Crystal structure of diethyl [(4-nitro­phenyl­amino)(2-hy­droxy­phen­yl)meth­yl]phospho­nate methanol monosolvate

Wang, Q.M.; Su, F.; Yang, T.T.; Lu, L.P.; Zhu, M.L.

doi:10.1107/S1600536814018649

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1053-o1054

doi:10.1107/S1600536814018649

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Crystal structure of diethyl [(4-nitrophenylamino)(2-hydroxyphenyl)methyl]phosphonate methanol monosolvate

QingMing Wang,^a Feng Su,^b TingTing Yang,^a LiPing Lu ^b and MiaoLi Zhu ^b ^*

^aSchool of Pharmacy, Yancheng Teachers' University, Yancheng, Jiangsu 224051, People's Republic of China, and ^bInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: miaoli@sxu.edu.cn

Edited by S. Parkin, University of Kentucky, USA (Received 9 July 2014; accepted 17 August 2014; online 30 August 2014)

In the title compound, C₁₇H₂₁N₂O₆P·CH₃OH, the planes of the 4-nitroaniline and 2-hydroxyphenyl groups form a dihedral angle of 84.04 (8)°. The P atom exhibits tetrahedral geometry involving two O-ethyl groups, a Cα atom and a double-bonded O atom. In the crystal, O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds link the α-aminophosphonic acid and methanol molecules into chains that propagate parallel to the a axis.

Keywords: crystal structure; α-aminophosphonic acids; phosphonate salts; hydrogen bonding.

CCDC reference: 1019639

1. Related literature

For background to the synthesis and properties of α-aminophosphonic acids, see: Allen et al. (1978 ); Arizpe et al. (2011 ); Cherkasov & Galkin (1998 ); Sieńczyk & Oleksyszyn (2009 ). For structures of related compounds, see: Li et al. (2008 ); Wang et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₇H₂₁N₂O₆P·CH₄O
M_r = 412.37
Triclinic, $[P \overline 1]$
a = 9.401 (6) Å
b = 10.061 (6) Å
c = 11.963 (7) Å
α = 101.328 (10)°
β = 94.183 (10)°
γ = 104.549 (9)°
V = 1065.0 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 296 K
0.40 × 0.34 × 0.30 mm

2.2. Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.935, T_max = 0.951
14569 measured reflections
5230 independent reflections
2934 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.138
S = 1.01
5230 reflections
262 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4ⁱ	0.82	2.00	2.819 (3)	172
O1—H1⋯O7	0.82	1.95	2.757 (3)	170
C10—H10⋯O5ⁱⁱ	0.93	2.53	3.308 (4)	141
N1—H1A⋯O4ⁱⁱⁱ	0.82 (2)	2.14 (2)	2.959 (3)	171 (2)
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z-1; (iii) -x, -y+1, -z.

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/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1019639

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018649/pk2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018649/pk2529Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018649/pk2529Isup3.cml

checkCIF report

Introduction top

As mimics of natural amino acids, α-aminophosphonic acids and related derivatives are currently attracting a great deal of interest in medicinal chemistry due to their important biological effects (Arizpe, et al., 2011). They have been reported to possess a wide range of biological functions. These include antibacterial activities (Allen et al., 1978), action as inhibitors of enzymes such as rennin, HIV proteases, serine proteases and so on (Sieńczyk, et al., 2009).

Experimental top

Synthesis and crystallization top

The synthesis of o-cresol α-aminophosphonate N-derivatives with rigid structures was achieved through the Pudovik reaction reaction (Cherkasov et al., 1998). We obtained the title compound following our earlier report (Wang et al., 2012). The synthesis involved two steps: a) the Schiff bases were first prepared in a condensation of 4-nitroaniline and salicylaldehyde in methanol solvent by refluxing equimolar amounts of reagents; b ) reaction of Schiff base with a diethyl phosphonate in methanol solvent under reflux. The title compound was obtained from the filtrate after three days.

Refinement top

The amine H atom was located in a difference Fourier map and refined freely. All other H atoms were placed in geometrically idealized positions and refined as riding, with C–H = 0.93-0.98 Å, O–H = 0.82 Å, and the Uiso(H) = 1.2Ueq (C) for benzene ring, C7, C14, C16 and Uiso(H) = 1.5Ueq (O, C) for O—H groups and C15, C17, C18.

Results and discussion top

The crystal structure of the title compound is triclinic, with space group P1. As seen from Fig. 1, the P atom has tetrahedral geometry involving two O-ethyl groups (O2, O3), one Cα atom (C7), and a double bond O atom (O4), which is the same as our earlier reports (Li et al., 2008; Wang et al., 2012). The C—P and P═O bond lengths are comparable to those in similar structures (Li et al. 2008; Wang et al., 2012). Several hydrogen bonding interactions [O7—H7A···O4ⁱ (i = x+1,y,z), O1—H1···O7, C10—H10···O5ⁱⁱ (ii=-x, -y, -z-1), N1—H1A···O4ⁱⁱⁱ (iii=-x, -y+1, -z)] exist within in the crystal structure. The dihedral angle formed by the planes of the 4-nitroaniline and 2-hydroxyphenyl groups is 84.08 (8)°.

Related literature top

For background to the synthesis and properties of α-aminophosphonic acids, see: Allen et al. (1978); Arizpe et al. (2011); Cherkasov & Galkin (1998); Sieńczyk & Oleksyszyn (2009). For structures of related compounds, see: Li et al. (2008); Wang et al. (2012).

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/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound, drawn so as to highlight the hydrogen-bonding interactions between molecules.

Diethyl [(4-nitrophenylamino)(2-hydroxyphenyl)methyl]phosphonate methanol monosolvate top

Crystal data top

C₁₇H₂₁N₂O₆P·CH₄O	Z = 2
M_r = 412.37	F(000) = 436
Triclinic, P1	D_x = 1.286 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.401 (6) Å	Cell parameters from 1930 reflections
b = 10.061 (6) Å	θ = 1.8–28.3°
c = 11.963 (7) Å	µ = 0.17 mm⁻¹
α = 101.328 (10)°	T = 296 K
β = 94.183 (10)°	Block, yellow
γ = 104.549 (9)°	0.4 × 0.34 × 0.3 mm
V = 1065.0 (12) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5230 independent reflections
Radiation source: fine-focus sealed tube	2934 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 28.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→12
T_min = 0.935, T_max = 0.951	k = −13→13
14569 measured reflections	l = −15→15

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0575P)² + 0.0659P] where P = (F_o² + 2F_c²)/3
5230 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₂₁N₂O₆P·CH₄O	γ = 104.549 (9)°
M_r = 412.37	V = 1065.0 (12) Å³
Triclinic, P1	Z = 2
a = 9.401 (6) Å	Mo Kα radiation
b = 10.061 (6) Å	µ = 0.17 mm⁻¹
c = 11.963 (7) Å	T = 296 K
α = 101.328 (10)°	0.4 × 0.34 × 0.3 mm
β = 94.183 (10)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5230 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2934 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.951	R_int = 0.051
14569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.31 e Å⁻³
5230 reflections	Δρ_min = −0.27 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
C1	0.4255 (3)	0.3224 (2)	0.17400 (19)	0.0408 (5)
C2	0.4364 (3)	0.2362 (3)	0.2493 (2)	0.0538 (7)
H2	0.5292	0.2347	0.2808	0.065*
C3	0.3111 (4)	0.1532 (3)	0.2778 (2)	0.0655 (8)
H3	0.3192	0.0962	0.3291	0.079*
C4	0.1720 (4)	0.1538 (3)	0.2302 (3)	0.0692 (8)
H4	0.0868	0.0979	0.2497	0.083*
C5	0.1618 (3)	0.2385 (3)	0.1535 (2)	0.0538 (7)
H5	0.0688	0.2379	0.1207	0.065*
C6	0.2871 (3)	0.3241 (2)	0.12431 (18)	0.0378 (5)
C7	0.2760 (2)	0.4232 (2)	0.04485 (17)	0.0348 (5)
H7	0.3749	0.4597	0.0239	0.042*
C8	0.2056 (2)	0.2631 (2)	−0.14895 (19)	0.0372 (5)
C9	0.1083 (3)	0.2150 (2)	−0.2517 (2)	0.0467 (6)
H9	0.0257	0.2492	−0.2595	0.056*
C10	0.1327 (3)	0.1185 (3)	−0.3410 (2)	0.0526 (7)
H10	0.0681	0.0884	−0.4092	0.063*
C11	0.2548 (3)	0.0660 (2)	−0.3287 (2)	0.0449 (6)
C12	0.3527 (3)	0.1124 (3)	−0.2294 (2)	0.0472 (6)
H12	0.4347	0.0772	−0.2227	0.057*
C13	0.3303 (3)	0.2105 (2)	−0.1397 (2)	0.0428 (6)
H13	0.3976	0.2422	−0.0729	0.051*
C14	0.3182 (4)	0.6256 (4)	0.3468 (2)	0.0941 (12)
H14A	0.2782	0.7004	0.3841	0.113*
H14B	0.2476	0.5363	0.3455	0.113*
C15	0.4561 (4)	0.6334 (4)	0.4116 (3)	0.0989 (12)
H15A	0.5020	0.5674	0.3700	0.148*
H15B	0.4377	0.6111	0.4846	0.148*
H15C	0.5206	0.7269	0.4237	0.148*
C16	0.2262 (3)	0.8152 (3)	0.0724 (2)	0.0600 (7)
H16A	0.2731	0.8615	0.1500	0.072*
H16B	0.1208	0.8069	0.0696	0.072*
C17	0.2894 (4)	0.8987 (3)	−0.0089 (3)	0.0853 (10)
H17A	0.3945	0.9110	−0.0026	0.128*
H17B	0.2697	0.9891	0.0087	0.128*
H17C	0.2453	0.8505	−0.0858	0.128*
C18	0.8676 (5)	0.4263 (6)	0.3596 (3)	0.154 (2)
H18A	0.9379	0.3743	0.3716	0.232*
H18B	0.7854	0.3987	0.4010	0.232*
H18C	0.9143	0.5253	0.3868	0.232*
N1	0.1748 (2)	0.3567 (2)	−0.06050 (16)	0.0415 (5)
N2	0.2802 (3)	−0.0373 (3)	−0.4225 (2)	0.0650 (7)
O1	0.54719 (18)	0.4078 (2)	0.14493 (15)	0.0566 (5)
H1	0.6220	0.4018	0.1811	0.085*
O2	0.33759 (18)	0.63846 (17)	0.22920 (13)	0.0518 (4)
O3	0.25022 (19)	0.67641 (16)	0.04156 (14)	0.0525 (5)
O4	0.06458 (17)	0.53339 (17)	0.14848 (13)	0.0478 (4)
O5	0.1927 (3)	−0.0771 (3)	−0.51111 (19)	0.1029 (9)
O6	0.3885 (3)	−0.0818 (2)	−0.41134 (17)	0.0919 (8)
O7	0.8177 (2)	0.3987 (3)	0.24407 (17)	0.0785 (6)
H7A	0.8843	0.4359	0.2104	0.118*
P1	0.21847 (7)	0.57045 (6)	0.12230 (5)	0.03809 (18)
H1A	0.107 (3)	0.391 (2)	−0.077 (2)	0.045 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0458 (14)	0.0433 (14)	0.0362 (12)	0.0202 (11)	0.0041 (11)	0.0060 (11)
C2	0.0633 (18)	0.0542 (16)	0.0482 (15)	0.0253 (14)	−0.0009 (13)	0.0122 (13)
C3	0.092 (2)	0.0552 (18)	0.0595 (18)	0.0284 (17)	0.0110 (17)	0.0260 (14)
C4	0.073 (2)	0.0569 (18)	0.081 (2)	0.0077 (16)	0.0271 (17)	0.0307 (16)
C5	0.0478 (16)	0.0494 (16)	0.0677 (18)	0.0133 (12)	0.0112 (13)	0.0202 (14)
C6	0.0427 (13)	0.0345 (12)	0.0383 (12)	0.0170 (10)	0.0074 (10)	0.0043 (10)
C7	0.0304 (12)	0.0384 (12)	0.0371 (12)	0.0127 (10)	0.0051 (10)	0.0069 (10)
C8	0.0386 (13)	0.0356 (12)	0.0384 (12)	0.0127 (10)	0.0057 (10)	0.0070 (10)
C9	0.0420 (14)	0.0532 (15)	0.0473 (14)	0.0244 (12)	−0.0002 (11)	0.0041 (12)
C10	0.0521 (16)	0.0589 (16)	0.0433 (14)	0.0201 (13)	−0.0072 (12)	0.0010 (12)
C11	0.0521 (15)	0.0439 (14)	0.0401 (13)	0.0229 (12)	0.0043 (11)	0.0008 (11)
C12	0.0491 (15)	0.0530 (15)	0.0478 (15)	0.0301 (12)	0.0070 (12)	0.0093 (12)
C13	0.0401 (13)	0.0476 (14)	0.0421 (13)	0.0196 (11)	0.0015 (11)	0.0047 (11)
C14	0.077 (2)	0.154 (4)	0.0440 (17)	0.040 (2)	0.0036 (17)	−0.005 (2)
C15	0.131 (3)	0.117 (3)	0.0546 (19)	0.058 (3)	−0.007 (2)	0.008 (2)
C16	0.0649 (18)	0.0428 (15)	0.0774 (19)	0.0221 (14)	0.0101 (15)	0.0153 (14)
C17	0.102 (3)	0.0560 (19)	0.106 (3)	0.0203 (18)	0.030 (2)	0.0333 (19)
C18	0.090 (3)	0.273 (6)	0.081 (3)	−0.008 (3)	−0.006 (2)	0.074 (4)
N1	0.0372 (11)	0.0475 (12)	0.0416 (11)	0.0229 (10)	−0.0020 (9)	0.0017 (9)
N2	0.0834 (18)	0.0676 (16)	0.0481 (14)	0.0422 (14)	−0.0002 (13)	−0.0021 (12)
O1	0.0382 (10)	0.0749 (13)	0.0640 (12)	0.0186 (9)	0.0022 (9)	0.0298 (10)
O2	0.0484 (10)	0.0560 (11)	0.0440 (10)	0.0116 (8)	−0.0047 (8)	0.0020 (8)
O3	0.0708 (12)	0.0400 (9)	0.0556 (11)	0.0256 (9)	0.0171 (9)	0.0143 (8)
O4	0.0395 (9)	0.0560 (10)	0.0531 (10)	0.0234 (8)	0.0092 (8)	0.0094 (8)
O5	0.1169 (19)	0.120 (2)	0.0634 (14)	0.0713 (16)	−0.0256 (14)	−0.0358 (13)
O6	0.1136 (18)	0.1124 (18)	0.0664 (14)	0.0860 (16)	−0.0014 (13)	−0.0079 (12)
O7	0.0485 (12)	0.1205 (19)	0.0717 (14)	0.0160 (12)	0.0039 (10)	0.0441 (13)
P1	0.0382 (3)	0.0382 (3)	0.0402 (3)	0.0168 (3)	0.0047 (3)	0.0059 (3)

Geometric parameters (Å, º) top

C1—O1	1.360 (3)	C14—C15	1.438 (4)
C1—C2	1.382 (3)	C14—O2	1.458 (3)
C1—C6	1.396 (3)	C14—H14A	0.9700
C2—C3	1.370 (4)	C14—H14B	0.9700
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.390 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.383 (4)	C16—O3	1.451 (3)
C4—H4	0.9300	C16—C17	1.469 (4)
C5—C6	1.386 (3)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.522 (3)	C17—H17A	0.9600
C7—N1	1.454 (3)	C17—H17B	0.9600
C7—P1	1.812 (2)	C17—H17C	0.9600
C7—H7	0.9800	C18—O7	1.377 (4)
C8—N1	1.371 (3)	C18—H18A	0.9600
C8—C9	1.401 (3)	C18—H18B	0.9600
C8—C13	1.407 (3)	C18—H18C	0.9600
C9—C10	1.371 (3)	N1—H1A	0.82 (2)
C9—H9	0.9300	N2—O6	1.219 (3)
C10—C11	1.389 (3)	N2—O5	1.225 (3)
C10—H10	0.9300	O1—H1	0.8200
C11—C12	1.372 (3)	O2—P1	1.5557 (18)
C11—N2	1.450 (3)	O3—P1	1.5638 (18)
C12—C13	1.376 (3)	O4—P1	1.4734 (18)
C12—H12	0.9300	O7—H7A	0.8200
C13—H13	0.9300

O1—C1—C2	122.1 (2)	O2—C14—H14A	109.3
O1—C1—C6	117.4 (2)	C15—C14—H14B	109.3
C2—C1—C6	120.6 (2)	O2—C14—H14B	109.3
C3—C2—C1	120.4 (3)	H14A—C14—H14B	108.0
C3—C2—H2	119.8	C14—C15—H15A	109.5
C1—C2—H2	119.8	C14—C15—H15B	109.5
C2—C3—C4	120.2 (3)	H15A—C15—H15B	109.5
C2—C3—H3	119.9	C14—C15—H15C	109.5
C4—C3—H3	119.9	H15A—C15—H15C	109.5
C5—C4—C3	119.2 (3)	H15B—C15—H15C	109.5
C5—C4—H4	120.4	O3—C16—C17	109.0 (2)
C3—C4—H4	120.4	O3—C16—H16A	109.9
C4—C5—C6	121.5 (3)	C17—C16—H16A	109.9
C4—C5—H5	119.3	O3—C16—H16B	109.9
C6—C5—H5	119.3	C17—C16—H16B	109.9
C5—C6—C1	118.2 (2)	H16A—C16—H16B	108.3
C5—C6—C7	121.6 (2)	C16—C17—H17A	109.5
C1—C6—C7	120.2 (2)	C16—C17—H17B	109.5
N1—C7—C6	113.91 (19)	H17A—C17—H17B	109.5
N1—C7—P1	109.45 (15)	C16—C17—H17C	109.5
C6—C7—P1	108.85 (14)	H17A—C17—H17C	109.5
N1—C7—H7	108.2	H17B—C17—H17C	109.5
C6—C7—H7	108.2	O7—C18—H18A	109.5
P1—C7—H7	108.2	O7—C18—H18B	109.5
N1—C8—C9	119.2 (2)	H18A—C18—H18B	109.5
N1—C8—C13	122.4 (2)	O7—C18—H18C	109.5
C9—C8—C13	118.4 (2)	H18A—C18—H18C	109.5
C10—C9—C8	121.1 (2)	H18B—C18—H18C	109.5
C10—C9—H9	119.5	C8—N1—C7	123.21 (19)
C8—C9—H9	119.5	C8—N1—H1A	115.2 (17)
C9—C10—C11	119.4 (2)	C7—N1—H1A	119.4 (17)
C9—C10—H10	120.3	O6—N2—O5	121.8 (2)
C11—C10—H10	120.3	O6—N2—C11	119.1 (2)
C12—C11—C10	120.7 (2)	O5—N2—C11	119.1 (2)
C12—C11—N2	119.7 (2)	C1—O1—H1	109.5
C10—C11—N2	119.6 (2)	C14—O2—P1	125.58 (18)
C11—C12—C13	120.4 (2)	C16—O3—P1	121.48 (16)
C11—C12—H12	119.8	C18—O7—H7A	109.5
C13—C12—H12	119.8	O4—P1—O2	114.76 (10)
C12—C13—C8	120.0 (2)	O4—P1—O3	114.66 (10)
C12—C13—H13	120.0	O2—P1—O3	104.51 (10)
C8—C13—H13	120.0	O4—P1—C7	114.21 (10)
C15—C14—O2	111.4 (3)	O2—P1—C7	105.37 (10)
C15—C14—H14A	109.3	O3—P1—C7	101.94 (10)

O1—C1—C2—C3	179.0 (2)	C9—C8—C13—C12	−1.3 (3)
C6—C1—C2—C3	−1.2 (4)	C9—C8—N1—C7	−173.7 (2)
C1—C2—C3—C4	0.7 (4)	C13—C8—N1—C7	7.8 (3)
C2—C3—C4—C5	0.4 (4)	C6—C7—N1—C8	−72.5 (3)
C3—C4—C5—C6	−0.9 (4)	P1—C7—N1—C8	165.39 (18)
C4—C5—C6—C1	0.4 (4)	C12—C11—N2—O6	0.2 (4)
C4—C5—C6—C7	−176.7 (2)	C10—C11—N2—O6	179.3 (3)
O1—C1—C6—C5	−179.6 (2)	C12—C11—N2—O5	−179.4 (3)
C2—C1—C6—C5	0.6 (3)	C10—C11—N2—O5	−0.3 (4)
O1—C1—C6—C7	−2.4 (3)	C15—C14—O2—P1	150.2 (2)
C2—C1—C6—C7	177.8 (2)	C17—C16—O3—P1	170.2 (2)
C5—C6—C7—N1	−49.0 (3)	C14—O2—P1—O4	21.6 (3)
C1—C6—C7—N1	133.9 (2)	C14—O2—P1—O3	148.0 (2)
C5—C6—C7—P1	73.4 (2)	C14—O2—P1—C7	−104.9 (2)
C1—C6—C7—P1	−103.7 (2)	C16—O3—P1—O4	58.8 (2)
N1—C8—C9—C10	−178.1 (2)	C16—O3—P1—O2	−67.7 (2)
C13—C8—C9—C10	0.5 (4)	C16—O3—P1—C7	−177.30 (19)
C8—C9—C10—C11	0.9 (4)	N1—C7—P1—O4	56.04 (18)
C9—C10—C11—C12	−1.6 (4)	C6—C7—P1—O4	−69.04 (17)
C9—C10—C11—N2	179.3 (2)	N1—C7—P1—O2	−177.09 (14)
C10—C11—C12—C13	0.8 (4)	C6—C7—P1—O2	57.82 (17)
N2—C11—C12—C13	179.9 (2)	N1—C7—P1—O3	−68.20 (17)
C11—C12—C13—C8	0.6 (4)	C6—C7—P1—O3	166.71 (15)
N1—C8—C13—C12	177.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.82	2.00	2.819 (3)	172
O1—H1···O7	0.82	1.95	2.757 (3)	170
C10—H10···O5ⁱⁱ	0.93	2.53	3.308 (4)	141
N1—H1A···O4ⁱⁱⁱ	0.82 (2)	2.14 (2)	2.959 (3)	171 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.82	2.00	2.819 (3)	172.2
O1—H1···O7	0.82	1.95	2.757 (3)	169.5
C10—H10···O5ⁱⁱ	0.93	2.53	3.308 (4)	141.2
N1—H1A···O4ⁱⁱⁱ	0.82 (2)	2.14 (2)	2.959 (3)	171 (2)

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation for Young Scientists of China (grant No. 21301150), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (grant No. 13KJB150037), the Foundation of Jiangsu Provincial Key Laboratory of Solonchak (grant No. JKLBS2012022), the Doctor and Professor Foundation of Yancheng Teachers' University (grant No. 12YSYJB0117) and the Practice Innovation Training Program Projects for the Jiangsu College Students (grant Nos. 201310324034Y and 201410324038Y).

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Volume 70| Part 9| September 2014| Pages o1053-o1054

doi:10.1107/S1600536814018649

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

Crystal structure of di­ethyl [(4-nitro­phenyl­amino)(2-hy­dr­oxy­phen­yl)meth­yl]phospho­nate methanol monosolvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of diethyl [(4-nitrophenylamino)(2-hydroxyphenyl)methyl]phosphonate methanol monosolvate