1-(3-{4-[(2,4-Dinitroanilino)methyl]­phenoxy}propyl)piperidinium chloride

Stark, H.; Amon, M.; Bolte, M.

doi:10.1107/S1600536807044157

1-(3-{4-[(2,4-Dinitroanilino)methyl]phenoxy}propyl)piperidinium chloride

The title compound, C₂₁H₂₇N₄O₅⁺·Cl⁻, is one of the parent compounds for a recently developed series of novel potent histamine H₃ receptor antagonists having additional fluorescent properties. The crystal structure is composed of discrete cations and anions connected by classical N—H

O and N—H

Cl hydrogen bonds. The crystal packing is further stabilized by weak C—H

Cl and C—H

O contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044157/hb2536sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044157/hb2536Isup2.hkl Contains datablock I

CCDC reference: 663778

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.072
wR factor = 0.128
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.75 Ratio
PLAT430_ALERT_2_B Short Inter D...A Contact  O122   ..  O122    ..       2.74 Ang.

Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Histamine H₃ receptors are important targets for different central nervous system disorders (Celanire et al., 2007). Within a recently developed series of novel potent histamine H₃ receptor antagonists having additional fluorescent properties the title compound can be taken as one of the parent molecules (Amon et al., 2007). The compound showed subnanomolar affinity at human histamine H₃ receptors (K_i value of 0.6nM) and a good Stokes shift of 100 nm.

The structure of the title compound, C₂₁H₂₇N₄O₅⁺ Cl^-, (I), is composed of discrete cations and anions. The bond lengths and angles in (I) are in the usual ranges. The piperidine ring adopts a chair conformation with the amino H atom in an axial position. Whereas one of the methylene C—C single bonds is in an antiperiplanar conformation [C2—C3—C4—N41 = 172.9 (3)°], the other one adopts a synclinal conformation [O1—C2—C3—C4 = 68.3 (4)°]. Both nitro groups are slightly tilted with respect to the aromatic ring to which they are attached: the dihedral angles between the planes of the nitro groups and the aromatic ring are 11.1 (5)° and 11.5 (6)° for the nitro groups N12, O121, O122 and N14, O141, O142, respectively. The dihedral angle between the two aromatic rings is 64.20 (11)°.

The amino H atom of the piperidine ring forms a classical N—H···Cl hydrogen bond (Table 1). The other amino H atom forms a bifurcated hydrogen bond. There is an intramolecular contact to one of the nitro O atoms of the aromatic ring attached to the amino group and there is an intermolecular contact to a symmetry equivalent of the same nitro O atom. As a result, a centrosymmetric dimer is formed (Fig. 2). In addition to these classical hydrogen bonds, the crystal packing is further stabilized by weak C—H···Cl and C—H···O contacts.

Related literature top

For related literature, see: Amon et al. (2007); Celanire et al. (2007).

Experimental top

The appropriate benzyl amine derivative was prepared in four steps by classical coupling reactions starting from piperidine and 3-chloropropanol. Alcohol chlorination, ether formation with 4-cyanophenol, and catalytic reduction led to the primary benzylamine which then was reacted with Sanger's reagent (1-fluoro-2,4-dinitrobenzen) in a nucleophilic aromatic substitution (Amon et al., 2007). The reaction product was purified chromatographically over silica gel with dichloromethane/methanol (95:5) and NH₃ gas. Yellow blocks of (I) were obtained from a mixture of ethanol/diethyl ether (1:6 v/v) with three drops of HCl at approximately 280 K.

Structure description top

For related literature, see: Amon et al. (2007); Celanire et al. (2007).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of (I) with displacement ellipsoids shown at the 50% probability level (arbitrary spheres for the hydrogen atoms).
	Fig. 2. Packing diagram of (I) viewed onto the ac plane. The classical hydrogen bonds shown as dashed lines.

1-(3-{4-[(2,4-Dinitroanilino)methyl]phenoxy}propyl)piperidinium chloride top

Crystal data top

C₂₁H₂₇N₄O₅⁺·Cl⁻	F(000) = 952
M_r = 450.92	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9924 reflections
a = 19.4030 (15) Å	θ = 3.5–25.6°
b = 7.2300 (5) Å	µ = 0.21 mm⁻¹
c = 17.2830 (13) Å	T = 173 K
β = 110.583 (6)°	Block, yellow
V = 2269.8 (3) Å³	0.27 × 0.12 × 0.11 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	4261 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ω scans	θ_max = 25.7°, θ_min = 3.6°
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)]	h = −23→23
T_min = 0.946, T_max = 0.968	k = −8→8
27016 measured reflections	l = −21→21

Refinement top

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)] = 0.072	Hydrogen site location: difmap and geom
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
4261 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₇N₄O₅⁺·Cl⁻	V = 2269.8 (3) Å³
M_r = 450.92	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.4030 (15) Å	µ = 0.21 mm⁻¹
b = 7.2300 (5) Å	T = 173 K
c = 17.2830 (13) Å	0.27 × 0.12 × 0.11 mm
β = 110.583 (6)°

Data collection top

Stoe IPDS II two-circle diffractometer	4261 independent reflections
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)]	2776 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.968	R_int = 0.074
27016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.26 e Å⁻³
4261 reflections	Δρ_min = −0.24 e Å⁻³
288 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.06439 (14)	0.7518 (4)	0.45674 (16)	0.0220 (6)
H1	0.0424 (17)	0.661 (5)	0.4681 (19)	0.012 (8)*
C1	0.06952 (17)	0.7550 (4)	0.37402 (19)	0.0234 (7)
H1A	0.0679	0.8852	0.3557	0.028*
H1B	0.0260	0.6911	0.3351	0.028*
O1	0.32321 (13)	0.4100 (3)	0.34329 (16)	0.0323 (6)
C2	0.34155 (18)	0.2203 (5)	0.3692 (2)	0.0307 (8)
H2A	0.3002	0.1372	0.3393	0.037*
H2B	0.3519	0.2077	0.4292	0.037*
C3	0.40978 (17)	0.1709 (5)	0.3488 (2)	0.0309 (8)
H3A	0.4009	0.2000	0.2901	0.037*
H3B	0.4195	0.0366	0.3569	0.037*
C4	0.47691 (17)	0.2788 (5)	0.4039 (2)	0.0249 (7)
H4A	0.4695	0.4122	0.3906	0.030*
H4B	0.4819	0.2624	0.4624	0.030*
C11	0.09157 (16)	0.8805 (4)	0.51601 (19)	0.0193 (7)
C12	0.07709 (17)	0.8840 (4)	0.5918 (2)	0.0201 (7)
C13	0.09925 (16)	1.0306 (4)	0.64785 (19)	0.0217 (7)
H13	0.0872	1.0315	0.6966	0.026*
C14	0.13877 (19)	1.1733 (4)	0.6314 (2)	0.0282 (8)
C15	0.1599 (2)	1.1705 (5)	0.5615 (2)	0.0326 (8)
H15	0.1906	1.2654	0.5534	0.039*
C16	0.13618 (18)	1.0301 (4)	0.5051 (2)	0.0276 (7)
H16	0.1496	1.0317	0.4572	0.033*
N12	0.03606 (14)	0.7389 (3)	0.61389 (16)	0.0246 (6)
O121	0.01389 (15)	0.7619 (4)	0.67164 (15)	0.0392 (6)
O122	0.02439 (16)	0.5931 (3)	0.57364 (16)	0.0428 (7)
N14	0.15790 (19)	1.3301 (4)	0.6881 (2)	0.0417 (8)
O141	0.12909 (19)	1.3407 (4)	0.74137 (19)	0.0527 (8)
O142	0.2012 (2)	1.4472 (4)	0.6795 (2)	0.0675 (10)
C21	0.26258 (17)	0.4855 (5)	0.3546 (2)	0.0243 (7)
C22	0.24320 (19)	0.6651 (5)	0.3233 (2)	0.0277 (8)
H22	0.2719	0.7271	0.2968	0.033*
C23	0.18216 (17)	0.7521 (4)	0.3311 (2)	0.0247 (7)
H23	0.1699	0.8738	0.3100	0.030*
C24	0.13876 (17)	0.6646 (4)	0.36916 (19)	0.0201 (7)
C25	0.15833 (17)	0.4860 (5)	0.3999 (2)	0.0280 (7)
H25	0.1287	0.4233	0.4251	0.034*
C26	0.22036 (18)	0.3975 (4)	0.3944 (2)	0.0290 (8)
H26	0.2338	0.2780	0.4177	0.035*
N41	0.54659 (14)	0.2151 (4)	0.39226 (16)	0.0198 (5)
H41	0.5459 (19)	0.081 (5)	0.393 (2)	0.029 (9)*
C42	0.55035 (18)	0.2777 (5)	0.3111 (2)	0.0304 (8)
H42A	0.5507	0.4146	0.3093	0.036*
H42B	0.5063	0.2336	0.2655	0.036*
C43	0.6197 (2)	0.2028 (6)	0.2993 (2)	0.0397 (9)
H43A	0.6175	0.0660	0.2969	0.048*
H43B	0.6219	0.2485	0.2462	0.048*
C44	0.6888 (2)	0.2630 (6)	0.3697 (3)	0.0476 (10)
H44A	0.6941	0.3990	0.3686	0.057*
H44B	0.7326	0.2057	0.3629	0.057*
C45	0.68359 (18)	0.2042 (6)	0.4524 (2)	0.0371 (9)
H45A	0.7272	0.2508	0.4980	0.044*
H45B	0.6839	0.0674	0.4557	0.044*
C46	0.61356 (17)	0.2785 (5)	0.4630 (2)	0.0294 (7)
H46A	0.6107	0.2335	0.5159	0.035*
H46B	0.6151	0.4153	0.4648	0.035*
Cl1	0.55483 (6)	−0.21420 (11)	0.40105 (6)	0.0365 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0251 (14)	0.0192 (14)	0.0246 (14)	−0.0060 (11)	0.0125 (11)	−0.0030 (11)
C1	0.0246 (16)	0.0261 (17)	0.0199 (15)	0.0035 (13)	0.0085 (12)	0.0025 (13)
O1	0.0265 (13)	0.0330 (12)	0.0454 (16)	0.0112 (10)	0.0224 (11)	0.0127 (11)
C2	0.0217 (16)	0.0248 (16)	0.045 (2)	0.0040 (14)	0.0114 (15)	0.0001 (16)
C3	0.0214 (17)	0.0348 (19)	0.035 (2)	0.0043 (14)	0.0087 (15)	−0.0092 (15)
C4	0.0255 (16)	0.0261 (15)	0.0256 (17)	0.0028 (14)	0.0121 (13)	−0.0029 (14)
C11	0.0185 (16)	0.0155 (14)	0.0214 (16)	0.0041 (11)	0.0037 (13)	0.0018 (12)
C12	0.0190 (15)	0.0174 (15)	0.0234 (17)	−0.0002 (12)	0.0068 (13)	0.0035 (12)
C13	0.0228 (16)	0.0212 (15)	0.0184 (16)	0.0012 (12)	0.0040 (13)	−0.0023 (13)
C14	0.0346 (19)	0.0202 (16)	0.0232 (17)	−0.0062 (14)	0.0020 (15)	−0.0015 (13)
C15	0.038 (2)	0.0248 (17)	0.034 (2)	−0.0115 (15)	0.0110 (16)	0.0034 (15)
C16	0.0318 (18)	0.0276 (17)	0.0251 (18)	−0.0077 (14)	0.0120 (14)	0.0005 (14)
N12	0.0292 (14)	0.0220 (14)	0.0232 (14)	−0.0078 (12)	0.0100 (11)	−0.0048 (11)
O121	0.0519 (15)	0.0431 (15)	0.0337 (14)	−0.0181 (13)	0.0291 (12)	−0.0121 (12)
O122	0.073 (2)	0.0291 (13)	0.0383 (16)	−0.0257 (13)	0.0346 (14)	−0.0162 (12)
N14	0.056 (2)	0.0226 (16)	0.042 (2)	−0.0121 (14)	0.0116 (17)	−0.0057 (14)
O141	0.091 (2)	0.0304 (14)	0.0421 (17)	−0.0175 (14)	0.0300 (17)	−0.0156 (13)
O142	0.098 (3)	0.0437 (17)	0.069 (2)	−0.0476 (18)	0.041 (2)	−0.0229 (16)
C21	0.0229 (16)	0.0280 (16)	0.0247 (17)	0.0043 (14)	0.0114 (13)	0.0042 (14)
C22	0.0316 (18)	0.0292 (17)	0.0312 (19)	0.0018 (14)	0.0219 (15)	0.0107 (14)
C23	0.0299 (17)	0.0187 (16)	0.0285 (17)	0.0031 (13)	0.0139 (13)	0.0072 (13)
C24	0.0207 (16)	0.0207 (15)	0.0174 (16)	0.0012 (12)	0.0048 (13)	0.0013 (12)
C25	0.0231 (17)	0.0269 (16)	0.039 (2)	0.0003 (14)	0.0169 (15)	0.0106 (15)
C26	0.0255 (18)	0.0217 (16)	0.042 (2)	0.0035 (13)	0.0149 (16)	0.0112 (15)
N41	0.0222 (13)	0.0190 (12)	0.0202 (13)	0.0005 (11)	0.0099 (11)	0.0008 (11)
C42	0.0313 (18)	0.0391 (18)	0.0240 (17)	0.0090 (16)	0.0139 (14)	0.0092 (16)
C43	0.038 (2)	0.057 (2)	0.033 (2)	0.0114 (18)	0.0238 (17)	0.0091 (19)
C44	0.035 (2)	0.052 (3)	0.065 (3)	0.0037 (19)	0.0290 (19)	0.011 (2)
C45	0.0201 (17)	0.045 (2)	0.041 (2)	0.0007 (16)	0.0042 (15)	−0.0030 (18)
C46	0.0256 (17)	0.0300 (16)	0.0277 (18)	−0.0040 (14)	0.0034 (14)	−0.0081 (15)
Cl1	0.0588 (6)	0.0208 (4)	0.0265 (4)	0.0016 (4)	0.0107 (4)	0.0010 (4)

Geometric parameters (Å, º) top

N1—C11	1.346 (4)	N14—O141	1.236 (4)
N1—C1	1.468 (4)	N14—O142	1.238 (4)
N1—H1	0.84 (3)	C21—C26	1.396 (5)
C1—C24	1.523 (4)	C21—C22	1.406 (5)
C1—H1A	0.9900	C22—C23	1.389 (5)
C1—H1B	0.9900	C22—H22	0.9500
O1—C21	1.371 (4)	C23—C24	1.390 (4)
O1—C2	1.448 (4)	C23—H23	0.9500
C2—C3	1.527 (5)	C24—C25	1.397 (4)
C2—H2A	0.9900	C25—C26	1.395 (5)
C2—H2B	0.9900	C25—H25	0.9500
C3—C4	1.530 (4)	C26—H26	0.9500
C3—H3A	0.9900	N41—C42	1.500 (4)
C3—H3B	0.9900	N41—C46	1.509 (4)
C4—N41	1.507 (4)	N41—H41	0.97 (4)
C4—H4A	0.9900	C42—C43	1.529 (5)
C4—H4B	0.9900	C42—H42A	0.9900
C11—C12	1.434 (5)	C42—H42B	0.9900
C11—C16	1.439 (4)	C43—C44	1.523 (6)
C12—C13	1.397 (4)	C43—H43A	0.9900
C12—N12	1.447 (4)	C43—H43B	0.9900
C13—C14	1.374 (5)	C44—C45	1.528 (6)
C13—H13	0.9500	C44—H44A	0.9900
C14—C15	1.406 (5)	C44—H44B	0.9900
C14—N14	1.459 (4)	C45—C46	1.531 (5)
C15—C16	1.370 (5)	C45—H45A	0.9900
C15—H15	0.9500	C45—H45B	0.9900
C16—H16	0.9500	C46—H46A	0.9900
N12—O121	1.229 (4)	C46—H46B	0.9900
N12—O122	1.239 (3)

C11—N1—C1	126.0 (3)	O1—C21—C22	116.1 (3)
C11—N1—H1	117 (2)	C26—C21—C22	119.1 (3)
C1—N1—H1	117 (2)	C23—C22—C21	120.2 (3)
N1—C1—C24	114.2 (3)	C23—C22—H22	119.9
N1—C1—H1A	108.7	C21—C22—H22	119.9
C24—C1—H1A	108.7	C22—C23—C24	121.2 (3)
N1—C1—H1B	108.7	C22—C23—H23	119.4
C24—C1—H1B	108.7	C24—C23—H23	119.4
H1A—C1—H1B	107.6	C23—C24—C25	118.2 (3)
C21—O1—C2	117.6 (3)	C23—C24—C1	121.6 (3)
O1—C2—C3	106.8 (3)	C25—C24—C1	120.2 (3)
O1—C2—H2A	110.4	C26—C25—C24	121.6 (3)
C3—C2—H2A	110.4	C26—C25—H25	119.2
O1—C2—H2B	110.4	C24—C25—H25	119.2
C3—C2—H2B	110.4	C25—C26—C21	119.6 (3)
H2A—C2—H2B	108.6	C25—C26—H26	120.2
C2—C3—C4	110.8 (3)	C21—C26—H26	120.2
C2—C3—H3A	109.5	C42—N41—C4	111.9 (2)
C4—C3—H3A	109.5	C42—N41—C46	110.8 (3)
C2—C3—H3B	109.5	C4—N41—C46	110.9 (2)
C4—C3—H3B	109.5	C42—N41—H41	109 (2)
H3A—C3—H3B	108.1	C4—N41—H41	107 (2)
N41—C4—C3	111.6 (3)	C46—N41—H41	108 (2)
N41—C4—H4A	109.3	N41—C42—C43	110.6 (3)
C3—C4—H4A	109.3	N41—C42—H42A	109.5
N41—C4—H4B	109.3	C43—C42—H42A	109.5
C3—C4—H4B	109.3	N41—C42—H42B	109.5
H4A—C4—H4B	108.0	C43—C42—H42B	109.5
N1—C11—C12	123.9 (3)	H42A—C42—H42B	108.1
N1—C11—C16	120.8 (3)	C44—C43—C42	111.1 (3)
C12—C11—C16	115.3 (3)	C44—C43—H43A	109.4
C13—C12—C11	122.4 (3)	C42—C43—H43A	109.4
C13—C12—N12	115.5 (3)	C44—C43—H43B	109.4
C11—C12—N12	122.1 (3)	C42—C43—H43B	109.4
C14—C13—C12	119.0 (3)	H43A—C43—H43B	108.0
C14—C13—H13	120.5	C43—C44—C45	109.8 (3)
C12—C13—H13	120.5	C43—C44—H44A	109.7
C13—C14—C15	121.3 (3)	C45—C44—H44A	109.7
C13—C14—N14	118.2 (3)	C43—C44—H44B	109.7
C15—C14—N14	120.5 (3)	C45—C44—H44B	109.7
C16—C15—C14	119.7 (3)	H44A—C44—H44B	108.2
C16—C15—H15	120.2	C44—C45—C46	111.6 (3)
C14—C15—H15	120.2	C44—C45—H45A	109.3
C15—C16—C11	122.1 (3)	C46—C45—H45A	109.3
C15—C16—H16	119.0	C44—C45—H45B	109.3
C11—C16—H16	119.0	C46—C45—H45B	109.3
O121—N12—O122	121.6 (3)	H45A—C45—H45B	108.0
O121—N12—C12	119.9 (3)	N41—C46—C45	110.1 (3)
O122—N12—C12	118.5 (3)	N41—C46—H46A	109.6
O141—N14—O142	123.5 (3)	C45—C46—H46A	109.6
O141—N14—C14	118.3 (3)	N41—C46—H46B	109.6
O142—N14—C14	118.2 (3)	C45—C46—H46B	109.6
O1—C21—C26	124.8 (3)	H46A—C46—H46B	108.2

C11—N1—C1—C24	88.5 (4)	C15—C14—N14—O142	−9.5 (5)
C21—O1—C2—C3	179.2 (3)	C2—O1—C21—C26	4.8 (5)
O1—C2—C3—C4	68.3 (4)	C2—O1—C21—C22	−175.5 (3)
C2—C3—C4—N41	172.9 (3)	O1—C21—C22—C23	179.4 (3)
C1—N1—C11—C12	171.6 (3)	C26—C21—C22—C23	−0.9 (5)
C1—N1—C11—C16	−6.3 (5)	C21—C22—C23—C24	−0.4 (5)
N1—C11—C12—C13	−172.7 (3)	C22—C23—C24—C25	0.3 (5)
C16—C11—C12—C13	5.3 (4)	C22—C23—C24—C1	−176.8 (3)
N1—C11—C12—N12	5.0 (5)	N1—C1—C24—C23	−131.3 (3)
C16—C11—C12—N12	−177.0 (3)	N1—C1—C24—C25	51.7 (4)
C11—C12—C13—C14	−2.5 (5)	C23—C24—C25—C26	1.2 (5)
N12—C12—C13—C14	179.7 (3)	C1—C24—C25—C26	178.3 (3)
C12—C13—C14—C15	−2.9 (5)	C24—C25—C26—C21	−2.5 (5)
C12—C13—C14—N14	176.6 (3)	O1—C21—C26—C25	−178.0 (3)
C13—C14—C15—C16	5.1 (5)	C22—C21—C26—C25	2.4 (5)
N14—C14—C15—C16	−174.4 (3)	C3—C4—N41—C42	72.8 (3)
C14—C15—C16—C11	−1.9 (5)	C3—C4—N41—C46	−162.9 (3)
N1—C11—C16—C15	175.0 (3)	C4—N41—C42—C43	−177.2 (3)
C12—C11—C16—C15	−3.0 (5)	C46—N41—C42—C43	58.5 (4)
C13—C12—N12—O121	10.4 (4)	N41—C42—C43—C44	−57.5 (4)
C11—C12—N12—O121	−167.4 (3)	C42—C43—C44—C45	55.4 (4)
C13—C12—N12—O122	−169.4 (3)	C43—C44—C45—C46	−55.4 (4)
C11—C12—N12—O122	12.8 (4)	C42—N41—C46—C45	−58.0 (4)
C13—C14—N14—O141	−10.2 (5)	C4—N41—C46—C45	177.1 (3)
C15—C14—N14—O141	169.2 (3)	C44—C45—C46—N41	56.7 (4)
C13—C14—N14—O142	171.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N41—H41···Cl1	0.97 (4)	2.14 (4)	3.109 (3)	175 (3)
N1—H1···O122	0.84 (3)	2.03 (3)	2.665 (4)	131 (3)
N1—H1···O122ⁱ	0.84 (3)	2.22 (3)	2.971 (4)	149 (3)
C4—H4B···Cl1ⁱⁱ	0.99	2.72	3.664 (3)	161
C23—H23···O141ⁱⁱⁱ	0.95	2.37	3.318 (4)	173
C42—H42B···Cl1^iv	0.99	2.73	3.514 (3)	137

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, −y+5/2, z−1/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₇N₄O₅⁺·Cl⁻
M_r	450.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	19.4030 (15), 7.2300 (5), 17.2830 (13)
β (°)	110.583 (6)
V (Å³)	2269.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.27 × 0.12 × 0.11

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan [MULABS (Spek, 2003; Blessing, 1995)]
T_min, T_max	0.946, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	27016, 4261, 2776
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.128, 1.07
No. of reflections	4261
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.24

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PLATON (Spek, 2003).