O-Phenyl (tert-butyl-amido)(p-tolyl-amido)-phosphinate.

In the title mol-ecule, C(17)H(23)N(2)O(2)P, the P atom has a distorted tetra-hedral environment. The P-N bond to the tolyl-amido fragment is 1.642 (4) Å while that to the butyl-amido fragment is 1.629 (3) Å. The dihedral angle between the two benzene rings is 82.3 (2)°. In the crystal, adjacent mol-ecules are linked via weak N-H⋯(O)P and N-H⋯N hydrogen-bonding inter-actions into an extended chain parallel to the b axis. The three methyl groups of the tert-butyl-amido substituent are disordered over two sets of sites with equal occupancies. The crystal studied was found to be a non-merohedral twin with the minor twin component = 23.1 (1)%.

Related literature

For background to mixed-<span class="Chemical">amido phosphinates, see: Pourayoubi et al. (2011a ▶); Sabbaghi et al. (2011 ▶). For the sp 2 character of the nitro­gen atom of the P(=O)N unit and also for its low Lewis-base character in acting as a <span class="Chemical">hydrogen-bond acceptor, see: Toghraee et al. (2011 ▶); Pourayoubi et al. (2011b ▶,c ▶). For a description of the Cambridge Structure Database, see: Allen (2002 ▶).

Experimental

Crystal data

<span class="Chemical">C17H23N2O2P

M = 318.34

Monoclinic,

a = 11.412 (5) Å

b = 9.519 (4) Å

c = 15.768 (6) Å

β = 104.332 (5)°

V = 1659.5 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a ▶) T min = 0.966, T max = 0.974

18075 measured reflections

3860 independent reflections

2497 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.089

wR(F 2) = 0.203

S = 1.08

3860 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: CELL_NOW (Sheldrick, 2008a ▶) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048537/wm2550sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048537/wm2550Isup2.hkl

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

C17H23N2O2P	F(000) = 680
Mr = 318.34	Dx = 1.274 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2700 reflections
a = 11.412 (5) Å	θ = 2.5–27.3°
b = 9.519 (4) Å	µ = 0.18 mm−1
c = 15.768 (6) Å	T = 100 K
β = 104.332 (5)°	Block, colourless
V = 1659.5 (12) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Bruker APEX CCD diffractometer	18075 independent reflections
Radiation source: fine-focus sealed tube	2497 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a)	h = −15→14
Tmin = 0.966, Tmax = 0.974	k = 0→12
3860 measured reflections	l = 0→20

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)] = 0.089	H-atom parameters constrained
wR(F2) = 0.203	w = 1/[σ2(Fo2) + (0.032P)2 + 5.6384P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3860 reflections	Δρmax = 0.36 e Å−3
235 parameters	Δρmin = −0.42 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (8)

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	Occ. (<1)
C1	−0.3828 (4)	0.3138 (7)	0.1636 (3)	0.0484 (14)
H1A	−0.4241	0.3213	0.1014	0.073*
H1B	−0.4038	0.3950	0.1951	0.073*
H1C	−0.4083	0.2273	0.1876	0.073*
C2	−0.2482 (4)	0.3104 (6)	0.1738 (3)	0.0375 (11)
C3	−0.1876 (4)	0.1854 (5)	0.1663 (2)	0.0330 (10)
H3	−0.2329	0.1008	0.1548	0.040*
C4	−0.0631 (4)	0.1802 (5)	0.1750 (2)	0.0293 (9)
H4	−0.0249	0.0933	0.1688	0.035*
C5	0.0049 (3)	0.3026 (5)	0.1927 (2)	0.0264 (9)
C6	−0.0545 (3)	0.4307 (5)	0.1998 (2)	0.0288 (9)
H6	−0.0095	0.5155	0.2113	0.035*
C7	−0.1785 (4)	0.4320 (5)	0.1901 (2)	0.0338 (10)
H7	−0.2174	0.5189	0.1948	0.041*
C8	0.2197 (4)	0.1078 (5)	0.0673 (3)	0.0323 (10)
C9	0.1197 (4)	0.1458 (5)	0.0015 (3)	0.0362 (11)
H9	0.0411	0.1470	0.0118	0.043*
C10	0.1373 (5)	0.1821 (6)	−0.0801 (3)	0.0449 (12)
H10	0.0700	0.2084	−0.1261	0.054*
C11	0.2522 (5)	0.1802 (6)	−0.0946 (3)	0.0450 (12)
H11	0.2638	0.2068	−0.1500	0.054*
C12	0.3495 (5)	0.1395 (6)	−0.0283 (3)	0.0439 (12)
H12	0.4277	0.1364	−0.0391	0.053*
C13	0.3357 (4)	0.1030 (5)	0.0541 (3)	0.0369 (11)
H13	0.4031	0.0757	0.0998	0.044*
C14	0.2211 (4)	0.1101 (5)	0.3984 (2)	0.0286 (9)
C15	0.3531 (8)	0.0707 (13)	0.4489 (6)	0.041 (2)	0.50
H15A	0.3657	−0.0303	0.4432	0.061*	0.50
H15B	0.3653	0.0948	0.5109	0.061*	0.50
H15C	0.4108	0.1231	0.4242	0.061*	0.50
C16	0.1961 (10)	0.2594 (11)	0.4144 (6)	0.038 (2)	0.50
H16A	0.2495	0.3199	0.3905	0.058*	0.50
H16B	0.2105	0.2757	0.4775	0.058*	0.50
H16C	0.1116	0.2811	0.3858	0.058*	0.50
C17	0.1378 (10)	0.0128 (12)	0.4394 (6)	0.043 (2)	0.50
H17A	0.0529	0.0386	0.4154	0.065*	0.50
H17B	0.1588	0.0247	0.5031	0.065*	0.50
H17C	0.1500	−0.0855	0.4251	0.065*	0.50
C15'	0.3377 (8)	0.1837 (13)	0.4350 (5)	0.041 (2)	0.50
H15D	0.4046	0.1256	0.4264	0.062*	0.50
H15E	0.3473	0.2002	0.4977	0.062*	0.50
H15F	0.3378	0.2739	0.4050	0.062*	0.50
C16'	0.1147 (9)	0.2038 (12)	0.4044 (6)	0.042 (2)	0.50
H16D	0.1245	0.2966	0.3802	0.063*	0.50
H16E	0.1123	0.2135	0.4658	0.063*	0.50
H16F	0.0391	0.1613	0.3710	0.063*	0.50
C17'	0.2138 (9)	−0.0251 (11)	0.4441 (5)	0.034 (2)	0.50
H17D	0.1421	−0.0773	0.4126	0.051*	0.50
H17E	0.2080	−0.0063	0.5040	0.051*	0.50
H17F	0.2865	−0.0810	0.4457	0.051*	0.50
N1	0.1321 (3)	0.3055 (4)	0.2034 (2)	0.0272 (8)
H1	0.1619	0.3882	0.1951	0.033*
N2	0.2060 (3)	0.0744 (4)	0.3037 (2)	0.0281 (8)
H2	0.1806	−0.0109	0.2871	0.034*
O1	0.3536 (2)	0.2436 (3)	0.24577 (18)	0.0325 (7)
O2	0.2020 (2)	0.0677 (3)	0.14980 (17)	0.0304 (7)
P1	0.23229 (9)	0.17878 (13)	0.22865 (6)	0.0262 (3)

	U11	U22	U33	U12	U13	U23
C1	0.028 (2)	0.083 (4)	0.036 (2)	−0.002 (3)	0.0118 (19)	−0.001 (3)
C2	0.024 (2)	0.070 (4)	0.0189 (19)	−0.006 (2)	0.0061 (15)	−0.004 (2)
C3	0.029 (2)	0.048 (3)	0.0203 (19)	−0.008 (2)	0.0044 (16)	0.003 (2)
C4	0.028 (2)	0.037 (2)	0.0229 (19)	−0.0024 (19)	0.0063 (15)	0.0036 (19)
C5	0.0230 (19)	0.040 (2)	0.0163 (17)	0.0016 (18)	0.0043 (14)	0.0045 (17)
C6	0.024 (2)	0.041 (3)	0.0214 (19)	−0.0008 (18)	0.0050 (15)	−0.0012 (18)
C7	0.029 (2)	0.054 (3)	0.0192 (19)	0.008 (2)	0.0083 (16)	−0.003 (2)
C8	0.038 (2)	0.038 (3)	0.022 (2)	−0.001 (2)	0.0106 (17)	−0.0050 (19)
C9	0.036 (2)	0.048 (3)	0.025 (2)	0.000 (2)	0.0081 (17)	−0.004 (2)
C10	0.057 (3)	0.053 (3)	0.024 (2)	0.010 (3)	0.009 (2)	−0.003 (2)
C11	0.063 (3)	0.051 (3)	0.027 (2)	−0.002 (3)	0.022 (2)	−0.008 (2)
C12	0.048 (3)	0.055 (3)	0.035 (2)	−0.007 (2)	0.023 (2)	−0.011 (2)
C13	0.034 (2)	0.045 (3)	0.033 (2)	−0.004 (2)	0.0097 (19)	−0.008 (2)
C14	0.031 (2)	0.037 (3)	0.0199 (19)	0.0019 (19)	0.0097 (16)	−0.0009 (18)
C15	0.038 (5)	0.063 (7)	0.019 (4)	0.001 (5)	0.002 (4)	−0.002 (5)
C16	0.047 (6)	0.049 (6)	0.023 (4)	0.000 (5)	0.015 (4)	0.006 (4)
C17	0.057 (7)	0.052 (7)	0.023 (5)	−0.018 (6)	0.016 (5)	0.001 (4)
C15'	0.040 (5)	0.066 (7)	0.019 (4)	−0.019 (5)	0.009 (4)	−0.009 (5)
C16'	0.041 (5)	0.063 (7)	0.024 (4)	0.021 (5)	0.012 (4)	−0.004 (4)
C17'	0.040 (5)	0.046 (6)	0.019 (4)	0.002 (5)	0.011 (4)	0.004 (4)
N1	0.0212 (16)	0.038 (2)	0.0229 (16)	−0.0022 (15)	0.0067 (13)	0.0015 (15)
N2	0.0318 (18)	0.035 (2)	0.0169 (16)	−0.0020 (16)	0.0045 (13)	−0.0002 (14)
O1	0.0238 (14)	0.0463 (19)	0.0275 (15)	−0.0002 (13)	0.0067 (11)	−0.0013 (14)
O2	0.0316 (15)	0.0385 (18)	0.0216 (14)	−0.0021 (13)	0.0079 (11)	−0.0046 (13)
P1	0.0215 (5)	0.0383 (6)	0.0184 (5)	0.0005 (5)	0.0045 (4)	−0.0014 (5)

C1—C2	1.506 (6)	C14—C17'	1.488 (10)
C1—H1A	0.9800	C14—N2	1.500 (5)
C1—H1B	0.9800	C14—C16'	1.528 (10)
C1—H1C	0.9800	C14—C15	1.565 (10)
C2—C7	1.391 (7)	C14—C17	1.576 (10)
C2—C3	1.396 (7)	C15—H15A	0.9800
C3—C4	1.394 (5)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.390 (6)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.413 (6)	C16—H16C	0.9800
C5—N1	1.419 (5)	C17—H17A	0.9800
C6—C7	1.386 (5)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C7—H7	0.9500	C15'—H15D	0.9800
C8—C9	1.386 (6)	C15'—H15E	0.9800
C8—C13	1.391 (6)	C15'—H15F	0.9800
C8—O2	1.417 (5)	C16'—H16D	0.9800
C9—C10	1.395 (6)	C16'—H16E	0.9800
C9—H9	0.9500	C16'—H16F	0.9800
C10—C11	1.385 (7)	C17'—H17D	0.9800
C10—H10	0.9500	C17'—H17E	0.9800
C11—C12	1.379 (7)	C17'—H17F	0.9800
C11—H11	0.9500	N1—P1	1.642 (4)
C12—C13	1.392 (6)	N1—H1	0.8800
C12—H12	0.9500	N2—P1	1.629 (3)
C13—H13	0.9500	N2—H2	0.8800
C14—C16	1.483 (11)	O1—P1	1.478 (3)
C14—C15'	1.487 (10)	O2—P1	1.603 (3)
C2—C1—H1A	109.5	N2—C14—C16'	107.3 (4)
C2—C1—H1B	109.5	C16—C14—C15	110.2 (7)
H1A—C1—H1B	109.5	C17'—C14—C15	73.1 (6)
C2—C1—H1C	109.5	N2—C14—C15	108.1 (4)
H1A—C1—H1C	109.5	C16'—C14—C15	142.0 (6)
H1B—C1—H1C	109.5	C16—C14—C17	109.4 (6)
C7—C2—C3	116.9 (4)	C15'—C14—C17	133.6 (6)
C7—C2—C1	121.5 (5)	N2—C14—C17	110.0 (5)
C3—C2—C1	121.5 (5)	C16'—C14—C17	75.4 (6)
C4—C3—C2	122.4 (4)	C15—C14—C17	104.6 (6)
C4—C3—H3	118.8	C14—C15—H15A	109.5
C2—C3—H3	118.8	C14—C15—H15B	109.5
C5—C4—C3	119.6 (4)	C14—C15—H15C	109.5
C5—C4—H4	120.2	C14—C16—H16A	109.5
C3—C4—H4	120.2	C14—C16—H16B	109.5
C4—C5—C6	119.0 (4)	C14—C16—H16C	109.5
C4—C5—N1	122.9 (4)	C14—C17—H17A	109.5
C6—C5—N1	118.1 (4)	C14—C17—H17B	109.5
C7—C6—C5	119.8 (4)	C14—C17—H17C	109.5
C7—C6—H6	120.1	C14—C15'—H15D	109.5
C5—C6—H6	120.1	C14—C15'—H15E	109.5
C6—C7—C2	122.3 (4)	H15D—C15'—H15E	109.5
C6—C7—H7	118.9	C14—C15'—H15F	109.5
C2—C7—H7	118.9	H15D—C15'—H15F	109.5
C9—C8—C13	122.3 (4)	H15E—C15'—H15F	109.5
C9—C8—O2	118.6 (4)	C14—C16'—H16D	109.5
C13—C8—O2	119.0 (4)	C14—C16'—H16E	109.5
C8—C9—C10	118.4 (4)	H16D—C16'—H16E	109.5
C8—C9—H9	120.8	C14—C16'—H16F	109.5
C10—C9—H9	120.8	H16D—C16'—H16F	109.5
C11—C10—C9	120.5 (4)	H16E—C16'—H16F	109.5
C11—C10—H10	119.8	C14—C17'—H17D	109.5
C9—C10—H10	119.8	C14—C17'—H17E	109.5
C12—C11—C10	119.7 (4)	H17D—C17'—H17E	109.5
C12—C11—H11	120.1	C14—C17'—H17F	109.5
C10—C11—H11	120.1	H17D—C17'—H17F	109.5
C11—C12—C13	121.5 (5)	H17E—C17'—H17F	109.5
C11—C12—H12	119.2	C5—N1—P1	130.2 (3)
C13—C12—H12	119.2	C5—N1—H1	114.9
C8—C13—C12	117.6 (4)	P1—N1—H1	114.9
C8—C13—H13	121.2	C14—N2—P1	126.0 (3)
C12—C13—H13	121.2	C14—N2—H2	117.0
C16—C14—C15'	71.0 (7)	P1—N2—H2	117.0
C16—C14—C17'	135.3 (6)	C8—O2—P1	118.8 (3)
C15'—C14—C17'	111.8 (6)	O1—P1—O2	115.41 (16)
C16—C14—N2	114.0 (5)	O1—P1—N2	117.03 (17)
C15'—C14—N2	111.4 (4)	O2—P1—N2	96.76 (17)
C17'—C14—N2	106.2 (5)	O1—P1—N1	107.61 (19)
C15'—C14—C16'	110.4 (7)	O2—P1—N1	107.01 (16)
C17'—C14—C16'	109.5 (6)	N2—P1—N1	112.47 (17)
C7—C2—C3—C4	0.3 (6)	C6—C5—N1—P1	159.1 (3)
C1—C2—C3—C4	179.6 (4)	C16—C14—N2—P1	32.5 (6)
C2—C3—C4—C5	0.7 (6)	C15'—C14—N2—P1	−45.5 (7)
C3—C4—C5—C6	−1.2 (5)	C17'—C14—N2—P1	−167.5 (5)
C3—C4—C5—N1	179.3 (3)	C16'—C14—N2—P1	75.5 (6)
C4—C5—C6—C7	0.7 (6)	C15—C14—N2—P1	−90.4 (6)
N1—C5—C6—C7	−179.8 (3)	C17—C14—N2—P1	155.9 (6)
C5—C6—C7—C2	0.3 (6)	C9—C8—O2—P1	−101.8 (4)
C3—C2—C7—C6	−0.8 (6)	C13—C8—O2—P1	80.5 (5)
C1—C2—C7—C6	179.9 (4)	C8—O2—P1—O1	−51.6 (3)
C13—C8—C9—C10	−1.0 (7)	C8—O2—P1—N2	−175.9 (3)
O2—C8—C9—C10	−178.6 (4)	C8—O2—P1—N1	68.1 (3)
C8—C9—C10—C11	0.0 (8)	C14—N2—P1—O1	54.8 (4)
C9—C10—C11—C12	1.2 (8)	C14—N2—P1—O2	177.8 (3)
C10—C11—C12—C13	−1.4 (8)	C14—N2—P1—N1	−70.6 (4)
C9—C8—C13—C12	0.7 (7)	C5—N1—P1—O1	−170.6 (3)
O2—C8—C13—C12	178.3 (4)	C5—N1—P1—O2	64.8 (3)
C11—C12—C13—C8	0.5 (8)	C5—N1—P1—N2	−40.3 (4)
C4—C5—N1—P1	−21.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88	2.32	3.175 (5)	163.
N2—H2···O1ii	0.88	2.40	3.275 (5)	170.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88	2.32	3.175 (5)	163
N2—H2⋯O1ii	0.88	2.40	3.275 (5)	170

Symmetry codes: (i) ; (ii) .