N,N'-Bis(2-methyl-phen-yl)-N''-(2,2,2-trichloro-acet-yl)phospho-ric triamide.

In the title compound, C(16)H(17)Cl(3)N(3)O(2)P, the P-N bonds in the P(O)[NH(2-CH(3))C(6)H(4)](2) unit [1.623 (4) and 1.637 (3) Å] are shorter than the P-N bond in the C(O)NHP(O) fragment [1.704 (3) Å]. The phosphoryl and carbonyl groups are anti with respect to each other and the P atom has a distorted tetra-hedral configuration. In the crystal, adjacent mol-ecules are linked via N-H⋯O(P) and N-H⋯O(C) hydrogen bonds into an extended chain parallel to [101].

Related literature

For background to compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011 ▶); Pourayoubi, Tarahhomi et al. (2011 ▶). For bond lengths and angles in a related structure, see: Pourayoubi, Fadaei & Parvez (2011 ▶).

Experimental

Crystal data

C16H17Cl3N3O2P

M = 420.65

Monoclinic,

a = 14.2030 (5) Å

b = 16.1935 (6) Å

c = 16.9107 (6) Å

β = 102.3720 (19)°

V = 3799.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 173 K

0.10 × 0.09 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer with APEXII CCD

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.944, T max = 0.955

8110 measured reflections

4296 independent reflections

3031 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.141

S = 1.11

4296 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039511/jj2101sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039511/jj2101Isup2.hkl

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

C16H17Cl3N3O2P	F(000) = 1728
Mr = 420.65	Dx = 1.471 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4137 reflections
a = 14.2030 (5) Å	θ = 2.5–27.5°
b = 16.1935 (6) Å	µ = 0.58 mm−1
c = 16.9107 (6) Å	T = 173 K
β = 102.3720 (19)°	Prism, colorless
V = 3799.1 (2) Å3	0.10 × 0.09 × 0.08 mm
Z = 8

Nonius KappaCCD diffractometer with APEXII CCD	4296 independent reflections
Radiation source: fine-focus sealed tube	3031 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω and φ scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −18→18
Tmin = 0.944, Tmax = 0.955	k = −20→21
8110 measured reflections	l = −21→21

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.P)2 + 26.070P] where P = (Fo2 + 2Fc2)/3
4296 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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
Cl1	0.23160 (9)	0.15298 (9)	0.78649 (8)	0.0533 (4)
Cl2	0.09485 (7)	0.26270 (8)	0.68962 (7)	0.0474 (3)
Cl3	0.27140 (8)	0.32851 (9)	0.78607 (8)	0.0513 (3)
P1	0.44011 (7)	0.21369 (7)	0.61189 (6)	0.0253 (2)
O1	0.2270 (2)	0.2435 (2)	0.58675 (16)	0.0383 (7)
O2	0.53687 (18)	0.20089 (18)	0.66214 (15)	0.0312 (6)
N1	0.3656 (2)	0.2181 (2)	0.67847 (18)	0.0264 (7)
H1	0.3904	0.2094	0.7301	0.032*
N2	0.4268 (2)	0.2961 (2)	0.5559 (2)	0.0350 (8)
H2	0.3841	0.2950	0.5098	0.042*
N3	0.3973 (2)	0.1417 (2)	0.54605 (19)	0.0288 (7)
H3	0.3750	0.1581	0.4959	0.035*
C1	0.2710 (3)	0.2342 (2)	0.6560 (2)	0.0274 (8)
C2	0.2186 (3)	0.2441 (3)	0.7272 (2)	0.0349 (10)
C3	0.4812 (3)	0.3707 (3)	0.5776 (3)	0.0379 (10)
C4	0.5651 (3)	0.3852 (3)	0.5521 (3)	0.0430 (11)
C5	0.6135 (4)	0.4609 (3)	0.5734 (3)	0.0556 (15)
H5	0.6720	0.4722	0.5570	0.067*
C6	0.5758 (5)	0.5179 (4)	0.6178 (4)	0.0661 (17)
H6	0.6082	0.5691	0.6306	0.079*
C7	0.4923 (6)	0.5032 (4)	0.6446 (4)	0.0733 (19)
H7	0.4682	0.5432	0.6762	0.088*
C8	0.4446 (4)	0.4301 (3)	0.6250 (3)	0.0565 (14)
H8	0.3869	0.4191	0.6431	0.068*
C9	0.6031 (4)	0.3245 (3)	0.5022 (3)	0.0573 (14)
H9A	0.6592	0.3478	0.4850	0.069*
H9B	0.5531	0.3108	0.4544	0.069*
H9C	0.6223	0.2743	0.5340	0.069*
C10	0.3923 (3)	0.0558 (3)	0.5609 (2)	0.0284 (9)
C11	0.3738 (3)	0.0013 (3)	0.4949 (3)	0.0319 (9)
C12	0.3716 (3)	−0.0828 (3)	0.5109 (3)	0.0384 (10)
H12	0.3599	−0.1207	0.4670	0.046*
C13	0.3860 (3)	−0.1126 (3)	0.5889 (3)	0.0426 (11)
H13	0.3840	−0.1703	0.5983	0.051*
C14	0.4031 (3)	−0.0585 (3)	0.6528 (3)	0.0391 (10)
H14	0.4121	−0.0790	0.7065	0.047*
C15	0.4074 (3)	0.0250 (3)	0.6399 (3)	0.0345 (10)
H15	0.4206	0.0619	0.6846	0.041*
C16	0.3589 (3)	0.0325 (3)	0.4097 (3)	0.0421 (11)
H16A	0.3531	−0.0143	0.3723	0.051*
H16B	0.4141	0.0667	0.4040	0.051*
H16C	0.2999	0.0657	0.3970	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0420 (6)	0.0706 (9)	0.0466 (7)	−0.0022 (6)	0.0080 (5)	0.0227 (6)
Cl2	0.0251 (5)	0.0693 (9)	0.0452 (7)	0.0064 (5)	0.0018 (5)	−0.0046 (6)
Cl3	0.0384 (6)	0.0659 (8)	0.0473 (7)	0.0042 (6)	0.0041 (5)	−0.0278 (6)
P1	0.0242 (5)	0.0315 (6)	0.0181 (5)	−0.0012 (4)	0.0003 (4)	0.0003 (4)
O1	0.0291 (15)	0.057 (2)	0.0239 (15)	0.0055 (14)	−0.0050 (12)	0.0003 (14)
O2	0.0252 (14)	0.0454 (18)	0.0206 (14)	0.0009 (13)	−0.0009 (11)	−0.0016 (13)
N1	0.0251 (16)	0.0362 (19)	0.0149 (15)	0.0026 (14)	−0.0026 (12)	−0.0019 (14)
N2	0.0348 (19)	0.038 (2)	0.0263 (18)	−0.0065 (16)	−0.0060 (15)	0.0049 (16)
N3	0.0327 (18)	0.0355 (19)	0.0160 (16)	0.0003 (15)	0.0004 (13)	0.0005 (14)
C1	0.0258 (19)	0.030 (2)	0.0238 (19)	−0.0002 (16)	−0.0010 (15)	−0.0006 (16)
C2	0.024 (2)	0.049 (3)	0.029 (2)	0.0001 (19)	0.0010 (17)	−0.004 (2)
C3	0.044 (3)	0.035 (2)	0.030 (2)	−0.004 (2)	−0.0019 (19)	0.0095 (19)
C4	0.043 (3)	0.039 (3)	0.041 (3)	−0.005 (2)	−0.003 (2)	0.010 (2)
C5	0.062 (3)	0.044 (3)	0.048 (3)	−0.013 (3)	−0.018 (3)	0.015 (3)
C6	0.092 (5)	0.042 (3)	0.054 (4)	−0.012 (3)	−0.008 (3)	0.007 (3)
C7	0.120 (6)	0.052 (4)	0.046 (3)	0.007 (4)	0.012 (4)	−0.008 (3)
C8	0.074 (4)	0.049 (3)	0.042 (3)	0.001 (3)	0.003 (3)	−0.003 (3)
C9	0.057 (3)	0.054 (3)	0.060 (4)	0.002 (3)	0.013 (3)	0.004 (3)
C10	0.0262 (19)	0.031 (2)	0.028 (2)	−0.0005 (17)	0.0059 (16)	−0.0030 (17)
C11	0.025 (2)	0.041 (2)	0.030 (2)	−0.0028 (18)	0.0072 (17)	−0.0067 (19)
C12	0.037 (2)	0.038 (3)	0.041 (3)	−0.005 (2)	0.009 (2)	−0.010 (2)
C13	0.045 (3)	0.033 (2)	0.051 (3)	−0.004 (2)	0.012 (2)	0.001 (2)
C14	0.038 (2)	0.042 (3)	0.038 (3)	0.000 (2)	0.010 (2)	0.004 (2)
C15	0.038 (2)	0.037 (2)	0.027 (2)	−0.0035 (19)	0.0045 (18)	0.0002 (19)
C16	0.049 (3)	0.046 (3)	0.031 (2)	−0.009 (2)	0.010 (2)	−0.009 (2)

Cl1—C2	1.771 (5)	C6—H6	0.9500
Cl2—C2	1.762 (4)	C7—C8	1.369 (8)
Cl3—C2	1.762 (4)	C7—H7	0.9500
P1—O2	1.468 (3)	C8—H8	0.9500
P1—N2	1.623 (4)	C9—H9A	0.9800
P1—N3	1.637 (3)	C9—H9B	0.9800
P1—N1	1.704 (3)	C9—H9C	0.9800
O1—C1	1.213 (4)	C10—C15	1.397 (6)
N1—C1	1.341 (5)	C10—C11	1.404 (5)
N1—H1	0.8800	C11—C12	1.390 (6)
N2—C3	1.439 (5)	C11—C16	1.499 (6)
N2—H2	0.8800	C12—C13	1.377 (6)
N3—C10	1.419 (5)	C12—H12	0.9500
N3—H3	0.8800	C13—C14	1.372 (6)
C1—C2	1.554 (6)	C13—H13	0.9500
C3—C4	1.371 (6)	C14—C15	1.373 (6)
C3—C8	1.420 (7)	C14—H14	0.9500
C4—C5	1.413 (7)	C15—H15	0.9500
C4—C9	1.472 (7)	C16—H16A	0.9800
C5—C6	1.369 (8)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.377 (9)
O2—P1—N2	115.54 (18)	C8—C7—C6	119.1 (6)
O2—P1—N3	117.28 (17)	C8—C7—H7	120.4
N2—P1—N3	102.06 (17)	C6—C7—H7	120.4
O2—P1—N1	105.08 (15)	C7—C8—C3	120.0 (6)
N2—P1—N1	109.89 (18)	C7—C8—H8	120.0
N3—P1—N1	106.68 (16)	C3—C8—H8	120.0
C1—N1—P1	123.1 (3)	C4—C9—H9A	109.5
C1—N1—H1	118.4	C4—C9—H9B	109.5
P1—N1—H1	118.4	H9A—C9—H9B	109.5
C3—N2—P1	123.6 (3)	C4—C9—H9C	109.5
C3—N2—H2	118.2	H9A—C9—H9C	109.5
P1—N2—H2	118.2	H9B—C9—H9C	109.5
C10—N3—P1	127.1 (3)	C15—C10—C11	120.0 (4)
C10—N3—H3	116.4	C15—C10—N3	121.0 (4)
P1—N3—H3	116.4	C11—C10—N3	118.9 (4)
O1—C1—N1	125.2 (4)	C12—C11—C10	118.0 (4)
O1—C1—C2	120.1 (3)	C12—C11—C16	120.9 (4)
N1—C1—C2	114.7 (3)	C10—C11—C16	121.1 (4)
C1—C2—Cl2	110.2 (3)	C13—C12—C11	121.7 (4)
C1—C2—Cl3	107.5 (3)	C13—C12—H12	119.2
Cl2—C2—Cl3	110.0 (2)	C11—C12—H12	119.2
C1—C2—Cl1	110.1 (3)	C14—C13—C12	119.7 (4)
Cl2—C2—Cl1	108.8 (2)	C14—C13—H13	120.2
Cl3—C2—Cl1	110.3 (2)	C12—C13—H13	120.2
C4—C3—C8	120.6 (5)	C13—C14—C15	120.7 (4)
C4—C3—N2	121.2 (4)	C13—C14—H14	119.7
C8—C3—N2	118.1 (4)	C15—C14—H14	119.7
C3—C4—C5	118.4 (5)	C14—C15—C10	120.0 (4)
C3—C4—C9	121.0 (4)	C14—C15—H15	120.0
C5—C4—C9	120.5 (5)	C10—C15—H15	120.0
C6—C5—C4	119.9 (6)	C11—C16—H16A	109.5
C6—C5—H5	120.0	C11—C16—H16B	109.5
C4—C5—H5	120.0	H16A—C16—H16B	109.5
C5—C6—C7	121.9 (6)	C11—C16—H16C	109.5
C5—C6—H6	119.0	H16A—C16—H16C	109.5
C7—C6—H6	119.0	H16B—C16—H16C	109.5
O2—P1—N1—C1	176.0 (3)	N2—C3—C4—C9	−0.6 (7)
N2—P1—N1—C1	51.1 (4)	C3—C4—C5—C6	−0.6 (7)
N3—P1—N1—C1	−58.9 (4)	C9—C4—C5—C6	178.1 (5)
O2—P1—N2—C3	−29.9 (4)	C4—C5—C6—C7	1.6 (8)
N3—P1—N2—C3	−158.3 (4)	C5—C6—C7—C8	−1.2 (9)
N1—P1—N2—C3	88.8 (4)	C6—C7—C8—C3	−0.1 (8)
O2—P1—N3—C10	51.5 (4)	C4—C3—C8—C7	1.0 (8)
N2—P1—N3—C10	178.8 (3)	N2—C3—C8—C7	−177.7 (5)
N1—P1—N3—C10	−65.9 (4)	P1—N3—C10—C15	12.9 (6)
P1—N1—C1—O1	3.5 (6)	P1—N3—C10—C11	−165.8 (3)
P1—N1—C1—C2	−174.1 (3)	C15—C10—C11—C12	−0.3 (6)
O1—C1—C2—Cl2	3.5 (5)	N3—C10—C11—C12	178.4 (4)
N1—C1—C2—Cl2	−178.7 (3)	C15—C10—C11—C16	−179.1 (4)
O1—C1—C2—Cl3	−116.4 (4)	N3—C10—C11—C16	−0.3 (6)
N1—C1—C2—Cl3	61.4 (4)	C10—C11—C12—C13	0.7 (6)
O1—C1—C2—Cl1	123.5 (4)	C16—C11—C12—C13	179.4 (4)
N1—C1—C2—Cl1	−58.8 (4)	C11—C12—C13—C14	−0.1 (7)
P1—N2—C3—C4	93.0 (5)	C12—C13—C14—C15	−0.8 (7)
P1—N2—C3—C8	−88.3 (5)	C13—C14—C15—C10	1.2 (7)
C8—C3—C4—C5	−0.6 (7)	C11—C10—C15—C14	−0.6 (6)
N2—C3—C4—C5	178.1 (4)	N3—C10—C15—C14	−179.4 (4)
C8—C3—C4—C9	−179.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.90	2.768 (4)	170.
N2—H2···O1ii	0.88	2.11	2.957 (4)	162.
N3—H3···O1ii	0.88	2.39	3.149 (4)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	1.90	2.768 (4)	170
N2—H2⋯O1ii	0.88	2.11	2.957 (4)	162
N3—H3⋯O1ii	0.88	2.39	3.149 (4)	144

Symmetry codes: (i) ; (ii) .