3-[(4-Amino-5-chloro-2-ethoxy­benz­amido)meth­yl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate

Tong, T.-F.; Zhao, J.; Cheng, L.; Zhang, Y.-H.

doi:10.1107/S160053680803986X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o14

doi:10.1107/S160053680803986X

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3-[(4-Amino-5-chloro-2-ethoxybenzamido)methyl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate

Tai-Feng Tong,^a Jian Zhao,^b Lin Cheng ^b and Yi-Hua Zhang ^a ^*

^aCollege of Pharmacy, China Pharmaceutical University, Nanjing 210009, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: cep02chl@yahoo.cn

(Received 8 November 2008; accepted 26 November 2008; online 3 December 2008)

The title compound, C₁₇H₂₅ClN₃O₃⁺·Cl⁻·H₂O, is a monohydrated hydrochloride salt of a new derivative of mosapride, which is a pharmaceutical compound possessing gastrointestinal pro-kinetic activity. The chloride anion accepts hydrogen bonds from the NH group of the pyrrolooxazine fused-ring system and from the amine group, and the water molecules form hydrogen bonds that bridge between the chloride anion and the C=O bond of the amide.

Related literature

For related structures and background information concerning mosapride, see: Kakigami et al. (1998 ); Morie et al. (1995 ); Omae et al. (2002 ); Aoki et al. (2007 ).

Experimental

Crystal data

C₁₇H₂₅ClN₃O₃⁺·Cl⁻·H₂O
M_r = 408.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0984 (9) Å
b = 11.1594 (13) Å
c = 21.843 (3) Å
V = 1974.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 (2) K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.919, T_max = 0.945
10642 measured reflections
3848 independent reflections
3188 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.096
S = 1.06
3848 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1631 Friedel pairs
Flack parameter: −0.02 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.84 (4)	2.66 (4)	3.384 (3)	146 (3)
N1—H1B⋯Cl1ⁱⁱ	0.85 (3)	2.45 (3)	3.281 (3)	169 (3)
N3—H3C⋯Cl1	0.92 (3)	2.18 (3)	3.077 (3)	164 (2)
O1W—H1WA⋯Cl1ⁱⁱⁱ	0.79 (3)	2.62 (3)	3.410 (4)	176 (3)
O1W—H1WB⋯O2	0.88 (4)	1.95 (5)	2.800 (4)	161 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803986X/bi2322sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803986X/bi2322Isup2.hkl

checkCIF report

Comment top

Mosapride citrate is a benzamide derivative that possesses a gastrointestinal prokinetic activity (Aoki et al. 2007). The title compound (Fig. 1) is a new mosapride derivative, and crystals of its hydrochloride salt were obtained by acidifying with hydrochloric acid then recrystallizing from methanol.

In the benzamide unit, the C=O bond distance of 1.229 (3) Å is much shorter than the C—O bond distances (1.359 (3)–1.432 (3) Å), showing it to have full double-bond character. Meanwhile, the C9—N2 distance of 1.330 (4) Å is comparable with that of C4—N1 (1.352 (4) Å), but much shorter than N2—C10 (1.441 (3) Å), N3—C13 (1.493 (4) Å), N3—C14 (1.489 (4) Å) and N3—C17 (1.492 (4) Å). Thus, the C4—N1 bond has partial double-bond character.

Related literature top

For related structures and background information concerning mosapride, see: Kakigami et al. (1998); Morie et al. (1995); Omae et al. (2002); Aoki et al. (2007).

Experimental top

A mixture of 4-amino-5-chloro-2-ethoxybenzoic acid (8.613 g, 40 mmol), (hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-3-yl)methanamine (4.8 g, 30.72 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (11.8 g, 61.8 mmol) in CH₂Cl₂ (60 ml) was stirred for two hours under an argon atmosphere. The products were treated with saturated NaHCO₃ (200 ml) and extracted with CH₂Cl₂ (3 × 300 ml), then the organic layer was dried with anhydrous MgSO₄ and distilled under vacuum. The white solids were collected and dried (yield 5.856 g, 54.0%). Crystals of the title compound were obtained by acidifying with hydrochloric acid then recrystallizing from methanol.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with 30% displacement ellipsoids for non-H atoms.

3-[(4-Amino-5-chloro-2-ethoxybenzamido)methyl]pyrrolo[2,1- c][1,4]oxazin-5-ium chloride monohydrate top

Crystal data top

C₁₇H₂₅ClN₃O₃⁺·Cl⁻·H₂O	F(000) = 864
M_r = 408.32	D_x = 1.374 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 735 reflections
a = 8.0984 (9) Å	θ = 2.5–28.0°
b = 11.1594 (13) Å	µ = 0.36 mm⁻¹
c = 21.843 (3) Å	T = 293 K
V = 1974.0 (4) Å³	Block, colourless
Z = 4	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker APEX CCD diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	3188 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.919, T_max = 0.945	k = −10→13
10642 measured reflections	l = −26→25

Refinement top

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0412P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3848 reflections	Δρ_max = 0.32 e Å⁻³
261 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1631 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (7)

Crystal data top

C₁₇H₂₅ClN₃O₃⁺·Cl⁻·H₂O	V = 1974.0 (4) Å³
M_r = 408.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0984 (9) Å	µ = 0.36 mm⁻¹
b = 11.1594 (13) Å	T = 293 K
c = 21.843 (3) Å	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker APEX CCD diffractometer	3848 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3188 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.945	R_int = 0.037
10642 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.32 e Å⁻³
S = 1.06	Δρ_min = −0.22 e Å⁻³
3848 reflections	Absolute structure: Flack (1983), 1631 Friedel pairs
261 parameters	Absolute structure parameter: −0.02 (7)
0 restraints

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
C1	0.6257 (3)	0.7564 (2)	0.77046 (11)	0.0307 (6)
C2	0.4701 (4)	0.8084 (3)	0.76571 (13)	0.0364 (7)
C3	0.3807 (3)	0.8034 (3)	0.71361 (13)	0.0376 (7)
C4	0.4363 (4)	0.7438 (2)	0.66142 (12)	0.0344 (6)
C5	0.5913 (4)	0.6900 (3)	0.66594 (13)	0.0368 (7)
C6	0.6851 (3)	0.6961 (2)	0.71801 (12)	0.0323 (6)
C7	0.9124 (4)	0.5928 (3)	0.66895 (12)	0.0443 (8)
H7A	0.9261	0.6511	0.6364	0.053*
H7B	0.8429	0.5283	0.6541	0.053*
C8	1.0757 (4)	0.5452 (3)	0.68833 (13)	0.0455 (8)
H8A	1.0590	0.4780	0.7150	0.068*
H8B	1.1371	0.5201	0.6530	0.068*
H8C	1.1360	0.6065	0.7096	0.068*
C9	0.7127 (4)	0.7704 (2)	0.82975 (12)	0.0309 (6)
C10	0.9629 (4)	0.7321 (3)	0.88920 (13)	0.0452 (8)
H10A	0.8921	0.7486	0.9240	0.054*
H10B	1.0431	0.7964	0.8860	0.054*
C11	1.0507 (4)	0.6148 (3)	0.89873 (12)	0.0374 (7)
H11	0.9690	0.5504	0.9021	0.045*
C12	1.2222 (4)	0.4781 (3)	0.84947 (14)	0.0523 (10)
H12A	1.2880	0.4646	0.8130	0.063*
H12B	1.1348	0.4186	0.8502	0.063*
C13	1.3298 (4)	0.4625 (3)	0.90549 (13)	0.0408 (8)
H13	1.3596	0.3777	0.9090	0.049*
C14	1.1561 (4)	0.6167 (3)	0.95570 (11)	0.0345 (7)
H14A	1.2381	0.6798	0.9527	0.041*
H14B	1.0878	0.6323	0.9913	0.041*
C15	1.4860 (4)	0.5363 (3)	0.90920 (16)	0.0545 (9)
H15A	1.4693	0.6151	0.8916	0.065*
H15B	1.5759	0.4969	0.8878	0.065*
C16	1.5225 (5)	0.5453 (4)	0.97717 (17)	0.0689 (11)
H16A	1.6182	0.4971	0.9876	0.083*
H16B	1.5443	0.6278	0.9886	0.083*
C17	1.3705 (4)	0.4991 (3)	1.01002 (14)	0.0511 (9)
H17A	1.3891	0.4191	1.0259	0.061*
H17B	1.3406	0.5516	1.0436	0.061*
Cl1	0.92851 (11)	0.35057 (8)	0.99188 (4)	0.0554 (3)
Cl2	0.18901 (10)	0.87543 (9)	0.70977 (4)	0.0614 (3)
N1	0.3486 (4)	0.7381 (3)	0.60884 (12)	0.0482 (7)
H1A	0.266 (5)	0.780 (3)	0.5990 (16)	0.072*
H1B	0.394 (4)	0.717 (3)	0.5755 (15)	0.072*
N2	0.8652 (3)	0.7270 (2)	0.83413 (10)	0.0438 (7)
H2A	0.9079	0.6941	0.8023	0.053*
N3	1.2391 (3)	0.4983 (2)	0.96212 (11)	0.0363 (6)
O1	0.8390 (2)	0.64810 (19)	0.72151 (8)	0.0410 (5)
O2	0.6491 (3)	0.8222 (2)	0.87342 (8)	0.0453 (6)
O3	1.1512 (3)	0.59417 (19)	0.84669 (9)	0.0478 (6)
O1W	0.3524 (4)	0.8923 (3)	0.92869 (14)	0.0712 (8)
H2	0.426 (3)	0.845 (2)	0.8005 (12)	0.038 (8)*
H5	0.627 (3)	0.648 (3)	0.6312 (12)	0.043 (8)*
H3C	1.161 (3)	0.443 (2)	0.9736 (11)	0.031 (8)*
H1WA	0.368 (4)	0.954 (3)	0.9456 (15)	0.049 (12)*
H1WB	0.444 (6)	0.887 (4)	0.9073 (18)	0.103 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0306 (16)	0.0293 (15)	0.0321 (14)	−0.0011 (13)	0.0022 (12)	0.0019 (12)
C2	0.0337 (18)	0.0426 (18)	0.0329 (16)	0.0061 (14)	0.0033 (13)	−0.0059 (14)
C3	0.0220 (15)	0.0445 (18)	0.0461 (17)	0.0067 (13)	−0.0004 (13)	0.0014 (15)
C4	0.0289 (15)	0.0347 (16)	0.0395 (16)	0.0000 (14)	−0.0011 (14)	0.0037 (13)
C5	0.0427 (19)	0.0369 (17)	0.0308 (15)	−0.0003 (14)	0.0093 (14)	−0.0037 (13)
C6	0.0295 (16)	0.0310 (16)	0.0364 (15)	0.0031 (13)	0.0027 (13)	0.0048 (13)
C7	0.046 (2)	0.0475 (19)	0.0396 (17)	0.0091 (16)	0.0043 (15)	−0.0063 (15)
C8	0.0380 (19)	0.0496 (19)	0.0488 (18)	0.0063 (17)	0.0112 (16)	−0.0018 (15)
C9	0.0303 (16)	0.0275 (15)	0.0350 (15)	0.0027 (12)	0.0025 (13)	0.0008 (13)
C10	0.045 (2)	0.0479 (19)	0.0430 (18)	0.0126 (16)	−0.0087 (15)	−0.0073 (15)
C11	0.0368 (16)	0.0376 (17)	0.0380 (15)	0.0030 (15)	−0.0034 (14)	−0.0028 (14)
C12	0.052 (2)	0.063 (2)	0.0426 (18)	0.0179 (19)	−0.0069 (16)	−0.0193 (17)
C13	0.0390 (19)	0.0365 (17)	0.0468 (17)	0.0072 (15)	−0.0058 (15)	−0.0087 (14)
C14	0.0361 (16)	0.0335 (16)	0.0338 (14)	0.0030 (14)	−0.0013 (13)	−0.0051 (13)
C15	0.038 (2)	0.054 (2)	0.071 (2)	0.0050 (16)	0.0032 (18)	−0.0074 (19)
C16	0.043 (2)	0.077 (3)	0.087 (3)	−0.0011 (19)	−0.016 (2)	−0.024 (2)
C17	0.059 (2)	0.0451 (19)	0.0486 (19)	0.0065 (17)	−0.0229 (17)	−0.0012 (16)
Cl1	0.0476 (5)	0.0593 (5)	0.0594 (5)	−0.0128 (4)	−0.0147 (4)	0.0070 (4)
Cl2	0.0388 (5)	0.0819 (7)	0.0635 (5)	0.0261 (5)	−0.0107 (4)	−0.0162 (5)
N1	0.0410 (17)	0.067 (2)	0.0367 (15)	0.0077 (15)	−0.0072 (13)	−0.0028 (14)
N2	0.0434 (16)	0.0529 (16)	0.0350 (13)	0.0173 (13)	−0.0074 (12)	−0.0107 (12)
N3	0.0367 (15)	0.0338 (14)	0.0385 (14)	−0.0018 (12)	−0.0079 (11)	0.0017 (12)
O1	0.0352 (12)	0.0515 (13)	0.0364 (10)	0.0138 (10)	0.0004 (9)	−0.0086 (10)
O2	0.0358 (12)	0.0588 (15)	0.0415 (11)	0.0069 (11)	0.0012 (10)	−0.0108 (11)
O3	0.0531 (14)	0.0558 (14)	0.0346 (10)	0.0229 (12)	−0.0035 (10)	−0.0039 (10)
O1W	0.0479 (18)	0.088 (2)	0.078 (2)	0.0005 (17)	0.0099 (15)	−0.0155 (18)

Geometric parameters (Å, º) top

C1—C2	1.391 (4)	C11—H11	0.980
C1—C6	1.413 (4)	C12—O3	1.419 (4)
C1—C9	1.483 (4)	C12—C13	1.512 (4)
C2—C3	1.350 (4)	C12—H12A	0.970
C2—H2	0.93 (3)	C12—H12B	0.970
C3—C4	1.394 (4)	C13—N3	1.493 (4)
C3—Cl2	1.750 (3)	C13—C15	1.511 (4)
C4—N1	1.352 (4)	C13—H13	0.980
C4—C5	1.395 (4)	C14—N3	1.489 (4)
C5—C6	1.369 (4)	C14—H14A	0.970
C5—H5	0.94 (3)	C14—H14B	0.970
C6—O1	1.359 (3)	C15—C16	1.517 (4)
C7—O1	1.432 (3)	C15—H15A	0.970
C7—C8	1.486 (4)	C15—H15B	0.970
C7—H7A	0.970	C16—C17	1.515 (5)
C7—H7B	0.970	C16—H16A	0.970
C8—H8A	0.960	C16—H16B	0.970
C8—H8B	0.960	C17—N3	1.492 (4)
C8—H8C	0.960	C17—H17A	0.970
C9—O2	1.229 (3)	C17—H17B	0.970
C9—N2	1.330 (4)	N1—H1A	0.84 (4)
C10—N2	1.441 (3)	N1—H1B	0.85 (3)
C10—C11	1.504 (4)	N2—H2A	0.860
C10—H10A	0.970	N3—H3C	0.92 (3)
C10—H10B	0.970	O1W—H1WA	0.79 (3)
C11—O3	1.417 (3)	O1W—H1WB	0.88 (4)
C11—C14	1.509 (4)

C2—C1—C6	116.5 (3)	O3—C12—H12B	109.2
C2—C1—C9	116.8 (2)	C13—C12—H12B	109.2
C6—C1—C9	126.7 (2)	H12A—C12—H12B	107.9
C3—C2—C1	122.1 (3)	N3—C13—C15	102.8 (2)
C3—C2—H2	120.1 (17)	N3—C13—C12	110.9 (2)
C1—C2—H2	117.8 (17)	C15—C13—C12	117.6 (3)
C2—C3—C4	122.4 (3)	N3—C13—H13	108.4
C2—C3—Cl2	119.8 (2)	C15—C13—H13	108.4
C4—C3—Cl2	117.8 (2)	C12—C13—H13	108.4
N1—C4—C3	123.2 (3)	N3—C14—C11	108.7 (2)
N1—C4—C5	120.8 (3)	N3—C14—H14A	109.9
C3—C4—C5	116.0 (3)	C11—C14—H14A	109.9
C6—C5—C4	122.4 (3)	N3—C14—H14B	109.9
C6—C5—H5	122.0 (18)	C11—C14—H14B	109.9
C4—C5—H5	115.6 (18)	H14A—C14—H14B	108.3
O1—C6—C5	122.4 (2)	C13—C15—C16	104.6 (3)
O1—C6—C1	117.0 (2)	C13—C15—H15A	110.8
C5—C6—C1	120.6 (3)	C16—C15—H15A	110.8
O1—C7—C8	107.1 (2)	C13—C15—H15B	110.8
O1—C7—H7A	110.3	C16—C15—H15B	110.8
C8—C7—H7A	110.3	H15A—C15—H15B	108.9
O1—C7—H7B	110.3	C17—C16—C15	106.4 (3)
C8—C7—H7B	110.3	C17—C16—H16A	110.4
H7A—C7—H7B	108.5	C15—C16—H16A	110.4
C7—C8—H8A	109.1	C17—C16—H16B	110.4
C7—C8—H8B	109.7	C15—C16—H16B	110.4
H8A—C8—H8B	109.5	H16A—C16—H16B	108.6
C7—C8—H8C	109.7	N3—C17—C16	104.4 (3)
H8A—C8—H8C	109.5	N3—C17—H17A	110.9
H8B—C8—H8C	109.5	C16—C17—H17A	110.9
O2—C9—N2	120.3 (3)	N3—C17—H17B	110.9
O2—C9—C1	121.9 (2)	C16—C17—H17B	110.9
N2—C9—C1	117.7 (2)	H17A—C17—H17B	108.9
N2—C10—C11	109.9 (2)	C4—N1—H1A	127 (3)
N2—C10—H10A	109.7	C4—N1—H1B	121 (3)
C11—C10—H10A	109.7	H1A—N1—H1B	106 (3)
N2—C10—H10B	109.7	C9—N2—C10	123.8 (2)
C11—C10—H10B	109.7	C9—N2—H2A	118.1
H10A—C10—H10B	108.2	C10—N2—H2A	118.1
O3—C11—C10	107.6 (2)	C14—N3—C17	112.5 (2)
O3—C11—C14	109.8 (2)	C14—N3—C13	112.4 (2)
C10—C11—C14	111.7 (2)	C17—N3—C13	103.4 (2)
O3—C11—H11	109.2	C14—N3—H3C	108.4 (17)
C10—C11—H11	109.2	C17—N3—H3C	107.6 (16)
C14—C11—H11	109.2	C13—N3—H3C	112.4 (16)
O3—C12—C13	111.9 (3)	C6—O1—C7	120.4 (2)
O3—C12—H12A	109.2	C11—O3—C12	110.3 (2)
C13—C12—H12A	109.2	H1WA—O1W—H1WB	100 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.84 (4)	2.66 (4)	3.384 (3)	146 (3)
N1—H1B···Cl1ⁱⁱ	0.85 (3)	2.45 (3)	3.281 (3)	169 (3)
N3—H3C···Cl1	0.92 (3)	2.18 (3)	3.077 (3)	164 (2)
O1W—H1WA···Cl1ⁱⁱⁱ	0.79 (3)	2.62 (3)	3.410 (4)	176 (3)
O1W—H1WB···O2	0.88 (4)	1.95 (5)	2.800 (4)	161 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z−1/2; (iii) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅ClN₃O₃⁺·Cl⁻·H₂O
M_r	408.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.0984 (9), 11.1594 (13), 21.843 (3)
V (Å³)	1974.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.919, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	10642, 3848, 3188
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.096, 1.06
No. of reflections	3848
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22
Absolute structure	Flack (1983), 1631 Friedel pairs
Absolute structure parameter	−0.02 (7)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.84 (4)	2.66 (4)	3.384 (3)	146 (3)
N1—H1B···Cl1ⁱⁱ	0.85 (3)	2.45 (3)	3.281 (3)	169 (3)
N3—H3C···Cl1	0.92 (3)	2.18 (3)	3.077 (3)	164 (2)
O1W—H1WA···Cl1ⁱⁱⁱ	0.79 (3)	2.62 (3)	3.410 (4)	176 (3)
O1W—H1WB···O2	0.88 (4)	1.95 (5)	2.800 (4)	161 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, −y+1, z−1/2; (iii) x−1/2, −y+3/2, −z+2.

Acknowledgements

The authors thank the Program for Young Excellent Talents in China Pharmaceutical University for financial support.

References

Aoki, Y., Hakamata, H., Igarashi, Y., Uchida, K., Kobayashi, H., Hirayama, N., Kotani, A. & Kusu, F. (2007). J. Chromatogr. B858, 135–142. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kakigami, T., Usui, T., Ikami, T., Tsukamoto, K., Miwa, Y., Taga, T. & Kataoka, T. (1998). Chem. Pharm. Bull. 46, 1039–1043. Web of Science CrossRef CAS PubMed Google Scholar
Morie, T., Kato, S., Harada, H., Yoshida, N., Fujiwara, I. & Matsumoto, J.-I. (1995). Chem. Pharm. Bull. 43, 1137–1147. CrossRef CAS PubMed Web of Science Google Scholar
Omae, T., Sakurai, M., Ashizawa, K. & Kajima, T. (2002). Anal. Sci. 18, 729–730. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[(4-Amino-5-chloro-2-eth­oxy­benz­amido)meth­yl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-[(4-Amino-5-chloro-2-ethoxybenzamido)methyl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate