N-(2-Fluoro-benzo-yl)-N',N''-bis-(4-methyl-phen-yl)phospho-ric triamide.

The P atom in the title compound, C(21)H(21)FN(3)O(2)P, is in a tetra-hedral coordination environment and the environment of each N atom is essentially planar (sums of angles = 359.7, 359.9 and 358.4°). The phosphoryl and carbonyl groups adopt anti orientations with respect to each other. In the crystal, adjacent mol-ecules are linked via N-H⋯O=P and two N-H⋯O=C hydrogen bonds into an extended chain parallel to the a axis.

Related literature

For a phospho­rus ligand having a C(O)NHP(O) skeleton, see: Gholivand et al. (2010 ▶). For a related structure, see: Pourayoubi et al. (2010 ▶). For bond lengths in related structures, see: Sabbaghi et al. (2010 ▶) and references cited therein.

Experimental

Crystal data

C21H21FN3O2P

M = 397.38

Monoclinic,

a = 9.7697 (9) Å

b = 10.2197 (9) Å

c = 20.2404 (18) Å

β = 96.605 (1)°

V = 2007.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 100 K

0.25 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.975

15865 measured reflections

4551 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.05

4551 reflections

264 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.26 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009640/nc2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009640/nc2222Isup2.hkl

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

C21H21FN3O2P	F(000) = 832
Mr = 397.38	Dx = 1.315 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7697 (9) Å	Cell parameters from 5744 reflections
b = 10.2197 (9) Å	θ = 2.2–27.5°
c = 20.2404 (18) Å	µ = 0.17 mm−1
β = 96.605 (1)°	T = 100 K
V = 2007.5 (3) Å3	Block, colourless
Z = 4	0.25 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	4551 independent reflections
Radiation source: fine-focus sealed tube	3411 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.959, Tmax = 0.975	k = −11→13
15865 measured reflections	l = −25→25

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.498P] where P = (Fo2 + 2Fc2)/3
4551 reflections	(Δ/σ)max = 0.007
264 parameters	Δρmax = 0.41 e Å−3
3 restraints	Δρmin = −0.26 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	0.72255 (5)	0.92119 (4)	0.50855 (2)	0.02136 (14)
F1	0.92737 (14)	1.40039 (12)	0.55287 (6)	0.0441 (3)
O1	0.91560 (13)	1.14443 (13)	0.50431 (6)	0.0293 (3)
O2	0.58757 (12)	0.86140 (12)	0.51487 (6)	0.0250 (3)
N1	0.69300 (16)	1.08365 (14)	0.50258 (7)	0.0210 (3)
H1N	0.6074 (11)	1.1095 (19)	0.4983 (9)	0.025*
N2	0.79772 (16)	0.87866 (15)	0.44363 (8)	0.0240 (3)
H2N	0.8811 (12)	0.8507 (19)	0.4525 (10)	0.029*
N3	0.84260 (16)	0.88686 (16)	0.56874 (8)	0.0267 (4)
H3N	0.9270 (12)	0.905 (2)	0.5636 (10)	0.032*
C1	0.8139 (2)	1.41838 (19)	0.50898 (9)	0.0296 (4)
C2	0.7701 (2)	1.5451 (2)	0.49516 (11)	0.0381 (5)
H2C	0.8194	1.6173	0.5157	0.046*
C3	0.6533 (2)	1.5647 (2)	0.45090 (11)	0.0379 (5)
H3B	0.6219	1.6511	0.4408	0.045*
C4	0.5822 (2)	1.4596 (2)	0.42132 (11)	0.0344 (5)
H4A	0.5029	1.4737	0.3903	0.041*
C5	0.6265 (2)	1.33331 (19)	0.43680 (9)	0.0278 (4)
H5A	0.5765	1.2612	0.4166	0.033*
C6	0.74372 (19)	1.31052 (17)	0.48164 (9)	0.0230 (4)
C7	0.79305 (18)	1.17460 (18)	0.49728 (8)	0.0220 (4)
C8	0.7441 (2)	0.89104 (17)	0.37612 (9)	0.0244 (4)
C9	0.6203 (2)	0.9545 (2)	0.35614 (10)	0.0319 (5)
H9A	0.5685	0.9914	0.3884	0.038*
C10	0.5725 (2)	0.9640 (2)	0.28921 (10)	0.0360 (5)
H10A	0.4886	1.0089	0.2762	0.043*
C11	0.6439 (2)	0.9096 (2)	0.24070 (10)	0.0404 (5)
C12	0.7657 (2)	0.8443 (2)	0.26118 (10)	0.0419 (6)
H12A	0.8157	0.8051	0.2288	0.050*
C13	0.8164 (2)	0.8347 (2)	0.32801 (10)	0.0341 (5)
H13A	0.9004	0.7898	0.3409	0.041*
C14	0.5884 (3)	0.9202 (3)	0.16774 (11)	0.0561 (7)
H14A	0.6098	0.8398	0.1446	0.084*
H14B	0.6313	0.9950	0.1479	0.084*
H14C	0.4884	0.9326	0.1636	0.084*
C15	0.8269 (2)	0.85706 (18)	0.63606 (9)	0.0260 (4)
C16	0.7217 (2)	0.7756 (2)	0.65213 (10)	0.0406 (5)
H16A	0.6570	0.7408	0.6180	0.049*
C17	0.7115 (2)	0.7452 (3)	0.71817 (11)	0.0506 (7)
H17A	0.6367	0.6929	0.7288	0.061*
C18	0.8072 (3)	0.7891 (2)	0.76906 (10)	0.0435 (6)
C19	0.9162 (3)	0.8633 (2)	0.75138 (11)	0.0507 (7)
H19A	0.9862	0.8909	0.7850	0.061*
C20	0.9253 (3)	0.8980 (2)	0.68584 (11)	0.0427 (6)
H20A	1.0000	0.9504	0.6752	0.051*
C21	0.7964 (3)	0.7510 (3)	0.84055 (11)	0.0657 (8)
H21A	0.8791	0.7801	0.8687	0.099*
H21B	0.7879	0.6557	0.8437	0.099*
H21C	0.7150	0.7926	0.8556	0.099*

	U11	U22	U33	U12	U13	U23
P1	0.0143 (3)	0.0263 (2)	0.0236 (2)	0.00103 (18)	0.00229 (18)	0.00314 (18)
F1	0.0442 (8)	0.0440 (7)	0.0404 (7)	−0.0137 (6)	−0.0116 (6)	−0.0023 (5)
O1	0.0150 (7)	0.0379 (8)	0.0351 (8)	−0.0004 (6)	0.0030 (6)	0.0005 (6)
O2	0.0142 (7)	0.0278 (7)	0.0330 (7)	−0.0001 (5)	0.0025 (5)	0.0038 (5)
N1	0.0143 (8)	0.0244 (8)	0.0245 (8)	0.0002 (6)	0.0038 (6)	0.0007 (6)
N2	0.0158 (8)	0.0297 (8)	0.0262 (8)	0.0048 (6)	0.0015 (6)	−0.0003 (6)
N3	0.0133 (8)	0.0388 (9)	0.0279 (9)	0.0000 (7)	0.0018 (7)	0.0086 (6)
C1	0.0288 (11)	0.0346 (11)	0.0252 (10)	−0.0079 (9)	0.0024 (8)	−0.0004 (8)
C2	0.0497 (15)	0.0292 (10)	0.0368 (12)	−0.0104 (10)	0.0106 (10)	−0.0051 (9)
C3	0.0433 (14)	0.0280 (11)	0.0443 (12)	0.0005 (9)	0.0135 (11)	0.0062 (9)
C4	0.0271 (11)	0.0353 (11)	0.0411 (12)	0.0002 (9)	0.0058 (9)	0.0084 (9)
C5	0.0231 (10)	0.0292 (10)	0.0317 (10)	−0.0033 (8)	0.0057 (8)	0.0011 (8)
C6	0.0202 (10)	0.0273 (9)	0.0227 (9)	−0.0035 (7)	0.0073 (7)	−0.0015 (7)
C7	0.0167 (10)	0.0303 (9)	0.0192 (9)	−0.0013 (7)	0.0033 (7)	−0.0019 (7)
C8	0.0212 (10)	0.0274 (9)	0.0247 (9)	−0.0034 (8)	0.0032 (8)	0.0010 (7)
C9	0.0270 (11)	0.0404 (11)	0.0278 (10)	0.0020 (9)	0.0019 (8)	−0.0030 (8)
C10	0.0290 (12)	0.0461 (12)	0.0313 (11)	0.0001 (10)	−0.0038 (9)	0.0029 (9)
C11	0.0345 (13)	0.0601 (15)	0.0262 (11)	−0.0110 (11)	0.0015 (9)	0.0024 (9)
C12	0.0351 (13)	0.0624 (15)	0.0300 (12)	−0.0047 (11)	0.0109 (10)	−0.0062 (10)
C13	0.0254 (11)	0.0452 (12)	0.0324 (11)	0.0013 (9)	0.0060 (9)	−0.0017 (9)
C14	0.0465 (16)	0.095 (2)	0.0262 (12)	−0.0108 (14)	0.0008 (11)	0.0069 (12)
C15	0.0234 (10)	0.0299 (10)	0.0248 (10)	0.0057 (8)	0.0040 (8)	0.0025 (7)
C16	0.0266 (12)	0.0627 (15)	0.0318 (11)	−0.0063 (10)	0.0001 (9)	0.0129 (10)
C17	0.0322 (13)	0.0782 (18)	0.0421 (14)	−0.0019 (12)	0.0075 (11)	0.0229 (12)
C18	0.0496 (15)	0.0558 (14)	0.0263 (11)	0.0136 (12)	0.0098 (10)	0.0039 (9)
C19	0.0709 (19)	0.0504 (14)	0.0284 (12)	−0.0100 (13)	−0.0048 (12)	−0.0038 (10)
C20	0.0499 (15)	0.0433 (13)	0.0336 (12)	−0.0166 (11)	−0.0006 (10)	0.0005 (9)
C21	0.074 (2)	0.095 (2)	0.0310 (13)	0.0190 (17)	0.0163 (13)	0.0111 (13)

P1—O2	1.4723 (13)	C9—H9A	0.9500
P1—N3	1.6291 (17)	C10—C11	1.385 (3)
P1—N2	1.6361 (15)	C10—H10A	0.9500
P1—N1	1.6872 (15)	C11—C12	1.386 (3)
F1—C1	1.351 (2)	C11—C14	1.517 (3)
O1—C7	1.229 (2)	C12—C13	1.389 (3)
N1—C7	1.362 (2)	C12—H12A	0.9500
N1—H1N	0.872 (9)	C13—H13A	0.9500
N2—C8	1.412 (2)	C14—H14A	0.9800
N2—H2N	0.862 (9)	C14—H14B	0.9800
N3—C15	1.422 (2)	C14—H14C	0.9800
N3—H3N	0.863 (9)	C15—C20	1.375 (3)
C1—C6	1.380 (3)	C15—C16	1.390 (3)
C1—C2	1.382 (3)	C16—C17	1.387 (3)
C2—C3	1.382 (3)	C16—H16A	0.9500
C2—H2C	0.9500	C17—C18	1.384 (3)
C3—C4	1.378 (3)	C17—H17A	0.9500
C3—H3B	0.9500	C18—C19	1.387 (3)
C4—C5	1.385 (3)	C18—C21	1.514 (3)
C4—H4A	0.9500	C19—C20	1.386 (3)
C5—C6	1.396 (3)	C19—H19A	0.9500
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.492 (3)	C21—H21A	0.9800
C8—C9	1.391 (3)	C21—H21B	0.9800
C8—C13	1.392 (3)	C21—H21C	0.9800
C9—C10	1.384 (3)
O2—P1—N3	114.88 (8)	C9—C10—C11	121.7 (2)
O2—P1—N2	116.67 (8)	C9—C10—H10A	119.2
N3—P1—N2	101.09 (8)	C11—C10—H10A	119.2
O2—P1—N1	105.49 (8)	C10—C11—C12	117.8 (2)
N3—P1—N1	111.59 (8)	C10—C11—C14	120.6 (2)
N2—P1—N1	107.03 (8)	C12—C11—C14	121.6 (2)
C7—N1—P1	123.97 (13)	C11—C12—C13	121.5 (2)
C7—N1—H1N	118.3 (13)	C11—C12—H12A	119.2
P1—N1—H1N	117.4 (13)	C13—C12—H12A	119.2
C8—N2—P1	127.06 (13)	C12—C13—C8	120.0 (2)
C8—N2—H2N	117.9 (13)	C12—C13—H13A	120.0
P1—N2—H2N	114.9 (13)	C8—C13—H13A	120.0
C15—N3—P1	127.97 (13)	C11—C14—H14A	109.5
C15—N3—H3N	111.7 (14)	C11—C14—H14B	109.5
P1—N3—H3N	118.7 (14)	H14A—C14—H14B	109.5
F1—C1—C6	119.15 (18)	C11—C14—H14C	109.5
F1—C1—C2	118.14 (18)	H14A—C14—H14C	109.5
C6—C1—C2	122.7 (2)	H14B—C14—H14C	109.5
C3—C2—C1	118.7 (2)	C20—C15—C16	118.94 (18)
C3—C2—H2C	120.7	C20—C15—N3	119.60 (18)
C1—C2—H2C	120.7	C16—C15—N3	121.11 (18)
C4—C3—C2	120.4 (2)	C17—C16—C15	119.8 (2)
C4—C3—H3B	119.8	C17—C16—H16A	120.1
C2—C3—H3B	119.8	C15—C16—H16A	120.1
C3—C4—C5	119.9 (2)	C18—C17—C16	121.8 (2)
C3—C4—H4A	120.0	C18—C17—H17A	119.1
C5—C4—H4A	120.0	C16—C17—H17A	119.1
C4—C5—C6	120.93 (19)	C17—C18—C19	117.3 (2)
C4—C5—H5A	119.5	C17—C18—C21	120.8 (2)
C6—C5—H5A	119.5	C19—C18—C21	121.8 (2)
C1—C6—C5	117.37 (18)	C20—C19—C18	121.5 (2)
C1—C6—C7	121.68 (18)	C20—C19—H19A	119.2
C5—C6—C7	120.92 (16)	C18—C19—H19A	119.2
O1—C7—N1	121.22 (17)	C15—C20—C19	120.5 (2)
O1—C7—C6	123.01 (16)	C15—C20—H20A	119.8
N1—C7—C6	115.77 (15)	C19—C20—H20A	119.8
C9—C8—C13	118.93 (18)	C18—C21—H21A	109.5
C9—C8—N2	122.47 (16)	C18—C21—H21B	109.5
C13—C8—N2	118.58 (17)	H21A—C21—H21B	109.5
C10—C9—C8	120.08 (18)	C18—C21—H21C	109.5
C10—C9—H9A	120.0	H21A—C21—H21C	109.5
C8—C9—H9A	120.0	H21B—C21—H21C	109.5
O2—P1—N1—C7	178.66 (14)	C5—C6—C7—N1	−39.0 (2)
N3—P1—N1—C7	53.27 (16)	P1—N2—C8—C9	6.1 (3)
N2—P1—N1—C7	−56.46 (16)	P1—N2—C8—C13	−172.26 (15)
O2—P1—N2—C8	57.27 (18)	C13—C8—C9—C10	−1.7 (3)
N3—P1—N2—C8	−177.42 (15)	N2—C8—C9—C10	179.93 (18)
N1—P1—N2—C8	−60.53 (17)	C8—C9—C10—C11	1.1 (3)
O2—P1—N3—C15	−28.7 (2)	C9—C10—C11—C12	0.3 (3)
N2—P1—N3—C15	−155.21 (16)	C9—C10—C11—C14	179.3 (2)
N1—P1—N3—C15	91.30 (17)	C10—C11—C12—C13	−0.9 (3)
F1—C1—C2—C3	−179.31 (17)	C14—C11—C12—C13	180.0 (2)
C6—C1—C2—C3	−1.7 (3)	C11—C12—C13—C8	0.3 (3)
C1—C2—C3—C4	0.1 (3)	C9—C8—C13—C12	1.0 (3)
C2—C3—C4—C5	1.1 (3)	N2—C8—C13—C12	179.47 (19)
C3—C4—C5—C6	−0.7 (3)	P1—N3—C15—C20	−144.91 (18)
F1—C1—C6—C5	179.64 (15)	P1—N3—C15—C16	41.9 (3)
C2—C1—C6—C5	2.0 (3)	C20—C15—C16—C17	4.9 (3)
F1—C1—C6—C7	−2.4 (3)	N3—C15—C16—C17	178.1 (2)
C2—C1—C6—C7	179.95 (17)	C15—C16—C17—C18	−3.0 (4)
C4—C5—C6—C1	−0.8 (3)	C16—C17—C18—C19	−1.2 (4)
C4—C5—C6—C7	−178.77 (17)	C16—C17—C18—C21	−178.0 (2)
P1—N1—C7—O1	−8.6 (2)	C17—C18—C19—C20	3.3 (4)
P1—N1—C7—C6	170.55 (12)	C21—C18—C19—C20	−179.9 (2)
C1—C6—C7—O1	−37.7 (3)	C16—C15—C20—C19	−2.8 (3)
C5—C6—C7—O1	140.17 (18)	N3—C15—C20—C19	−176.1 (2)
C1—C6—C7—N1	143.13 (17)	C18—C19—C20—C15	−1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.87 (1)	1.92 (1)	2.780 (2)	171 (2)
N2—H2N···O1ii	0.86 (1)	2.08 (1)	2.886 (2)	156 (2)
N3—H3N···O1ii	0.86 (1)	2.24 (2)	2.945 (2)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.87 (1)	1.92 (1)	2.780 (2)	171 (2)
N2—H2N⋯O1ii	0.86 (1)	2.08 (1)	2.886 (2)	156 (2)
N3—H3N⋯O1ii	0.86 (1)	2.24 (2)	2.945 (2)	139 (2)

Symmetry codes: (i) ; (ii) .