N-(4-Chloro­phen­yl)-6,7-bis­(2-methoxy­ethoxy)quinazolin-4-amine monohydrate

Li, S.-C.; Xu, H.; Huang, W.-L.

doi:10.1107/S1600536807059466

N-(4-Chlorophenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine monohydrate

In the title compound, C₂₀H₂₂ClN₃O₄·H₂O, the quinazoline and benzene ring systems are oriented at a dihedral angle of 4.99 (3)°. Intramolecular C—H

N hydrogen bonding results in the formation of a nearly planar six-membered ring, which is nearly coplanar with the adjacent quinazoline ring system and the benzene ring, making dihedral angles of 2.39 (3) and 3.32 (3)°, respectively. In the crystal structure, intermolecular N—H

O and C—H

O hydrogen bonds link the molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059466/hk2380sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059466/hk2380Isup2.hkl Contains datablock I

CCDC reference: 673011

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.067
wR factor = 0.179
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C20 H22 Cl N3 O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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

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

Comment top

The title compound, C₂₀H₂₄ClN₃O₅, is one of quinazolins which are an important class of aromatic compounds and have widespread applications from pharmaceuticals (Dolle et al., 1994) to agronomy environmental microbiology (Aislabie et al., 1990). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C7—C12), B (N1/N2/C10/C11/C13/C14) and C (C15—C20) are, of course, planar and the dihedral angles between them are A/B = 0.50 (3)°, A/C = 5.06 (3)° and B/C = 4.89 (2)°. So, rings A and B are also co-planar. The nearly planar quinazoline ring system is oriented with respect to ring C at a dihedral angle of 4.99 (3)°. The intramolecular C—H···N hydrogen bond (Table 1) causes to the formation of the nearly planar six-membered ring; D (N2/N3/C14—C16/H16A), in which it is also nearly co-planar with the adjacent quinazoline ring system and ring C with dihedral angles of 2.39 (3)° and 3.32 (3)°, respectively.

In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules, in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Dolle et al. (1994); Aislabie et al. (1990). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a solution of 4-chloro-6,7-bis -(2-methoxyethoxy)-quinazoline (2.0 g, 6.4 mmol) and 4-chlorobenzenamine (1.0 g, 7.8 mmol) in i-PrOH(15.0 ml) was stirred and heated at reflux for 6 h under N₂ atmosphere resulting in the precipitation of a colorless solid. After stirring at room temperature overnight the precipitation was filtered, washed with hot i-PrOH and dried on the air to afford the crude hydrochloride product (yield; 2.7 g, 94%). To isolate the free base, the crude product (0.5 g) was dissolved in water (10 ml) and basified using conc. aq. ammonia (5 ml). Extraction with dichloromethane (4 x 20 ml), gave after drying and evaporation, the title compound as colorless crystals. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

N-(4-chlorophenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine monohydrate top

Crystal data top

C₂₀H₂₂ClN₃O₄·H₂O	F(000) = 888
M_r = 421.87	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 411(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.8850 (12) Å	Cell parameters from 25 reflections
b = 16.231 (3) Å	θ = 10–13°
c = 21.723 (4) Å	µ = 0.22 mm⁻¹
β = 93.93 (3)°	T = 298 K
V = 2070.1 (7) Å³	Block, colorless
Z = 4	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1956 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 26.0°, θ_min = 1.6°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
T_min = 0.937, T_max = 0.978	l = 0→26
4474 measured reflections	3 standard reflections every 120 min
4064 independent reflections	intensity decay: none

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
4064 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₂ClN₃O₄·H₂O	V = 2070.1 (7) Å³
M_r = 421.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8850 (12) Å	µ = 0.22 mm⁻¹
b = 16.231 (3) Å	T = 298 K
c = 21.723 (4) Å	0.30 × 0.10 × 0.10 mm
β = 93.93 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1956 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.036
T_min = 0.937, T_max = 0.978	3 standard reflections every 120 min
4474 measured reflections	intensity decay: none
4064 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 0.99	Δρ_max = 0.20 e Å⁻³
4064 reflections	Δρ_min = −0.26 e Å⁻³
262 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
Cl	0.28318 (19)	0.54760 (8)	0.08634 (6)	0.0852 (4)
OW	2.2216 (5)	0.58666 (15)	0.30954 (12)	0.0652 (8)
HWB	2.3512	0.6041	0.3004	0.078*
HWA	2.1409	0.6263	0.3214	0.078*
O1	2.2847 (5)	0.23685 (18)	0.48805 (14)	0.0734 (8)
O2	2.0330 (5)	0.31921 (15)	0.38367 (12)	0.0610 (7)
O3	2.0406 (5)	0.60395 (19)	0.42442 (13)	0.0790 (9)
O4	1.8136 (5)	0.45376 (15)	0.39496 (12)	0.0634 (8)
N1	1.5256 (6)	0.23193 (19)	0.21452 (16)	0.0678 (10)
N2	1.2049 (6)	0.3156 (2)	0.18159 (16)	0.0699 (10)
N3	1.1257 (5)	0.43964 (18)	0.22824 (13)	0.0520 (8)
H3A	1.1693	0.4744	0.2565	0.062*
C1	2.1970 (9)	0.1593 (3)	0.5006 (2)	0.0893 (15)
H1B	2.1511	0.1582	0.5422	0.134*
H1C	2.3119	0.1182	0.4959	0.134*
H1D	2.0678	0.1481	0.4725	0.134*
C2	2.3533 (7)	0.2472 (3)	0.4277 (2)	0.0675 (12)
H2B	2.4608	0.2039	0.4195	0.081*
H2C	2.4330	0.2994	0.4257	0.081*
C3	2.1656 (7)	0.2459 (2)	0.37812 (19)	0.0614 (11)
H3B	2.2280	0.2440	0.3379	0.074*
H3C	2.0710	0.1976	0.3824	0.074*
C4	2.1759 (7)	0.6585 (3)	0.4609 (2)	0.0865 (15)
H4A	2.3114	0.6712	0.4406	0.130*
H4B	2.2169	0.6334	0.5002	0.130*
H4C	2.0922	0.7083	0.4671	0.130*
C5	1.8353 (7)	0.5800 (2)	0.44938 (18)	0.0596 (11)
H5A	1.7497	0.6285	0.4599	0.071*
H5B	1.8683	0.5481	0.4867	0.071*
C6	1.6987 (7)	0.5297 (2)	0.40302 (18)	0.0604 (11)
H6A	1.5485	0.5195	0.4172	0.072*
H6B	1.6810	0.5590	0.3641	0.072*
C7	1.7244 (7)	0.4023 (2)	0.34991 (17)	0.0497 (9)
C8	1.8498 (7)	0.3282 (2)	0.34302 (17)	0.0500 (9)
C9	1.7805 (7)	0.2744 (2)	0.29797 (17)	0.0542 (10)
H9A	1.8631	0.2263	0.2931	0.065*
C10	1.5872 (7)	0.2897 (2)	0.25873 (17)	0.0534 (10)
C11	1.4585 (6)	0.3615 (2)	0.26580 (16)	0.0475 (9)
C12	1.5328 (6)	0.4175 (2)	0.31264 (17)	0.0502 (9)
H12A	1.4501	0.4654	0.3182	0.060*
C13	1.3404 (9)	0.2501 (3)	0.1796 (2)	0.0801 (14)
H13A	1.2983	0.2116	0.1492	0.096*
C14	1.2607 (6)	0.3716 (2)	0.22432 (17)	0.0506 (9)
C15	0.9255 (6)	0.4610 (2)	0.19267 (17)	0.0490 (9)
C16	0.8334 (7)	0.4174 (3)	0.1424 (2)	0.0710 (12)
H16A	0.9033	0.3693	0.1303	0.085*
C17	0.6390 (8)	0.4448 (3)	0.1103 (2)	0.0782 (14)
H17A	0.5801	0.4155	0.0760	0.094*
C18	0.5306 (7)	0.5149 (3)	0.1279 (2)	0.0598 (11)
C19	0.6159 (7)	0.5582 (2)	0.17804 (19)	0.0608 (11)
H19A	0.5421	0.6053	0.1906	0.073*
C20	0.8115 (7)	0.5316 (2)	0.20973 (18)	0.0601 (11)
H20A	0.8699	0.5617	0.2437	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0616 (7)	0.0858 (9)	0.1056 (10)	−0.0049 (6)	−0.0127 (6)	0.0152 (7)
OW	0.0705 (18)	0.0484 (16)	0.0770 (19)	−0.0015 (14)	0.0064 (15)	−0.0136 (14)
O1	0.081 (2)	0.066 (2)	0.072 (2)	0.0037 (17)	0.0000 (17)	−0.0073 (16)
O2	0.0661 (18)	0.0464 (16)	0.0693 (18)	0.0151 (14)	−0.0037 (15)	−0.0044 (13)
O3	0.077 (2)	0.087 (2)	0.074 (2)	−0.0186 (18)	0.0123 (17)	−0.0290 (17)
O4	0.0768 (18)	0.0420 (15)	0.0692 (18)	0.0147 (14)	−0.0109 (15)	−0.0117 (14)
N1	0.088 (3)	0.045 (2)	0.069 (2)	0.0070 (19)	−0.004 (2)	−0.0126 (17)
N2	0.090 (3)	0.045 (2)	0.072 (2)	0.0072 (19)	−0.011 (2)	−0.0171 (18)
N3	0.057 (2)	0.0486 (19)	0.0499 (19)	−0.0026 (16)	−0.0017 (16)	−0.0052 (15)
C1	0.118 (4)	0.075 (3)	0.073 (3)	−0.002 (3)	−0.004 (3)	0.015 (3)
C2	0.065 (3)	0.056 (3)	0.083 (3)	0.006 (2)	0.010 (3)	−0.003 (2)
C3	0.068 (3)	0.049 (2)	0.067 (3)	0.012 (2)	0.008 (2)	0.005 (2)
C4	0.067 (3)	0.095 (4)	0.097 (4)	−0.011 (3)	0.003 (3)	−0.037 (3)
C5	0.064 (3)	0.054 (2)	0.060 (3)	0.007 (2)	0.001 (2)	−0.009 (2)
C6	0.067 (3)	0.044 (2)	0.069 (3)	0.007 (2)	−0.005 (2)	−0.010 (2)
C7	0.061 (2)	0.037 (2)	0.052 (2)	−0.0016 (19)	0.006 (2)	−0.0028 (18)
C8	0.058 (2)	0.040 (2)	0.051 (2)	0.0072 (19)	0.003 (2)	0.0046 (18)
C9	0.070 (3)	0.035 (2)	0.059 (2)	0.0044 (19)	0.011 (2)	−0.0046 (18)
C10	0.069 (3)	0.039 (2)	0.053 (2)	−0.001 (2)	0.008 (2)	−0.0019 (19)
C11	0.058 (2)	0.036 (2)	0.049 (2)	−0.0050 (18)	0.0080 (19)	0.0011 (17)
C12	0.057 (2)	0.037 (2)	0.056 (2)	0.0032 (19)	0.005 (2)	−0.0010 (18)
C13	0.113 (4)	0.051 (3)	0.073 (3)	0.003 (3)	−0.013 (3)	−0.021 (2)
C14	0.060 (3)	0.042 (2)	0.050 (2)	−0.006 (2)	0.005 (2)	0.0001 (18)
C15	0.051 (2)	0.046 (2)	0.049 (2)	−0.008 (2)	0.0041 (18)	−0.0016 (18)
C16	0.058 (3)	0.068 (3)	0.085 (3)	0.001 (2)	−0.003 (2)	−0.015 (2)
C17	0.070 (3)	0.083 (4)	0.079 (3)	−0.005 (3)	−0.013 (3)	−0.018 (3)
C18	0.052 (2)	0.059 (3)	0.069 (3)	−0.008 (2)	0.004 (2)	0.013 (2)
C19	0.067 (3)	0.050 (2)	0.066 (3)	0.004 (2)	0.005 (2)	0.006 (2)
C20	0.075 (3)	0.048 (2)	0.058 (3)	−0.006 (2)	0.000 (2)	0.003 (2)

Geometric parameters (Å, º) top

Cl—C18	1.742 (4)	C4—H4B	0.9600
OW—HWB	0.8500	C4—H4C	0.9600
OW—HWA	0.8501	C5—C6	1.489 (5)
N1—C13	1.318 (5)	C5—H5A	0.9700
N1—C10	1.374 (4)	C5—H5B	0.9700
O1—C1	1.394 (5)	C6—H6A	0.9700
O1—C2	1.408 (5)	C6—H6B	0.9700
C1—H1B	0.9600	C7—C12	1.365 (5)
C1—H1C	0.9600	C7—C8	1.424 (5)
C1—H1D	0.9600	C8—C9	1.354 (5)
O2—C8	1.354 (4)	C9—C10	1.396 (5)
O2—C3	1.433 (4)	C9—H9A	0.9300
N2—C14	1.324 (4)	C10—C11	1.403 (5)
N2—C13	1.332 (5)	C11—C12	1.412 (5)
C2—C3	1.490 (5)	C11—C14	1.432 (5)
C2—H2B	0.9700	C12—H12A	0.9300
C2—H2C	0.9700	C13—H13A	0.9300
N3—C14	1.366 (4)	C15—C16	1.380 (5)
N3—C15	1.408 (4)	C15—C20	1.391 (5)
N3—H3A	0.8600	C16—C17	1.373 (5)
O3—C4	1.400 (5)	C16—H16A	0.9300
O3—C5	1.412 (5)	C17—C18	1.371 (6)
C3—H3B	0.9700	C17—H17A	0.9300
C3—H3C	0.9700	C18—C19	1.363 (5)
O4—C7	1.364 (4)	C19—C20	1.370 (5)
O4—C6	1.423 (4)	C19—H19A	0.9300
C4—H4A	0.9600	C20—H20A	0.9300

HWB—OW—HWA	110.3	C5—C6—H6B	110.0
C13—N1—C10	114.7 (4)	H6A—C6—H6B	108.3
C1—O1—C2	115.1 (3)	O4—C7—C12	125.2 (3)
O1—C1—H1B	109.5	O4—C7—C8	114.6 (3)
O1—C1—H1C	109.5	C12—C7—C8	120.2 (3)
H1B—C1—H1C	109.5	C9—C8—O2	126.1 (3)
O1—C1—H1D	109.5	C9—C8—C7	119.2 (4)
H1B—C1—H1D	109.5	O2—C8—C7	114.7 (3)
H1C—C1—H1D	109.5	C8—C9—C10	121.3 (4)
C8—O2—C3	116.7 (3)	C8—C9—H9A	119.4
C14—N2—C13	116.8 (4)	C10—C9—H9A	119.4
O1—C2—C3	115.2 (3)	N1—C10—C9	118.0 (4)
O1—C2—H2B	108.5	N1—C10—C11	121.6 (4)
C3—C2—H2B	108.5	C9—C10—C11	120.3 (4)
O1—C2—H2C	108.5	C10—C11—C12	118.1 (4)
C3—C2—H2C	108.5	C10—C11—C14	116.6 (3)
H2B—C2—H2C	107.5	C12—C11—C14	125.3 (3)
C14—N3—C15	129.3 (3)	C7—C12—C11	120.9 (3)
C14—N3—H3A	115.3	C7—C12—H12A	119.5
C15—N3—H3A	115.3	C11—C12—H12A	119.5
C4—O3—C5	115.1 (3)	N1—C13—N2	129.3 (4)
O2—C3—C2	107.9 (3)	N1—C13—H13A	115.4
O2—C3—H3B	110.1	N2—C13—H13A	115.4
C2—C3—H3B	110.1	N2—C14—N3	118.7 (3)
O2—C3—H3C	110.1	N2—C14—C11	120.9 (4)
C2—C3—H3C	110.1	N3—C14—C11	120.3 (3)
H3B—C3—H3C	108.4	C16—C15—C20	117.6 (4)
C7—O4—C6	117.1 (3)	C16—C15—N3	125.2 (4)
O3—C4—H4A	109.5	C20—C15—N3	117.2 (3)
O3—C4—H4B	109.5	C17—C16—C15	120.3 (4)
H4A—C4—H4B	109.5	C17—C16—H16A	119.8
O3—C4—H4C	109.5	C15—C16—H16A	119.8
H4A—C4—H4C	109.5	C18—C17—C16	121.0 (4)
H4B—C4—H4C	109.5	C18—C17—H17A	119.5
O3—C5—C6	109.1 (3)	C16—C17—H17A	119.5
O3—C5—H5A	109.9	C19—C18—C17	119.8 (4)
C6—C5—H5A	109.9	C19—C18—Cl	120.4 (4)
O3—C5—H5B	109.9	C17—C18—Cl	119.8 (4)
C6—C5—H5B	109.9	C18—C19—C20	119.3 (4)
H5A—C5—H5B	108.3	C18—C19—H19A	120.3
O4—C6—C5	108.6 (3)	C20—C19—H19A	120.3
O4—C6—H6A	110.0	C19—C20—C15	122.0 (4)
C5—C6—H6A	110.0	C19—C20—H20A	119.0
O4—C6—H6B	110.0	C15—C20—H20A	119.0

C1—O1—C2—C3	67.2 (5)	C8—C7—C12—C11	−1.6 (5)
C8—O2—C3—C2	−178.6 (3)	C10—C11—C12—C7	0.0 (5)
O1—C2—C3—O2	69.4 (4)	C14—C11—C12—C7	−179.9 (3)
C4—O3—C5—C6	174.0 (3)	C10—N1—C13—N2	−0.8 (7)
C7—O4—C6—C5	−174.2 (3)	C14—N2—C13—N1	0.2 (8)
O3—C5—C6—O4	67.7 (4)	C13—N2—C14—N3	−179.6 (4)
C6—O4—C7—C12	−0.8 (5)	C13—N2—C14—C11	0.3 (6)
C6—O4—C7—C8	178.5 (3)	C15—N3—C14—N2	0.4 (6)
C3—O2—C8—C9	0.2 (5)	C15—N3—C14—C11	−179.6 (3)
C3—O2—C8—C7	−179.5 (3)	C10—C11—C14—N2	−0.2 (5)
O4—C7—C8—C9	−177.5 (3)	C12—C11—C14—N2	179.8 (4)
C12—C7—C8—C9	1.9 (5)	C10—C11—C14—N3	179.8 (3)
O4—C7—C8—O2	2.2 (5)	C12—C11—C14—N3	−0.3 (5)
C12—C7—C8—O2	−178.4 (3)	C14—N3—C15—C16	−4.6 (6)
O2—C8—C9—C10	179.6 (3)	C14—N3—C15—C20	175.2 (3)
C7—C8—C9—C10	−0.8 (6)	C20—C15—C16—C17	1.4 (6)
C13—N1—C10—C9	179.4 (4)	N3—C15—C16—C17	−178.8 (4)
C13—N1—C10—C11	0.9 (6)	C15—C16—C17—C18	−1.1 (7)
C8—C9—C10—N1	−179.3 (4)	C16—C17—C18—C19	−0.1 (7)
C8—C9—C10—C11	−0.8 (6)	C16—C17—C18—Cl	−179.6 (3)
N1—C10—C11—C12	179.6 (3)	C17—C18—C19—C20	0.9 (6)
C9—C10—C11—C12	1.1 (5)	Cl—C18—C19—C20	−179.6 (3)
N1—C10—C11—C14	−0.5 (5)	C18—C19—C20—C15	−0.6 (6)
C9—C10—C11—C14	−178.9 (3)	C16—C15—C20—C19	−0.5 (6)
O4—C7—C12—C11	177.8 (3)	N3—C15—C20—C19	179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···O3	0.85	2.38	2.794 (4)	110
C16—H16A···N2	0.93	2.21	2.825 (6)	123
N3—H3A···OWⁱ	0.86	2.17	2.999 (4)	163
C12—H12A···OWⁱ	0.93	2.38	3.299 (4)	168
C20—H20A···OWⁱ	0.93	2.47	3.257 (5)	143

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂ClN₃O₄·H₂O
M_r	421.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	5.8850 (12), 16.231 (3), 21.723 (4)
β (°)	93.93 (3)
V (Å³)	2070.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.937, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	4474, 4064, 1956
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.179, 0.99
No. of reflections	4064
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Siemens, 1996).