Erlotinib hydro­chloride: an anti­cancer agent

Selvanayagam, S.; Sridhar, B.; Ravikumar, K.

doi:10.1107/S1600536808011707

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o931

doi:10.1107/S1600536808011707

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Erlotinib hydrochloride: an anticancer agent

S. Selvanayagam,^a ^* B. Sridhar ^b and K. Ravikumar ^b

^aDepartment of Physics, Kalasalingam University, Krishnankoil 626 190, India, and ^bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 11 April 2008; accepted 23 April 2008; online 30 April 2008)

In the cation of the title compound, C₂₂H₂₄N₃O₄⁺·Cl⁻, an active ingredient of the anticancer drug also known as Tarceva, the quinazoline ring system is planar within 0.044 (3) Å. The dihedral angle formed by the mean planes of the two six-membered quinazoline rings is 3.2 (1)°. Both N-bound H atoms participate in N—H⋯Cl bonds, which link the ions into infinite chains running along the b axis. C—H⋯O interactions involving neighboring cations provide additional stabilization of these aggregates.

Related literature

For related literature, see: Herbst et al. (2005 ); Minna & Dowell (2005 ); Li et al. (2007 ); Xia (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₂₄N₃O₄⁺·Cl⁻
M_r = 429.89
Monoclinic, P 2₁ /c
a = 14.5351 (15) Å
b = 18.4863 (19) Å
c = 8.1222 (8) Å
β = 102.966 (2)°
V = 2126.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 (2) K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: none
24377 measured reflections
5001 independent reflections
3649 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.151
S = 1.16
5001 reflections
275 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Cl1	0.86	2.46	3.277 (2)	160
N1—HN1⋯Cl1ⁱ	0.86	2.23	3.066 (2)	165
C1—H1⋯O4ⁱ	0.93	2.46	3.372 (3)	167
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808011707/ya2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011707/ya2075Isup2.hkl

checkCIF report

Comment top

Erlotinib hydrochloride, (I), also known under its tradename Tarceva, is a potent reversible epidermal growth factor receptor tyrosine kinase inhibitor with single agent activity in patients with non-small lung cancer, pancreatic cancer and several other types of cancer (Herbst et al., 2005). It is the first drug to demonstrate an increase in survival in phase III trials in patients with advanced non-small cell lung cancer (Minna & Dowell, 2005). It has recently been shown to be potent inhibitor of JAK2 V617F activity; JAK2 V617F is a mutant of tyrosine kinase JAK2 (Li et al., 2007). As no crystal structure of the title compound has yet been published, we have undertaken the single-crystal X-ray diffraction study and report here its results.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The C21—C22 bond length [1.170 (4) Å] is consistent with its acetylenic character, as evidenced by literature value of 1.174 (11) Å (see Allen et al., 1987). The geometry of the quinazoline ring system is comparable to that in the reported related structure (Xia, 2005).

The bicyclic system is effectively planar with a maximum deviation of 0.044 (3) Å for the C1 atom. The dihedral angle formed by the mean planes of two six membered rings of quinazoline moiety is 3.2 (1)°. The benzene ring C15—C20 and its attached ethynyl group are coplanar with a maximum deviation -0.011 (3) Å for the C20 atom. The dihedral angle between this ring and quinazoline ring system is 34.4 (1)°. The short contacts H3···H4 (2.12 Å) and H7···H9A (2.14 Å) result in substantial widening of the C2—N3—C15 and C6—O1—C9 bond angles [127.4 (2)° and 117.1 (2)°, respectively].

Both N-bound H atoms (HN1 and H3) participate in H-bonds with the Cl1 anion (Table 2). These bonds link cations and anions into the infinite chains running along the b axis of the crystal. The C1—H1···O4 interactions involving neighboring cations provide additional stabilization for these chains (Fig. 2).

Related literature top

For related literature, see: Herbst et al. (2005); Minna & Dowell (2005); Li et al. (2007); Xia (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

In order to obtain crystals suitable for X-ray study, commercially available erlotinib hydrochloride was dissolved in a methanol-water solution (90:10v/v); the solvents were then allowed to evaporate slowly.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The structure and atom-numbering scheme for (I); displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Molecular packing of (I) viewed along the c axis; H-bonds are shown as dashed lines; H atoms, not involved in H-bonds, have been omitted.

Erlotinib hydrochloride top

Crystal data top

C₂₂H₂₄N₃O₄⁺·Cl⁻	F(000) = 904
M_r = 429.89	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9448 reflections
a = 14.5351 (15) Å	θ = 2.2–23.4°
b = 18.4863 (19) Å	µ = 0.21 mm⁻¹
c = 8.1222 (8) Å	T = 293 K
β = 102.966 (2)°	Block, colourless
V = 2126.8 (4) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	3649 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 28.0°, θ_min = 1.8°
ω scans	h = −18→19
24377 measured reflections	k = −24→24
5001 independent reflections	l = −10→10

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0551P)² + 0.7563P] where P = (F_o² + 2F_c²)/3
5001 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₂₄N₃O₄⁺·Cl⁻	V = 2126.8 (4) Å³
M_r = 429.89	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.5351 (15) Å	µ = 0.21 mm⁻¹
b = 18.4863 (19) Å	T = 293 K
c = 8.1222 (8) Å	0.26 × 0.22 × 0.20 mm
β = 102.966 (2)°

Data collection top

Bruker APEX area-detector diffractometer	3649 reflections with I > 2σ(I)
24377 measured reflections	R_int = 0.050
5001 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	Δρ_max = 0.33 e Å⁻³
5001 reflections	Δρ_min = −0.25 e Å⁻³
275 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
Cl1	0.50200 (5)	0.34427 (3)	0.62635 (9)	0.0469 (2)
O1	0.27725 (11)	0.61695 (9)	0.9544 (2)	0.0395 (4)
O2	0.10485 (14)	0.70220 (13)	0.9170 (3)	0.0648 (6)
O3	0.29876 (12)	0.48732 (9)	0.8521 (2)	0.0417 (4)
O4	0.20059 (13)	0.31485 (10)	0.6875 (3)	0.0514 (5)
N1	0.57019 (14)	0.69146 (10)	0.8273 (3)	0.0395 (5)
HN1	0.5603	0.7355	0.8527	0.047*
N2	0.67238 (14)	0.60941 (11)	0.7423 (3)	0.0408 (5)
N3	0.63506 (13)	0.48880 (10)	0.7058 (3)	0.0350 (5)
H3	0.5945	0.4550	0.7065	0.042*
C1	0.64787 (18)	0.67467 (13)	0.7780 (4)	0.0435 (7)
H1	0.6887	0.7123	0.7678	0.052*
C2	0.61060 (16)	0.55508 (12)	0.7464 (3)	0.0318 (5)
C3	0.52182 (16)	0.56803 (12)	0.7918 (3)	0.0310 (5)
C4	0.45169 (16)	0.51536 (12)	0.7961 (3)	0.0321 (5)
H4	0.4604	0.4681	0.7637	0.039*
C5	0.37123 (16)	0.53333 (13)	0.8474 (3)	0.0324 (5)
C6	0.35795 (16)	0.60529 (13)	0.9019 (3)	0.0326 (5)
C7	0.42426 (17)	0.65734 (12)	0.8963 (3)	0.0346 (5)
H7	0.4158	0.7044	0.9305	0.042*
C8	0.50471 (16)	0.63882 (12)	0.8385 (3)	0.0320 (5)
C9	0.26703 (18)	0.68616 (14)	1.0300 (4)	0.0417 (6)
H9A	0.2742	0.7248	0.9530	0.050*
H9B	0.3151	0.6919	1.1333	0.050*
C10	0.17127 (19)	0.68926 (15)	1.0675 (4)	0.0448 (6)
H10A	0.1574	0.6439	1.1166	0.054*
H10B	0.1689	0.7277	1.1478	0.054*
C11	0.0123 (3)	0.7093 (3)	0.9450 (7)	0.1109 (16)
H11A	−0.0314	0.7178	0.8392	0.166*
H11B	0.0106	0.7492	1.0197	0.166*
H11C	−0.0047	0.6656	0.9949	0.166*
C12	0.30023 (17)	0.41876 (13)	0.7695 (4)	0.0422 (6)
H12A	0.3512	0.3889	0.8318	0.051*
H12B	0.3093	0.4256	0.6558	0.051*
C13	0.2062 (2)	0.38355 (15)	0.7650 (4)	0.0510 (7)
H13A	0.1974	0.3784	0.8793	0.061*
H13B	0.1560	0.4142	0.7029	0.061*
C14	0.1801 (3)	0.3188 (2)	0.5094 (5)	0.0765 (11)
H14A	0.1774	0.2709	0.4631	0.115*
H14B	0.2286	0.3460	0.4740	0.115*
H14C	0.1203	0.3423	0.4699	0.115*
C15	0.72087 (16)	0.46773 (12)	0.6616 (3)	0.0327 (5)
C16	0.71529 (18)	0.41268 (14)	0.5436 (3)	0.0396 (6)
H16	0.6575	0.3912	0.4968	0.048*
C17	0.7960 (2)	0.38986 (16)	0.4959 (4)	0.0474 (7)
H17	0.7922	0.3529	0.4169	0.057*
C18	0.88191 (19)	0.42120 (15)	0.5641 (4)	0.0473 (7)
H18	0.9356	0.4060	0.5296	0.057*
C19	0.88874 (17)	0.47541 (13)	0.6842 (3)	0.0395 (6)
C20	0.80763 (17)	0.49842 (13)	0.7347 (3)	0.0371 (6)
H20	0.8118	0.5341	0.8168	0.045*
C21	0.9793 (2)	0.50773 (16)	0.7563 (4)	0.0490 (7)
C22	1.0541 (2)	0.5325 (2)	0.8100 (5)	0.0653 (9)
H22	1.115 (2)	0.5534 (16)	0.849 (4)	0.063 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0508 (4)	0.0276 (3)	0.0642 (5)	−0.0062 (3)	0.0173 (3)	−0.0023 (3)
O1	0.0339 (9)	0.0328 (9)	0.0559 (11)	−0.0003 (7)	0.0190 (8)	−0.0044 (8)
O2	0.0438 (12)	0.0814 (16)	0.0696 (15)	0.0176 (11)	0.0135 (10)	0.0081 (12)
O3	0.0353 (9)	0.0315 (9)	0.0628 (12)	−0.0071 (7)	0.0207 (9)	−0.0071 (8)
O4	0.0525 (12)	0.0327 (10)	0.0694 (14)	−0.0093 (9)	0.0145 (10)	−0.0046 (9)
N1	0.0373 (12)	0.0223 (10)	0.0611 (14)	−0.0008 (9)	0.0158 (10)	−0.0023 (10)
N2	0.0325 (11)	0.0270 (11)	0.0661 (15)	−0.0004 (9)	0.0181 (10)	0.0036 (10)
N3	0.0276 (10)	0.0264 (10)	0.0527 (13)	−0.0003 (8)	0.0127 (9)	0.0009 (9)
C1	0.0330 (14)	0.0291 (13)	0.0715 (19)	−0.0040 (11)	0.0184 (13)	0.0048 (12)
C2	0.0279 (12)	0.0266 (12)	0.0412 (14)	0.0007 (9)	0.0083 (10)	0.0030 (10)
C3	0.0280 (12)	0.0289 (12)	0.0361 (13)	0.0010 (9)	0.0073 (10)	0.0027 (10)
C4	0.0311 (12)	0.0232 (11)	0.0424 (14)	0.0007 (9)	0.0091 (10)	0.0008 (10)
C5	0.0299 (12)	0.0299 (12)	0.0377 (13)	−0.0032 (10)	0.0080 (10)	0.0028 (10)
C6	0.0297 (12)	0.0329 (13)	0.0361 (13)	0.0023 (10)	0.0095 (10)	0.0009 (10)
C7	0.0361 (13)	0.0237 (11)	0.0447 (14)	0.0023 (10)	0.0107 (11)	−0.0030 (10)
C8	0.0299 (12)	0.0263 (12)	0.0394 (13)	−0.0007 (9)	0.0068 (10)	0.0027 (10)
C9	0.0431 (15)	0.0349 (14)	0.0490 (16)	0.0055 (12)	0.0147 (12)	−0.0035 (12)
C10	0.0493 (16)	0.0390 (15)	0.0512 (16)	0.0085 (12)	0.0221 (13)	0.0014 (13)
C11	0.045 (2)	0.152 (4)	0.135 (4)	0.034 (2)	0.019 (2)	−0.013 (4)
C12	0.0350 (14)	0.0305 (13)	0.0636 (18)	−0.0034 (11)	0.0162 (12)	−0.0027 (12)
C13	0.0448 (16)	0.0404 (15)	0.073 (2)	−0.0095 (12)	0.0240 (15)	−0.0085 (14)
C14	0.093 (3)	0.066 (2)	0.077 (3)	−0.032 (2)	0.031 (2)	−0.0167 (19)
C15	0.0338 (13)	0.0260 (12)	0.0403 (14)	0.0051 (10)	0.0125 (11)	0.0077 (10)
C16	0.0385 (14)	0.0353 (14)	0.0443 (15)	0.0027 (11)	0.0079 (11)	0.0015 (11)
C17	0.0542 (17)	0.0441 (16)	0.0466 (16)	0.0070 (13)	0.0167 (13)	−0.0070 (13)
C18	0.0421 (16)	0.0517 (17)	0.0538 (17)	0.0127 (13)	0.0230 (13)	0.0022 (14)
C19	0.0330 (13)	0.0352 (14)	0.0533 (17)	0.0038 (11)	0.0158 (12)	0.0107 (12)
C20	0.0346 (13)	0.0285 (12)	0.0496 (16)	0.0018 (10)	0.0123 (11)	−0.0001 (11)
C21	0.0387 (16)	0.0495 (17)	0.064 (2)	0.0052 (13)	0.0237 (14)	0.0062 (14)
C22	0.0416 (19)	0.077 (2)	0.082 (2)	−0.0098 (17)	0.0233 (17)	−0.0084 (19)

Geometric parameters (Å, º) top

O1—C6	1.352 (3)	C9—H9B	0.9700
O1—C9	1.441 (3)	C10—H10A	0.9700
O2—C10	1.397 (3)	C10—H10B	0.9700
O2—C11	1.419 (4)	C11—H11A	0.9600
O3—C5	1.361 (3)	C11—H11B	0.9600
O3—C12	1.436 (3)	C11—H11C	0.9600
O4—C13	1.412 (3)	C12—C13	1.507 (3)
O4—C14	1.412 (4)	C12—H12A	0.9700
N1—C1	1.317 (3)	C12—H12B	0.9700
N1—C8	1.378 (3)	C13—H13A	0.9700
N1—HN1	0.8600	C13—H13B	0.9700
N2—C1	1.309 (3)	C14—H14A	0.9600
N2—C2	1.353 (3)	C14—H14B	0.9600
N3—C2	1.337 (3)	C14—H14C	0.9600
N3—C15	1.427 (3)	C15—C16	1.388 (3)
N3—H3	0.8600	C15—C20	1.389 (3)
C1—H1	0.9300	C16—C17	1.382 (4)
C2—C3	1.440 (3)	C16—H16	0.9300
C3—C8	1.400 (3)	C17—C18	1.375 (4)
C3—C4	1.416 (3)	C17—H17	0.9300
C4—C5	1.368 (3)	C18—C19	1.386 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.429 (3)	C19—C20	1.399 (3)
C6—C7	1.370 (3)	C19—C21	1.444 (4)
C7—C8	1.397 (3)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.170 (4)
C9—C10	1.491 (3)	C22—H22	0.95 (3)
C9—H9A	0.9700

C6—O1—C9	117.09 (19)	H10A—C10—H10B	108.3
C10—O2—C11	111.7 (3)	O2—C11—H11A	109.5
C5—O3—C12	116.48 (18)	O2—C11—H11B	109.5
C13—O4—C14	112.8 (2)	H11A—C11—H11B	109.5
C1—N1—C8	120.4 (2)	O2—C11—H11C	109.5
C1—N1—HN1	119.8	H11A—C11—H11C	109.5
C8—N1—HN1	119.8	H11B—C11—H11C	109.5
C1—N2—C2	117.6 (2)	O3—C12—C13	106.5 (2)
C2—N3—C15	127.4 (2)	O3—C12—H12A	110.4
C2—N3—H3	116.3	C13—C12—H12A	110.4
C15—N3—H3	116.3	O3—C12—H12B	110.4
N2—C1—N1	125.4 (2)	C13—C12—H12B	110.4
N2—C1—H1	117.3	H12A—C12—H12B	108.6
N1—C1—H1	117.3	O4—C13—C12	111.1 (2)
N3—C2—N2	117.4 (2)	O4—C13—H13A	109.4
N3—C2—C3	121.2 (2)	C12—C13—H13A	109.4
N2—C2—C3	121.4 (2)	O4—C13—H13B	109.4
C8—C3—C4	117.6 (2)	C12—C13—H13B	109.4
C8—C3—C2	116.7 (2)	H13A—C13—H13B	108.0
C4—C3—C2	125.7 (2)	O4—C14—H14A	109.5
C5—C4—C3	120.7 (2)	O4—C14—H14B	109.5
C5—C4—H4	119.7	H14A—C14—H14B	109.5
C3—C4—H4	119.7	O4—C14—H14C	109.5
O3—C5—C4	125.2 (2)	H14A—C14—H14C	109.5
O3—C5—C6	114.5 (2)	H14B—C14—H14C	109.5
C4—C5—C6	120.3 (2)	C16—C15—C20	120.1 (2)
O1—C6—C7	124.4 (2)	C16—C15—N3	117.1 (2)
O1—C6—C5	115.7 (2)	C20—C15—N3	122.8 (2)
C7—C6—C5	119.9 (2)	C17—C16—C15	119.7 (2)
C6—C7—C8	119.2 (2)	C17—C16—H16	120.1
C6—C7—H7	120.4	C15—C16—H16	120.1
C8—C7—H7	120.4	C18—C17—C16	120.6 (3)
N1—C8—C7	119.4 (2)	C18—C17—H17	119.7
N1—C8—C3	118.3 (2)	C16—C17—H17	119.7
C7—C8—C3	122.2 (2)	C17—C18—C19	120.2 (2)
O1—C9—C10	108.1 (2)	C17—C18—H18	119.9
O1—C9—H9A	110.1	C19—C18—H18	119.9
C10—C9—H9A	110.1	C18—C19—C20	119.6 (2)
O1—C9—H9B	110.1	C18—C19—C21	120.0 (2)
C10—C9—H9B	110.1	C20—C19—C21	120.4 (2)
H9A—C9—H9B	108.4	C15—C20—C19	119.6 (2)
O2—C10—C9	108.7 (2)	C15—C20—H20	120.2
O2—C10—H10A	109.9	C19—C20—H20	120.2
C9—C10—H10A	109.9	C22—C21—C19	177.3 (3)
O2—C10—H10B	109.9	C21—C22—H22	178 (2)
C9—C10—H10B	109.9

C2—N2—C1—N1	4.2 (4)	C1—N1—C8—C3	−1.7 (4)
C8—N1—C1—N2	−2.7 (4)	C6—C7—C8—N1	177.9 (2)
C15—N3—C2—N2	1.5 (4)	C6—C7—C8—C3	−2.4 (4)
C15—N3—C2—C3	−178.7 (2)	C4—C3—C8—N1	−177.0 (2)
C1—N2—C2—N3	178.4 (2)	C2—C3—C8—N1	4.1 (3)
C1—N2—C2—C3	−1.3 (4)	C4—C3—C8—C7	3.4 (4)
N3—C2—C3—C8	177.5 (2)	C2—C3—C8—C7	−175.5 (2)
N2—C2—C3—C8	−2.7 (3)	C6—O1—C9—C10	176.3 (2)
N3—C2—C3—C4	−1.2 (4)	C11—O2—C10—C9	−177.2 (3)
N2—C2—C3—C4	178.5 (2)	O1—C9—C10—O2	−76.9 (3)
C8—C3—C4—C5	−1.2 (3)	C5—O3—C12—C13	−170.3 (2)
C2—C3—C4—C5	177.5 (2)	C14—O4—C13—C12	−79.6 (3)
C12—O3—C5—C4	−11.3 (3)	O3—C12—C13—O4	−179.3 (2)
C12—O3—C5—C6	168.7 (2)	C2—N3—C15—C16	−146.2 (2)
C3—C4—C5—O3	178.3 (2)	C2—N3—C15—C20	35.6 (4)
C3—C4—C5—C6	−1.7 (4)	C20—C15—C16—C17	−1.7 (4)
C9—O1—C6—C7	−8.6 (3)	N3—C15—C16—C17	−179.9 (2)
C9—O1—C6—C5	172.4 (2)	C15—C16—C17—C18	−0.1 (4)
O3—C5—C6—O1	1.8 (3)	C16—C17—C18—C19	1.1 (4)
C4—C5—C6—O1	−178.3 (2)	C17—C18—C19—C20	−0.5 (4)
O3—C5—C6—C7	−177.3 (2)	C17—C18—C19—C21	179.5 (3)
C4—C5—C6—C7	2.7 (4)	C16—C15—C20—C19	2.4 (4)
O1—C6—C7—C8	−179.6 (2)	N3—C15—C20—C19	−179.6 (2)
C5—C6—C7—C8	−0.6 (4)	C18—C19—C20—C15	−1.3 (4)
C1—N1—C8—C7	177.9 (2)	C21—C19—C20—C15	178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1	0.86	2.46	3.277 (2)	160
N1—HN1···Cl1ⁱ	0.86	2.23	3.066 (2)	165
C1—H1···O4ⁱ	0.93	2.46	3.372 (3)	167

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₃O₄⁺·Cl⁻
M_r	429.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.5351 (15), 18.4863 (19), 8.1222 (8)
β (°)	102.966 (2)
V (Å³)	2126.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24377, 5001, 3649
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.151, 1.16
No. of reflections	5001
No. of parameters	275
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)', SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Cl1	0.86	2.46	3.277 (2)	160
N1—HN1···Cl1ⁱ	0.86	2.23	3.066 (2)	165
C1—H1···O4ⁱ	0.93	2.46	3.372 (3)	167

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

SS thanks the Vice Chancellor and the management of Kalasalingam University, Anand Nagar, Krishnankoil, for their support and encouragement.

References

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