N,N'-Dicyclo-hexyl-N,N'-dimethyl-N''-(4-nitro-benzo-yl)phospho-ric triamide.

The P atom in the title compound, C(21)H(33)N(4)O(4)P, is in a slightly distorted tetra-hedral coordination environment and the phosphoryl and carbonyl groups are anti to each other. The environment of each N atom is essentially planar (average angles of 119.9 and 118.4°). In the crystal structure, the H atom of the C(=O)NHP(=O) group is involved in an inter-molecular -P=O⋯H-N- hydrogen bond, forming centrosymmetric dimers.

Related literature

For applications of compounds containing the –C(=O)NHP(=O)– skeleton, see: Gholivand et al. (2010 ▶). For related structures, see: Pourayoubi & Sabbaghi (2009 ▶); Sabbaghi et al. (2010 ▶).

Experimental

Crystal data

C21H33N4O4P

M = 436.48

Triclinic,

a = 8.6118 (16) Å

b = 10.838 (2) Å

c = 12.711 (2) Å

α = 93.089 (4)°

β = 106.792 (4)°

γ = 95.105 (3)°

V = 1127.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 120 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.959, T max = 0.969

12417 measured reflections

5955 independent reflections

4603 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.103

S = 1.00

5955 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023524/lh5061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023524/lh5061Isup2.hkl

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

C21H33N4O4P	Z = 2
Mr = 436.48	F(000) = 468
Triclinic, P1	Dx = 1.286 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6118 (16) Å	Cell parameters from 2045 reflections
b = 10.838 (2) Å	θ = 2–25°
c = 12.711 (2) Å	µ = 0.16 mm−1
α = 93.089 (4)°	T = 120 K
β = 106.792 (4)°	Prism, colorless
γ = 95.105 (3)°	0.40 × 0.20 × 0.20 mm
V = 1127.4 (4) Å3

Bruker SMART 1000 CCD area detector diffractometer	5955 independent reflections
Radiation source: fine-focus sealed tube	4603 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 29.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.959, Tmax = 0.969	k = −14→14
12417 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: mixed
wR(F2) = 0.103	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.001P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3
5955 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.43 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
P1	0.45851 (5)	0.82031 (4)	0.58020 (3)	0.02026 (10)
O1	0.48700 (15)	0.85007 (11)	0.47427 (9)	0.0235 (3)
O2	0.37428 (15)	0.88786 (11)	0.78908 (10)	0.0269 (3)
O3	0.60736 (19)	1.44437 (13)	1.10559 (11)	0.0390 (3)
O4	0.7761 (2)	1.49349 (14)	1.01319 (12)	0.0453 (4)
N1	0.47053 (17)	0.95776 (12)	0.65239 (11)	0.0199 (3)
H1N	0.4965	1.0218	0.6211	0.024*
N2	0.6661 (2)	1.42572 (14)	1.02941 (12)	0.0305 (3)
N3	0.28286 (18)	0.73684 (13)	0.55664 (11)	0.0240 (3)
N4	0.59191 (18)	0.74205 (13)	0.66231 (12)	0.0247 (3)
C1	0.43680 (19)	0.97284 (15)	0.75065 (13)	0.0200 (3)
C2	0.48973 (19)	1.09818 (15)	0.81576 (13)	0.0197 (3)
C3	0.5913 (2)	1.19046 (16)	0.78890 (14)	0.0246 (3)
H3A	0.6219	1.1794	0.7232	0.030*
C4	0.6481 (2)	1.29926 (16)	0.85839 (14)	0.0263 (4)
H4A	0.7182	1.3626	0.8413	0.032*
C5	0.5999 (2)	1.31276 (15)	0.95283 (13)	0.0232 (3)
C6	0.4977 (2)	1.22431 (16)	0.98073 (14)	0.0244 (3)
H6A	0.4653	1.2369	1.0455	0.029*
C7	0.4429 (2)	1.11573 (16)	0.91131 (13)	0.0229 (3)
H7A	0.3729	1.0528	0.9292	0.027*
C8	0.2412 (2)	0.65393 (18)	0.63379 (15)	0.0335 (4)
H8A	0.1906	0.5735	0.5943	0.050*
H8B	0.1646	0.6909	0.6668	0.050*
H8C	0.3405	0.6418	0.6920	0.050*
C9	0.1508 (2)	0.75515 (15)	0.45520 (13)	0.0217 (3)
H9A	0.1909	0.8281	0.4217	0.026*
C10	−0.0048 (2)	0.78658 (18)	0.47985 (15)	0.0306 (4)
H10A	0.0200	0.8621	0.5318	0.037*
H10B	−0.0464	0.7174	0.5156	0.037*
C11	−0.1361 (2)	0.80878 (19)	0.37426 (16)	0.0342 (4)
H11A	−0.2379	0.8235	0.3920	0.041*
H11B	−0.0995	0.8839	0.3430	0.041*
C12	−0.1699 (2)	0.69742 (19)	0.28905 (17)	0.0382 (5)
H12A	−0.2174	0.6243	0.3172	0.046*
H12B	−0.2504	0.7160	0.2202	0.046*
C13	−0.0139 (3)	0.6671 (2)	0.26434 (16)	0.0393 (5)
H13A	0.0280	0.7371	0.2296	0.047*
H13B	−0.0382	0.5923	0.2116	0.047*
C14	0.1171 (2)	0.64358 (17)	0.37005 (15)	0.0297 (4)
H14A	0.0798	0.5685	0.4010	0.036*
H14B	0.2189	0.6285	0.3525	0.036*
C15	0.6164 (3)	0.62277 (18)	0.61104 (17)	0.0404 (5)
H15A	0.6089	0.5568	0.6597	0.061*
H15B	0.7243	0.6294	0.5993	0.061*
H15C	0.5321	0.6029	0.5400	0.061*
C16	0.7269 (2)	0.79996 (16)	0.75819 (13)	0.0226 (3)
H16A	0.6797	0.8608	0.7989	0.027*
C17	0.7955 (2)	0.70390 (17)	0.83827 (14)	0.0279 (4)
H17A	0.8455	0.6425	0.8016	0.034*
H17B	0.7059	0.6590	0.8601	0.034*
C18	0.9245 (2)	0.76902 (19)	0.94149 (15)	0.0329 (4)
H18A	0.8718	0.8248	0.9816	0.040*
H18B	0.9714	0.7059	0.9913	0.040*
C19	1.0606 (2)	0.8443 (2)	0.91066 (16)	0.0363 (5)
H19A	1.1212	0.7874	0.8780	0.044*
H19B	1.1380	0.8891	0.9780	0.044*
C20	0.9923 (2)	0.9376 (2)	0.82845 (17)	0.0361 (5)
H20A	1.0822	0.9815	0.8063	0.043*
H20B	0.9424	1.0003	0.8640	0.043*
C21	0.8637 (2)	0.87251 (19)	0.72583 (15)	0.0306 (4)
H21A	0.8179	0.9352	0.6752	0.037*
H21B	0.9156	0.8150	0.6866	0.037*

	U11	U22	U33	U12	U13	U23
P1	0.0236 (2)	0.0180 (2)	0.01684 (19)	0.00119 (16)	0.00277 (16)	0.00079 (15)
O1	0.0288 (6)	0.0206 (6)	0.0198 (6)	0.0005 (5)	0.0062 (5)	−0.0009 (4)
O2	0.0322 (7)	0.0247 (6)	0.0249 (6)	0.0000 (5)	0.0108 (5)	0.0037 (5)
O3	0.0589 (10)	0.0343 (8)	0.0216 (6)	0.0068 (7)	0.0091 (6)	−0.0052 (5)
O4	0.0593 (10)	0.0356 (8)	0.0337 (8)	−0.0152 (7)	0.0101 (7)	−0.0085 (6)
N1	0.0244 (7)	0.0173 (6)	0.0174 (6)	0.0013 (5)	0.0058 (5)	0.0014 (5)
N2	0.0421 (9)	0.0260 (8)	0.0192 (7)	0.0045 (7)	0.0025 (7)	−0.0004 (6)
N3	0.0262 (7)	0.0240 (7)	0.0177 (7)	−0.0025 (6)	0.0004 (6)	0.0062 (5)
N4	0.0282 (8)	0.0191 (7)	0.0223 (7)	0.0061 (6)	−0.0002 (6)	−0.0017 (5)
C1	0.0182 (7)	0.0223 (8)	0.0181 (7)	0.0043 (6)	0.0023 (6)	0.0028 (6)
C2	0.0193 (8)	0.0213 (8)	0.0172 (7)	0.0047 (6)	0.0028 (6)	0.0011 (6)
C3	0.0277 (9)	0.0273 (9)	0.0186 (8)	−0.0001 (7)	0.0075 (7)	0.0002 (6)
C4	0.0310 (9)	0.0256 (9)	0.0203 (8)	−0.0020 (7)	0.0058 (7)	0.0010 (7)
C5	0.0274 (9)	0.0218 (8)	0.0164 (7)	0.0046 (7)	0.0001 (6)	−0.0009 (6)
C6	0.0280 (9)	0.0282 (9)	0.0176 (8)	0.0082 (7)	0.0063 (7)	0.0025 (6)
C7	0.0243 (8)	0.0246 (8)	0.0199 (8)	0.0042 (7)	0.0061 (6)	0.0033 (6)
C8	0.0365 (10)	0.0313 (10)	0.0265 (9)	−0.0097 (8)	0.0021 (8)	0.0110 (7)
C9	0.0236 (8)	0.0219 (8)	0.0166 (7)	0.0012 (6)	0.0014 (6)	0.0028 (6)
C10	0.0325 (10)	0.0333 (10)	0.0259 (9)	0.0075 (8)	0.0077 (8)	0.0015 (7)
C11	0.0286 (10)	0.0361 (10)	0.0372 (11)	0.0117 (8)	0.0058 (8)	0.0063 (8)
C12	0.0287 (10)	0.0354 (11)	0.0394 (11)	0.0051 (8)	−0.0076 (8)	0.0013 (9)
C13	0.0389 (11)	0.0436 (12)	0.0246 (9)	0.0118 (9)	−0.0075 (8)	−0.0085 (8)
C14	0.0275 (9)	0.0305 (9)	0.0250 (9)	0.0079 (7)	−0.0021 (7)	−0.0045 (7)
C15	0.0504 (13)	0.0275 (10)	0.0350 (11)	0.0144 (9)	−0.0020 (9)	−0.0058 (8)
C16	0.0219 (8)	0.0252 (8)	0.0189 (8)	0.0050 (6)	0.0024 (6)	0.0005 (6)
C17	0.0269 (9)	0.0315 (9)	0.0246 (9)	0.0057 (7)	0.0048 (7)	0.0068 (7)
C18	0.0291 (10)	0.0429 (11)	0.0238 (9)	0.0041 (8)	0.0019 (7)	0.0091 (8)
C19	0.0229 (9)	0.0521 (13)	0.0301 (10)	0.0038 (8)	0.0011 (8)	0.0071 (9)
C20	0.0248 (9)	0.0440 (12)	0.0354 (10)	−0.0041 (8)	0.0039 (8)	0.0093 (9)
C21	0.0274 (9)	0.0392 (10)	0.0259 (9)	0.0048 (8)	0.0074 (7)	0.0100 (8)

P1—O1	1.4834 (13)	C10—H10B	0.9900
P1—N3	1.6315 (15)	C11—C12	1.526 (3)
P1—N4	1.6446 (15)	C11—H11A	0.9900
P1—N1	1.6859 (14)	C11—H11B	0.9900
O2—C1	1.220 (2)	C12—C13	1.524 (3)
O3—N2	1.231 (2)	C12—H12A	0.9900
O4—N2	1.219 (2)	C12—H12B	0.9900
N1—C1	1.366 (2)	C13—C14	1.534 (2)
N1—H1N	0.8628	C13—H13A	0.9900
N2—C5	1.483 (2)	C13—H13B	0.9900
N3—C8	1.462 (2)	C14—H14A	0.9900
N3—C9	1.489 (2)	C14—H14B	0.9900
N4—C15	1.476 (2)	C15—H15A	0.9800
N4—C16	1.483 (2)	C15—H15B	0.9800
C1—C2	1.513 (2)	C15—H15C	0.9800
C2—C3	1.391 (2)	C16—C21	1.525 (2)
C2—C7	1.395 (2)	C16—C17	1.531 (2)
C3—C4	1.395 (2)	C16—H16A	1.0000
C3—H3A	0.9500	C17—C18	1.540 (3)
C4—C5	1.383 (2)	C17—H17A	0.9900
C4—H4A	0.9500	C17—H17B	0.9900
C5—C6	1.374 (2)	C18—C19	1.524 (3)
C6—C7	1.391 (2)	C18—H18A	0.9900
C6—H6A	0.9500	C18—H18B	0.9900
C7—H7A	0.9500	C19—C20	1.525 (3)
C8—H8A	0.9800	C19—H19A	0.9900
C8—H8B	0.9800	C19—H19B	0.9900
C8—H8C	0.9800	C20—C21	1.534 (3)
C9—C10	1.523 (2)	C20—H20A	0.9900
C9—C14	1.527 (2)	C20—H20B	0.9900
C9—H9A	1.0000	C21—H21A	0.9900
C10—C11	1.531 (3)	C21—H21B	0.9900
C10—H10A	0.9900
O1—P1—N3	109.91 (7)	H11A—C11—H11B	108.0
O1—P1—N4	117.28 (8)	C13—C12—C11	111.06 (16)
N3—P1—N4	105.39 (8)	C13—C12—H12A	109.4
O1—P1—N1	106.20 (7)	C11—C12—H12A	109.4
N3—P1—N1	113.38 (8)	C13—C12—H12B	109.4
N4—P1—N1	104.81 (7)	C11—C12—H12B	109.4
C1—N1—P1	125.20 (12)	H12A—C12—H12B	108.0
C1—N1—H1N	120.1	C12—C13—C14	111.07 (17)
P1—N1—H1N	114.6	C12—C13—H13A	109.4
O4—N2—O3	124.33 (16)	C14—C13—H13A	109.4
O4—N2—C5	117.72 (15)	C12—C13—H13B	109.4
O3—N2—C5	117.95 (16)	C14—C13—H13B	109.4
C8—N3—C9	117.46 (14)	H13A—C13—H13B	108.0
C8—N3—P1	124.25 (12)	C9—C14—C13	110.50 (15)
C9—N3—P1	118.02 (11)	C9—C14—H14A	109.5
C15—N4—C16	116.81 (14)	C13—C14—H14A	109.5
C15—N4—P1	114.39 (12)	C9—C14—H14B	109.5
C16—N4—P1	124.01 (11)	C13—C14—H14B	109.5
O2—C1—N1	122.38 (15)	H14A—C14—H14B	108.1
O2—C1—C2	119.89 (15)	N4—C15—H15A	109.5
N1—C1—C2	117.61 (14)	N4—C15—H15B	109.5
C3—C2—C7	119.80 (15)	H15A—C15—H15B	109.5
C3—C2—C1	122.95 (15)	N4—C15—H15C	109.5
C7—C2—C1	117.06 (15)	H15A—C15—H15C	109.5
C2—C3—C4	119.99 (16)	H15B—C15—H15C	109.5
C2—C3—H3A	120.0	N4—C16—C21	113.46 (14)
C4—C3—H3A	120.0	N4—C16—C17	111.50 (14)
C5—C4—C3	118.47 (16)	C21—C16—C17	110.48 (14)
C5—C4—H4A	120.8	N4—C16—H16A	107.0
C3—C4—H4A	120.8	C21—C16—H16A	107.0
C6—C5—C4	122.96 (16)	C17—C16—H16A	107.0
C6—C5—N2	118.42 (15)	C16—C17—C18	110.00 (15)
C4—C5—N2	118.59 (16)	C16—C17—H17A	109.7
C5—C6—C7	118.05 (16)	C18—C17—H17A	109.7
C5—C6—H6A	121.0	C16—C17—H17B	109.7
C7—C6—H6A	121.0	C18—C17—H17B	109.7
C6—C7—C2	120.72 (16)	H17A—C17—H17B	108.2
C6—C7—H7A	119.6	C19—C18—C17	111.18 (16)
C2—C7—H7A	119.6	C19—C18—H18A	109.4
N3—C8—H8A	109.5	C17—C18—H18A	109.4
N3—C8—H8B	109.5	C19—C18—H18B	109.4
H8A—C8—H8B	109.5	C17—C18—H18B	109.4
N3—C8—H8C	109.5	H18A—C18—H18B	108.0
H8A—C8—H8C	109.5	C18—C19—C20	111.10 (16)
H8B—C8—H8C	109.5	C18—C19—H19A	109.4
N3—C9—C10	112.56 (14)	C20—C19—H19A	109.4
N3—C9—C14	111.46 (14)	C18—C19—H19B	109.4
C10—C9—C14	111.44 (15)	C20—C19—H19B	109.4
N3—C9—H9A	107.0	H19A—C19—H19B	108.0
C10—C9—H9A	107.0	C19—C20—C21	111.01 (17)
C14—C9—H9A	107.0	C19—C20—H20A	109.4
C9—C10—C11	111.17 (15)	C21—C20—H20A	109.4
C9—C10—H10A	109.4	C19—C20—H20B	109.4
C11—C10—H10A	109.4	C21—C20—H20B	109.4
C9—C10—H10B	109.4	H20A—C20—H20B	108.0
C11—C10—H10B	109.4	C16—C21—C20	110.50 (15)
H10A—C10—H10B	108.0	C16—C21—H21A	109.5
C12—C11—C10	111.01 (16)	C20—C21—H21A	109.5
C12—C11—H11A	109.4	C16—C21—H21B	109.5
C10—C11—H11A	109.4	C20—C21—H21B	109.5
C12—C11—H11B	109.4	H21A—C21—H21B	108.1
C10—C11—H11B	109.4
O1—P1—N1—C1	173.62 (13)	C4—C5—C6—C7	1.1 (3)
N3—P1—N1—C1	52.83 (15)	N2—C5—C6—C7	−176.72 (15)
N4—P1—N1—C1	−61.59 (15)	C5—C6—C7—C2	−0.6 (2)
O1—P1—N3—C8	156.29 (15)	C3—C2—C7—C6	−0.5 (2)
N4—P1—N3—C8	29.03 (17)	C1—C2—C7—C6	174.68 (15)
N1—P1—N3—C8	−85.04 (17)	C8—N3—C9—C10	49.4 (2)
O1—P1—N3—C9	−29.95 (15)	P1—N3—C9—C10	−124.79 (14)
N4—P1—N3—C9	−157.20 (12)	C8—N3—C9—C14	−76.7 (2)
N1—P1—N3—C9	88.73 (13)	P1—N3—C9—C14	109.15 (15)
O1—P1—N4—C15	−55.86 (16)	N3—C9—C10—C11	178.22 (15)
N3—P1—N4—C15	66.78 (16)	C14—C9—C10—C11	−55.7 (2)
N1—P1—N4—C15	−173.32 (14)	C9—C10—C11—C12	55.4 (2)
O1—P1—N4—C16	98.72 (15)	C10—C11—C12—C13	−55.9 (2)
N3—P1—N4—C16	−138.64 (14)	C11—C12—C13—C14	56.5 (2)
N1—P1—N4—C16	−18.74 (16)	N3—C9—C14—C13	−177.44 (16)
P1—N1—C1—O2	−9.5 (2)	C10—C9—C14—C13	55.9 (2)
P1—N1—C1—C2	166.63 (11)	C12—C13—C14—C9	−56.2 (2)
O2—C1—C2—C3	166.11 (16)	C15—N4—C16—C21	81.6 (2)
N1—C1—C2—C3	−10.1 (2)	P1—N4—C16—C21	−72.46 (19)
O2—C1—C2—C7	−8.9 (2)	C15—N4—C16—C17	−43.9 (2)
N1—C1—C2—C7	174.87 (14)	P1—N4—C16—C17	162.03 (13)
C7—C2—C3—C4	1.1 (3)	N4—C16—C17—C18	−174.96 (15)
C1—C2—C3—C4	−173.82 (16)	C21—C16—C17—C18	57.9 (2)
C2—C3—C4—C5	−0.5 (3)	C16—C17—C18—C19	−56.7 (2)
C3—C4—C5—C6	−0.6 (3)	C17—C18—C19—C20	55.6 (2)
C3—C4—C5—N2	177.27 (16)	C18—C19—C20—C21	−55.6 (2)
O4—N2—C5—C6	168.44 (17)	N4—C16—C21—C20	175.75 (15)
O3—N2—C5—C6	−11.0 (2)	C17—C16—C21—C20	−58.2 (2)
O4—N2—C5—C4	−9.5 (2)	C19—C20—C21—C16	56.9 (2)
O3—N2—C5—C4	171.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	1.91	2.7622 (18)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	1.91	2.7622 (18)	167

Symmetry code: (i) .