(S)-Methyl 3-(3,4-dimeth­oxy­phen­yl)-2-[2-(diphenyl­phosphan­yl)benzamido]­propano­ate

Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811047179

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3285

https://doi.org/10.1107/S1600536811047179

Open

access

(S)-Methyl 3-(3,4-dimethoxyphenyl)-2-[2-(diphenylphosphanyl)benzamido]propanoate

Tricia Naicker,^a Thavendran Govender,^a Hendrick G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, and ^bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 12 October 2011; accepted 8 November 2011; online 12 November 2011)

Molecules of the title compound, C₃₁H₃₀NO₅P, show a sttagered conformation about the C—C bond joining the dimethoxybenzene group to the chiral centre, with the dimethoxybenzene ring gauche to the amide group and anti to the ester group. In the crystal, weak intermolecular N—H⋯O and C—H⋯O hydrogen bonds form layers parallel to (110).

Related literature

For related structures, see: Clegg & Elsegood, (2003 ). For organocatalysts prepared from a related precursor, see: Naicker et al. (2010 , 2011 ). For analogous precusors to several biologically active compounds, see: Zalán et al. (2006 ).

Experimental

Crystal data

C₃₁H₃₀NO₅P
M_r = 527.53
Monoclinic, P 2₁
a = 10.2218 (3) Å
b = 8.4535 (2) Å
c = 15.7633 (4) Å
β = 100.300 (2)°
V = 1340.16 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 173 K
0.18 × 0.15 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer
6654 measured reflections
6654 independent reflections
5550 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.079
S = 1.04
6654 reflections
350 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 3108 Friedel pairs
Flack parameter: −0.08 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.816 (17)	2.345 (17)	3.1428 (17)	166 (15)
C10—H10A⋯O3ⁱ	0.98	2.56	3.371 (2)	140
C21—H21⋯O4ⁱⁱ	0.95	2.58	3.279 (2)	131
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811047179/lr2034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047179/lr2034Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047179/lr2034Isup3.cml

checkCIF report

Comment top

The title compound is being used as a precusor to novel chiral organocatalysts (Naicker et al. 2010 and 2011). Analogous structures are well known precusors to several biologically active compounds (Zalán et al., 2006).

There is an analogous X-ray crystal structure reported (Clegg and Elsegood, 2003), which has a tert-butoxy group at the ester carboxyl carbon and a (9-H-Fluoren-9-yl)-methoxy group attached to the amide carboxyl carbon. The title compound has a methoxy and a 2-diphenylphoshinobenzene group at the these positions respectively.

The title compound exists in a well ordered staggered conformation about the C7—C8 bond (Fig. 1). As in the analogous X-ray structure, the dimethoxybenzene ring is gauche to the amide group and anti to the ester group. The configuration at C8 was confirmed to be S, on the basis of anomalous scaterring effects, Flack x parameter = -0.08 (6).

The molecules in the crystal are connected by relatively weak hydrogen bond interactions (Fig. 2) in which the N1—H1···O2 and the C10—H10A···O3 interactions give chains along the b axis. These chains are interconnected via the C21—H21···O4 interaction giving a layered packing system.

Related literature top

For related structures, see: Clegg & Elsegood, (2003). For organocatalysts prepared from a related precursor, see: Naicker et al. (2010, 2011). For analogous precusors to several biologically active compounds, see: Zalán et al. (2006).

Experimental top

2-(diphenylphosphanyl)benzoic acid (1.3 g, 4.2 mmol) was dissolved was dissolved in DMF (15 ml) and THF (5 ml) followed by addition of HBTU (4.6 mmol), DIPEA (8.4 mmol) and (S)-methyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate (1.0 g, 4.2 mmol). The reaction mixture was then stirred at room temperature until no more starting material could be detected by TLC analysis. The reaction mixture was poured into 30 volumes of chilled water; the mixture was then extracted thrice with ethyl acetate (20 ml). The combined extracts were dried over anhydrous sodium sulfate and then concentrated to dryness affording the crude product. This crude product was purified by column chromatography (50:50 EtOAc/Hexane, R_f = 0.6) to afford the product 2.20 g (98%) as a white solid. M.p. = 420 K.

Recrystallization from ethyl acetate at room temperature afforded crystals suitable for X-ray analysis.

Structure description top

For related structures, see: Clegg & Elsegood, (2003). For organocatalysts prepared from a related precursor, see: Naicker et al. (2010, 2011). For analogous precusors to several biologically active compounds, see: Zalán et al. (2006).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. A view of packing of the the title compound along the a axis.

(S)-Methyl 3-(3,4-dimethoxyphenyl)-2-[2-(diphenylphosphanyl)benzamido]propanoate top

Crystal data top

C₃₁H₃₀NO₅P	F(000) = 556
M_r = 527.53	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁	Melting point: 420 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.2218 (3) Å	Cell parameters from 6654 reflections
b = 8.4535 (2) Å	θ = 2.6–28.3°
c = 15.7633 (4) Å	µ = 0.14 mm⁻¹
β = 100.300 (2)°	T = 173 K
V = 1340.16 (6) Å³	Needle, colourless
Z = 2	0.18 × 0.15 × 0.14 mm

Data collection top

Nonius KappaCCD diffractometer	5550 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 28.3°, θ_min = 2.6°
1.2° φ scans and ω scans	h = −13→13
6654 measured reflections	k = −11→11
6654 independent reflections	l = −21→20

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0449P)² + 0.0315P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
6654 reflections	Δρ_max = 0.17 e Å⁻³
350 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3108 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (6)

Crystal data top

C₃₁H₃₀NO₅P	V = 1340.16 (6) Å³
M_r = 527.53	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.2218 (3) Å	µ = 0.14 mm⁻¹
b = 8.4535 (2) Å	T = 173 K
c = 15.7633 (4) Å	0.18 × 0.15 × 0.14 mm
β = 100.300 (2)°

Data collection top

Nonius KappaCCD diffractometer	5550 reflections with I > 2σ(I)
6654 measured reflections	R_int = 0.000
6654 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.17 e Å⁻³
S = 1.04	Δρ_min = −0.25 e Å⁻³
6654 reflections	Absolute structure: Flack (1983), 3108 Friedel pairs
350 parameters	Absolute structure parameter: −0.08 (6)
1 restraint

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
P1	0.92652 (4)	0.26037 (5)	0.25790 (2)	0.02523 (9)
O1	0.48837 (10)	0.38280 (13)	−0.10867 (6)	0.0317 (2)
O2	0.32444 (10)	0.23354 (13)	−0.07247 (7)	0.0307 (2)
O3	0.74192 (10)	0.13486 (13)	0.08701 (8)	0.0350 (3)
O4	0.59931 (12)	0.12392 (14)	0.36882 (7)	0.0368 (3)
O5	0.60041 (13)	0.38582 (16)	0.45360 (7)	0.0418 (3)
N1	0.63147 (12)	0.36602 (16)	0.05671 (8)	0.0245 (3)
H1N	0.6418 (16)	0.461 (2)	0.0513 (10)	0.028 (5)*
C1	0.50466 (14)	0.2509 (2)	0.23296 (9)	0.0284 (3)
H1	0.5024	0.1538	0.2024	0.034*
C2	0.55163 (14)	0.2534 (2)	0.32072 (9)	0.0285 (3)
C3	0.55354 (16)	0.3961 (2)	0.36673 (10)	0.0315 (4)
C4	0.51056 (17)	0.5329 (2)	0.32311 (11)	0.0349 (4)
H4	0.5119	0.6301	0.3535	0.042*
C5	0.46479 (16)	0.52901 (19)	0.23368 (11)	0.0334 (4)
H5	0.4364	0.6242	0.2040	0.040*
C6	0.46036 (14)	0.38986 (19)	0.18847 (9)	0.0275 (3)
C7	0.40679 (15)	0.3851 (2)	0.09251 (9)	0.0295 (3)
H7A	0.3922	0.4949	0.0710	0.035*
H7B	0.3195	0.3310	0.0828	0.035*
C8	0.49880 (13)	0.30031 (16)	0.03990 (9)	0.0239 (3)
H8	0.5042	0.1861	0.0567	0.029*
C9	0.43998 (14)	0.31191 (17)	−0.05562 (9)	0.0243 (3)
C10	0.24347 (15)	0.2574 (2)	−0.15711 (10)	0.0361 (4)
H10A	0.2296	0.3709	−0.1677	0.054*
H10B	0.1573	0.2051	−0.1595	0.054*
H10C	0.2889	0.2123	−0.2012	0.054*
C11	0.74258 (13)	0.27876 (18)	0.07843 (8)	0.0227 (3)
C12	0.86721 (14)	0.37492 (18)	0.08839 (9)	0.0226 (3)
C13	0.88991 (15)	0.4619 (2)	0.01690 (9)	0.0288 (3)
H13	0.8264	0.4589	−0.0351	0.035*
C14	1.00365 (17)	0.5522 (2)	0.02102 (10)	0.0332 (4)
H14	1.0202	0.6074	−0.0285	0.040*
C15	1.09289 (15)	0.56158 (19)	0.09765 (11)	0.0318 (4)
H15	1.1694	0.6269	0.1016	0.038*
C16	1.07142 (14)	0.47595 (19)	0.16908 (10)	0.0281 (3)
H16	1.1339	0.4838	0.2213	0.034*
C17	0.96012 (13)	0.37840 (18)	0.16613 (9)	0.0235 (3)
C18	1.01378 (14)	0.37421 (19)	0.35058 (9)	0.0266 (3)
C19	0.93471 (16)	0.4673 (2)	0.39468 (10)	0.0344 (4)
H19	0.8411	0.4685	0.3760	0.041*
C20	0.99036 (18)	0.5573 (2)	0.46472 (11)	0.0420 (4)
H20	0.9349	0.6192	0.4940	0.050*
C21	1.12645 (18)	0.5579 (2)	0.49259 (11)	0.0390 (4)
H21	1.1648	0.6214	0.5403	0.047*
C22	1.20615 (16)	0.4658 (2)	0.45073 (10)	0.0361 (4)
H22	1.2997	0.4655	0.4700	0.043*
C23	1.15084 (15)	0.3736 (2)	0.38064 (10)	0.0321 (3)
H23	1.2067	0.3093	0.3528	0.039*
C24	1.04146 (15)	0.09383 (18)	0.25728 (9)	0.0263 (3)
C25	1.01978 (17)	−0.0371 (2)	0.30662 (10)	0.0346 (4)
H25	0.9461	−0.0375	0.3358	0.042*
C26	1.10386 (19)	−0.1664 (2)	0.31385 (12)	0.0435 (4)
H26	1.0882	−0.2541	0.3483	0.052*
C27	1.21046 (17)	−0.1684 (2)	0.27115 (11)	0.0395 (4)
H27	1.2688	−0.2568	0.2768	0.047*
C28	1.23209 (16)	−0.0417 (2)	0.22019 (11)	0.0351 (4)
H28	1.3042	−0.0439	0.1897	0.042*
C29	1.14867 (15)	0.0889 (2)	0.21343 (10)	0.0313 (4)
H29	1.1646	0.1760	0.1786	0.038*
C30	0.6152 (2)	−0.0166 (2)	0.32221 (12)	0.0446 (4)
H30A	0.5276	−0.0568	0.2954	0.067*
H30B	0.6613	−0.0964	0.3617	0.067*
H30C	0.6676	0.0066	0.2774	0.067*
C31	0.6213 (2)	0.5309 (2)	0.50066 (12)	0.0485 (5)
H31A	0.6819	0.5985	0.4751	0.073*
H31B	0.6603	0.5085	0.5609	0.073*
H31C	0.5360	0.5854	0.4982	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.02244 (17)	0.02806 (19)	0.02497 (18)	−0.00083 (17)	0.00365 (14)	0.00163 (17)
O1	0.0317 (6)	0.0349 (6)	0.0290 (5)	−0.0030 (5)	0.0067 (5)	0.0031 (5)
O2	0.0272 (5)	0.0309 (6)	0.0307 (5)	−0.0069 (5)	−0.0039 (4)	0.0041 (5)
O3	0.0266 (6)	0.0204 (6)	0.0570 (8)	0.0016 (5)	0.0046 (5)	0.0029 (5)
O4	0.0513 (7)	0.0302 (6)	0.0272 (6)	0.0053 (5)	0.0022 (5)	0.0015 (5)
O5	0.0531 (7)	0.0453 (7)	0.0255 (6)	0.0012 (6)	0.0026 (5)	−0.0058 (5)
N1	0.0206 (6)	0.0188 (7)	0.0326 (7)	−0.0002 (5)	0.0005 (5)	0.0012 (5)
C1	0.0275 (7)	0.0292 (8)	0.0285 (7)	−0.0016 (7)	0.0048 (6)	−0.0028 (7)
C2	0.0280 (7)	0.0297 (8)	0.0275 (7)	0.0004 (7)	0.0040 (6)	0.0050 (7)
C3	0.0304 (8)	0.0375 (9)	0.0266 (8)	−0.0006 (7)	0.0052 (7)	−0.0031 (7)
C4	0.0378 (9)	0.0319 (9)	0.0357 (9)	0.0024 (7)	0.0085 (7)	−0.0056 (7)
C5	0.0354 (9)	0.0298 (9)	0.0362 (9)	0.0037 (7)	0.0092 (7)	0.0025 (7)
C6	0.0213 (7)	0.0329 (8)	0.0285 (8)	0.0010 (6)	0.0051 (6)	0.0030 (7)
C7	0.0246 (7)	0.0343 (8)	0.0293 (8)	0.0039 (7)	0.0040 (6)	0.0050 (7)
C8	0.0204 (7)	0.0225 (8)	0.0279 (8)	−0.0023 (6)	0.0016 (6)	0.0029 (6)
C9	0.0234 (7)	0.0201 (7)	0.0290 (8)	0.0004 (6)	0.0038 (6)	−0.0008 (6)
C10	0.0340 (8)	0.0364 (8)	0.0324 (8)	−0.0055 (8)	−0.0090 (6)	0.0034 (8)
C11	0.0243 (7)	0.0253 (8)	0.0186 (6)	−0.0001 (6)	0.0038 (5)	−0.0019 (6)
C12	0.0203 (7)	0.0222 (7)	0.0251 (7)	0.0025 (6)	0.0037 (6)	−0.0029 (6)
C13	0.0289 (8)	0.0311 (8)	0.0258 (8)	−0.0007 (7)	0.0031 (6)	0.0029 (7)
C14	0.0317 (8)	0.0358 (9)	0.0334 (9)	−0.0033 (7)	0.0089 (7)	0.0071 (7)
C15	0.0233 (7)	0.0306 (9)	0.0413 (9)	−0.0051 (7)	0.0048 (7)	0.0054 (7)
C16	0.0233 (7)	0.0296 (8)	0.0297 (8)	−0.0016 (7)	0.0002 (6)	0.0010 (7)
C17	0.0207 (7)	0.0221 (7)	0.0275 (7)	0.0033 (6)	0.0036 (6)	0.0000 (6)
C18	0.0280 (8)	0.0285 (8)	0.0232 (7)	0.0004 (7)	0.0045 (6)	0.0028 (6)
C19	0.0305 (8)	0.0414 (9)	0.0318 (9)	0.0010 (8)	0.0068 (7)	−0.0020 (8)
C20	0.0456 (10)	0.0476 (11)	0.0342 (9)	0.0021 (9)	0.0111 (8)	−0.0087 (8)
C21	0.0453 (10)	0.0445 (10)	0.0257 (8)	−0.0064 (9)	0.0022 (7)	−0.0053 (8)
C22	0.0325 (8)	0.0438 (10)	0.0296 (8)	−0.0029 (8)	−0.0014 (7)	0.0015 (8)
C23	0.0283 (8)	0.0382 (9)	0.0291 (8)	0.0029 (7)	0.0031 (6)	0.0028 (7)
C24	0.0273 (8)	0.0278 (8)	0.0220 (7)	−0.0023 (6)	−0.0003 (6)	−0.0017 (6)
C25	0.0392 (9)	0.0328 (9)	0.0320 (8)	−0.0003 (8)	0.0069 (7)	0.0050 (7)
C26	0.0565 (11)	0.0281 (9)	0.0454 (10)	0.0043 (8)	0.0079 (9)	0.0089 (8)
C27	0.0393 (9)	0.0325 (9)	0.0437 (10)	0.0092 (8)	−0.0012 (8)	−0.0057 (8)
C28	0.0294 (8)	0.0384 (9)	0.0372 (9)	0.0030 (8)	0.0049 (7)	−0.0069 (8)
C29	0.0317 (8)	0.0323 (9)	0.0302 (8)	0.0002 (7)	0.0063 (7)	0.0030 (7)
C30	0.0605 (12)	0.0277 (9)	0.0394 (10)	0.0049 (9)	−0.0076 (9)	0.0004 (8)
C31	0.0547 (12)	0.0533 (12)	0.0361 (10)	−0.0007 (10)	0.0049 (9)	−0.0177 (9)

Geometric parameters (Å, º) top

P1—C24	1.8348 (16)	C13—H13	0.9500
P1—C17	1.8395 (15)	C14—C15	1.380 (2)
P1—C18	1.8413 (15)	C14—H14	0.9500
O1—C9	1.2046 (17)	C15—C16	1.389 (2)
O2—C9	1.3387 (18)	C15—H15	0.9500
O2—C10	1.4529 (17)	C16—C17	1.399 (2)
O3—C11	1.2242 (18)	C16—H16	0.9500
O4—C2	1.371 (2)	C18—C23	1.396 (2)
O4—C30	1.421 (2)	C18—C19	1.399 (2)
O5—C3	1.3703 (19)	C19—C20	1.377 (2)
O5—C31	1.430 (2)	C19—H19	0.9500
N1—C11	1.3462 (19)	C20—C21	1.382 (2)
N1—C8	1.4454 (18)	C20—H20	0.9500
N1—H1N	0.82 (2)	C21—C22	1.377 (2)
C1—C2	1.381 (2)	C21—H21	0.9500
C1—C6	1.401 (2)	C22—C23	1.388 (2)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.406 (2)	C23—H23	0.9500
C3—C4	1.377 (2)	C24—C25	1.393 (2)
C4—C5	1.404 (2)	C24—C29	1.397 (2)
C4—H4	0.9500	C25—C26	1.383 (2)
C5—C6	1.372 (2)	C25—H25	0.9500
C5—H5	0.9500	C26—C27	1.380 (3)
C6—C7	1.514 (2)	C26—H26	0.9500
C7—C8	1.538 (2)	C27—C28	1.380 (3)
C7—H7A	0.9900	C27—H27	0.9500
C7—H7B	0.9900	C28—C29	1.388 (2)
C8—C9	1.521 (2)	C28—H28	0.9500
C8—H8	1.0000	C29—H29	0.9500
C10—H10A	0.9800	C30—H30A	0.9800
C10—H10B	0.9800	C30—H30B	0.9800
C10—H10C	0.9800	C30—H30C	0.9800
C11—C12	1.496 (2)	C31—H31A	0.9800
C12—C13	1.399 (2)	C31—H31B	0.9800
C12—C17	1.4101 (19)	C31—H31C	0.9800
C13—C14	1.383 (2)

C24—P1—C17	101.67 (7)	C13—C14—H14	120.3
C24—P1—C18	100.69 (7)	C14—C15—C16	120.29 (15)
C17—P1—C18	102.03 (7)	C14—C15—H15	119.9
C9—O2—C10	116.81 (12)	C16—C15—H15	119.9
C2—O4—C30	116.35 (12)	C15—C16—C17	121.72 (14)
C3—O5—C31	117.21 (14)	C15—C16—H16	119.1
C11—N1—C8	123.87 (13)	C17—C16—H16	119.1
C11—N1—H1N	116.5 (12)	C16—C17—C12	117.29 (13)
C8—N1—H1N	119.6 (12)	C16—C17—P1	123.97 (11)
C2—C1—C6	120.78 (16)	C12—C17—P1	118.72 (11)
C2—C1—H1	119.6	C23—C18—C19	117.87 (14)
C6—C1—H1	119.6	C23—C18—P1	125.55 (12)
O4—C2—C1	124.56 (15)	C19—C18—P1	116.58 (11)
O4—C2—C3	115.41 (12)	C20—C19—C18	121.10 (15)
C1—C2—C3	120.03 (15)	C20—C19—H19	119.4
O5—C3—C4	125.14 (15)	C18—C19—H19	119.4
O5—C3—C2	115.56 (15)	C19—C20—C21	120.34 (16)
C4—C3—C2	119.31 (14)	C19—C20—H20	119.8
C3—C4—C5	120.05 (15)	C21—C20—H20	119.8
C3—C4—H4	120.0	C22—C21—C20	119.57 (16)
C5—C4—H4	120.0	C22—C21—H21	120.2
C6—C5—C4	121.06 (15)	C20—C21—H21	120.2
C6—C5—H5	119.5	C21—C22—C23	120.49 (16)
C4—C5—H5	119.5	C21—C22—H22	119.8
C5—C6—C1	118.76 (14)	C23—C22—H22	119.8
C5—C6—C7	120.94 (14)	C22—C23—C18	120.61 (15)
C1—C6—C7	120.29 (14)	C22—C23—H23	119.7
C6—C7—C8	113.84 (12)	C18—C23—H23	119.7
C6—C7—H7A	108.8	C25—C24—C29	118.02 (14)
C8—C7—H7A	108.8	C25—C24—P1	116.15 (11)
C6—C7—H7B	108.8	C29—C24—P1	125.82 (12)
C8—C7—H7B	108.8	C26—C25—C24	121.04 (15)
H7A—C7—H7B	107.7	C26—C25—H25	119.5
N1—C8—C9	110.39 (11)	C24—C25—H25	119.5
N1—C8—C7	111.48 (12)	C27—C26—C25	120.21 (16)
C9—C8—C7	109.39 (11)	C27—C26—H26	119.9
N1—C8—H8	108.5	C25—C26—H26	119.9
C9—C8—H8	108.5	C26—C27—C28	119.80 (16)
C7—C8—H8	108.5	C26—C27—H27	120.1
O1—C9—O2	124.44 (13)	C28—C27—H27	120.1
O1—C9—C8	125.49 (13)	C27—C28—C29	120.14 (15)
O2—C9—C8	110.06 (12)	C27—C28—H28	119.9
O2—C10—H10A	109.5	C29—C28—H28	119.9
O2—C10—H10B	109.5	C28—C29—C24	120.76 (15)
H10A—C10—H10B	109.5	C28—C29—H29	119.6
O2—C10—H10C	109.5	C24—C29—H29	119.6
H10A—C10—H10C	109.5	O4—C30—H30A	109.5
H10B—C10—H10C	109.5	O4—C30—H30B	109.5
O3—C11—N1	123.47 (13)	H30A—C30—H30B	109.5
O3—C11—C12	123.36 (13)	O4—C30—H30C	109.5
N1—C11—C12	113.14 (13)	H30A—C30—H30C	109.5
C13—C12—C17	120.39 (13)	H30B—C30—H30C	109.5
C13—C12—C11	117.51 (12)	O5—C31—H31A	109.5
C17—C12—C11	122.10 (12)	O5—C31—H31B	109.5
C14—C13—C12	120.76 (14)	H31A—C31—H31B	109.5
C14—C13—H13	119.6	O5—C31—H31C	109.5
C12—C13—H13	119.6	H31A—C31—H31C	109.5
C15—C14—C13	119.45 (14)	H31B—C31—H31C	109.5
C15—C14—H14	120.3

C30—O4—C2—C1	7.8 (2)	C12—C13—C14—C15	−2.7 (2)
C30—O4—C2—C3	−171.77 (14)	C13—C14—C15—C16	2.6 (3)
C6—C1—C2—O4	−178.59 (14)	C14—C15—C16—C17	0.0 (2)
C6—C1—C2—C3	1.0 (2)	C15—C16—C17—C12	−2.4 (2)
C31—O5—C3—C4	−8.0 (2)	C15—C16—C17—P1	179.37 (12)
C31—O5—C3—C2	171.56 (14)	C13—C12—C17—C16	2.3 (2)
O4—C2—C3—O5	−1.2 (2)	C11—C12—C17—C16	−178.21 (13)
C1—C2—C3—O5	179.23 (13)	C13—C12—C17—P1	−179.38 (11)
O4—C2—C3—C4	178.39 (15)	C11—C12—C17—P1	0.11 (18)
C1—C2—C3—C4	−1.2 (2)	C24—P1—C17—C16	−77.33 (14)
O5—C3—C4—C5	179.85 (15)	C18—P1—C17—C16	26.42 (14)
C2—C3—C4—C5	0.3 (2)	C24—P1—C17—C12	104.47 (12)
C3—C4—C5—C6	0.8 (2)	C18—P1—C17—C12	−151.78 (11)
C4—C5—C6—C1	−1.1 (2)	C24—P1—C18—C23	26.80 (15)
C4—C5—C6—C7	178.01 (14)	C17—P1—C18—C23	−77.71 (15)
C2—C1—C6—C5	0.2 (2)	C24—P1—C18—C19	−152.39 (12)
C2—C1—C6—C7	−178.91 (13)	C17—P1—C18—C19	103.10 (12)
C5—C6—C7—C8	130.11 (15)	C23—C18—C19—C20	0.9 (2)
C1—C6—C7—C8	−50.83 (19)	P1—C18—C19—C20	−179.80 (14)
C11—N1—C8—C9	−109.43 (14)	C18—C19—C20—C21	0.4 (3)
C11—N1—C8—C7	128.76 (13)	C19—C20—C21—C22	−1.1 (3)
C6—C7—C8—N1	−53.92 (17)	C20—C21—C22—C23	0.4 (3)
C6—C7—C8—C9	−176.30 (13)	C21—C22—C23—C18	0.9 (3)
C10—O2—C9—O1	−10.2 (2)	C19—C18—C23—C22	−1.6 (2)
C10—O2—C9—C8	168.85 (12)	P1—C18—C23—C22	179.23 (13)
N1—C8—C9—O1	−8.7 (2)	C17—P1—C24—C25	−165.63 (12)
C7—C8—C9—O1	114.33 (16)	C18—P1—C24—C25	89.57 (13)
N1—C8—C9—O2	172.30 (12)	C17—P1—C24—C29	15.66 (15)
C7—C8—C9—O2	−64.66 (15)	C18—P1—C24—C29	−89.14 (14)
C8—N1—C11—O3	−0.8 (2)	C29—C24—C25—C26	1.7 (2)
C8—N1—C11—C12	177.40 (12)	P1—C24—C25—C26	−177.15 (14)
O3—C11—C12—C13	119.27 (17)	C24—C25—C26—C27	−0.8 (3)
N1—C11—C12—C13	−58.97 (17)	C25—C26—C27—C28	−0.8 (3)
O3—C11—C12—C17	−60.23 (19)	C26—C27—C28—C29	1.4 (3)
N1—C11—C12—C17	121.52 (14)	C27—C28—C29—C24	−0.5 (2)
C17—C12—C13—C14	0.2 (2)	C25—C24—C29—C28	−1.0 (2)
C11—C12—C13—C14	−179.31 (14)	P1—C24—C29—C28	177.64 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.816 (17)	2.345 (17)	3.1428 (17)	166 (15)
C10—H10A···O3ⁱ	0.98	2.56	3.371 (2)	140
C21—H21···O4ⁱⁱ	0.95	2.58	3.279 (2)	131

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

Experimental details

Crystal data
Chemical formula	C₃₁H₃₀NO₅P
M_r	527.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	10.2218 (3), 8.4535 (2), 15.7633 (4)
β (°)	100.300 (2)
V (Å³)	1340.16 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.18 × 0.15 × 0.14

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6654, 6654, 5550
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.079, 1.04
No. of reflections	6654
No. of parameters	350
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.25
Absolute structure	Flack (1983), 3108 Friedel pairs
Absolute structure parameter	−0.08 (6)

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.816 (17)	2.345 (17)	3.1428 (17)	166 (15)
C10—H10A···O3ⁱ	0.98	2.56	3.371 (2)	140
C21—H21···O4ⁱⁱ	0.95	2.58	3.279 (2)	131

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

Acknowledgements

The authors wish to thank Dr Hong Su of the Chemistry Department of the University of Cape Town for her assistance with the crystallographic data collection.

References

Clegg, W. & Elsegood, M. R. J. (2003). Acta Cryst. E59, o1946–o1948. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Naicker, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2011). Eur. J. Org. Chem. In the press. doi:10.1002/ejoc.201100923. Google Scholar
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859–2867. Web of Science CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zalán, Z., Martinek, T. A., Lázár, L., Sillanpää, R. & Fülöp, F. (2006). Tetrahedron, 62, 2883–2891. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3285

https://doi.org/10.1107/S1600536811047179

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(S)-Methyl 3-(3,4-dimeth­­oxy­phen­yl)-2-[2-(di­phenyl­phosphan­yl)benzamido]­propano­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(S)-Methyl 3-(3,4-dimethoxyphenyl)-2-[2-(diphenylphosphanyl)benzamido]propanoate