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

The P atom in the title compound, C(23)H(25)N(4)O(4)P, is in a slightly distorted tetra-hedral coordination environment and the N atoms show sp(2) character. The phosphoryl group and the NH unit are syn with respect to each other. In the crystal, pairs of inter-molecular N-H⋯O(P) hydrogen bonds form centrosymmetric dimers.

Related literature

For phospho­rus compounds with general formula XP(O)[N(CH3)(CH2C6H5)]2, see: Gholivand et al. (2005 ▶). For bond lengths in a related structure, see: Sabbaghi et al. (2010 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H25N4O4P

M = 452.44

Triclinic,

a = 8.3526 (5) Å

b = 11.8150 (5) Å

c = 12.2668 (4) Å

α = 77.184 (3)°

β = 81.289 (4)°

γ = 71.928 (4)°

V = 1117.70 (9) Å3

Z = 2

Cu Kα radiation

μ = 1.41 mm−1

T = 297 K

0.24 × 0.14 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.941, T max = 1.000

8669 measured reflections

4203 independent reflections

3779 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.05

4203 reflections

390 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011275/ng5139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011275/ng5139Isup2.hkl

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

C23H25N4O4P	Z = 2
Mr = 452.44	F(000) = 476
Triclinic, P1	Dx = 1.344 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.3526 (5) Å	Cell parameters from 5608 reflections
b = 11.8150 (5) Å	θ = 3.7–70.5°
c = 12.2668 (4) Å	µ = 1.41 mm−1
α = 77.184 (3)°	T = 297 K
β = 81.289 (4)°	Prismatic, colorless
γ = 71.928 (4)°	0.24 × 0.14 × 0.05 mm
V = 1117.70 (9) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4203 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3779 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.2673 pixels mm-1	θmax = 70.6°, θmin = 3.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→14
Tmin = 0.941, Tmax = 1.000	l = −14→14
8669 measured reflections

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)] = 0.035	All H-atom parameters refined
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.049P)2 + 0.1381P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4203 reflections	Δρmax = 0.21 e Å−3
390 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (5)

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	0.37947 (4)	0.43216 (3)	0.68154 (3)	0.03514 (12)
O2	0.39241 (13)	0.55008 (8)	0.61457 (8)	0.0441 (2)
O3	0.40102 (16)	0.16957 (10)	0.70306 (10)	0.0570 (3)
O4	1.0449 (2)	−0.09851 (14)	0.30155 (13)	0.0866 (5)
O5	0.9874 (2)	−0.24087 (12)	0.42737 (14)	0.0867 (5)
N6	0.18214 (15)	0.43519 (10)	0.71762 (10)	0.0422 (3)
N7	0.46802 (15)	0.38121 (10)	0.80040 (10)	0.0415 (3)
N8	0.48310 (16)	0.32916 (10)	0.59984 (10)	0.0404 (3)
N9	0.9666 (2)	−0.13399 (13)	0.38622 (13)	0.0594 (4)
C10	−0.08796 (18)	0.59948 (13)	0.70707 (13)	0.0455 (3)
C11	−0.2562 (2)	0.61378 (15)	0.69736 (16)	0.0559 (4)
C12	−0.3838 (2)	0.69259 (18)	0.7548 (2)	0.0693 (6)
C13	−0.3441 (3)	0.75656 (19)	0.82172 (19)	0.0718 (6)
C14	−0.1776 (3)	0.7439 (2)	0.8315 (2)	0.0717 (5)
C15	−0.0499 (2)	0.66649 (16)	0.77376 (17)	0.0587 (4)
C16	0.0512 (2)	0.51473 (15)	0.64516 (14)	0.0494 (4)
C17	0.1226 (2)	0.34870 (15)	0.80655 (16)	0.0537 (4)
C18	0.3946 (3)	0.44794 (17)	0.89219 (14)	0.0563 (4)
C19	0.6514 (2)	0.32321 (15)	0.80428 (14)	0.0484 (3)
C20	0.69385 (18)	0.22357 (14)	0.90560 (12)	0.0451 (3)
C21	0.7774 (2)	0.2365 (2)	0.98905 (15)	0.0615 (4)
C22	0.8215 (3)	0.1426 (3)	1.08008 (17)	0.0796 (6)
C23	0.7830 (3)	0.0367 (2)	1.08917 (18)	0.0742 (6)
C24	0.7001 (3)	0.02349 (18)	1.00715 (18)	0.0697 (5)
C25	0.6558 (3)	0.11582 (16)	0.91598 (16)	0.0592 (4)
C26	0.48804 (18)	0.20940 (12)	0.62439 (11)	0.0402 (3)
C27	0.61200 (18)	0.12548 (12)	0.55456 (11)	0.0392 (3)
C28	0.7086 (2)	0.16247 (13)	0.45913 (12)	0.0478 (4)
C29	0.8241 (2)	0.07733 (14)	0.40268 (13)	0.0526 (4)
C30	0.8402 (2)	−0.04361 (13)	0.44417 (13)	0.0461 (3)
C31	0.7468 (2)	−0.08292 (14)	0.53841 (15)	0.0543 (4)
C32	0.6313 (2)	0.00252 (14)	0.59370 (15)	0.0515 (4)
H11	−0.278 (3)	0.569 (2)	0.6490 (18)	0.069 (6)*
H12	−0.499 (4)	0.701 (2)	0.745 (2)	0.092 (7)*
H13	−0.432 (3)	0.809 (2)	0.860 (2)	0.087 (7)*
H14	−0.154 (3)	0.786 (2)	0.882 (2)	0.093 (8)*
H15	0.067 (3)	0.6575 (19)	0.7821 (18)	0.070 (6)*
H16A	0.104 (2)	0.5613 (17)	0.5845 (17)	0.054 (5)*
H16B	0.001 (3)	0.4617 (19)	0.6165 (17)	0.061 (5)*
H17A	0.041 (3)	0.3951 (19)	0.8615 (18)	0.067 (6)*
H17B	0.218 (3)	0.292 (2)	0.843 (2)	0.076 (6)*
H17C	0.070 (3)	0.303 (2)	0.7758 (19)	0.076 (6)*
H18A	0.276 (3)	0.490 (2)	0.885 (2)	0.084 (7)*
H18B	0.444 (3)	0.512 (3)	0.892 (2)	0.096 (8)*
H18C	0.407 (3)	0.394 (2)	0.964 (2)	0.088 (7)*
H19A	0.702 (3)	0.3836 (19)	0.8089 (17)	0.061 (5)*
H19B	0.693 (2)	0.2926 (17)	0.7372 (17)	0.057 (5)*
H21	0.803 (3)	0.312 (2)	0.9826 (19)	0.074 (6)*
H22	0.878 (4)	0.154 (3)	1.137 (3)	0.117 (10)*
H23	0.810 (3)	−0.029 (3)	1.148 (2)	0.096 (8)*
H24	0.672 (3)	−0.051 (2)	1.009 (2)	0.078 (6)*
H25	0.600 (3)	0.1054 (19)	0.8612 (19)	0.069 (6)*
H28	0.698 (2)	0.2437 (19)	0.4309 (17)	0.061 (5)*
H29	0.894 (3)	0.101 (2)	0.3376 (19)	0.070 (6)*
H31	0.766 (3)	−0.165 (2)	0.5660 (18)	0.069 (6)*
H32	0.565 (3)	−0.0228 (19)	0.6597 (18)	0.066 (6)*
H8	0.533 (2)	0.3600 (17)	0.5403 (17)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
P1	0.0438 (2)	0.02572 (18)	0.03071 (18)	−0.00681 (13)	0.00261 (13)	−0.00327 (12)
O2	0.0586 (6)	0.0298 (5)	0.0380 (5)	−0.0110 (4)	0.0061 (4)	−0.0035 (4)
O3	0.0742 (7)	0.0362 (5)	0.0535 (6)	−0.0178 (5)	0.0162 (5)	−0.0060 (5)
O4	0.0973 (11)	0.0691 (9)	0.0630 (9)	0.0154 (8)	0.0114 (8)	−0.0189 (7)
O5	0.1171 (13)	0.0377 (7)	0.0854 (10)	0.0103 (7)	−0.0052 (9)	−0.0200 (7)
N6	0.0434 (6)	0.0352 (6)	0.0402 (6)	−0.0065 (5)	0.0002 (5)	−0.0006 (5)
N7	0.0460 (6)	0.0371 (6)	0.0354 (6)	−0.0048 (5)	−0.0009 (5)	−0.0064 (5)
N8	0.0530 (7)	0.0292 (5)	0.0337 (6)	−0.0098 (5)	0.0060 (5)	−0.0044 (4)
N9	0.0701 (9)	0.0463 (8)	0.0522 (8)	0.0072 (6)	−0.0137 (7)	−0.0185 (6)
C10	0.0418 (7)	0.0386 (7)	0.0505 (8)	−0.0079 (6)	−0.0075 (6)	0.0004 (6)
C11	0.0500 (9)	0.0452 (8)	0.0674 (10)	−0.0159 (7)	−0.0141 (8)	0.0087 (8)
C12	0.0398 (9)	0.0600 (11)	0.0866 (14)	−0.0080 (8)	−0.0010 (8)	0.0178 (10)
C13	0.0578 (11)	0.0591 (11)	0.0732 (12)	0.0025 (9)	0.0135 (9)	−0.0011 (10)
C14	0.0686 (12)	0.0629 (11)	0.0768 (13)	−0.0026 (9)	−0.0034 (10)	−0.0243 (10)
C15	0.0469 (9)	0.0555 (10)	0.0723 (11)	−0.0054 (7)	−0.0089 (8)	−0.0198 (8)
C16	0.0514 (8)	0.0469 (8)	0.0468 (8)	−0.0072 (7)	−0.0101 (7)	−0.0086 (7)
C17	0.0516 (9)	0.0425 (8)	0.0578 (10)	−0.0134 (7)	0.0105 (8)	−0.0012 (7)
C18	0.0698 (11)	0.0528 (10)	0.0400 (8)	−0.0051 (8)	−0.0041 (7)	−0.0146 (7)
C19	0.0449 (8)	0.0500 (9)	0.0451 (8)	−0.0141 (7)	−0.0012 (6)	0.0005 (7)
C20	0.0377 (7)	0.0486 (8)	0.0418 (7)	−0.0068 (6)	−0.0007 (5)	−0.0036 (6)
C21	0.0593 (10)	0.0786 (13)	0.0509 (9)	−0.0310 (9)	−0.0070 (7)	−0.0029 (8)
C22	0.0693 (12)	0.1179 (19)	0.0511 (10)	−0.0358 (12)	−0.0214 (9)	0.0091 (11)
C23	0.0635 (11)	0.0782 (14)	0.0599 (11)	−0.0073 (10)	−0.0144 (9)	0.0174 (10)
C24	0.0835 (14)	0.0454 (10)	0.0674 (12)	−0.0087 (9)	−0.0101 (10)	0.0039 (8)
C25	0.0723 (11)	0.0496 (9)	0.0524 (9)	−0.0128 (8)	−0.0143 (8)	−0.0037 (7)
C26	0.0502 (8)	0.0306 (6)	0.0365 (7)	−0.0097 (6)	−0.0020 (6)	−0.0034 (5)
C27	0.0493 (7)	0.0294 (6)	0.0370 (7)	−0.0073 (5)	−0.0076 (6)	−0.0056 (5)
C28	0.0675 (10)	0.0283 (7)	0.0388 (7)	−0.0052 (6)	−0.0007 (7)	−0.0035 (6)
C29	0.0698 (10)	0.0393 (8)	0.0377 (7)	−0.0044 (7)	0.0022 (7)	−0.0058 (6)
C30	0.0548 (8)	0.0353 (7)	0.0434 (8)	0.0017 (6)	−0.0126 (6)	−0.0128 (6)
C31	0.0673 (10)	0.0279 (7)	0.0617 (10)	−0.0059 (7)	−0.0064 (8)	−0.0069 (7)
C32	0.0605 (9)	0.0320 (7)	0.0558 (9)	−0.0105 (6)	0.0018 (7)	−0.0042 (6)

P1—O2	1.4787 (10)	C17—H17C	0.95 (2)
P1—N6	1.6319 (13)	C18—H18A	0.97 (3)
P1—N7	1.6420 (12)	C18—H18B	0.96 (3)
P1—N8	1.6910 (11)	C18—H18C	0.97 (3)
O3—C26	1.2163 (18)	C19—C20	1.510 (2)
O4—N9	1.206 (2)	C19—H19A	0.95 (2)
O5—N9	1.219 (2)	C19—H19B	0.95 (2)
N6—C17	1.462 (2)	C20—C25	1.380 (3)
N6—C16	1.4684 (19)	C20—C21	1.382 (2)
N7—C18	1.4663 (19)	C21—C22	1.391 (3)
N7—C19	1.474 (2)	C21—H21	0.96 (2)
N8—C26	1.3686 (18)	C22—C23	1.364 (4)
N8—H8	0.85 (2)	C22—H22	0.96 (3)
N9—C30	1.4729 (19)	C23—C24	1.365 (3)
C10—C11	1.383 (2)	C23—H23	0.93 (3)
C10—C15	1.385 (2)	C24—C25	1.383 (3)
C10—C16	1.509 (2)	C24—H24	0.97 (2)
C11—C12	1.395 (3)	C25—H25	0.92 (2)
C11—H11	0.95 (2)	C26—C27	1.5035 (19)
C12—C13	1.367 (3)	C27—C28	1.385 (2)
C12—H12	0.96 (3)	C27—C32	1.391 (2)
C13—C14	1.373 (3)	C28—C29	1.388 (2)
C13—H13	0.94 (3)	C28—H28	0.93 (2)
C14—C15	1.389 (3)	C29—C30	1.377 (2)
C14—H14	0.96 (3)	C29—H29	0.96 (2)
C15—H15	0.97 (2)	C30—C31	1.369 (2)
C16—H16A	0.96 (2)	C31—C32	1.383 (2)
C16—H16B	1.00 (2)	C31—H31	0.92 (2)
C17—H17A	1.01 (2)	C32—H32	0.96 (2)
C17—H17B	0.96 (2)
O2—P1—N6	110.89 (6)	H18A—C18—H18B	104 (2)
O2—P1—N7	118.67 (6)	N7—C18—H18C	110.9 (15)
N6—P1—N7	103.85 (6)	H18A—C18—H18C	110 (2)
O2—P1—N8	105.24 (6)	H18B—C18—H18C	108 (2)
N6—P1—N8	113.52 (6)	N7—C19—C20	112.83 (12)
N7—P1—N8	104.82 (6)	N7—C19—H19A	107.8 (12)
C17—N6—C16	113.89 (13)	C20—C19—H19A	107.4 (12)
C17—N6—P1	125.48 (11)	N7—C19—H19B	108.0 (11)
C16—N6—P1	119.62 (10)	C20—C19—H19B	110.6 (12)
C18—N7—C19	112.51 (13)	H19A—C19—H19B	110.2 (17)
C18—N7—P1	117.29 (10)	C25—C20—C21	118.07 (16)
C19—N7—P1	122.11 (10)	C25—C20—C19	121.29 (15)
C26—N8—P1	124.98 (10)	C21—C20—C19	120.60 (16)
C26—N8—H8	122.7 (12)	C20—C21—C22	120.3 (2)
P1—N8—H8	112.4 (12)	C20—C21—H21	118.3 (14)
O4—N9—O5	123.56 (15)	C22—C21—H21	121.4 (14)
O4—N9—C30	118.42 (14)	C23—C22—C21	121.0 (2)
O5—N9—C30	118.01 (16)	C23—C22—H22	120.3 (19)
C11—C10—C15	118.31 (16)	C21—C22—H22	118.7 (19)
C11—C10—C16	121.02 (15)	C22—C23—C24	119.00 (19)
C15—C10—C16	120.65 (14)	C22—C23—H23	124.1 (17)
C10—C11—C12	120.54 (18)	C24—C23—H23	116.9 (17)
C10—C11—H11	116.3 (13)	C23—C24—C25	120.7 (2)
C12—C11—H11	123.1 (13)	C23—C24—H24	121.8 (14)
C13—C12—C11	120.40 (18)	C25—C24—H24	117.5 (14)
C13—C12—H12	121.6 (16)	C20—C25—C24	120.95 (19)
C11—C12—H12	118.0 (16)	C20—C25—H25	119.4 (13)
C12—C13—C14	119.66 (19)	C24—C25—H25	119.6 (14)
C12—C13—H13	119.4 (15)	O3—C26—N8	121.84 (13)
C14—C13—H13	120.9 (16)	O3—C26—C27	120.11 (12)
C13—C14—C15	120.3 (2)	N8—C26—C27	117.97 (12)
C13—C14—H14	117.8 (16)	C28—C27—C32	119.72 (13)
C15—C14—H14	121.8 (17)	C28—C27—C26	124.63 (12)
C10—C15—C14	120.80 (18)	C32—C27—C26	115.62 (13)
C10—C15—H15	119.7 (13)	C27—C28—C29	120.19 (14)
C14—C15—H15	119.5 (13)	C27—C28—H28	121.6 (12)
N6—C16—C10	112.55 (12)	C29—C28—H28	118.2 (12)
N6—C16—H16A	108.2 (11)	C30—C29—C28	118.48 (15)
C10—C16—H16A	109.3 (11)	C30—C29—H29	120.0 (13)
N6—C16—H16B	107.3 (12)	C28—C29—H29	121.5 (13)
C10—C16—H16B	108.7 (12)	C31—C30—C29	122.66 (14)
H16A—C16—H16B	110.8 (16)	C31—C30—N9	118.90 (14)
N6—C17—H17A	108.4 (12)	C29—C30—N9	118.42 (15)
N6—C17—H17B	109.0 (14)	C30—C31—C32	118.49 (14)
H17A—C17—H17B	110.9 (18)	C30—C31—H31	120.1 (13)
N6—C17—H17C	110.5 (14)	C32—C31—H31	121.3 (14)
H17A—C17—H17C	110.8 (18)	C31—C32—C27	120.47 (16)
H17B—C17—H17C	107 (2)	C31—C32—H32	120.0 (13)
N7—C18—H18A	110.9 (15)	C27—C32—H32	119.6 (13)
N7—C18—H18B	113.1 (17)
O2—P1—N6—C17	−162.93 (13)	N7—C19—C20—C21	−112.67 (17)
N7—P1—N6—C17	−34.39 (15)	C25—C20—C21—C22	0.2 (3)
N8—P1—N6—C17	78.85 (14)	C19—C20—C21—C22	−177.67 (17)
O2—P1—N6—C16	29.27 (13)	C20—C21—C22—C23	−0.2 (3)
N7—P1—N6—C16	157.80 (11)	C21—C22—C23—C24	0.1 (3)
N8—P1—N6—C16	−88.96 (12)	C22—C23—C24—C25	0.1 (3)
O2—P1—N7—C18	67.60 (14)	C21—C20—C25—C24	−0.1 (3)
N6—P1—N7—C18	−56.00 (14)	C19—C20—C25—C24	177.82 (17)
N8—P1—N7—C18	−175.36 (13)	C23—C24—C25—C20	−0.1 (3)
O2—P1—N7—C19	−78.73 (13)	P1—N8—C26—O3	8.3 (2)
N6—P1—N7—C19	157.67 (12)	P1—N8—C26—C27	−168.53 (10)
N8—P1—N7—C19	38.30 (13)	O3—C26—C27—C28	175.52 (15)
O2—P1—N8—C26	−173.12 (12)	N8—C26—C27—C28	−7.6 (2)
N6—P1—N8—C26	−51.67 (14)	O3—C26—C27—C32	−6.7 (2)
N7—P1—N8—C26	60.98 (14)	N8—C26—C27—C32	170.15 (14)
C15—C10—C11—C12	−0.9 (2)	C32—C27—C28—C29	0.0 (2)
C16—C10—C11—C12	−179.86 (15)	C26—C27—C28—C29	177.69 (15)
C10—C11—C12—C13	−0.2 (3)	C27—C28—C29—C30	−0.3 (3)
C11—C12—C13—C14	0.6 (3)	C28—C29—C30—C31	0.2 (3)
C12—C13—C14—C15	−0.1 (3)	C28—C29—C30—N9	−178.13 (15)
C11—C10—C15—C14	1.5 (3)	O4—N9—C30—C31	177.97 (17)
C16—C10—C15—C14	−179.55 (18)	O5—N9—C30—C31	−2.8 (2)
C13—C14—C15—C10	−1.0 (3)	O4—N9—C30—C29	−3.7 (2)
C17—N6—C16—C10	65.91 (18)	O5—N9—C30—C29	175.58 (17)
P1—N6—C16—C10	−124.93 (13)	C29—C30—C31—C32	0.2 (3)
C11—C10—C16—N6	−132.44 (15)	N9—C30—C31—C32	178.54 (15)
C15—C10—C16—N6	48.6 (2)	C30—C31—C32—C27	−0.5 (3)
C18—N7—C19—C20	66.18 (18)	C28—C27—C32—C31	0.4 (2)
P1—N7—C19—C20	−146.04 (12)	C26—C27—C32—C31	−177.47 (15)
N7—C19—C20—C25	69.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O2i	0.85 (2)	2.07 (2)	2.909 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O2i	0.85 (2)	2.07 (2)	2.909 (2)	169 (2)

Symmetry code: (i) .