Methyl 2-[(carbamoyl­amino)­imino]-2-(3-{1-[(carbamoyl­amino)­imino]-2-meth­oxy-2-oxoeth­yl}phen­yl)acetate ethanol monosolvate monohydrate

Ismatov, D.; Azizov, U.; Ashurov, J.; Talipov, S.

doi:10.1107/S1600536812001237

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o464

doi:10.1107/S1600536812001237

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Methyl 2-[(carbamoylamino)imino]-2-(3-{1-[(carbamoylamino)imino]-2-methoxy-2-oxoethyl}phenyl)acetate ethanol monosolvate monohydrate

Dilmurot Ismatov,^a ^* Umarkhon Azizov,^b Jamshid Ashurov ^c and Samat Talipov ^c

^aTashkent Chemical Technology Institute, A. Navoyi 11, Tashkent, Uzbekistan, ^bUzbekistan Scientific Research Pharmacological Chemistry Institute (named after A. Sultonov), Durmon Yuli str. 40, Tashkent, Uzbekistan, and ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Street 83, Tashkent, 100125 Uzbekistan
^*Correspondence e-mail: x-ray.uz@mail.ru

(Received 2 November 2011; accepted 11 January 2012; online 21 January 2012)

In the title compound, C₁₄H₁₆N₆O₆·C₂H₆O·H₂O, both substituents of the benzene ring are approximately planar with maximum deviations from the mean plane of 0.0561 (12) (an imine N atom) and 0.1419 (11) Å (a methoxy O atom). The substituents are tilted out of the plane of the benzene ring by 64.48 (4) and 70.08 (5)°, respectively. In the crystal, molecules form centrosymmetric dimers associated via pairs of N—H⋯O hydrogen bonds. The dimers are linked via the water and ethanol molecules, forming two-dimensional hydrogen-bond networks lying parallel to (100).

Related literature

For details of the synthesis of 1,4-benzodiketodicarboxylic acid and its derivatives, see: Ismatov et al. (1991 ). For the synthesis and biological activity of 1,3-benzodiketodicarboxylic acid and its derivatives, see: Ismatov et al. (1998 , 2001 ).

Experimental

Crystal data

C₁₄H₁₆N₆O₆·C₂H₆O·H₂O
M_r = 428.41
Monoclinic, P 2₁ /c
a = 7.5810 (2) Å
b = 12.1216 (3) Å
c = 23.0379 (7) Å
β = 97.254 (3)°
V = 2100.11 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.94 mm⁻¹
T = 294 K
0.41 × 0.32 × 0.26 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.700, T_max = 1.000
15863 measured reflections
4317 independent reflections
2927 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 0.98
4317 reflections
298 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O6	0.85	2.05	2.879 (3)	166
O1W—H1WB⋯O5ⁱ	0.85	2.16	2.941 (3)	152
N3—H3A⋯O7	0.86 (4)	2.13 (4)	2.980 (2)	169 (3)
N3—H3B⋯O5ⁱⁱ	0.85 (3)	2.61 (2)	3.082 (2)	116.7 (18)
N5—H5A⋯O3ⁱⁱⁱ	0.86	2.19	3.010 (2)	160
N6—H6A⋯O1W^iv	0.84 (3)	2.34 (3)	3.137 (3)	158 (3)
N6—H6B⋯O7^v	0.90 (3)	1.99 (3)	2.871 (3)	166 (2)
O7—H7⋯O2	0.88 (3)	1.96 (3)	2.801 (2)	158 (3)
O7—H7⋯N1	0.88 (3)	2.52 (3)	3.0677 (19)	121 (2)
C4—H4⋯O6^vi	0.93	2.57	3.493 (2)	173
C13—H13C⋯N6^vii	0.96	2.62	3.405 (3)	139
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) x+1, y, z; (vii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001237/fy2032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001237/fy2032Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001237/fy2032Isup3.cml

checkCIF report

Comment top

It has been reported previously that arylketodicarbonicacid derivatives possess antiinflammatory activity (Ismatov et al., 1991, Ismatov et al., 1998, Ismatov et al., 2001). We report herein the X-ray crystallographic study of a disemicarbazonodimethylether-1,3-benzenediketodicarbonic acid monohydrate ethanol solvate.

The asymmetric unit of the title compound, C₁₄H₁₆N₆O₆.C₂H₆O.H₂O, contains a disemicarbazonodimethylether-1,3-benzenediketodicarbonic acid (DBA), an ethanol and a water molecule as shown in Fig. 1. In the DBA molecule the planes of the substituent fragments (C1/C7/C8/N1/N2/O1/O2 and C3/C11/C12/N4/N5/O4/O5) are tilted out of the mean plane of the benzene ring by 64.48 (4)° and 70.08 (5)°, respectively.

In the crystal structure (Fig. 2), DBA molecules form centrosymmetric pair associates via N2—H···O3 and N5—H···O3 H-bonds and the associates are linked via H-bonds by water (O1W—H1···O5, O1W—H2···O6, N6—H···O1W) and ethanol (N6—H···O7, N3—H3···O7,O7—H7···O2) molecules forming two-dimensional networks parallel to the (100) plane (Table 1).

Related literature top

For details of the synthesis of 1,4-benzodiketodicarboxylic acid and its derivatives, see: Ismatov et al. (1991). For the synthesis and biological activity of 1,3-benzodiketodicarboxylic acid and its derivatives, see: Ismatov et al. (1998, 2001).

Experimental top

In a round bottom flask, dimethylether-1,3-benzodiketodicarboxylic acid (0.02 mol, 0.51 g) was dissolved in 5 ml methanol. Drops of semicarbazide chloride (0.04 mol, 0.44 g) dissolved in ethanol (5 ml) were then added. The reaction mixture was refluxed for 30 min. The precipitate (0.44 g )formed after 24 h was filtered. The precipitate was then dissolved in ethanol at room temperature. After few days, colorless crystals (m.p. 120–121°C) were formed by slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of title compound, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram for title compound.

Methyl 2-[(carbamoylamino)imino]-2-(3-{1-[(carbamoylamino)imino]- 2-methoxy-2-oxoethyl}phenyl)acetate ethanol monosolvate monohydrate top

Crystal data top

C₁₄H₁₆N₆O₆·C₂H₆O·H₂O	Z = 4
M_r = 428.41	F(000) = 904
Monoclinic, P2₁/c	D_x = 1.355 Mg m⁻³
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 7.5810 (2) Å	θ = 3.6–75.7°
b = 12.1216 (3) Å	µ = 0.94 mm⁻¹
c = 23.0379 (7) Å	T = 294 K
β = 97.254 (3)°	Block, colourless
V = 2100.11 (10) Å³	0.41 × 0.32 × 0.26 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	4317 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.2576 pixels mm^-1	θ_max = 75.9°, θ_min = 3.9°
ω scans	h = −8→9
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→15
T_min = 0.700, T_max = 1.000	l = −27→28
15863 measured reflections

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0775P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.002
4317 reflections	Δρ_max = 0.27 e Å⁻³
298 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Crystal data top

C₁₄H₁₆N₆O₆·C₂H₆O·H₂O	V = 2100.11 (10) Å³
M_r = 428.41	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.5810 (2) Å	µ = 0.94 mm⁻¹
b = 12.1216 (3) Å	T = 294 K
c = 23.0379 (7) Å	0.41 × 0.32 × 0.26 mm
β = 97.254 (3)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	4317 independent reflections
Absorption correction: multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2009)	2927 reflections with I > 2σ(I)
T_min = 0.700, T_max = 1.000	R_int = 0.035
15863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.27 e Å⁻³
4317 reflections	Δρ_min = −0.18 e Å⁻³
298 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
C1	0.2929 (2)	0.25039 (12)	0.51014 (7)	0.0377 (4)
C2	0.3041 (2)	0.27386 (13)	0.56962 (7)	0.0400 (4)
H2	0.2219	0.3212	0.5831	0.048*
C3	0.4375 (2)	0.22701 (13)	0.60902 (7)	0.0427 (4)
C4	0.5626 (2)	0.15889 (14)	0.58852 (8)	0.0501 (4)
H4	0.6537	0.1288	0.6145	0.060*
C5	0.5520 (2)	0.13560 (14)	0.52931 (9)	0.0526 (4)
H5	0.6362	0.0897	0.5157	0.063*
C6	0.4171 (2)	0.18025 (13)	0.49020 (8)	0.0457 (4)
H6	0.4096	0.1633	0.4506	0.055*
C7	0.1457 (2)	0.29742 (13)	0.46895 (7)	0.0385 (4)
C8	0.1357 (2)	0.41831 (13)	0.45552 (7)	0.0412 (4)
C9	0.2828 (3)	0.58940 (15)	0.47140 (10)	0.0582 (5)
H9A	0.2586	0.6042	0.4302	0.087*
H9B	0.3987	0.6170	0.4860	0.087*
H9C	0.1951	0.6251	0.4915	0.087*
C10	−0.1273 (2)	0.07098 (14)	0.42197 (7)	0.0455 (4)
C11	0.4352 (2)	0.25050 (14)	0.67237 (7)	0.0475 (4)
C12	0.5777 (3)	0.31779 (15)	0.70685 (8)	0.0553 (5)
C13	0.8581 (3)	0.4016 (2)	0.70538 (13)	0.0876 (8)
H13A	0.9592	0.3958	0.6843	0.131*
H13B	0.8902	0.3768	0.7449	0.131*
H13C	0.8199	0.4771	0.7056	0.131*
C14	0.0394 (3)	0.12867 (16)	0.70835 (9)	0.0583 (5)
N1	0.01612 (18)	0.24187 (11)	0.44138 (6)	0.0408 (3)
N2	0.00539 (19)	0.13309 (10)	0.45248 (6)	0.0446 (3)
H2A	0.0812	0.1026	0.4785	0.053*
N3	−0.2322 (3)	0.12126 (15)	0.37973 (8)	0.0628 (5)
N4	0.3108 (2)	0.22112 (12)	0.70208 (7)	0.0528 (4)
N5	0.1754 (2)	0.15785 (13)	0.67639 (7)	0.0560 (4)
H5A	0.1739	0.1361	0.6408	0.067*
N6	0.0482 (3)	0.17095 (18)	0.76207 (9)	0.0713 (5)
O1	0.27699 (16)	0.47111 (9)	0.48126 (6)	0.0489 (3)
O2	0.01418 (18)	0.46321 (10)	0.42578 (6)	0.0585 (4)
O3	−0.14134 (19)	−0.02689 (10)	0.43545 (6)	0.0583 (4)
O4	0.7144 (2)	0.33357 (12)	0.67710 (7)	0.0670 (4)
O5	0.5688 (2)	0.35432 (13)	0.75522 (6)	0.0767 (5)
O6	−0.0770 (2)	0.06677 (13)	0.68590 (7)	0.0725 (4)
C15	−0.3706 (4)	0.4190 (2)	0.32573 (11)	0.0836 (8)
H15A	−0.4259	0.3992	0.2869	0.100*
H15B	−0.3366	0.4961	0.3249	0.100*
C16	−0.4991 (4)	0.4054 (3)	0.36663 (16)	0.1227 (12)
H16A	−0.6073	0.4428	0.3520	0.184*
H16B	−0.4523	0.4361	0.4038	0.184*
H16C	−0.5229	0.3283	0.3712	0.184*
O7	−0.2166 (2)	0.35452 (12)	0.33981 (7)	0.0649 (4)
O1W	−0.2726 (4)	−0.13725 (18)	0.67387 (11)	0.1195 (8)
H1WA	−0.2003	−0.0837	0.6802	0.179*
H1WB	−0.3699	−0.1212	0.6866	0.179*
H3A	−0.212 (4)	0.188 (3)	0.3697 (13)	0.106 (10)*
H3B	−0.317 (3)	0.084 (2)	0.3617 (10)	0.073 (7)*
H6A	0.132 (4)	0.212 (2)	0.7761 (12)	0.095 (10)*
H6B	−0.046 (4)	0.158 (2)	0.7812 (11)	0.081 (8)*
H7	−0.156 (4)	0.376 (2)	0.3730 (13)	0.111 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (8)	0.0285 (7)	0.0444 (8)	−0.0087 (6)	−0.0032 (6)	0.0021 (6)
C2	0.0412 (9)	0.0310 (8)	0.0458 (9)	−0.0047 (6)	−0.0024 (7)	−0.0002 (6)
C3	0.0459 (9)	0.0318 (8)	0.0466 (9)	−0.0088 (7)	−0.0094 (7)	0.0010 (6)
C4	0.0473 (10)	0.0358 (8)	0.0623 (11)	−0.0004 (7)	−0.0120 (8)	0.0012 (8)
C5	0.0463 (10)	0.0410 (9)	0.0688 (12)	0.0020 (7)	0.0005 (9)	−0.0042 (8)
C6	0.0502 (10)	0.0364 (8)	0.0495 (9)	−0.0061 (7)	0.0019 (8)	−0.0041 (7)
C7	0.0408 (8)	0.0352 (8)	0.0385 (8)	−0.0059 (6)	0.0007 (7)	0.0027 (6)
C8	0.0417 (9)	0.0356 (8)	0.0455 (9)	−0.0049 (7)	0.0022 (7)	0.0032 (7)
C9	0.0573 (11)	0.0344 (9)	0.0817 (14)	−0.0099 (8)	0.0041 (10)	0.0042 (9)
C10	0.0529 (10)	0.0399 (9)	0.0402 (8)	−0.0106 (7)	−0.0078 (7)	0.0024 (7)
C11	0.0530 (10)	0.0392 (9)	0.0459 (9)	−0.0043 (8)	−0.0110 (8)	0.0042 (7)
C12	0.0653 (13)	0.0402 (9)	0.0524 (11)	−0.0038 (8)	−0.0231 (9)	0.0046 (8)
C13	0.0760 (16)	0.0672 (14)	0.1084 (19)	−0.0257 (12)	−0.0323 (14)	−0.0023 (14)
C14	0.0591 (12)	0.0493 (11)	0.0636 (12)	0.0003 (9)	−0.0030 (10)	0.0152 (9)
N1	0.0460 (8)	0.0343 (7)	0.0397 (7)	−0.0063 (6)	−0.0043 (6)	0.0042 (5)
N2	0.0496 (8)	0.0340 (7)	0.0452 (7)	−0.0086 (6)	−0.0131 (6)	0.0074 (6)
N3	0.0705 (11)	0.0482 (10)	0.0599 (10)	−0.0145 (8)	−0.0302 (8)	0.0064 (8)
N4	0.0620 (10)	0.0447 (8)	0.0470 (8)	−0.0047 (7)	−0.0112 (7)	0.0032 (6)
N5	0.0623 (10)	0.0561 (10)	0.0474 (8)	−0.0137 (8)	−0.0021 (7)	−0.0009 (7)
N6	0.0813 (15)	0.0677 (12)	0.0659 (12)	−0.0023 (11)	0.0131 (11)	0.0088 (10)
O1	0.0457 (7)	0.0326 (6)	0.0661 (8)	−0.0088 (5)	−0.0019 (6)	0.0034 (5)
O2	0.0556 (8)	0.0396 (7)	0.0740 (9)	−0.0047 (6)	−0.0157 (7)	0.0123 (6)
O3	0.0735 (9)	0.0405 (7)	0.0540 (7)	−0.0196 (6)	−0.0186 (6)	0.0065 (5)
O4	0.0638 (9)	0.0579 (8)	0.0729 (9)	−0.0211 (7)	−0.0159 (7)	−0.0047 (7)
O5	0.0873 (11)	0.0771 (10)	0.0574 (9)	−0.0112 (8)	−0.0233 (8)	−0.0126 (7)
O6	0.0637 (9)	0.0672 (9)	0.0839 (11)	−0.0132 (7)	−0.0017 (8)	0.0137 (8)
C15	0.0932 (19)	0.0754 (16)	0.0761 (15)	0.0252 (13)	−0.0131 (14)	0.0127 (12)
C16	0.095 (2)	0.151 (3)	0.125 (3)	0.047 (2)	0.026 (2)	0.030 (2)
O7	0.0647 (9)	0.0672 (9)	0.0588 (8)	0.0062 (7)	−0.0071 (7)	0.0032 (7)
O1W	0.154 (2)	0.1015 (16)	0.1034 (16)	−0.0471 (15)	0.0175 (16)	0.0006 (12)

Geometric parameters (Å, º) top

C1—C6	1.389 (2)	C12—O4	1.326 (3)
C1—C2	1.392 (2)	C13—O4	1.454 (2)
C1—C7	1.484 (2)	C13—H13A	0.9600
C2—C3	1.392 (2)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.385 (3)	C14—O6	1.222 (2)
C3—C11	1.489 (2)	C14—N6	1.333 (3)
C4—C5	1.385 (3)	C14—N5	1.387 (3)
C4—H4	0.9300	N1—N2	1.3476 (17)
C5—C6	1.385 (2)	N2—H2A	0.8600
C5—H5	0.9300	N3—H3A	0.86 (3)
C6—H6	0.9300	N3—H3B	0.85 (3)
C7—N1	1.290 (2)	N4—N5	1.356 (2)
C7—C8	1.498 (2)	N5—H5A	0.8600
C8—O2	1.206 (2)	N6—H6A	0.84 (3)
C8—O1	1.3224 (19)	N6—H6B	0.90 (3)
C9—O1	1.453 (2)	C15—O7	1.408 (3)
C9—H9A	0.9600	C15—C16	1.448 (4)
C9—H9B	0.9600	C15—H15A	0.9700
C9—H9C	0.9600	C15—H15B	0.9700
C10—O3	1.234 (2)	C16—H16A	0.9600
C10—N3	1.325 (2)	C16—H16B	0.9600
C10—N2	1.377 (2)	C16—H16C	0.9600
C11—N4	1.283 (2)	O7—H7	0.88 (3)
C11—C12	1.499 (2)	O1W—H1WA	0.8501
C12—O5	1.209 (2)	O1W—H1WB	0.8495

C6—C1—C2	119.41 (15)	O4—C13—H13A	109.5
C6—C1—C7	120.66 (15)	O4—C13—H13B	109.5
C2—C1—C7	119.90 (15)	H13A—C13—H13B	109.5
C1—C2—C3	120.53 (16)	O4—C13—H13C	109.5
C1—C2—H2	119.7	H13A—C13—H13C	109.5
C3—C2—H2	119.7	H13B—C13—H13C	109.5
C4—C3—C2	119.55 (16)	O6—C14—N6	125.3 (2)
C4—C3—C11	122.79 (15)	O6—C14—N5	118.5 (2)
C2—C3—C11	117.63 (16)	N6—C14—N5	116.2 (2)
C3—C4—C5	120.03 (16)	C7—N1—N2	118.53 (13)
C3—C4—H4	120.0	N1—N2—C10	119.73 (13)
C5—C4—H4	120.0	N1—N2—H2A	120.1
C6—C5—C4	120.47 (18)	C10—N2—H2A	120.1
C6—C5—H5	119.8	C10—N3—H3A	121 (2)
C4—C5—H5	119.8	C10—N3—H3B	117.5 (16)
C5—C6—C1	119.98 (17)	H3A—N3—H3B	121 (2)
C5—C6—H6	120.0	C11—N4—N5	119.39 (15)
C1—C6—H6	120.0	N4—N5—C14	119.03 (16)
N1—C7—C1	125.35 (14)	N4—N5—H5A	120.5
N1—C7—C8	113.16 (14)	C14—N5—H5A	120.5
C1—C7—C8	121.49 (13)	C14—N6—H6A	122 (2)
O2—C8—O1	123.61 (15)	C14—N6—H6B	115.9 (16)
O2—C8—C7	125.05 (15)	H6A—N6—H6B	122 (3)
O1—C8—C7	111.33 (14)	C8—O1—C9	116.52 (14)
O1—C9—H9A	109.5	C12—O4—C13	116.15 (18)
O1—C9—H9B	109.5	O7—C15—C16	113.2 (2)
H9A—C9—H9B	109.5	O7—C15—H15A	108.9
O1—C9—H9C	109.5	C16—C15—H15A	108.9
H9A—C9—H9C	109.5	O7—C15—H15B	108.9
H9B—C9—H9C	109.5	C16—C15—H15B	108.9
O3—C10—N3	124.35 (16)	H15A—C15—H15B	107.8
O3—C10—N2	118.54 (15)	C15—C16—H16A	109.5
N3—C10—N2	117.12 (15)	C15—C16—H16B	109.5
N4—C11—C3	124.74 (15)	H16A—C16—H16B	109.5
N4—C11—C12	113.41 (16)	C15—C16—H16C	109.5
C3—C11—C12	121.77 (17)	H16A—C16—H16C	109.5
O5—C12—O4	124.16 (18)	H16B—C16—H16C	109.5
O5—C12—C11	124.6 (2)	C15—O7—H7	111 (2)
O4—C12—C11	111.25 (17)	H1WA—O1W—H1WB	109.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O6	0.85	2.05	2.879 (3)	166
O1W—H1WB···O5ⁱ	0.85	2.16	2.941 (3)	152
N3—H3A···O7	0.86 (4)	2.13 (4)	2.980 (2)	169 (3)
N3—H3B···O5ⁱⁱ	0.85 (3)	2.61 (2)	3.082 (2)	116.7 (18)
N5—H5A···O3ⁱⁱⁱ	0.86	2.19	3.010 (2)	160
N6—H6A···O1W^iv	0.84 (3)	2.34 (3)	3.137 (3)	158 (3)
N6—H6B···O7^v	0.90 (3)	1.99 (3)	2.871 (3)	166 (2)
O7—H7···O2	0.88 (3)	1.96 (3)	2.801 (2)	158 (3)
O7—H7···N1	0.88 (3)	2.52 (3)	3.0677 (19)	121 (2)
C4—H4···O6^vi	0.93	2.57	3.493 (2)	173
C13—H13C···N6^vii	0.96	2.62	3.405 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₆O₆·C₂H₆O·H₂O
M_r	428.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.5810 (2), 12.1216 (3), 23.0379 (7)
β (°)	97.254 (3)
V (Å³)	2100.11 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.41 × 0.32 × 0.26

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (ABSPACK in CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.700, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15863, 4317, 2927
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 0.98
No. of reflections	4317
No. of parameters	298
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O6	0.85	2.05	2.879 (3)	166
O1W—H1WB···O5ⁱ	0.85	2.16	2.941 (3)	152
N3—H3A···O7	0.86 (4)	2.13 (4)	2.980 (2)	169 (3)
N3—H3B···O5ⁱⁱ	0.85 (3)	2.61 (2)	3.082 (2)	116.7 (18)
N5—H5A···O3ⁱⁱⁱ	0.86	2.19	3.010 (2)	160
N6—H6A···O1W^iv	0.84 (3)	2.34 (3)	3.137 (3)	158 (3)
N6—H6B···O7^v	0.90 (3)	1.99 (3)	2.871 (3)	166 (2)
O7—H7···O2	0.88 (3)	1.96 (3)	2.801 (2)	158 (3)
O7—H7···N1	0.88 (3)	2.52 (3)	3.0677 (19)	121 (2)
C4—H4···O6^vi	0.93	2.57	3.493 (2)	173
C13—H13C···N6^vii	0.96	2.62	3.405 (3)	139

Acknowledgements

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (No. FA—F3–T-141)

References

Ismatov, D. N., Azizov, U. M., Leonteva, L. I., Zakirov, A. U. & Yuldashev, S. Z. (2001). Pharm. Chem. J. 35, 418–420. CrossRef CAS Google Scholar
Ismatov, D. N., Azizov, U. M., Nurullaeva, M. K. & Iskandarov, S. I. (1991). Pharm. Chem. J., 25, 498–502. CrossRef Google Scholar
Ismatov, D. N., Leonteva, L. I., Azizov, U. M., Karshiev, D. N. & Zakirov, U. B. (1998). Pharm. Chem. J., 32, 593–594. CrossRef Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o464

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Methyl 2-[(carbamoyl­amino)­imino]-2-(3-{1-[(carbamoyl­amino)­imino]-2-meth­­oxy-2-oxoeth­yl}phen­yl)acetate ethanol monosolvate monohydrate

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Experimental

Crystal data

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organic compounds

Methyl 2-[(carbamoylamino)imino]-2-(3-{1-[(carbamoylamino)imino]-2-methoxy-2-oxoethyl}phenyl)acetate ethanol monosolvate monohydrate