N,N,N',N'-Tetra-benzyl-N''-(2,6-difluoro-benzo-yl)phospho-ric triamide.

In the C(O)NHP(O) fragment of the title compound, C(35)H(32)F(2)N(3)O(2)P, the P-N bond is longer and the O-P-N angle is contracted compared with the other two P-N bonds and O-P-N angles. The P atom adopts a distorted tetra-hedral environment and the phosphoryl and carbonyl groups are anti with respect to each other. The two tertiary N atoms of the dibenzyl-amido groups show sp(2) character with a slight deviation from planarity. In the crystal, pairs of N-H⋯O(P) hydrogen bonds form inversion dimers.

Related literature

For related structures with a [C(O)NH]P(O)[N]2 configuration, see: Sabbaghi et al. (2010 ▶); Pourayoubi et al. (2010 ▶). For the geometries of the tertiary N atoms in phospho­ric triamides with a C(O)NHP(O)[N]2 core, see: Pourayoubi et al. (2012 ▶).

Experimental

Crystal data

C35H32F2N3O2P

M = 595.61

Monoclinic,

a = 12.3079 (7) Å

b = 19.5089 (12) Å

c = 13.0131 (6) Å

β = 105.430 (3)°

V = 3012.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 100 K

0.18 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.975, T max = 0.986

23928 measured reflections

6199 independent reflections

4332 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.111

S = 1.01

6199 reflections

391 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042481/sj5269sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042481/sj5269Isup2.hkl

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

C35H32F2N3O2P	F(000) = 1248
Mr = 595.61	Dx = 1.313 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3822 reflections
a = 12.3079 (7) Å	θ = 2.7–25.0°
b = 19.5089 (12) Å	µ = 0.14 mm−1
c = 13.0131 (6) Å	T = 100 K
β = 105.430 (3)°	Block, colourless
V = 3012.0 (3) Å3	0.18 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	6199 independent reflections
Radiation source: fine-focus sealed tube	4332 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 26.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.975, Tmax = 0.986	k = −24→24
23928 measured reflections	l = −10→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.6985P] where P = (Fo2 + 2Fc2)/3
6199 reflections	(Δ/σ)max = 0.001
391 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.39 e Å−3

Experimental. IR (KBr, ν, cm-1): 3052, 2885, 1699, 1609, 1471, 1353, 1277, 1186, 1115, 1077, 1011, 930, 854, 802, 745.

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	0.59266 (4)	0.54027 (3)	0.16718 (4)	0.01441 (13)
F1	0.85267 (11)	0.58682 (6)	−0.04221 (9)	0.0281 (3)
F2	0.78767 (12)	0.36483 (7)	0.05916 (11)	0.0416 (4)
O1	0.84569 (11)	0.52129 (7)	0.18588 (11)	0.0207 (3)
O2	0.47271 (11)	0.53813 (7)	0.10611 (10)	0.0172 (3)
N1	0.66497 (13)	0.50969 (8)	0.08388 (13)	0.0156 (4)
H1N	0.6240 (16)	0.4957 (10)	0.0232 (13)	0.019*
N2	0.62881 (13)	0.61912 (8)	0.20347 (12)	0.0155 (4)
N3	0.63429 (13)	0.49405 (8)	0.27580 (12)	0.0149 (4)
C1	0.85840 (17)	0.51846 (10)	−0.05653 (16)	0.0185 (4)
C2	0.90366 (17)	0.49400 (11)	−0.13495 (16)	0.0226 (5)
H2A	0.9310	0.5245	−0.1792	0.027*
C3	0.90846 (17)	0.42409 (12)	−0.14784 (16)	0.0244 (5)
H3A	0.9400	0.4062	−0.2014	0.029*
C4	0.86834 (19)	0.37989 (12)	−0.08434 (18)	0.0288 (5)
H4A	0.8703	0.3317	−0.0941	0.035*
C5	0.82520 (18)	0.40748 (11)	−0.00619 (17)	0.0238 (5)
C6	0.81866 (16)	0.47654 (10)	0.01110 (15)	0.0157 (4)
C7	0.77876 (17)	0.50491 (10)	0.10290 (16)	0.0166 (4)
C8	0.72603 (16)	0.63857 (10)	0.29096 (15)	0.0173 (4)
H8A	0.7710	0.5970	0.3171	0.021*
H8B	0.6984	0.6567	0.3504	0.021*
C9	0.80209 (16)	0.69147 (10)	0.26126 (16)	0.0171 (4)
C10	0.84585 (16)	0.74433 (10)	0.33157 (16)	0.0202 (5)
H10A	0.8213	0.7496	0.3944	0.024*
C11	0.92460 (18)	0.78945 (11)	0.31167 (18)	0.0253 (5)
H11A	0.9546	0.8247	0.3614	0.030*
C12	0.95970 (18)	0.78337 (11)	0.21971 (18)	0.0266 (5)
H12A	1.0141	0.8141	0.2061	0.032*
C13	0.91462 (17)	0.73200 (11)	0.14762 (17)	0.0238 (5)
H13A	0.9376	0.7279	0.0837	0.029*
C14	0.83644 (17)	0.68657 (10)	0.16778 (16)	0.0200 (5)
H14A	0.8059	0.6517	0.1174	0.024*
C15	0.55331 (17)	0.67630 (10)	0.15645 (15)	0.0173 (4)
H15A	0.4978	0.6601	0.0912	0.021*
H15B	0.5982	0.7133	0.1356	0.021*
C16	0.49147 (17)	0.70473 (10)	0.23293 (15)	0.0187 (4)
C17	0.39712 (17)	0.67077 (11)	0.24741 (16)	0.0233 (5)
H17A	0.3712	0.6300	0.2086	0.028*
C18	0.34077 (19)	0.69638 (12)	0.31862 (17)	0.0289 (5)
H18A	0.2757	0.6735	0.3275	0.035*
C19	0.3792 (2)	0.75492 (12)	0.37635 (17)	0.0314 (6)
H19A	0.3412	0.7719	0.4258	0.038*
C20	0.4724 (2)	0.78869 (12)	0.36247 (17)	0.0298 (6)
H20A	0.4986	0.8290	0.4024	0.036*
C21	0.52835 (19)	0.76405 (10)	0.29027 (16)	0.0227 (5)
H21A	0.5920	0.7879	0.2802	0.027*
C22	0.67520 (17)	0.42326 (10)	0.27705 (16)	0.0190 (4)
H22A	0.7078	0.4168	0.2159	0.023*
H22B	0.6104	0.3916	0.2675	0.023*
C23	0.76288 (17)	0.40440 (10)	0.37836 (16)	0.0191 (5)
C24	0.77030 (18)	0.33680 (11)	0.41232 (16)	0.0231 (5)
H24A	0.7203	0.3035	0.3721	0.028*
C25	0.84993 (19)	0.31741 (11)	0.50427 (17)	0.0263 (5)
H25A	0.8552	0.2707	0.5258	0.032*
C26	0.92163 (18)	0.36505 (12)	0.56484 (18)	0.0284 (5)
H26A	0.9759	0.3514	0.6281	0.034*
C27	0.91417 (19)	0.43264 (12)	0.53319 (19)	0.0330 (6)
H27A	0.9623	0.4660	0.5754	0.040*
C28	0.83611 (18)	0.45199 (11)	0.43947 (18)	0.0297 (5)
H28A	0.8328	0.4984	0.4169	0.036*
C29	0.57861 (17)	0.50956 (10)	0.36177 (15)	0.0169 (4)
H29A	0.5423	0.5551	0.3480	0.020*
H29B	0.6370	0.5121	0.4307	0.020*
C30	0.49109 (16)	0.45744 (10)	0.37099 (15)	0.0162 (4)
C31	0.38563 (18)	0.45573 (11)	0.29768 (17)	0.0235 (5)
H31A	0.3682	0.4874	0.2402	0.028*
C32	0.30626 (18)	0.40808 (11)	0.30833 (18)	0.0265 (5)
H32A	0.2345	0.4073	0.2579	0.032*
C33	0.33008 (18)	0.36155 (11)	0.39148 (16)	0.0215 (5)
H33A	0.2748	0.3293	0.3987	0.026*
C34	0.43417 (17)	0.36235 (10)	0.46344 (16)	0.0193 (4)
H34A	0.4515	0.3303	0.5204	0.023*
C35	0.51438 (17)	0.41011 (10)	0.45299 (15)	0.0184 (4)
H35A	0.5864	0.4102	0.5030	0.022*

	U11	U22	U33	U12	U13	U23
P1	0.0122 (3)	0.0172 (3)	0.0140 (3)	0.0008 (2)	0.0036 (2)	−0.0007 (2)
F1	0.0412 (8)	0.0198 (6)	0.0268 (7)	0.0001 (6)	0.0154 (6)	0.0029 (5)
F2	0.0616 (10)	0.0199 (7)	0.0603 (9)	−0.0026 (6)	0.0459 (8)	0.0008 (6)
O1	0.0142 (7)	0.0271 (8)	0.0198 (8)	−0.0020 (6)	0.0027 (6)	−0.0038 (6)
O2	0.0133 (7)	0.0224 (7)	0.0157 (7)	0.0004 (6)	0.0034 (6)	−0.0037 (6)
N1	0.0120 (9)	0.0202 (9)	0.0142 (9)	0.0008 (7)	0.0028 (7)	−0.0015 (7)
N2	0.0139 (9)	0.0181 (9)	0.0135 (8)	0.0035 (7)	0.0018 (7)	0.0007 (7)
N3	0.0147 (9)	0.0157 (8)	0.0154 (9)	0.0019 (7)	0.0060 (7)	−0.0011 (7)
C1	0.0162 (11)	0.0189 (11)	0.0192 (11)	0.0005 (8)	0.0025 (9)	0.0006 (8)
C2	0.0170 (11)	0.0335 (13)	0.0169 (11)	0.0037 (9)	0.0039 (9)	0.0060 (9)
C3	0.0177 (11)	0.0370 (13)	0.0204 (11)	0.0052 (10)	0.0083 (9)	−0.0036 (10)
C4	0.0289 (13)	0.0242 (12)	0.0370 (13)	0.0029 (10)	0.0152 (11)	−0.0055 (10)
C5	0.0222 (12)	0.0226 (12)	0.0314 (13)	−0.0013 (9)	0.0157 (10)	0.0010 (9)
C6	0.0098 (10)	0.0202 (11)	0.0170 (10)	0.0014 (8)	0.0033 (8)	−0.0012 (8)
C7	0.0162 (10)	0.0148 (10)	0.0201 (11)	0.0005 (8)	0.0072 (9)	0.0030 (8)
C8	0.0189 (11)	0.0177 (10)	0.0131 (10)	0.0012 (8)	0.0002 (8)	−0.0017 (8)
C9	0.0134 (10)	0.0158 (10)	0.0202 (11)	0.0049 (8)	0.0011 (8)	0.0005 (8)
C10	0.0177 (11)	0.0188 (11)	0.0219 (11)	0.0050 (8)	0.0014 (9)	−0.0027 (8)
C11	0.0205 (12)	0.0184 (11)	0.0322 (13)	0.0002 (9)	−0.0014 (10)	−0.0043 (9)
C12	0.0164 (11)	0.0210 (11)	0.0418 (14)	−0.0001 (9)	0.0066 (10)	0.0042 (10)
C13	0.0200 (11)	0.0235 (12)	0.0290 (12)	0.0066 (9)	0.0086 (10)	0.0033 (9)
C14	0.0209 (11)	0.0172 (10)	0.0213 (11)	0.0026 (9)	0.0043 (9)	−0.0004 (8)
C15	0.0180 (11)	0.0176 (10)	0.0161 (10)	0.0042 (8)	0.0042 (8)	0.0027 (8)
C16	0.0194 (11)	0.0202 (11)	0.0153 (11)	0.0084 (8)	0.0026 (9)	0.0062 (8)
C17	0.0210 (12)	0.0259 (12)	0.0224 (12)	0.0069 (9)	0.0051 (9)	0.0043 (9)
C18	0.0230 (12)	0.0399 (14)	0.0265 (13)	0.0113 (10)	0.0115 (10)	0.0094 (10)
C19	0.0372 (14)	0.0391 (14)	0.0216 (12)	0.0224 (12)	0.0141 (11)	0.0070 (10)
C20	0.0453 (15)	0.0234 (12)	0.0193 (12)	0.0135 (11)	0.0063 (11)	0.0026 (9)
C21	0.0293 (12)	0.0200 (11)	0.0189 (11)	0.0078 (9)	0.0065 (9)	0.0046 (9)
C22	0.0185 (11)	0.0183 (10)	0.0220 (11)	0.0013 (8)	0.0085 (9)	0.0002 (9)
C23	0.0158 (11)	0.0216 (11)	0.0223 (11)	0.0031 (8)	0.0093 (9)	0.0028 (8)
C24	0.0275 (12)	0.0204 (11)	0.0235 (12)	0.0035 (9)	0.0104 (10)	−0.0012 (9)
C25	0.0343 (13)	0.0200 (11)	0.0268 (12)	0.0101 (10)	0.0118 (10)	0.0066 (9)
C26	0.0221 (12)	0.0338 (13)	0.0289 (13)	0.0105 (10)	0.0060 (10)	0.0104 (10)
C27	0.0229 (13)	0.0334 (13)	0.0374 (14)	−0.0028 (10)	−0.0009 (11)	0.0072 (11)
C28	0.0225 (12)	0.0242 (12)	0.0383 (14)	−0.0030 (9)	0.0009 (10)	0.0122 (10)
C29	0.0196 (11)	0.0174 (10)	0.0143 (10)	0.0002 (8)	0.0057 (8)	−0.0004 (8)
C30	0.0175 (11)	0.0174 (10)	0.0151 (10)	0.0003 (8)	0.0068 (8)	−0.0030 (8)
C31	0.0225 (12)	0.0221 (11)	0.0235 (11)	−0.0005 (9)	0.0016 (9)	0.0083 (9)
C32	0.0187 (11)	0.0280 (12)	0.0290 (12)	−0.0033 (9)	−0.0003 (10)	0.0050 (10)
C33	0.0222 (11)	0.0184 (11)	0.0261 (12)	−0.0045 (9)	0.0101 (9)	−0.0004 (9)
C34	0.0239 (12)	0.0180 (10)	0.0184 (11)	0.0030 (9)	0.0097 (9)	0.0035 (8)
C35	0.0196 (11)	0.0218 (11)	0.0140 (10)	0.0022 (8)	0.0051 (8)	−0.0003 (8)

P1—O2	1.4794 (14)	C16—C21	1.386 (3)
P1—N2	1.6358 (17)	C16—C17	1.393 (3)
P1—N3	1.6395 (16)	C17—C18	1.390 (3)
P1—N1	1.6841 (17)	C17—H17A	0.9500
F1—C1	1.351 (2)	C18—C19	1.380 (3)
F2—C5	1.356 (2)	C18—H18A	0.9500
O1—C7	1.214 (2)	C19—C20	1.376 (3)
N1—C7	1.359 (2)	C19—H19A	0.9500
N1—H1N	0.860 (15)	C20—C21	1.390 (3)
N2—C8	1.465 (2)	C20—H20A	0.9500
N2—C15	1.476 (2)	C21—H21A	0.9500
N3—C22	1.469 (2)	C22—C23	1.510 (3)
N3—C29	1.490 (2)	C22—H22A	0.9900
C1—C2	1.372 (3)	C22—H22B	0.9900
C1—C6	1.383 (3)	C23—C24	1.386 (3)
C2—C3	1.377 (3)	C23—C28	1.387 (3)
C2—H2A	0.9500	C24—C25	1.382 (3)
C3—C4	1.374 (3)	C24—H24A	0.9500
C3—H3A	0.9500	C25—C26	1.376 (3)
C4—C5	1.376 (3)	C25—H25A	0.9500
C4—H4A	0.9500	C26—C27	1.377 (3)
C5—C6	1.372 (3)	C26—H26A	0.9500
C6—C7	1.512 (3)	C27—C28	1.389 (3)
C8—C9	1.511 (3)	C27—H27A	0.9500
C8—H8A	0.9900	C28—H28A	0.9500
C8—H8B	0.9900	C29—C30	1.509 (3)
C9—C10	1.389 (3)	C29—H29A	0.9900
C9—C14	1.393 (3)	C29—H29B	0.9900
C10—C11	1.384 (3)	C30—C35	1.382 (3)
C10—H10A	0.9500	C30—C31	1.392 (3)
C11—C12	1.381 (3)	C31—C32	1.382 (3)
C11—H11A	0.9500	C31—H31A	0.9500
C12—C13	1.384 (3)	C32—C33	1.383 (3)
C12—H12A	0.9500	C32—H32A	0.9500
C13—C14	1.384 (3)	C33—C34	1.371 (3)
C13—H13A	0.9500	C33—H33A	0.9500
C14—H14A	0.9500	C34—C35	1.390 (3)
C15—C16	1.510 (3)	C34—H34A	0.9500
C15—H15A	0.9900	C35—H35A	0.9500
C15—H15B	0.9900
O2—P1—N2	109.73 (8)	C21—C16—C17	119.32 (19)
O2—P1—N3	119.07 (8)	C21—C16—C15	120.73 (19)
N2—P1—N3	105.64 (8)	C17—C16—C15	119.94 (18)
O2—P1—N1	105.49 (8)	C18—C17—C16	120.1 (2)
N2—P1—N1	111.66 (8)	C18—C17—H17A	120.0
N3—P1—N1	105.23 (8)	C16—C17—H17A	120.0
C7—N1—P1	127.05 (14)	C19—C18—C17	120.1 (2)
C7—N1—H1N	118.0 (14)	C19—C18—H18A	120.0
P1—N1—H1N	115.0 (14)	C17—C18—H18A	120.0
C8—N2—C15	114.85 (15)	C20—C19—C18	120.1 (2)
C8—N2—P1	124.82 (13)	C20—C19—H19A	119.9
C15—N2—P1	119.87 (13)	C18—C19—H19A	119.9
C22—N3—C29	114.04 (15)	C19—C20—C21	120.2 (2)
C22—N3—P1	123.66 (13)	C19—C20—H20A	119.9
C29—N3—P1	115.78 (12)	C21—C20—H20A	119.9
F1—C1—C2	119.50 (18)	C16—C21—C20	120.1 (2)
F1—C1—C6	117.12 (17)	C16—C21—H21A	119.9
C2—C1—C6	123.38 (19)	C20—C21—H21A	119.9
C1—C2—C3	118.3 (2)	N3—C22—C23	113.71 (16)
C1—C2—H2A	120.8	N3—C22—H22A	108.8
C3—C2—H2A	120.8	C23—C22—H22A	108.8
C4—C3—C2	121.0 (2)	N3—C22—H22B	108.8
C4—C3—H3A	119.5	C23—C22—H22B	108.8
C2—C3—H3A	119.5	H22A—C22—H22B	107.7
C3—C4—C5	118.0 (2)	C24—C23—C28	118.44 (19)
C3—C4—H4A	121.0	C24—C23—C22	118.76 (18)
C5—C4—H4A	121.0	C28—C23—C22	122.79 (18)
F2—C5—C6	117.08 (18)	C25—C24—C23	120.5 (2)
F2—C5—C4	119.10 (19)	C25—C24—H24A	119.8
C6—C5—C4	123.8 (2)	C23—C24—H24A	119.8
C5—C6—C1	115.49 (18)	C26—C25—C24	120.7 (2)
C5—C6—C7	122.33 (18)	C26—C25—H25A	119.7
C1—C6—C7	122.03 (18)	C24—C25—H25A	119.7
O1—C7—N1	124.51 (18)	C25—C26—C27	119.6 (2)
O1—C7—C6	120.86 (17)	C25—C26—H26A	120.2
N1—C7—C6	114.63 (17)	C27—C26—H26A	120.2
N2—C8—C9	114.30 (16)	C26—C27—C28	119.9 (2)
N2—C8—H8A	108.7	C26—C27—H27A	120.1
C9—C8—H8A	108.7	C28—C27—H27A	120.1
N2—C8—H8B	108.7	C23—C28—C27	120.9 (2)
C9—C8—H8B	108.7	C23—C28—H28A	119.5
H8A—C8—H8B	107.6	C27—C28—H28A	119.5
C10—C9—C14	118.14 (19)	N3—C29—C30	113.79 (15)
C10—C9—C8	119.78 (18)	N3—C29—H29A	108.8
C14—C9—C8	121.94 (17)	C30—C29—H29A	108.8
C11—C10—C9	121.1 (2)	N3—C29—H29B	108.8
C11—C10—H10A	119.4	C30—C29—H29B	108.8
C9—C10—H10A	119.4	H29A—C29—H29B	107.7
C12—C11—C10	120.2 (2)	C35—C30—C31	118.50 (19)
C12—C11—H11A	119.9	C35—C30—C29	120.37 (18)
C10—C11—H11A	119.9	C31—C30—C29	121.12 (18)
C11—C12—C13	119.2 (2)	C32—C31—C30	120.18 (19)
C11—C12—H12A	120.4	C32—C31—H31A	119.9
C13—C12—H12A	120.4	C30—C31—H31A	119.9
C14—C13—C12	120.6 (2)	C31—C32—C33	120.8 (2)
C14—C13—H13A	119.7	C31—C32—H32A	119.6
C12—C13—H13A	119.7	C33—C32—H32A	119.6
C13—C14—C9	120.63 (19)	C34—C33—C32	119.5 (2)
C13—C14—H14A	119.7	C34—C33—H33A	120.3
C9—C14—H14A	119.7	C32—C33—H33A	120.3
N2—C15—C16	112.12 (15)	C33—C34—C35	119.98 (19)
N2—C15—H15A	109.2	C33—C34—H34A	120.0
C16—C15—H15A	109.2	C35—C34—H34A	120.0
N2—C15—H15B	109.2	C30—C35—C34	121.09 (19)
C16—C15—H15B	109.2	C30—C35—H35A	119.5
H15A—C15—H15B	107.9	C34—C35—H35A	119.5
O2—P1—N1—C7	176.64 (16)	C10—C11—C12—C13	0.4 (3)
N2—P1—N1—C7	57.50 (19)	C11—C12—C13—C14	−0.9 (3)
N3—P1—N1—C7	−56.63 (18)	C12—C13—C14—C9	−0.3 (3)
O2—P1—N2—C8	159.51 (15)	C10—C9—C14—C13	2.0 (3)
N3—P1—N2—C8	29.97 (18)	C8—C9—C14—C13	−173.73 (19)
N1—P1—N2—C8	−83.90 (17)	C8—N2—C15—C16	−68.0 (2)
O2—P1—N2—C15	−12.28 (17)	P1—N2—C15—C16	104.57 (17)
N3—P1—N2—C15	−141.81 (14)	N2—C15—C16—C21	99.8 (2)
N1—P1—N2—C15	104.31 (15)	N2—C15—C16—C17	−79.4 (2)
O2—P1—N3—C22	90.02 (16)	C21—C16—C17—C18	0.1 (3)
N2—P1—N3—C22	−146.14 (15)	C15—C16—C17—C18	179.28 (18)
N1—P1—N3—C22	−27.88 (17)	C16—C17—C18—C19	−1.0 (3)
O2—P1—N3—C29	−59.88 (15)	C17—C18—C19—C20	1.0 (3)
N2—P1—N3—C29	63.95 (15)	C18—C19—C20—C21	0.0 (3)
N1—P1—N3—C29	−177.79 (13)	C17—C16—C21—C20	0.9 (3)
F1—C1—C2—C3	−179.99 (17)	C15—C16—C21—C20	−178.33 (18)
C6—C1—C2—C3	0.8 (3)	C19—C20—C21—C16	−0.9 (3)
C1—C2—C3—C4	0.4 (3)	C29—N3—C22—C23	−61.0 (2)
C2—C3—C4—C5	−1.2 (3)	P1—N3—C22—C23	148.61 (14)
C3—C4—C5—F2	−178.4 (2)	N3—C22—C23—C24	150.43 (18)
C3—C4—C5—C6	0.8 (3)	N3—C22—C23—C28	−29.2 (3)
F2—C5—C6—C1	179.56 (18)	C28—C23—C24—C25	−0.8 (3)
C4—C5—C6—C1	0.3 (3)	C22—C23—C24—C25	179.58 (18)
F2—C5—C6—C7	3.9 (3)	C23—C24—C25—C26	1.3 (3)
C4—C5—C6—C7	−175.3 (2)	C24—C25—C26—C27	−0.3 (3)
F1—C1—C6—C5	179.63 (17)	C25—C26—C27—C28	−1.3 (4)
C2—C1—C6—C5	−1.2 (3)	C24—C23—C28—C27	−0.8 (3)
F1—C1—C6—C7	−4.7 (3)	C22—C23—C28—C27	178.8 (2)
C2—C1—C6—C7	174.50 (18)	C26—C27—C28—C23	1.8 (4)
P1—N1—C7—O1	1.6 (3)	C22—N3—C29—C30	−48.9 (2)
P1—N1—C7—C6	−178.72 (14)	P1—N3—C29—C30	103.88 (17)
C5—C6—C7—O1	95.9 (2)	N3—C29—C30—C35	104.5 (2)
C1—C6—C7—O1	−79.5 (3)	N3—C29—C30—C31	−75.5 (2)
C5—C6—C7—N1	−83.8 (2)	C35—C30—C31—C32	0.8 (3)
C1—C6—C7—N1	100.8 (2)	C29—C30—C31—C32	−179.23 (19)
C15—N2—C8—C9	−58.6 (2)	C30—C31—C32—C33	0.0 (3)
P1—N2—C8—C9	129.21 (16)	C31—C32—C33—C34	−0.7 (3)
N2—C8—C9—C10	138.58 (18)	C32—C33—C34—C35	0.6 (3)
N2—C8—C9—C14	−45.8 (2)	C31—C30—C35—C34	−0.9 (3)
C14—C9—C10—C11	−2.4 (3)	C29—C30—C35—C34	179.13 (18)
C8—C9—C10—C11	173.37 (18)	C33—C34—C35—C30	0.2 (3)
C9—C10—C11—C12	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	1.90 (2)	2.761 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	1.90 (2)	2.761 (2)	176 (2)

Symmetry code: (i) .