Structural studies of (N-phenylthioureidoalkyl- and -aryl)phosphonates

The crystal structures of three (N-phenylthioureidoalkyl- and -aryl)phosphonates, i.e. diphenyl [(3-phenylthioureido)phenylpropyl]phosphonate, diphenyl [1-(3-phenylthioureido)benzyl]phosphonate and diphenyl [2,2-dimethyl-1-(3-phenylthioureido)propyl]phosphonate, have been determined by X-ray diffraction. The conformations of the title molecules, the geometry of the thioureide fragments and molecular packing arrangements are analyzed and compared with literature data.

Computing details

For all compounds, data collection: MSC/AFC Diffractometer Control Software (1989a); cell refinement: MSC/AFC Diffractometer Control Software (1989a); data reduction: TEXSAN (1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).

Figures

(I) diphenyl [(3-phenylthioureido)phenylpropyl]phosphonate

Crystal data

C28H27N2O3PS	Z = 2
Mr = 502.55	F(000) = 528
Triclinic, P1	Dx = 1.259 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.951 (1) Å	Cell parameters from 25 reflections
b = 12.201 (1) Å	θ = 38.2–39.9°
c = 11.844 (1) Å	µ = 1.91 mm^−1
α = 100.40 (1)°	T = 293 K
β = 102.90 (1)°	Prism, colourless
γ = 102.90 (1)°	0.50 × 0.30 × 0.20 mm
V = 1325.6 (2) Å^3

Data collection

AFC5S Rigaku diffractometer	3089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 67.5°, θmin = 3.8°
ω scans	h = −11→11
Absorption correction: analytical (De Meulenaer & Tompa, 1965)	k = −14→14
Tmin = 0.448, Tmax = 0.701	l = −11→14
4878 measured reflections	3 standard reflections every 150 reflections
4637 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0663P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
4637 reflections	Δρmax = 0.21 e Å^−3
325 parameters	Δρmin = −0.28 e Å^−3
8 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0146 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.44040 (7)	0.31491 (6)	0.19540 (5)	0.0739 (2)
C1	0.2730 (2)	0.23518 (19)	0.17094 (18)	0.0530 (5)
N1	0.2123 (2)	0.21260 (18)	0.25830 (16)	0.0604 (5)
H1	0.137 (2)	0.1608 (19)	0.235 (2)	0.071 (8)*
N2	0.1818 (2)	0.18510 (16)	0.05978 (15)	0.0554 (5)
H2	0.096 (2)	0.1402 (19)	0.056 (2)	0.068 (8)*
C2	0.2245 (2)	0.18120 (19)	−0.05049 (18)	0.0552 (6)
H201	0.3276	0.2191	−0.0288	0.066*
C3	0.1484 (3)	0.24601 (19)	−0.1320 (2)	0.0646 (6)
H301	0.1768	0.2368	−0.2056	0.078*
H302	0.0456	0.2123	−0.1520	0.078*
C4	0.1840 (3)	0.3743 (2)	−0.0734 (2)	0.0838 (9)
H401	0.1469	0.3833	−0.0042	0.101*
H402	0.2874	0.4058	−0.0457	0.101*
C51	0.1232 (3)	0.4429 (2)	−0.1559 (2)	0.0686 (7)
C52	−0.0046 (3)	0.4682 (2)	−0.1559 (2)	0.0789 (8)
H52	−0.0562	0.4412	−0.1053	0.095*
C53	−0.0573 (4)	0.5328 (3)	−0.2296 (3)	0.0950 (10)
H53	−0.1447	0.5479	−0.2290	0.114*
C54	0.0162 (4)	0.5749 (3)	−0.3031 (3)	0.1012 (10)
H54	−0.0186	0.6206	−0.3510	0.121*
C55	0.1432 (4)	0.5489 (3)	−0.3058 (3)	0.1078 (11)
H55	0.1931	0.5745	−0.3580	0.129*
C56	0.1965 (3)	0.4849 (3)	−0.2311 (3)	0.0896 (9)
H56	0.2839	0.4699	−0.2318	0.107*
P1	0.19730 (7)	0.03069 (5)	−0.11821 (5)	0.0559 (2)
O1	0.05416 (16)	−0.04412 (13)	−0.13141 (13)	0.0615 (4)
O2	0.23898 (18)	0.03783 (13)	−0.23782 (14)	0.0694 (5)
O3	0.32302 (17)	−0.00571 (15)	−0.04221 (16)	0.0721 (5)
C11	0.2849 (2)	0.2468 (2)	0.38339 (19)	0.0574 (6)
C12	0.3023 (3)	0.1639 (2)	0.4444 (2)	0.0766 (7)
H12	0.2708	0.0859	0.4046	0.092*
C13	0.3681 (3)	0.1975 (3)	0.5673 (3)	0.0926 (9)
H13	0.3817	0.1418	0.6097	0.111*
C14	0.4121 (3)	0.3114 (3)	0.6245 (2)	0.0910 (9)
H14	0.4547	0.3334	0.7065	0.109*
C15	0.3947 (3)	0.3942 (3)	0.5634 (2)	0.0851 (9)
H15	0.4266	0.4721	0.6036	0.102*
C16	0.3301 (3)	0.3627 (2)	0.4426 (2)	0.0683 (7)
H16	0.3168	0.4189	0.4010	0.082*
C21	0.2116 (3)	−0.0610 (2)	−0.33190 (19)	0.0593 (6)
C22	0.0807 (3)	−0.0978 (3)	−0.4139 (2)	0.0804 (8)
H22	0.0098	−0.0610	−0.4059	0.096*
C23	0.0554 (4)	−0.1902 (3)	−0.5085 (3)	0.1042 (11)
H23	−0.0340	−0.2171	−0.5643	0.125*
C24	0.1586 (5)	−0.2423 (3)	−0.5214 (3)	0.1074 (12)
H24	0.1407	−0.3037	−0.5869	0.129*
C25	0.2905 (5)	−0.2055 (3)	−0.4385 (3)	0.1025 (11)
H25	0.3610	−0.2426	−0.4472	0.123*
C26	0.3175 (3)	−0.1128 (3)	−0.3422 (3)	0.0806 (8)
H26	0.4063	−0.0865	−0.2856	0.097*
C31	0.3108 (2)	−0.08783 (19)	0.0249 (2)	0.0614 (6)
C32	0.3310 (4)	−0.1936 (2)	−0.0180 (3)	0.1039 (11)
H32	0.3452	−0.2120	−0.0934	0.125*
C33	0.3300 (4)	−0.2724 (3)	0.0526 (3)	0.1257 (14)
H33	0.3432	−0.3443	0.0245	0.151*
C34	0.3095 (3)	−0.2449 (3)	0.1646 (3)	0.1040 (11)
H34	0.3084	−0.2985	0.2115	0.125*
C35	0.2907 (4)	−0.1382 (3)	0.2071 (3)	0.1187 (12)
H35	0.2771	−0.1195	0.2826	0.142*
C36	0.2923 (4)	−0.0592 (3)	0.1371 (2)	0.1049 (11)
H36	0.2809	0.0133	0.1658	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0622 (4)	0.0842 (5)	0.0536 (4)	−0.0046 (3)	0.0118 (3)	−0.0013 (3)
C1	0.0558 (13)	0.0537 (12)	0.0438 (11)	0.0110 (10)	0.0114 (10)	0.0051 (10)
N1	0.0600 (13)	0.0648 (13)	0.0423 (10)	0.0005 (10)	0.0081 (9)	0.0061 (9)
N2	0.0550 (12)	0.0595 (12)	0.0406 (10)	0.0043 (10)	0.0084 (9)	0.0049 (8)
C2	0.0623 (14)	0.0537 (13)	0.0421 (11)	0.0075 (11)	0.0109 (10)	0.0076 (10)
C3	0.0807 (17)	0.0584 (14)	0.0485 (13)	0.0154 (13)	0.0110 (12)	0.0104 (11)
C4	0.122 (2)	0.0632 (16)	0.0594 (16)	0.0296 (16)	0.0113 (15)	0.0098 (13)
C51	0.087 (2)	0.0559 (14)	0.0590 (15)	0.0195 (14)	0.0158 (14)	0.0108 (12)
C52	0.089 (2)	0.088 (2)	0.0609 (16)	0.0228 (17)	0.0253 (14)	0.0181 (15)
C53	0.105 (2)	0.114 (3)	0.079 (2)	0.053 (2)	0.0272 (18)	0.0252 (19)
C54	0.129 (3)	0.100 (2)	0.097 (2)	0.053 (2)	0.033 (2)	0.047 (2)
C55	0.131 (3)	0.112 (3)	0.111 (3)	0.039 (2)	0.059 (2)	0.064 (2)
C56	0.095 (2)	0.099 (2)	0.098 (2)	0.0425 (19)	0.0428 (18)	0.0421 (19)
P1	0.0611 (4)	0.0535 (3)	0.0468 (3)	0.0071 (3)	0.0150 (3)	0.0073 (3)
O1	0.0564 (10)	0.0610 (9)	0.0529 (9)	−0.0003 (8)	0.0107 (7)	0.0050 (7)
O2	0.0926 (13)	0.0573 (9)	0.0559 (9)	0.0088 (9)	0.0330 (9)	0.0065 (8)
O3	0.0601 (10)	0.0740 (11)	0.0838 (12)	0.0153 (9)	0.0156 (9)	0.0326 (10)
C11	0.0588 (14)	0.0667 (14)	0.0416 (12)	0.0119 (11)	0.0115 (10)	0.0095 (11)
C12	0.088 (2)	0.0750 (17)	0.0690 (17)	0.0220 (15)	0.0209 (14)	0.0253 (14)
C13	0.099 (2)	0.124 (3)	0.0696 (19)	0.037 (2)	0.0234 (16)	0.051 (2)
C14	0.082 (2)	0.131 (3)	0.0495 (16)	0.020 (2)	0.0088 (14)	0.0183 (18)
C15	0.092 (2)	0.092 (2)	0.0517 (15)	0.0073 (17)	0.0134 (14)	−0.0020 (15)
C16	0.0815 (18)	0.0652 (15)	0.0479 (13)	0.0128 (13)	0.0096 (12)	0.0076 (12)
C21	0.0729 (16)	0.0600 (14)	0.0460 (12)	0.0154 (12)	0.0222 (12)	0.0114 (11)
C22	0.086 (2)	0.098 (2)	0.0550 (15)	0.0300 (17)	0.0132 (14)	0.0152 (15)
C23	0.121 (3)	0.107 (3)	0.0575 (18)	0.011 (2)	0.0061 (18)	0.0022 (17)
C24	0.168 (4)	0.081 (2)	0.065 (2)	0.016 (2)	0.047 (2)	−0.0013 (16)
C25	0.149 (3)	0.088 (2)	0.105 (3)	0.058 (2)	0.075 (3)	0.028 (2)
C26	0.082 (2)	0.092 (2)	0.0732 (18)	0.0307 (17)	0.0267 (15)	0.0180 (16)
C31	0.0552 (14)	0.0591 (14)	0.0671 (15)	0.0148 (11)	0.0114 (12)	0.0166 (12)
C32	0.152 (3)	0.073 (2)	0.089 (2)	0.038 (2)	0.036 (2)	0.0130 (17)
C33	0.175 (4)	0.065 (2)	0.134 (3)	0.038 (2)	0.028 (3)	0.030 (2)
C34	0.089 (2)	0.096 (3)	0.121 (3)	0.0116 (19)	0.005 (2)	0.057 (2)
C35	0.155 (4)	0.136 (3)	0.096 (3)	0.065 (3)	0.046 (2)	0.059 (3)
C36	0.165 (3)	0.092 (2)	0.082 (2)	0.064 (2)	0.045 (2)	0.0317 (18)

Geometric parameters (Å, º)

S1—C1	1.663 (2)	C11—C16	1.382 (3)
C1—N1	1.349 (3)	C12—C13	1.398 (4)
C1—N2	1.363 (3)	C12—H12	0.9300
N1—C11	1.434 (3)	C13—C14	1.356 (4)
N1—H1	0.821 (19)	C13—H13	0.9300
N2—C2	1.457 (3)	C14—C15	1.364 (4)
N2—H2	0.891 (19)	C14—H14	0.9300
C2—C3	1.532 (3)	C15—C16	1.374 (3)
C2—P1	1.799 (2)	C15—H15	0.9300
C2—H201	0.9800	C16—H16	0.9300
C3—C4	1.519 (3)	C21—C26	1.362 (3)
C3—H301	0.9700	C21—C22	1.363 (3)
C3—H302	0.9700	C22—C23	1.371 (4)
C4—C51	1.510 (3)	C22—H22	0.9300
C4—H401	0.9700	C23—C24	1.344 (5)
C4—H402	0.9700	C23—H23	0.9300
C51—C56	1.369 (4)	C24—C25	1.374 (5)
C51—C52	1.374 (4)	C24—H24	0.9300
C52—C53	1.373 (4)	C25—C26	1.383 (4)
C52—H52	0.9300	C25—H25	0.9300
C53—C54	1.354 (4)	C26—H26	0.9300
C53—H53	0.9300	C31—C36	1.3750 (18)
C54—C55	1.375 (4)	C31—C32	1.374 (4)
C54—H54	0.9300	C32—C33	1.383 (5)
C55—C56	1.378 (4)	C32—H32	0.9300
C55—H55	0.9300	C33—C34	1.380 (5)
C56—H56	0.9300	C33—H33	0.9300
P1—O1	1.4680 (15)	C34—C35	1.378 (5)
P1—O3	1.5691 (17)	C34—H34	0.9300
P1—O2	1.5740 (16)	C35—C36	1.380 (5)
O2—C21	1.415 (3)	C35—H35	0.9300
O3—C31	1.388 (3)	C36—H36	0.9300
C11—C12	1.364 (3)
N1—C1—N2	112.47 (19)	C12—C11—N1	119.5 (2)
N1—C1—S1	124.00 (17)	C16—C11—N1	120.0 (2)
N2—C1—S1	123.53 (17)	C11—C12—C13	119.3 (3)
C1—N1—C11	125.1 (2)	C11—C12—H12	120.3
C1—N1—H1	114.3 (17)	C13—C12—H12	120.3
C11—N1—H1	118.3 (17)	C14—C13—C12	119.8 (3)
C1—N2—C2	124.18 (19)	C14—C13—H13	120.1
C1—N2—H2	116.4 (15)	C12—C13—H13	120.1
C2—N2—H2	118.2 (15)	C13—C14—C15	120.8 (3)
N2—C2—C3	112.88 (19)	C13—C14—H14	119.6
N2—C2—P1	106.59 (14)	C15—C14—H14	119.6
C3—C2—P1	114.31 (15)	C14—C15—C16	120.1 (3)
N2—C2—H201	107.6	C14—C15—H15	120.0
C3—C2—H201	107.6	C16—C15—H15	120.0
P1—C2—H201	107.6	C15—C16—C11	119.6 (3)
C4—C3—C2	111.93 (19)	C15—C16—H16	120.2
C4—C3—H301	109.2	C11—C16—H16	120.2
C2—C3—H301	109.2	C26—C21—C22	121.7 (2)
C4—C3—H302	109.2	C26—C21—O2	119.8 (2)
C2—C3—H302	109.2	C22—C21—O2	118.4 (2)
H301—C3—H302	107.9	C21—C22—C23	118.8 (3)
C51—C4—C3	113.3 (2)	C21—C22—H22	120.6
C51—C4—H401	108.9	C23—C22—H22	120.6
C3—C4—H401	108.9	C24—C23—C22	120.6 (3)
C51—C4—H402	108.9	C24—C23—H23	119.7
C3—C4—H402	108.9	C22—C23—H23	119.7
H401—C4—H402	107.7	C23—C24—C25	120.6 (3)
C56—C51—C52	117.8 (3)	C23—C24—H24	119.7
C56—C51—C4	120.7 (3)	C25—C24—H24	119.7
C52—C51—C4	121.5 (3)	C24—C25—C26	119.5 (3)
C53—C52—C51	121.0 (3)	C24—C25—H25	120.2
C53—C52—H52	119.5	C26—C25—H25	120.2
C51—C52—H52	119.5	C21—C26—C25	118.7 (3)
C54—C53—C52	121.0 (3)	C21—C26—H26	120.6
C54—C53—H53	119.5	C25—C26—H26	120.6
C52—C53—H53	119.5	C36—C31—C32	120.9 (2)
C53—C54—C55	118.9 (3)	C36—C31—O3	120.1 (2)
C53—C54—H54	120.6	C32—C31—O3	118.7 (2)
C55—C54—H54	120.6	C31—C32—C33	118.9 (3)
C54—C55—C56	120.0 (3)	C31—C32—H32	120.5
C54—C55—H55	120.0	C33—C32—H32	120.5
C56—C55—H55	120.0	C34—C33—C32	120.5 (3)
C51—C56—C55	121.3 (3)	C34—C33—H33	119.7
C51—C56—H56	119.3	C32—C33—H33	119.7
C55—C56—H56	119.3	C35—C34—C33	120.0 (3)
O1—P1—O3	114.03 (9)	C35—C34—H34	120.0
O1—P1—O2	115.74 (9)	C33—C34—H34	120.0
O3—P1—O2	103.91 (10)	C34—C35—C36	119.7 (3)
O1—P1—C2	114.59 (10)	C34—C35—H35	120.1
O3—P1—C2	105.48 (10)	C36—C35—H35	120.1
O2—P1—C2	101.63 (9)	C31—C36—C35	119.9 (3)
C21—O2—P1	122.72 (14)	C31—C36—H36	120.0
C31—O3—P1	126.81 (15)	C35—C36—H36	120.0
C12—C11—C16	120.4 (2)
N2—C1—N1—C11	175.4 (2)	C1—N1—C11—C12	−115.1 (3)
S1—C1—N1—C11	−4.5 (4)	C1—N1—C11—C16	68.2 (3)
N1—C1—N2—C2	−170.9 (2)	C16—C11—C12—C13	−0.8 (4)
S1—C1—N2—C2	9.0 (3)	N1—C11—C12—C13	−177.5 (2)
C1—N2—C2—C3	−117.7 (2)	C11—C12—C13—C14	0.8 (5)
C1—N2—C2—P1	116.0 (2)	C12—C13—C14—C15	−0.8 (5)
N2—C2—C3—C4	62.1 (3)	C13—C14—C15—C16	0.9 (5)
P1—C2—C3—C4	−175.80 (19)	C14—C15—C16—C11	−1.0 (4)
C2—C3—C4—C51	174.0 (2)	C12—C11—C16—C15	0.9 (4)
C3—C4—C51—C56	−85.6 (3)	N1—C11—C16—C15	177.6 (2)
C3—C4—C51—C52	96.3 (3)	P1—O2—C21—C26	−97.4 (3)
C56—C51—C52—C53	0.4 (4)	P1—O2—C21—C22	86.1 (3)
C4—C51—C52—C53	178.6 (3)	C26—C21—C22—C23	0.6 (4)
C51—C52—C53—C54	−1.0 (5)	O2—C21—C22—C23	177.0 (2)
C52—C53—C54—C55	2.0 (5)	C21—C22—C23—C24	−1.2 (5)
C53—C54—C55—C56	−2.5 (6)	C22—C23—C24—C25	1.4 (6)
C52—C51—C56—C55	−1.0 (4)	C23—C24—C25—C26	−1.1 (5)
C4—C51—C56—C55	−179.2 (3)	C22—C21—C26—C25	−0.2 (4)
C54—C55—C56—C51	2.1 (5)	O2—C21—C26—C25	−176.6 (2)
N2—C2—P1—O1	51.62 (18)	C24—C25—C26—C21	0.4 (5)
C3—C2—P1—O1	−73.82 (19)	P1—O3—C31—C36	−80.9 (3)
N2—C2—P1—O3	−74.64 (16)	P1—O3—C31—C32	105.2 (3)
C3—C2—P1—O3	159.92 (16)	C36—C31—C32—C33	1.2 (5)
N2—C2—P1—O2	177.20 (14)	O3—C31—C32—C33	175.0 (3)
C3—C2—P1—O2	51.76 (19)	C31—C32—C33—C34	−0.2 (6)
O1—P1—O2—C21	−44.1 (2)	C32—C33—C34—C35	−0.4 (6)
O3—P1—O2—C21	81.70 (19)	C33—C34—C35—C36	0.1 (6)
C2—P1—O2—C21	−168.93 (19)	C32—C31—C36—C35	−1.4 (5)
O1—P1—O3—C31	−9.8 (2)	O3—C31—C36—C35	−175.2 (3)
O2—P1—O3—C31	−136.67 (18)	C34—C35—C36—C31	0.8 (6)
C2—P1—O3—C31	116.82 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.82 (2)	2.06 (2)	2.861 (2)	163 (2)
N2—H2···O1^i	0.89 (2)	2.14 (2)	2.967 (2)	153 (2)

Symmetry code: (i) −x, −y, −z.

(II) diphenyl [1-(3-phenylthioureido)benzyl]phosphonate

Crystal data

C26H23N2O3PS	Z = 2
Mr = 474.49	F(000) = 496
Triclinic, P1	Dx = 1.319 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 9.953 (1) Å	Cell parameters from 22 reflections
b = 10.046 (1) Å	θ = 22.6–29.5°
c = 12.701 (1) Å	µ = 2.09 mm^−1
α = 96.66 (1)°	T = 293 K
β = 104.45 (1)°	Plate, colourless
γ = 99.84 (1)°	0.2 × 0.2 × 0.1 mm
V = 1194.8 (2) Å^3

Data collection

AFC5S Rigaku diffractometer	2147 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 67.5°, θmin = 3.6°
ω scans	h = −11→11
Absorption correction: analytical (De Meulenaer & Tompa, 1965)	k = −11→12
Tmin = 0.675, Tmax = 0.836	l = −15→15
4431 measured reflections	3 standard reflections every 150 reflections
4169 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	[1.00000exp(3.00(sinθ/λ)^2)]/ [σ^2(Fo^2) + 0.0000*P + (0.029P)^2] where P = 0.33333Fo^2 + 0.66667Fc^2
S = 1.00	(Δ/σ)max < 0.001
4169 reflections	Δρmax = 0.19 e Å^−3
307 parameters	Δρmin = −0.23 e Å^−3
8 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0060 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.42318 (8)	0.35393 (8)	0.18474 (6)	0.0552 (2)
C1	0.2577 (3)	0.2655 (3)	0.1562 (2)	0.0434 (7)
N1	0.1930 (3)	0.2320 (3)	0.23379 (18)	0.0532 (6)
H1	0.117 (3)	0.170 (3)	0.206 (2)	0.086 (12)*
N2	0.1737 (3)	0.2185 (3)	0.05246 (18)	0.0515 (6)
H2	0.096 (3)	0.167 (3)	0.046 (2)	0.081 (12)*
C2	0.2215 (3)	0.2261 (3)	−0.0465 (2)	0.0479 (7)
H201	0.3243	0.2610	−0.0216	0.057*
C41	0.1596 (3)	0.3245 (3)	−0.1180 (2)	0.0488 (7)
C42	0.2302 (4)	0.3774 (3)	−0.1895 (2)	0.0681 (9)
H42	0.3126	0.3491	−0.1955	0.082*
C43	0.1817 (4)	0.4708 (4)	−0.2518 (3)	0.0806 (11)
H43	0.2311	0.5052	−0.2994	0.097*
C44	0.0609 (4)	0.5134 (4)	−0.2442 (3)	0.0809 (11)
H44	0.0275	0.5765	−0.2867	0.097*
C45	−0.0106 (4)	0.4630 (4)	−0.1739 (3)	0.0956 (13)
H45	−0.0925	0.4925	−0.1679	0.115*
C46	0.0386 (3)	0.3676 (4)	−0.1112 (3)	0.0773 (10)
H46	−0.0115	0.3328	−0.0641	0.093*
P1	0.19360 (8)	0.05058 (8)	−0.11229 (6)	0.0506 (2)
O1	0.05553 (19)	−0.03446 (19)	−0.11845 (14)	0.0566 (5)
O2	0.2266 (2)	0.06605 (19)	−0.22583 (14)	0.0612 (6)
O3	0.3242 (2)	−0.0014 (2)	−0.04599 (16)	0.0637 (6)
C11	0.2629 (3)	0.2483 (3)	0.3487 (2)	0.0521 (7)
C12	0.2855 (4)	0.1331 (4)	0.3931 (3)	0.0753 (10)
H12	0.2592	0.0474	0.3486	0.090*
C13	0.3482 (4)	0.1469 (5)	0.5051 (3)	0.1023 (15)
H13	0.3642	0.0697	0.5361	0.123*
C14	0.3869 (4)	0.2723 (6)	0.5703 (3)	0.1088 (18)
H14	0.4284	0.2802	0.6456	0.131*
C15	0.3648 (4)	0.3861 (5)	0.5256 (3)	0.0952 (13)
H15	0.3922	0.4718	0.5702	0.114*
C16	0.3015 (3)	0.3744 (3)	0.4136 (2)	0.0693 (9)
H16	0.2854	0.4518	0.3829	0.083*
C21	0.2082 (3)	−0.0483 (3)	−0.3075 (2)	0.0548 (8)
C22	0.0815 (4)	−0.0869 (4)	−0.3868 (3)	0.0732 (10)
H22	0.0075	−0.0426	−0.3840	0.088*
C23	0.0654 (4)	−0.1934 (4)	−0.4717 (3)	0.0915 (12)
H23	−0.0199	−0.2210	−0.5267	0.110*
C24	0.1753 (5)	−0.2579 (4)	−0.4745 (3)	0.0959 (13)
H24	0.1644	−0.3291	−0.5317	0.115*
C25	0.3000 (4)	−0.2188 (4)	−0.3944 (3)	0.0837 (11)
H25	0.3738	−0.2635	−0.3972	0.100*
C26	0.3183 (3)	−0.1131 (3)	−0.3088 (2)	0.0656 (9)
H26	0.4034	−0.0867	−0.2533	0.079*
C31	0.3225 (3)	−0.1048 (3)	0.0186 (2)	0.0526 (7)
C32	0.3441 (4)	−0.2300 (3)	−0.0224 (3)	0.0755 (10)
H32	0.3502	−0.2481	−0.0944	0.091*
C33	0.3566 (4)	−0.3286 (3)	0.0448 (2)	0.0800 (11)
H33	0.3713	−0.4133	0.0176	0.096*
C34	0.3475 (3)	−0.3036 (3)	0.1515 (2)	0.0736 (10)
H34	0.3556	−0.3706	0.1962	0.088*
C35	0.3262 (5)	−0.1772 (3)	0.1907 (3)	0.1026 (14)
H35	0.3204	−0.1591	0.2627	0.123*
C36	0.3132 (4)	−0.0769 (3)	0.1250 (2)	0.0889 (12)
H36	0.2984	0.0078	0.1521	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0522 (5)	0.0564 (5)	0.0503 (4)	0.0032 (4)	0.0088 (4)	0.0050 (4)
C1	0.0455 (17)	0.0445 (16)	0.0377 (14)	0.0113 (13)	0.0058 (12)	0.0066 (12)
N1	0.0537 (16)	0.0625 (17)	0.0371 (13)	0.0002 (14)	0.0104 (12)	0.0054 (12)
N2	0.0492 (16)	0.0641 (17)	0.0366 (13)	0.0042 (14)	0.0093 (12)	0.0063 (12)
C2	0.0482 (17)	0.0558 (18)	0.0387 (15)	0.0091 (14)	0.0113 (13)	0.0077 (13)
C41	0.0521 (18)	0.0516 (18)	0.0406 (15)	0.0092 (15)	0.0105 (13)	0.0064 (13)
C42	0.080 (2)	0.072 (2)	0.068 (2)	0.0296 (19)	0.0318 (18)	0.0279 (19)
C43	0.105 (3)	0.080 (3)	0.076 (2)	0.030 (2)	0.042 (2)	0.037 (2)
C44	0.090 (3)	0.083 (3)	0.073 (2)	0.029 (2)	0.014 (2)	0.031 (2)
C45	0.082 (3)	0.118 (4)	0.116 (3)	0.052 (3)	0.039 (2)	0.064 (3)
C46	0.071 (2)	0.097 (3)	0.083 (2)	0.031 (2)	0.0315 (19)	0.047 (2)
P1	0.0520 (5)	0.0547 (5)	0.0442 (4)	0.0090 (4)	0.0133 (4)	0.0068 (4)
O1	0.0473 (12)	0.0625 (13)	0.0517 (12)	−0.0036 (10)	0.0121 (9)	0.0023 (10)
O2	0.0854 (15)	0.0561 (13)	0.0467 (11)	0.0119 (11)	0.0302 (11)	0.0043 (10)
O3	0.0494 (12)	0.0654 (14)	0.0813 (15)	0.0161 (11)	0.0154 (10)	0.0314 (12)
C11	0.0557 (18)	0.062 (2)	0.0370 (15)	0.0095 (16)	0.0124 (13)	0.0078 (14)
C12	0.098 (3)	0.079 (2)	0.062 (2)	0.031 (2)	0.030 (2)	0.0263 (19)
C13	0.109 (3)	0.155 (5)	0.071 (3)	0.060 (3)	0.035 (3)	0.061 (3)
C14	0.084 (3)	0.200 (6)	0.044 (2)	0.034 (4)	0.014 (2)	0.028 (3)
C15	0.095 (3)	0.123 (4)	0.049 (2)	−0.002 (3)	0.015 (2)	−0.015 (2)
C16	0.080 (2)	0.072 (2)	0.0486 (18)	0.0083 (19)	0.0137 (17)	0.0002 (17)
C21	0.067 (2)	0.0546 (19)	0.0465 (17)	0.0156 (17)	0.0210 (15)	0.0068 (15)
C22	0.067 (2)	0.085 (3)	0.066 (2)	0.022 (2)	0.0147 (18)	0.005 (2)
C23	0.089 (3)	0.099 (3)	0.065 (2)	0.007 (2)	0.000 (2)	−0.004 (2)
C24	0.137 (4)	0.080 (3)	0.066 (2)	0.029 (3)	0.025 (3)	−0.008 (2)
C25	0.109 (3)	0.083 (3)	0.078 (3)	0.048 (2)	0.039 (2)	0.017 (2)
C26	0.073 (2)	0.073 (2)	0.0565 (19)	0.0268 (19)	0.0201 (17)	0.0126 (17)
C31	0.0459 (17)	0.0489 (19)	0.0618 (19)	0.0108 (14)	0.0109 (14)	0.0122 (15)
C32	0.097 (3)	0.060 (2)	0.072 (2)	0.025 (2)	0.026 (2)	0.0058 (19)
C33	0.094 (3)	0.050 (2)	0.092 (3)	0.0206 (19)	0.016 (2)	0.008 (2)
C34	0.077 (2)	0.060 (2)	0.079 (2)	0.0158 (19)	0.008 (2)	0.0211 (19)
C35	0.173 (4)	0.084 (3)	0.068 (2)	0.061 (3)	0.036 (3)	0.025 (2)
C36	0.150 (4)	0.064 (2)	0.064 (2)	0.053 (2)	0.028 (2)	0.0175 (19)

Geometric parameters (Å, º)

S1—C1	1.662 (3)	C13—C14	1.362 (5)
C1—N1	1.349 (3)	C13—H13	0.9300
C1—N2	1.352 (3)	C14—C15	1.361 (5)
N1—C11	1.429 (3)	C14—H14	0.9300
N1—H1	0.86 (2)	C15—C16	1.387 (4)
N2—C2	1.456 (3)	C15—H15	0.9300
N2—H2	0.84 (2)	C16—H16	0.9300
C2—C41	1.522 (3)	C21—C22	1.365 (4)
C2—P1	1.806 (3)	C21—C26	1.370 (4)
C2—H201	0.9800	C22—C23	1.386 (4)
C41—C46	1.367 (4)	C22—H22	0.9300
C41—C42	1.380 (4)	C23—C24	1.369 (5)
C42—C43	1.369 (4)	C23—H23	0.9300
C42—H42	0.9300	C24—C25	1.356 (5)
C43—C44	1.365 (4)	C24—H24	0.9300
C43—H43	0.9300	C25—C26	1.382 (4)
C44—C45	1.363 (4)	C25—H25	0.9300
C44—H44	0.9300	C26—H26	0.9300
C45—C46	1.391 (4)	C31—C36	1.377 (4)
C45—H45	0.9300	C31—C32	1.377 (4)
C46—H46	0.9300	C32—C33	1.382 (4)
P1—O1	1.4677 (19)	C32—H32	0.9300
P1—O3	1.5680 (19)	C33—C34	1.378 (4)
P1—O2	1.5757 (18)	C33—H33	0.9300
O2—C21	1.410 (3)	C34—C35	1.380 (5)
O3—C31	1.397 (3)	C34—H34	0.9300
C11—C16	1.365 (4)	C35—C36	1.383 (4)
C11—C12	1.373 (4)	C35—H35	0.9300
C12—C13	1.383 (4)	C36—H36	0.9300
C12—H12	0.9300
N1—C1—N2	112.7 (2)	C14—C13—H13	119.6
N1—C1—S1	123.7 (2)	C12—C13—H13	119.6
N2—C1—S1	123.5 (2)	C15—C14—C13	120.1 (4)
C1—N1—C11	124.6 (2)	C15—C14—H14	119.9
C1—N1—H1	112 (2)	C13—C14—H14	119.9
C11—N1—H1	119 (2)	C14—C15—C16	120.0 (4)
C1—N2—C2	124.2 (3)	C14—C15—H15	120.0
C1—N2—H2	117 (2)	C16—C15—H15	120.0
C2—N2—H2	118 (2)	C11—C16—C15	119.5 (3)
N2—C2—C41	114.5 (2)	C11—C16—H16	120.2
N2—C2—P1	105.27 (19)	C15—C16—H16	120.2
C41—C2—P1	116.62 (17)	C22—C21—C26	121.9 (3)
N2—C2—H201	106.6	C22—C21—O2	118.2 (3)
C41—C2—H201	106.6	C26—C21—O2	119.8 (3)
P1—C2—H201	106.6	C21—C22—C23	118.7 (3)
C46—C41—C42	118.0 (3)	C21—C22—H22	120.6
C46—C41—C2	122.4 (3)	C23—C22—H22	120.6
C42—C41—C2	119.5 (3)	C24—C23—C22	119.9 (3)
C43—C42—C41	121.5 (3)	C24—C23—H23	120.0
C43—C42—H42	119.3	C22—C23—H23	120.0
C41—C42—H42	119.3	C25—C24—C23	120.5 (4)
C44—C43—C42	120.1 (3)	C25—C24—H24	119.8
C44—C43—H43	120.0	C23—C24—H24	119.8
C42—C43—H43	120.0	C24—C25—C26	120.7 (4)
C45—C44—C43	119.6 (3)	C24—C25—H25	119.7
C45—C44—H44	120.2	C26—C25—H25	119.7
C43—C44—H44	120.2	C21—C26—C25	118.3 (3)
C44—C45—C46	120.1 (3)	C21—C26—H26	120.8
C44—C45—H45	119.9	C25—C26—H26	120.8
C46—C45—H45	119.9	C36—C31—C32	121.1 (3)
C41—C46—C45	120.7 (3)	C36—C31—O3	120.0 (2)
C41—C46—H46	119.6	C32—C31—O3	118.6 (2)
C45—C46—H46	119.6	C31—C32—C33	119.1 (3)
O1—P1—O3	114.26 (11)	C31—C32—H32	120.5
O1—P1—O2	116.08 (11)	C33—C32—H32	120.5
O3—P1—O2	103.52 (11)	C34—C33—C32	121.2 (3)
O1—P1—C2	114.70 (12)	C34—C33—H33	119.4
O3—P1—C2	103.79 (12)	C32—C33—H33	119.4
O2—P1—C2	102.91 (11)	C33—C34—C35	118.6 (3)
C21—O2—P1	121.86 (17)	C33—C34—H34	120.7
C31—O3—P1	127.39 (17)	C35—C34—H34	120.7
C16—C11—C12	120.9 (3)	C34—C35—C36	121.3 (3)
C16—C11—N1	120.9 (3)	C34—C35—H35	119.3
C12—C11—N1	118.2 (3)	C36—C35—H35	119.3
C11—C12—C13	118.7 (4)	C31—C36—C35	118.8 (3)
C11—C12—H12	120.6	C31—C36—H36	120.6
C13—C12—H12	120.6	C35—C36—H36	120.6
C14—C13—C12	120.8 (4)
N2—C1—N1—C11	169.3 (3)	C1—N1—C11—C16	76.1 (4)
S1—C1—N1—C11	−10.3 (4)	C1—N1—C11—C12	−106.3 (3)
N1—C1—N2—C2	−172.7 (3)	C16—C11—C12—C13	0.0 (5)
S1—C1—N2—C2	6.9 (4)	N1—C11—C12—C13	−177.5 (3)
C1—N2—C2—C41	−111.4 (3)	C11—C12—C13—C14	0.0 (6)
C1—N2—C2—P1	119.1 (3)	C12—C13—C14—C15	−0.4 (7)
N2—C2—C41—C46	−20.0 (4)	C13—C14—C15—C16	0.7 (6)
P1—C2—C41—C46	103.6 (3)	C12—C11—C16—C15	0.2 (5)
N2—C2—C41—C42	157.3 (3)	N1—C11—C16—C15	177.8 (3)
P1—C2—C41—C42	−79.2 (3)	C14—C15—C16—C11	−0.6 (6)
C46—C41—C42—C43	0.2 (5)	P1—O2—C21—C22	92.8 (3)
C2—C41—C42—C43	−177.1 (3)	P1—O2—C21—C26	−90.3 (3)
C41—C42—C43—C44	−0.1 (5)	C26—C21—C22—C23	−1.0 (5)
C42—C43—C44—C45	0.3 (6)	O2—C21—C22—C23	175.8 (3)
C43—C44—C45—C46	−0.7 (6)	C21—C22—C23—C24	0.2 (6)
C42—C41—C46—C45	−0.6 (5)	C22—C23—C24—C25	0.3 (6)
C2—C41—C46—C45	176.7 (3)	C23—C24—C25—C26	−0.1 (6)
C44—C45—C46—C41	0.8 (6)	C22—C21—C26—C25	1.2 (5)
N2—C2—P1—O1	45.4 (2)	O2—C21—C26—C25	−175.5 (3)
C41—C2—P1—O1	−82.7 (2)	C24—C25—C26—C21	−0.6 (5)
N2—C2—P1—O3	−79.93 (19)	P1—O3—C31—C36	−81.4 (3)
C41—C2—P1—O3	151.9 (2)	P1—O3—C31—C32	104.7 (3)
N2—C2—P1—O2	172.42 (17)	C36—C31—C32—C33	−0.1 (5)
C41—C2—P1—O2	44.3 (2)	O3—C31—C32—C33	173.7 (3)
O1—P1—O2—C21	−49.5 (3)	C31—C32—C33—C34	0.1 (5)
O3—P1—O2—C21	76.6 (2)	C32—C33—C34—C35	−0.3 (6)
C2—P1—O2—C21	−175.6 (2)	C33—C34—C35—C36	0.3 (6)
O1—P1—O3—C31	−9.7 (3)	C32—C31—C36—C35	0.1 (5)
O2—P1—O3—C31	−136.8 (2)	O3—C31—C36—C35	−173.6 (3)
C2—P1—O3—C31	116.0 (2)	C34—C35—C36—C31	−0.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86 (2)	1.98 (2)	2.836 (3)	170 (3)
N2—H2···O1^i	0.84 (2)	2.27 (3)	3.033 (3)	151 (3)

Symmetry code: (i) −x, −y, −z.

(III) diphenyl [2,2-dimethyl-1-(3-phenylthioureido)propyl]phosphonate

Crystal data

C24H27N2O3PS	F(000) = 960
Mr = 454.51	Dx = 1.256 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.688 (3) Å	θ = 22.7–28.8°
b = 9.888 (2) Å	µ = 2.04 mm^−1
c = 22.961 (2) Å	T = 293 K
β = 97.790 (1)°	Prism, colourless
V = 2404.2 (9) Å^3	0.5 × 0.5 × 0.45 mm
Z = 4

Data collection

AFC5S Rigaku diffractometer	3100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 67.5°, θmin = 3.9°
ω scans	h = −12→12
Absorption correction: analytical (De Meulenaer & Tompa, 1965)	k = −8→11
Tmin = 0.427, Tmax = 0.464	l = −27→27
4439 measured reflections	3 standard reflections every 150 reflections
4193 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0821P)^2 + 0.0698P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4193 reflections	Δρmax = 0.22 e Å^−3
289 parameters	Δρmin = −0.37 e Å^−3
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0108 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.17928 (6)	0.49548 (6)	0.62637 (3)	0.0770 (2)
C1	0.3152 (2)	0.5341 (2)	0.60363 (8)	0.0586 (5)
N1	0.3889 (2)	0.6401 (2)	0.62376 (8)	0.0699 (5)
H1	0.4647 (12)	0.642 (2)	0.6158 (11)	0.076 (8)*
N2	0.36643 (19)	0.46038 (19)	0.56292 (8)	0.0651 (5)
H2	0.4402 (12)	0.487 (2)	0.5564 (9)	0.061 (6)*
C2	0.3140 (2)	0.3335 (2)	0.53824 (9)	0.0652 (6)
H201	0.2330	0.3200	0.5529	0.078*
C3	0.3976 (3)	0.2084 (3)	0.55747 (11)	0.0802 (7)
C4	0.5148 (3)	0.2015 (3)	0.52621 (14)	0.1040 (10)
H401	0.5676	0.1282	0.5421	0.156*
H402	0.5607	0.2850	0.5320	0.156*
H403	0.4896	0.1871	0.4849	0.156*
C5	0.4382 (4)	0.2178 (3)	0.62412 (14)	0.1215 (13)
H501	0.4934	0.2939	0.6326	0.182*
H502	0.4817	0.1365	0.6378	0.182*
H503	0.3649	0.2289	0.6436	0.182*
C6	0.3178 (3)	0.0799 (3)	0.54434 (16)	0.1045 (10)
H601	0.2403	0.0886	0.5609	0.157*
H602	0.3639	0.0030	0.5614	0.157*
H603	0.2992	0.0677	0.5026	0.157*
P1	0.27923 (6)	0.37191 (6)	0.46068 (2)	0.0621 (2)
O1	0.38380 (14)	0.42621 (17)	0.43252 (7)	0.0715 (4)
O2	0.22051 (16)	0.23709 (15)	0.43225 (7)	0.0731 (4)
O3	0.16046 (15)	0.46780 (15)	0.45700 (7)	0.0702 (4)
C11	0.3580 (2)	0.7455 (2)	0.66184 (10)	0.0673 (6)
C12	0.2480 (3)	0.8163 (3)	0.65081 (14)	0.0951 (9)
H12	0.1889	0.7936	0.6187	0.114*
C13	0.2240 (4)	0.9214 (3)	0.68708 (19)	0.1168 (12)
H13	0.1477	0.9676	0.6797	0.140*
C14	0.3091 (4)	0.9587 (3)	0.73316 (16)	0.1100 (11)
H14	0.2914	1.0293	0.7575	0.132*
C15	0.4209 (4)	0.8918 (3)	0.74348 (14)	0.1235 (13)
H15	0.4812	0.9180	0.7745	0.148*
C16	0.4456 (3)	0.7832 (3)	0.70750 (12)	0.1001 (9)
H16	0.5218	0.7369	0.7149	0.120*
C21	0.1867 (3)	0.2258 (2)	0.37060 (10)	0.0705 (6)
C22	0.2550 (3)	0.1430 (3)	0.34030 (12)	0.0946 (9)
H22	0.3255	0.0976	0.3590	0.114*
C23	0.2165 (4)	0.1276 (4)	0.27988 (15)	0.1134 (11)
H23	0.2622	0.0714	0.2581	0.136*
C24	0.1141 (4)	0.1932 (4)	0.25290 (14)	0.1096 (10)
H24	0.0899	0.1826	0.2127	0.132*
C25	0.0467 (3)	0.2742 (4)	0.28439 (14)	0.1132 (11)
H25	−0.0239	0.3192	0.2657	0.136*
C26	0.0816 (3)	0.2909 (3)	0.34405 (12)	0.0950 (9)
H26	0.0343	0.3456	0.3658	0.114*
C31	0.1481 (2)	0.6040 (2)	0.44149 (11)	0.0689 (6)
C32	0.1780 (3)	0.6484 (3)	0.38863 (13)	0.0936 (9)
H32	0.2129	0.5903	0.3633	0.112*
C33	0.1541 (4)	0.7841 (4)	0.37403 (18)	0.1240 (14)
H33	0.1737	0.8187	0.3387	0.149*
C34	0.1005 (4)	0.8666 (4)	0.4132 (3)	0.1406 (17)
H34	0.0838	0.9567	0.4035	0.169*
C35	0.0724 (4)	0.8185 (4)	0.4650 (2)	0.1260 (13)
H35	0.0380	0.8757	0.4907	0.151*
C36	0.0946 (3)	0.6854 (3)	0.47959 (13)	0.0883 (8)
H36	0.0736	0.6510	0.5147	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0839 (5)	0.0743 (4)	0.0793 (4)	−0.0083 (3)	0.0346 (3)	−0.0059 (3)
C1	0.0676 (13)	0.0567 (11)	0.0533 (11)	0.0027 (10)	0.0144 (9)	−0.0011 (9)
N1	0.0722 (13)	0.0682 (12)	0.0736 (12)	−0.0074 (10)	0.0252 (10)	−0.0187 (9)
N2	0.0685 (12)	0.0645 (11)	0.0650 (11)	−0.0105 (9)	0.0194 (9)	−0.0140 (9)
C2	0.0771 (14)	0.0553 (12)	0.0656 (13)	−0.0041 (11)	0.0185 (11)	−0.0098 (10)
C3	0.0995 (19)	0.0645 (14)	0.0756 (15)	0.0098 (14)	0.0079 (13)	−0.0048 (12)
C4	0.097 (2)	0.092 (2)	0.121 (2)	0.0274 (18)	0.0086 (18)	−0.0111 (18)
C5	0.169 (3)	0.103 (2)	0.0840 (19)	0.035 (2)	−0.012 (2)	0.0042 (18)
C6	0.132 (3)	0.0607 (15)	0.121 (2)	0.0038 (17)	0.018 (2)	0.0073 (15)
P1	0.0689 (4)	0.0570 (3)	0.0622 (3)	−0.0041 (3)	0.0156 (3)	−0.0081 (2)
O1	0.0700 (10)	0.0784 (10)	0.0697 (9)	−0.0079 (8)	0.0229 (8)	−0.0067 (8)
O2	0.0911 (11)	0.0609 (9)	0.0673 (9)	−0.0085 (8)	0.0115 (8)	−0.0124 (7)
O3	0.0711 (10)	0.0563 (8)	0.0865 (10)	0.0016 (7)	0.0220 (8)	0.0029 (7)
C11	0.0885 (16)	0.0573 (12)	0.0592 (12)	−0.0021 (12)	0.0208 (11)	−0.0064 (9)
C12	0.096 (2)	0.0744 (16)	0.114 (2)	0.0073 (16)	0.0114 (17)	−0.0185 (15)
C13	0.111 (3)	0.080 (2)	0.164 (4)	0.0141 (19)	0.035 (2)	−0.030 (2)
C14	0.163 (3)	0.0755 (18)	0.101 (2)	0.010 (2)	0.051 (2)	−0.0159 (17)
C15	0.191 (4)	0.094 (2)	0.0776 (19)	0.014 (3)	−0.010 (2)	−0.0262 (16)
C16	0.126 (2)	0.0842 (18)	0.0835 (18)	0.0202 (18)	−0.0085 (17)	−0.0219 (15)
C21	0.0836 (16)	0.0635 (13)	0.0657 (13)	−0.0082 (12)	0.0146 (12)	−0.0148 (11)
C22	0.111 (2)	0.0879 (19)	0.0840 (18)	0.0190 (17)	0.0109 (16)	−0.0212 (15)
C23	0.136 (3)	0.117 (3)	0.088 (2)	0.024 (2)	0.020 (2)	−0.0365 (19)
C24	0.118 (3)	0.128 (3)	0.0808 (19)	0.000 (2)	0.0068 (18)	−0.0278 (19)
C25	0.103 (2)	0.138 (3)	0.092 (2)	0.016 (2)	−0.0092 (17)	−0.031 (2)
C26	0.0858 (18)	0.114 (2)	0.0839 (17)	0.0072 (17)	0.0059 (14)	−0.0325 (17)
C31	0.0689 (14)	0.0594 (13)	0.0754 (15)	−0.0075 (11)	−0.0011 (11)	0.0026 (11)
C32	0.100 (2)	0.093 (2)	0.0843 (17)	−0.0124 (17)	0.0016 (15)	0.0190 (15)
C33	0.124 (3)	0.117 (3)	0.121 (3)	−0.028 (2)	−0.020 (2)	0.050 (2)
C34	0.126 (3)	0.080 (2)	0.202 (5)	−0.002 (2)	−0.028 (3)	0.039 (3)
C35	0.129 (3)	0.0659 (18)	0.180 (4)	0.013 (2)	0.008 (3)	−0.007 (2)
C36	0.0911 (19)	0.0656 (15)	0.108 (2)	0.0069 (14)	0.0146 (15)	−0.0118 (14)

Geometric parameters (Å, º)

S1—C1	1.654 (2)	C12—H12	0.9300
C1—N1	1.354 (3)	C13—C14	1.350 (5)
C1—N2	1.358 (3)	C13—H13	0.9300
N1—C11	1.427 (3)	C14—C15	1.359 (5)
N1—H1	0.854 (10)	C14—H14	0.9300
N2—C2	1.457 (3)	C15—C16	1.401 (4)
N2—H2	0.864 (10)	C15—H15	0.9300
C2—C3	1.554 (3)	C16—H16	0.9300
C2—P1	1.809 (2)	C21—C22	1.350 (3)
C2—H201	0.9800	C21—C26	1.365 (4)
C3—C4	1.527 (4)	C22—C23	1.401 (4)
C3—C5	1.536 (4)	C22—H22	0.9300
C3—C6	1.538 (4)	C23—C24	1.348 (5)
C4—H401	0.9600	C23—H23	0.9300
C4—H402	0.9600	C24—C25	1.350 (4)
C4—H403	0.9600	C24—H24	0.9300
C5—H501	0.9600	C25—C26	1.380 (4)
C5—H502	0.9600	C25—H25	0.9300
C5—H503	0.9600	C26—H26	0.9300
C6—H601	0.9600	C31—C32	1.368 (3)
C6—H602	0.9600	C31—C36	1.370 (3)
C6—H603	0.9600	C32—C33	1.398 (5)
P1—O1	1.4668 (15)	C32—H32	0.9300
P1—O2	1.5768 (15)	C33—C34	1.394 (6)
P1—O3	1.5774 (16)	C33—H33	0.9300
O2—C21	1.417 (3)	C34—C35	1.352 (6)
O3—C31	1.395 (3)	C34—H34	0.9300
C11—C16	1.359 (4)	C35—C36	1.371 (4)
C11—C12	1.362 (4)	C35—H35	0.9300
C12—C13	1.378 (4)	C36—H36	0.9300
N1—C1—N2	112.37 (19)	C11—C12—H12	119.9
N1—C1—S1	124.48 (16)	C13—C12—H12	119.9
N2—C1—S1	123.14 (17)	C14—C13—C12	121.3 (3)
C1—N1—C11	127.0 (2)	C14—C13—H13	119.4
C1—N1—H1	117.9 (17)	C12—C13—H13	119.4
C11—N1—H1	114.8 (17)	C13—C14—C15	119.1 (3)
C1—N2—C2	124.09 (19)	C13—C14—H14	120.4
C1—N2—H2	114.6 (15)	C15—C14—H14	120.4
C2—N2—H2	120.7 (15)	C14—C15—C16	120.1 (3)
N2—C2—C3	113.50 (19)	C14—C15—H15	120.0
N2—C2—P1	102.66 (15)	C16—C15—H15	120.0
C3—C2—P1	118.69 (15)	C11—C16—C15	120.0 (3)
N2—C2—H201	107.1	C11—C16—H16	120.0
C3—C2—H201	107.1	C15—C16—H16	120.0
P1—C2—H201	107.1	C22—C21—C26	121.7 (3)
C4—C3—C5	109.4 (3)	C22—C21—O2	118.7 (2)
C4—C3—C6	109.9 (2)	C26—C21—O2	119.5 (2)
C5—C3—C6	108.6 (3)	C21—C22—C23	118.0 (3)
C4—C3—C2	112.2 (2)	C21—C22—H22	121.0
C5—C3—C2	108.0 (2)	C23—C22—H22	121.0
C6—C3—C2	108.6 (2)	C24—C23—C22	120.9 (3)
C3—C4—H401	109.5	C24—C23—H23	119.5
C3—C4—H402	109.5	C22—C23—H23	119.5
H401—C4—H402	109.5	C23—C24—C25	119.8 (3)
C3—C4—H403	109.5	C23—C24—H24	120.1
H401—C4—H403	109.5	C25—C24—H24	120.1
H402—C4—H403	109.5	C24—C25—C26	120.7 (3)
C3—C5—H501	109.5	C24—C25—H25	119.6
C3—C5—H502	109.5	C26—C25—H25	119.6
H501—C5—H502	109.5	C21—C26—C25	118.8 (3)
C3—C5—H503	109.5	C21—C26—H26	120.6
H501—C5—H503	109.5	C25—C26—H26	120.6
H502—C5—H503	109.5	C32—C31—C36	123.1 (3)
C3—C6—H601	109.5	C32—C31—O3	120.7 (2)
C3—C6—H602	109.5	C36—C31—O3	116.0 (2)
H601—C6—H602	109.5	C31—C32—C33	117.6 (3)
C3—C6—H603	109.5	C31—C32—H32	121.2
H601—C6—H603	109.5	C33—C32—H32	121.2
H602—C6—H603	109.5	C34—C33—C32	119.0 (4)
O1—P1—O2	114.28 (9)	C34—C33—H33	120.5
O1—P1—O3	114.33 (9)	C32—C33—H33	120.5
O2—P1—O3	102.34 (9)	C35—C34—C33	121.4 (4)
O1—P1—C2	116.32 (11)	C35—C34—H34	119.3
O2—P1—C2	104.31 (9)	C33—C34—H34	119.3
O3—P1—C2	103.62 (10)	C34—C35—C36	120.1 (4)
C21—O2—P1	120.91 (14)	C34—C35—H35	119.9
C31—O3—P1	129.93 (15)	C36—C35—H35	119.9
C16—C11—C12	119.3 (2)	C31—C36—C35	118.7 (3)
C16—C11—N1	118.7 (2)	C31—C36—H36	120.6
C12—C11—N1	121.8 (2)	C35—C36—H36	120.6
C11—C12—C13	120.1 (3)
N2—C1—N1—C11	173.0 (2)	N1—C11—C12—C13	−177.0 (3)
S1—C1—N1—C11	−8.1 (3)	C11—C12—C13—C14	1.5 (5)
N1—C1—N2—C2	173.6 (2)	C12—C13—C14—C15	0.6 (6)
S1—C1—N2—C2	−5.3 (3)	C13—C14—C15—C16	−1.7 (6)
C1—N2—C2—C3	−111.5 (3)	C12—C11—C16—C15	1.5 (5)
C1—N2—C2—P1	119.2 (2)	N1—C11—C16—C15	176.1 (3)
N2—C2—C3—C4	−74.6 (3)	C14—C15—C16—C11	0.6 (5)
P1—C2—C3—C4	46.1 (3)	P1—O2—C21—C22	110.7 (2)
N2—C2—C3—C5	46.1 (3)	P1—O2—C21—C26	−73.7 (3)
P1—C2—C3—C5	166.8 (2)	C26—C21—C22—C23	1.4 (5)
N2—C2—C3—C6	163.8 (2)	O2—C21—C22—C23	176.8 (3)
P1—C2—C3—C6	−75.6 (3)	C21—C22—C23—C24	−0.2 (5)
N2—C2—P1—O1	53.79 (18)	C22—C23—C24—C25	−0.5 (6)
C3—C2—P1—O1	−72.3 (2)	C23—C24—C25—C26	0.1 (6)
N2—C2—P1—O2	−179.35 (14)	C22—C21—C26—C25	−1.8 (5)
C3—C2—P1—O2	54.6 (2)	O2—C21—C26—C25	−177.2 (3)
N2—C2—P1—O3	−72.57 (16)	C24—C25—C26—C21	1.1 (5)
C3—C2—P1—O3	161.37 (18)	P1—O3—C31—C32	55.8 (3)
O1—P1—O2—C21	−48.7 (2)	P1—O3—C31—C36	−129.7 (2)
O3—P1—O2—C21	75.47 (19)	C36—C31—C32—C33	1.2 (4)
C2—P1—O2—C21	−176.79 (18)	O3—C31—C32—C33	175.2 (3)
O1—P1—O3—C31	−13.7 (2)	C31—C32—C33—C34	−0.6 (5)
O2—P1—O3—C31	−137.80 (19)	C32—C33—C34—C35	0.6 (6)
C2—P1—O3—C31	113.9 (2)	C33—C34—C35—C36	−1.1 (6)
C1—N1—C11—C16	134.8 (3)	C32—C31—C36—C35	−1.6 (4)
C1—N1—C11—C12	−50.7 (4)	O3—C31—C36—C35	−175.9 (3)
C16—C11—C12—C13	−2.6 (5)	C34—C35—C36—C31	1.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.85 (1)	2.19 (2)	2.976 (3)	153 (1)
N2—H2···O1^i	0.86 (1)	2.05 (1)	2.884 (3)	162 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.