3-[(4-Amino-5-chloro-2-ethoxy-benz-amido)meth-yl]pyrrolo[2,1-c][1,4]oxazin-5-ium chloride monohydrate.

The title compound, C(17)H(25)ClN(3)O(3) (+)·Cl(-)·H(2)O, is a monohydrated hydro-chloride 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 mol-ecules 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 = 408.32

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.096

S = 1.06

3848 reflections

261 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1631 Friedel pairs

Flack parameter: −0.02 (7)

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.

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

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

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

C17H25ClN3O3+·Cl−·H2O	F(000) = 864
Mr = 408.32	Dx = 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

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

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(Fo2) + (0.0412P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3848 reflections	Δρmax = 0.32 e Å−3
261 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 1631 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (7)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .