—C46	1.432 (2)
C13—H13	0.9500	C41—C42	1.442 (2)
C14—C15	1.379 (3)	C42—C43	1.369 (2)
C14—H14	0.9500	C43—C44	1.381 (2)
C15—C16	1.388 (3)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.378 (2)
C16—H16	0.9500	C45—C46	1.379 (2)
C21—C22	1.388 (2)	C45—H45	0.9500
C21—C26	1.395 (2)

C4—N1—C7	109.85 (11)	C15—C16—H16	119.6
C4—N1—C3	112.16 (12)	C11—C16—H16	119.6
C7—N1—C3	110.73 (11)	C22—C21—C26	118.69 (13)
C4—N1—H71	107.2 (12)	C22—C21—C8	119.03 (13)
C7—N1—H71	109.6 (12)	C26—C21—C8	122.28 (13)
C3—N1—H71	107.1 (13)	C21—C22—C23	120.60 (15)
C6—N2—C5	107.43 (11)	C21—C22—H22	119.7
C6—N2—C8	110.63 (11)	C23—C22—H22	119.7
C5—N2—C8	110.50 (11)	C24—C23—C22	120.24 (15)
C2—C1—C11	126.91 (15)	C24—C23—H23	119.9
C2—C1—H1A	116.5	C22—C23—H23	119.9
C11—C1—H1A	116.5	C25—C24—C23	119.60 (14)
C1—C2—C3	123.84 (15)	C25—C24—H24	120.2
C1—C2—H2	118.1	C23—C24—H24	120.2
C3—C2—H2	118.1	C24—C25—C26	120.50 (15)
C2—C3—N1	112.36 (12)	C24—C25—H25	119.8
C2—C3—H3A	109.1	C26—C25—H25	119.8
N1—C3—H3A	109.1	C25—C26—C21	120.35 (14)
C2—C3—H3B	109.1	C25—C26—H26	119.8
N1—C3—H3B	109.1	C21—C26—H26	119.8
H3A—C3—H3B	107.9	C36—C31—C32	118.51 (14)
N1—C4—C5	110.38 (12)	C36—C31—C8	121.53 (13)
N1—C4—H4A	109.6	C32—C31—C8	119.96 (13)
C5—C4—H4A	109.6	C31—C32—C33	120.64 (15)
N1—C4—H4B	109.6	C31—C32—H32	119.7
C5—C4—H4B	109.6	C33—C32—H32	119.7
H4A—C4—H4B	108.1	C34—C33—C32	120.22 (16)
N2—C5—C4	110.34 (12)	C34—C33—H33	119.9
N2—C5—H5A	109.6	C32—C33—H33	119.9
C4—C5—H5A	109.6	C33—C34—C35	119.77 (15)
N2—C5—H5B	109.6	C33—C34—H34	120.1
C4—C5—H5B	109.6	C35—C34—H34	120.1
H5A—C5—H5B	108.1	C34—C35—C36	120.18 (16)
N2—C6—C7	110.95 (12)	C34—C35—H35	119.9
N2—C6—H6A	109.4	C36—C35—H35	119.9
C7—C6—H6A	109.4	C31—C36—C35	120.65 (15)
N2—C6—H6B	109.4	C31—C36—H36	119.7
C7—C6—H6B	109.4	C35—C36—H36	119.7
H6A—C6—H6B	108.0	C9—O7—H7	109.5
N1—C7—C6	111.07 (11)	O3—N3—O2	122.94 (16)
N1—C7—H7A	109.4	O3—N3—C46	117.98 (14)
C6—C7—H7A	109.4	O2—N3—C46	119.07 (14)
N1—C7—H7B	109.4	O5—N4—O4	122.97 (16)
C6—C7—H7B	109.4	O5—N4—C44	118.25 (16)
H7A—C7—H7B	108.0	O4—N4—C44	118.78 (15)
N2—C8—C21	110.99 (11)	O6—C9—O7	122.73 (17)
N2—C8—C31	110.55 (11)	O6—C9—C42	122.32 (17)
C21—C8—C31	111.42 (11)	O7—C9—C42	114.95 (16)
N2—C8—H8	107.9	O1—C41—C46	124.92 (15)
C21—C8—H8	107.9	O1—C41—C42	120.16 (15)
C31—C8—H8	107.9	C46—C41—C42	114.92 (13)
C16—C11—C12	118.36 (16)	C43—C42—C41	121.77 (14)
C16—C11—C1	119.29 (15)	C43—C42—C9	116.64 (15)
C12—C11—C1	122.35 (16)	C41—C42—C9	121.59 (15)
C13—C12—C11	120.39 (18)	C42—C43—C44	120.03 (15)
C13—C12—H12	119.8	C42—C43—H43	120.0
C11—C12—H12	119.8	C44—C43—H43	120.0
C14—C13—C12	120.41 (19)	C45—C44—C43	121.62 (14)
C14—C13—H13	119.8	C45—C44—N4	118.47 (15)
C12—C13—H13	119.8	C43—C44—N4	119.91 (15)
C13—C14—C15	120.06 (18)	C44—C45—C46	118.90 (14)
C13—C14—H14	120.0	C44—C45—H45	120.5
C15—C14—H14	120.0	C46—C45—H45	120.5
C14—C15—C16	119.9 (2)	C45—C46—C41	122.74 (14)
C14—C15—H15	120.0	C45—C46—N3	116.77 (14)
C16—C15—H15	120.0	C41—C46—N3	120.48 (14)
C15—C16—C11	120.85 (18)

C11—C1—C2—C3	−179.12 (15)	N2—C8—C31—C36	−64.73 (17)
C1—C2—C3—N1	−114.54 (17)	C21—C8—C31—C36	59.19 (17)
C4—N1—C3—C2	63.88 (17)	N2—C8—C31—C32	115.63 (14)
C7—N1—C3—C2	−173.02 (13)	C21—C8—C31—C32	−120.45 (14)
C7—N1—C4—C5	54.46 (16)	C36—C31—C32—C33	0.8 (2)
C3—N1—C4—C5	178.06 (12)	C8—C31—C32—C33	−179.55 (14)
C6—N2—C5—C4	63.12 (15)	C31—C32—C33—C34	−0.8 (3)
C8—N2—C5—C4	−176.12 (11)	C32—C33—C34—C35	−0.4 (3)
N1—C4—C5—N2	−60.74 (15)	C33—C34—C35—C36	1.5 (3)
C5—N2—C6—C7	−61.67 (15)	C32—C31—C36—C35	0.3 (2)
C8—N2—C6—C7	177.64 (11)	C8—C31—C36—C35	−179.31 (14)
C4—N1—C7—C6	−53.14 (16)	C34—C35—C36—C31	−1.5 (3)
C3—N1—C7—C6	−177.57 (12)	O1—C41—C42—C43	179.06 (15)
N2—C6—C7—N1	57.82 (16)	C46—C41—C42—C43	−1.4 (2)
C6—N2—C8—C21	176.26 (11)	O1—C41—C42—C9	−1.3 (2)
C5—N2—C8—C21	57.42 (14)	C46—C41—C42—C9	178.26 (14)
C6—N2—C8—C31	−59.58 (14)	O6—C9—C42—C43	2.9 (2)
C5—N2—C8—C31	−178.42 (11)	O7—C9—C42—C43	−176.34 (15)
C2—C1—C11—C16	−169.51 (17)	O6—C9—C42—C41	−176.79 (16)
C2—C1—C11—C12	9.5 (3)	O7—C9—C42—C41	4.0 (2)
C16—C11—C12—C13	0.5 (3)	C41—C42—C43—C44	1.4 (2)
C1—C11—C12—C13	−178.46 (16)	C9—C42—C43—C44	−178.21 (14)
C11—C12—C13—C14	−0.9 (3)	C42—C43—C44—C45	−0.2 (2)
C12—C13—C14—C15	0.8 (3)	C42—C43—C44—N4	−179.44 (15)
C13—C14—C15—C16	−0.3 (3)	O5—N4—C44—C45	−176.60 (17)
C14—C15—C16—C11	−0.1 (3)	O4—N4—C44—C45	3.2 (2)
C12—C11—C16—C15	0.0 (3)	O5—N4—C44—C43	2.7 (2)
C1—C11—C16—C15	179.02 (17)	O4—N4—C44—C43	−177.57 (16)
N2—C8—C21—C22	−133.38 (14)	C43—C44—C45—C46	−1.0 (2)
C31—C8—C21—C22	102.95 (15)	N4—C44—C45—C46	178.23 (14)
N2—C8—C21—C26	46.96 (17)	C44—C45—C46—C41	1.0 (2)
C31—C8—C21—C26	−76.71 (17)	C44—C45—C46—N3	179.78 (14)
C26—C21—C22—C23	0.8 (2)	O1—C41—C46—C45	179.67 (15)
C8—C21—C22—C23	−178.82 (15)	C42—C41—C46—C45	0.1 (2)
C21—C22—C23—C24	0.3 (3)	O1—C41—C46—N3	1.0 (2)
C22—C23—C24—C25	−0.8 (3)	C42—C41—C46—N3	−178.57 (13)
C23—C24—C25—C26	0.2 (3)	O3—N3—C46—C45	−15.1 (2)
C24—C25—C26—C21	0.9 (2)	O2—N3—C46—C45	166.34 (17)
C22—C21—C26—C25	−1.4 (2)	O3—N3—C46—C41	163.64 (16)
C8—C21—C26—C25	178.21 (14)	O2—N3—C46—C41	−14.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H71···O1ⁱ	0.89 (2)	1.99 (2)	2.8105 (18)	153.5 (17)
N1—H71···O2ⁱ	0.89 (2)	2.36 (2)	3.037 (2)	132.4 (16)
O7—H7···O1	0.84	1.75	2.507 (2)	149
C3—H3A···O6ⁱⁱ	0.99	2.40	3.341 (2)	160
C32—H32···O5	0.95	2.52	3.453 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H71⋯O1ⁱ	0.89 (2)	1.99 (2)	2.8105 (18)	153.5 (17)
N1—H71⋯O2ⁱ	0.89 (2)	2.36 (2)	3.037 (2)	132.4 (16)
O7—H7⋯O1	0.84	1.75	2.507 (2)	149
C3—H3A⋯O6ⁱⁱ	0.99	2.40	3.341 (2)	160
C32—H32⋯O5	0.95	2.52	3.453 (2)	166

Symmetry codes: (i) ; (ii) .

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1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Graph-set analysis of hydrogen-bond patterns in organic crystals.

Authors: M C Etter; J C MacDonald; J Bernstein
Journal: Acta Crystallogr B Date: 1990-04-01

3. A clinical evaluation of cinnarizine (Mitronal) in various allergic disorders.

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Journal: J Maine Med Assoc Date: 1960-12

4. Cinnarizinium dipicrate.

Authors: Jerry P Jasinski; Ray J Butcher; M S Siddegowda; H S Yathirajan; C S Chidan Kumar
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-01-26

5. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

5 in total

1. A resonance-assisted intra-molecular hydrogen bond in compounds containing 2-hy-droxy-3,5-di-nitro-benzoic acid and its various deprotonated forms: redetermination of several related structures.

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Journal: Acta Crystallogr E Crystallogr Commun Date: 2018-08-24