A second monoclinic polymorph of N-[bis-(morpholin-4-yl)phosphino-yl]-4-fluoro-benzamide with the P2(1)/n space group.

A second monoclinic polymorph of the title mol-ecule, C(15)H(21)FN(3)O(4)P, is reported in the space group P2(1)/n and compared to the previously reported C2/c space group [Gholivand et al. (2006 ▶). Polyhedron, 25, 711-721]. The asymmetric unit of the title compound consists of two independent mol-ecules. The P atoms adopt a distorted tetra-hedral environment. In the C(O)NHP(O) fragment, the P=O and the N-H groups are in a syn conformation with respect to each other and in the crystal, inter-molecular N-H⋯O=P hydrogen bonds form dimeric aggregates.

Related literature

For the monoclinic polymorph of the title mol­ecule, in a C2/c space group, for bond lengths and angles and for preparation of the starting compound 4-F—C6H4C(O)NHP(O)Cl2, see: Gholivand et al. (2006 ▶). For related phospho­ramidates, see: Pourayoubi, Nečas & Negari (2012 ▶); Pourayoubi, Tarahhomi et al. (2012 ▶).

Experimental

Crystal data

C15H21FN3O4P

M = 357.32

Monoclinic,

a = 15.6093 (6) Å

b = 10.7114 (4) Å

c = 21.0045 (9) Å

β = 106.896 (2)°

V = 3360.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 100 K

0.18 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.965, T max = 0.980

25230 measured reflections

6912 independent reflections

5355 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.160

S = 1.03

6912 reflections

439 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.45 e Å−3

Δρmin = −0.73 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031418/jj2145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031418/jj2145Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031418/jj2145Isup3.cml

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

C15H21FN3O4P	F(000) = 1504
Mr = 357.32	Dx = 1.413 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7455 reflections
a = 15.6093 (6) Å	θ = 2.3–26.4°
b = 10.7114 (4) Å	µ = 0.20 mm−1
c = 21.0045 (9) Å	T = 100 K
β = 106.896 (2)°	Block, colourless
V = 3360.3 (2) Å3	0.18 × 0.15 × 0.10 mm
Z = 8

Bruker APEXII CCD diffractometer	6912 independent reflections
Radiation source: fine-focus sealed tube	5355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 8.33 pixels mm-1	θmax = 26.4°, θmin = 1.4°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −13→13
Tmin = 0.965, Tmax = 0.980	l = −22→26
25230 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0816P)2 + 4.9555P] where P = (Fo2 + 2Fc2)/3
6912 reflections	(Δ/σ)max < 0.001
439 parameters	Δρmax = 1.45 e Å−3
2 restraints	Δρmin = −0.73 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	0.47360 (4)	0.87432 (6)	0.15573 (3)	0.01350 (17)
P2	0.93848 (4)	0.36293 (6)	0.12376 (3)	0.01408 (17)
F1	0.07031 (11)	0.82774 (16)	0.31748 (9)	0.0255 (4)
F2	0.58872 (11)	0.32224 (15)	0.33946 (9)	0.0239 (4)
O1	0.30622 (14)	0.71437 (19)	0.12959 (10)	0.0250 (5)
O2	0.54401 (12)	0.95376 (17)	0.19942 (9)	0.0170 (4)
O3	0.26441 (14)	1.08121 (18)	0.01350 (10)	0.0263 (5)
O4	0.59087 (13)	0.54123 (18)	0.08540 (10)	0.0238 (5)
O5	0.76002 (14)	0.22559 (19)	0.10808 (10)	0.0246 (5)
O6	1.01711 (12)	0.43300 (18)	0.16535 (10)	0.0192 (4)
O7	0.74106 (13)	0.59113 (17)	−0.00982 (10)	0.0228 (4)
O8	1.08127 (14)	0.03799 (19)	0.09330 (11)	0.0294 (5)
N1	0.40849 (14)	0.8319 (2)	0.20362 (11)	0.0149 (5)
H1N	0.417 (2)	0.872 (3)	0.2410 (11)	0.018*
N2	0.41816 (15)	0.9499 (2)	0.08931 (11)	0.0165 (5)
N3	0.50455 (15)	0.7452 (2)	0.12658 (11)	0.0176 (5)
N4	0.87238 (15)	0.3430 (2)	0.17412 (11)	0.0157 (5)
H4N	0.8948 (19)	0.374 (3)	0.2123 (10)	0.019*
N5	0.88937 (14)	0.4404 (2)	0.05651 (11)	0.0164 (5)
N6	0.95166 (15)	0.2234 (2)	0.09645 (11)	0.0179 (5)
C1	0.27337 (18)	0.8749 (3)	0.27251 (14)	0.0186 (6)
H1A	0.3255	0.9257	0.2849	0.022*
C2	0.20861 (18)	0.8881 (3)	0.30509 (14)	0.0199 (6)
H2A	0.2152	0.9479	0.3396	0.024*
C3	0.13450 (17)	0.8125 (2)	0.28632 (14)	0.0172 (6)
C4	0.12203 (18)	0.7231 (3)	0.23765 (14)	0.0198 (6)
H4A	0.0707	0.6706	0.2269	0.024*
C5	0.18645 (17)	0.7119 (2)	0.20477 (14)	0.0173 (5)
H5A	0.1788	0.6520	0.1702	0.021*
C6	0.26243 (17)	0.7873 (2)	0.22151 (13)	0.0152 (5)
C7	0.32636 (18)	0.7737 (2)	0.18122 (13)	0.0168 (5)
C8	0.35807 (18)	0.8961 (3)	0.02858 (14)	0.0199 (6)
H8A	0.3567	0.8041	0.0330	0.024*
H8B	0.3805	0.9159	−0.0098	0.024*
C9	0.2642 (2)	0.9483 (3)	0.01647 (15)	0.0232 (6)
H9A	0.2249	0.9147	−0.0259	0.028*
H9B	0.2397	0.9213	0.0528	0.028*
C10	0.3181 (2)	1.1302 (3)	0.07509 (15)	0.0242 (6)
H10A	0.2939	1.1023	0.1114	0.029*
H10B	0.3160	1.2225	0.0735	0.029*
C11	0.4140 (2)	1.0871 (2)	0.08929 (15)	0.0226 (6)
H11A	0.4398	1.1206	0.0550	0.027*
H11B	0.4498	1.1193	0.1331	0.027*
C12	0.56485 (19)	0.7619 (3)	0.08400 (15)	0.0225 (6)
H12A	0.6268	0.7770	0.1122	0.027*
H12B	0.5454	0.8351	0.0546	0.027*
C13	0.5620 (2)	0.6472 (3)	0.04299 (15)	0.0249 (6)
H13A	0.5002	0.6333	0.0141	0.030*
H13B	0.6015	0.6582	0.0141	0.030*
C14	0.53270 (19)	0.5219 (3)	0.12520 (15)	0.0226 (6)
H14A	0.5529	0.4478	0.1538	0.027*
H14B	0.4715	0.5049	0.0960	0.027*
C15	0.53018 (19)	0.6333 (2)	0.16835 (14)	0.0204 (6)
H15A	0.4864	0.6186	0.1935	0.024*
H15B	0.5898	0.6459	0.2007	0.024*
C16	0.75142 (17)	0.3982 (2)	0.25373 (14)	0.0173 (5)
H16A	0.7956	0.4597	0.2545	0.021*
C17	0.70067 (17)	0.4068 (2)	0.29795 (14)	0.0177 (6)
H17A	0.7088	0.4741	0.3286	0.021*
C18	0.63820 (17)	0.3150 (2)	0.29609 (13)	0.0159 (5)
C19	0.62334 (16)	0.2167 (2)	0.25214 (14)	0.0158 (5)
H19A	0.5800	0.1546	0.2524	0.019*
C20	0.67331 (16)	0.2109 (2)	0.20749 (13)	0.0131 (5)
H20A	0.6630	0.1450	0.1759	0.016*
C21	0.73824 (17)	0.3000 (2)	0.20819 (13)	0.0142 (5)
C22	0.78981 (17)	0.2861 (2)	0.15893 (14)	0.0161 (5)
C23	0.81724 (17)	0.3917 (2)	0.00028 (13)	0.0171 (5)
H23A	0.8097	0.3012	0.0065	0.021*
H23B	0.8334	0.4033	−0.0415	0.021*
C24	0.73018 (18)	0.4588 (2)	−0.00470 (15)	0.0190 (6)
H24A	0.6832	0.4286	−0.0443	0.023*
H24B	0.7108	0.4401	0.0352	0.023*
C25	0.8061 (2)	0.6370 (3)	0.04805 (16)	0.0262 (7)
H25A	0.7871	0.6179	0.0880	0.031*
H25B	0.8112	0.7288	0.0449	0.031*
C26	0.89630 (19)	0.5771 (2)	0.05444 (16)	0.0244 (6)
H26A	0.9174	0.6018	0.0161	0.029*
H26B	0.9406	0.6070	0.0956	0.029*
C27	0.98143 (19)	0.2023 (3)	0.03698 (15)	0.0229 (6)
H27A	0.9799	0.2821	0.0129	0.027*
H27B	0.9401	0.1432	0.0068	0.027*
C28	1.0750 (2)	0.1502 (3)	0.05604 (18)	0.0305 (7)
H28A	1.0927	0.1334	0.0153	0.037*
H28B	1.1169	0.2127	0.0828	0.037*
C29	1.0563 (2)	0.0604 (3)	0.15248 (16)	0.0280 (7)
H29A	1.0983	0.1214	0.1806	0.034*
H29B	1.0610	−0.0184	0.1779	0.034*
C30	0.9619 (2)	0.1102 (3)	0.13704 (15)	0.0221 (6)
H30A	0.9191	0.0459	0.1129	0.027*
H30B	0.9479	0.1291	0.1791	0.027*

	U11	U22	U33	U12	U13	U23
P1	0.0156 (3)	0.0121 (3)	0.0144 (3)	0.0020 (2)	0.0069 (3)	0.0010 (3)
P2	0.0130 (3)	0.0138 (3)	0.0165 (4)	0.0014 (2)	0.0060 (3)	0.0030 (3)
F1	0.0196 (8)	0.0309 (9)	0.0323 (10)	0.0007 (7)	0.0173 (7)	−0.0010 (8)
F2	0.0236 (8)	0.0232 (8)	0.0321 (10)	−0.0011 (7)	0.0194 (7)	−0.0030 (7)
O1	0.0283 (11)	0.0296 (11)	0.0193 (11)	−0.0100 (9)	0.0104 (9)	−0.0112 (9)
O2	0.0146 (9)	0.0176 (9)	0.0180 (10)	0.0000 (7)	0.0034 (7)	0.0024 (8)
O3	0.0328 (11)	0.0195 (10)	0.0199 (11)	0.0081 (9)	−0.0026 (9)	−0.0024 (8)
O4	0.0260 (11)	0.0196 (10)	0.0305 (12)	0.0071 (8)	0.0155 (9)	0.0017 (9)
O5	0.0287 (11)	0.0272 (11)	0.0211 (11)	−0.0105 (9)	0.0124 (9)	−0.0097 (9)
O6	0.0142 (9)	0.0230 (10)	0.0201 (10)	−0.0004 (8)	0.0045 (8)	0.0065 (8)
O7	0.0235 (10)	0.0166 (9)	0.0240 (11)	0.0052 (8)	0.0002 (8)	0.0008 (8)
O8	0.0281 (11)	0.0238 (11)	0.0389 (13)	0.0130 (9)	0.0140 (10)	0.0058 (10)
N1	0.0151 (11)	0.0159 (10)	0.0157 (11)	−0.0010 (9)	0.0077 (9)	−0.0041 (9)
N2	0.0214 (11)	0.0114 (10)	0.0158 (11)	0.0024 (9)	0.0041 (9)	0.0001 (9)
N3	0.0260 (12)	0.0144 (11)	0.0162 (12)	0.0057 (9)	0.0120 (10)	0.0037 (9)
N4	0.0168 (11)	0.0171 (11)	0.0151 (11)	−0.0028 (9)	0.0075 (9)	−0.0033 (9)
N5	0.0145 (11)	0.0133 (10)	0.0198 (12)	0.0004 (8)	0.0026 (9)	0.0028 (9)
N6	0.0235 (12)	0.0165 (11)	0.0163 (11)	0.0052 (9)	0.0102 (9)	0.0030 (9)
C1	0.0153 (13)	0.0222 (14)	0.0196 (14)	−0.0039 (10)	0.0073 (11)	−0.0049 (11)
C2	0.0168 (13)	0.0239 (14)	0.0191 (14)	0.0007 (11)	0.0054 (11)	−0.0060 (11)
C3	0.0121 (12)	0.0205 (13)	0.0211 (14)	0.0046 (10)	0.0081 (11)	0.0060 (11)
C4	0.0133 (12)	0.0200 (13)	0.0259 (15)	−0.0025 (10)	0.0055 (11)	0.0016 (11)
C5	0.0154 (13)	0.0177 (13)	0.0169 (13)	−0.0003 (10)	0.0018 (10)	−0.0017 (11)
C6	0.0135 (12)	0.0150 (12)	0.0164 (13)	0.0011 (10)	0.0036 (10)	0.0008 (10)
C7	0.0205 (13)	0.0134 (12)	0.0168 (14)	−0.0010 (10)	0.0057 (11)	−0.0006 (10)
C8	0.0252 (14)	0.0183 (13)	0.0162 (14)	0.0028 (11)	0.0061 (11)	−0.0019 (11)
C9	0.0289 (15)	0.0178 (13)	0.0202 (15)	0.0035 (11)	0.0026 (12)	−0.0035 (11)
C10	0.0327 (16)	0.0163 (13)	0.0193 (15)	0.0074 (12)	0.0008 (12)	−0.0024 (11)
C11	0.0305 (16)	0.0130 (13)	0.0228 (15)	0.0008 (11)	0.0055 (12)	0.0020 (11)
C12	0.0262 (15)	0.0214 (14)	0.0241 (15)	0.0034 (12)	0.0140 (12)	0.0021 (12)
C13	0.0324 (16)	0.0238 (15)	0.0238 (16)	0.0070 (12)	0.0165 (13)	0.0015 (12)
C14	0.0240 (14)	0.0189 (13)	0.0280 (16)	0.0028 (11)	0.0122 (12)	0.0024 (12)
C15	0.0251 (14)	0.0175 (13)	0.0208 (14)	0.0038 (11)	0.0101 (12)	0.0047 (11)
C16	0.0127 (12)	0.0171 (13)	0.0229 (14)	−0.0039 (10)	0.0064 (10)	−0.0043 (11)
C17	0.0156 (13)	0.0187 (13)	0.0183 (14)	−0.0011 (10)	0.0042 (11)	−0.0068 (11)
C18	0.0124 (12)	0.0186 (13)	0.0190 (14)	0.0043 (10)	0.0084 (10)	0.0027 (11)
C19	0.0113 (12)	0.0129 (12)	0.0228 (14)	−0.0009 (9)	0.0043 (10)	0.0016 (10)
C20	0.0095 (11)	0.0120 (11)	0.0155 (13)	0.0020 (9)	−0.0002 (10)	0.0014 (10)
C21	0.0145 (12)	0.0131 (12)	0.0151 (13)	0.0003 (9)	0.0045 (10)	0.0017 (10)
C22	0.0180 (13)	0.0122 (12)	0.0187 (14)	−0.0033 (10)	0.0061 (11)	−0.0004 (10)
C23	0.0183 (13)	0.0167 (12)	0.0156 (13)	0.0021 (10)	0.0036 (11)	−0.0009 (10)
C24	0.0179 (13)	0.0159 (13)	0.0221 (14)	0.0012 (10)	0.0041 (11)	−0.0016 (11)
C25	0.0281 (15)	0.0127 (13)	0.0316 (17)	0.0043 (11)	−0.0010 (13)	−0.0011 (12)
C26	0.0226 (14)	0.0143 (13)	0.0307 (16)	−0.0031 (11)	−0.0011 (12)	0.0069 (12)
C27	0.0268 (15)	0.0242 (14)	0.0215 (15)	0.0043 (12)	0.0130 (12)	0.0026 (12)
C28	0.0291 (16)	0.0278 (16)	0.0419 (19)	0.0094 (13)	0.0221 (15)	0.0092 (14)
C29	0.0309 (16)	0.0234 (15)	0.0260 (16)	0.0081 (12)	0.0022 (13)	0.0091 (13)
C30	0.0296 (15)	0.0168 (13)	0.0210 (15)	0.0021 (11)	0.0091 (12)	0.0034 (11)

P1—O2	1.4791 (19)	C9—H9B	0.9900
P1—N2	1.628 (2)	C10—C11	1.511 (4)
P1—N3	1.641 (2)	C10—H10A	0.9900
P1—N1	1.687 (2)	C10—H10B	0.9900
P2—O6	1.4866 (19)	C11—H11A	0.9900
P2—N5	1.626 (2)	C11—H11B	0.9900
P2—N6	1.635 (2)	C12—C13	1.495 (4)
P2—N4	1.692 (2)	C12—H12A	0.9900
F1—C3	1.356 (3)	C12—H12B	0.9900
F2—C18	1.357 (3)	C13—H13A	0.9900
O1—C7	1.217 (3)	C13—H13B	0.9900
O3—C10	1.422 (3)	C14—C15	1.505 (4)
O3—C9	1.425 (3)	C14—H14A	0.9900
O4—C14	1.417 (3)	C14—H14B	0.9900
O4—C13	1.432 (3)	C15—H15A	0.9900
O5—C22	1.220 (3)	C15—H15B	0.9900
O7—C25	1.426 (3)	C16—C17	1.388 (4)
O7—C24	1.435 (3)	C16—C21	1.396 (4)
O8—C28	1.422 (4)	C16—H16A	0.9500
O8—C29	1.427 (4)	C17—C18	1.378 (4)
N1—C7	1.380 (3)	C17—H17A	0.9500
N1—H1N	0.869 (17)	C18—C19	1.375 (4)
N2—C8	1.464 (3)	C19—C20	1.385 (4)
N2—C11	1.471 (3)	C19—H19A	0.9500
N3—C15	1.471 (3)	C20—C21	1.389 (3)
N3—C12	1.486 (3)	C20—H20A	0.9500
N4—C22	1.377 (3)	C21—C22	1.491 (4)
N4—H4N	0.846 (18)	C23—C24	1.514 (4)
N5—C26	1.470 (3)	C23—H23A	0.9900
N5—C23	1.470 (3)	C23—H23B	0.9900
N6—C30	1.465 (3)	C24—H24A	0.9900
N6—C27	1.471 (3)	C24—H24B	0.9900
C1—C2	1.383 (4)	C25—C26	1.517 (4)
C1—C6	1.397 (4)	C25—H25A	0.9900
C1—H1A	0.9500	C25—H25B	0.9900
C2—C3	1.373 (4)	C26—H26A	0.9900
C2—H2A	0.9500	C26—H26B	0.9900
C3—C4	1.373 (4)	C27—C28	1.504 (4)
C4—C5	1.381 (4)	C27—H27A	0.9900
C4—H4A	0.9500	C27—H27B	0.9900
C5—C6	1.392 (4)	C28—H28A	0.9900
C5—H5A	0.9500	C28—H28B	0.9900
C6—C7	1.491 (4)	C29—C30	1.512 (4)
C8—C9	1.519 (4)	C29—H29A	0.9900
C8—H8A	0.9900	C29—H29B	0.9900
C8—H8B	0.9900	C30—H30A	0.9900
C9—H9A	0.9900	C30—H30B	0.9900
O2—P1—N2	111.08 (11)	O4—C13—H13A	109.7
O2—P1—N3	118.04 (11)	C12—C13—H13A	109.7
N2—P1—N3	103.92 (11)	O4—C13—H13B	109.7
O2—P1—N1	104.63 (11)	C12—C13—H13B	109.7
N2—P1—N1	112.50 (12)	H13A—C13—H13B	108.2
N3—P1—N1	106.82 (11)	O4—C14—C15	111.9 (2)
O6—P2—N5	110.68 (11)	O4—C14—H14A	109.2
O6—P2—N6	120.07 (12)	C15—C14—H14A	109.2
N5—P2—N6	103.74 (12)	O4—C14—H14B	109.2
O6—P2—N4	104.22 (11)	C15—C14—H14B	109.2
N5—P2—N4	112.86 (12)	H14A—C14—H14B	107.9
N6—P2—N4	105.41 (11)	N3—C15—C14	109.7 (2)
C10—O3—C9	109.7 (2)	N3—C15—H15A	109.7
C14—O4—C13	110.1 (2)	C14—C15—H15A	109.7
C25—O7—C24	110.3 (2)	N3—C15—H15B	109.7
C28—O8—C29	110.2 (2)	C14—C15—H15B	109.7
C7—N1—P1	125.42 (19)	H15A—C15—H15B	108.2
C7—N1—H1N	115 (2)	C17—C16—C21	120.6 (2)
P1—N1—H1N	116 (2)	C17—C16—H16A	119.7
C8—N2—C11	112.1 (2)	C21—C16—H16A	119.7
C8—N2—P1	126.66 (18)	C18—C17—C16	118.1 (2)
C11—N2—P1	120.65 (19)	C18—C17—H17A	121.0
C15—N3—C12	110.3 (2)	C16—C17—H17A	121.0
C15—N3—P1	121.53 (18)	F2—C18—C19	118.5 (2)
C12—N3—P1	115.43 (18)	F2—C18—C17	118.5 (2)
C22—N4—P2	127.66 (19)	C19—C18—C17	123.1 (2)
C22—N4—H4N	120 (2)	C18—C19—C20	118.1 (2)
P2—N4—H4N	113 (2)	C18—C19—H19A	121.0
C26—N5—C23	112.1 (2)	C20—C19—H19A	120.9
C26—N5—P2	120.94 (19)	C19—C20—C21	121.0 (2)
C23—N5—P2	125.07 (18)	C19—C20—H20A	119.5
C30—N6—C27	111.0 (2)	C21—C20—H20A	119.5
C30—N6—P2	123.80 (19)	C20—C21—C16	119.1 (2)
C27—N6—P2	122.78 (19)	C20—C21—C22	117.6 (2)
C2—C1—C6	120.3 (2)	C16—C21—C22	123.3 (2)
C2—C1—H1A	119.9	O5—C22—N4	122.1 (2)
C6—C1—H1A	119.9	O5—C22—C21	121.0 (2)
C3—C2—C1	118.3 (3)	N4—C22—C21	116.9 (2)
C3—C2—H2A	120.9	N5—C23—C24	110.5 (2)
C1—C2—H2A	120.9	N5—C23—H23A	109.6
F1—C3—C2	118.0 (2)	C24—C23—H23A	109.6
F1—C3—C4	118.6 (2)	N5—C23—H23B	109.6
C2—C3—C4	123.4 (2)	C24—C23—H23B	109.6
C3—C4—C5	117.8 (2)	H23A—C23—H23B	108.1
C3—C4—H4A	121.1	O7—C24—C23	110.5 (2)
C5—C4—H4A	121.1	O7—C24—H24A	109.5
C4—C5—C6	120.9 (3)	C23—C24—H24A	109.5
C4—C5—H5A	119.5	O7—C24—H24B	109.5
C6—C5—H5A	119.5	C23—C24—H24B	109.5
C5—C6—C1	119.2 (2)	H24A—C24—H24B	108.1
C5—C6—C7	117.5 (2)	O7—C25—C26	110.0 (2)
C1—C6—C7	123.2 (2)	O7—C25—H25A	109.7
O1—C7—N1	120.9 (2)	C26—C25—H25A	109.7
O1—C7—C6	121.0 (2)	O7—C25—H25B	109.7
N1—C7—C6	118.1 (2)	C26—C25—H25B	109.7
N2—C8—C9	110.1 (2)	H25A—C25—H25B	108.2
N2—C8—H8A	109.6	N5—C26—C25	110.5 (2)
C9—C8—H8A	109.6	N5—C26—H26A	109.6
N2—C8—H8B	109.6	C25—C26—H26A	109.6
C9—C8—H8B	109.6	N5—C26—H26B	109.6
H8A—C8—H8B	108.2	C25—C26—H26B	109.6
O3—C9—C8	111.1 (2)	H26A—C26—H26B	108.1
O3—C9—H9A	109.4	N6—C27—C28	110.7 (2)
C8—C9—H9A	109.4	N6—C27—H27A	109.5
O3—C9—H9B	109.4	C28—C27—H27A	109.5
C8—C9—H9B	109.4	N6—C27—H27B	109.5
H9A—C9—H9B	108.0	C28—C27—H27B	109.5
O3—C10—C11	110.8 (2)	H27A—C27—H27B	108.1
O3—C10—H10A	109.5	O8—C28—C27	111.5 (2)
C11—C10—H10A	109.5	O8—C28—H28A	109.3
O3—C10—H10B	109.5	C27—C28—H28A	109.3
C11—C10—H10B	109.5	O8—C28—H28B	109.3
H10A—C10—H10B	108.1	C27—C28—H28B	109.3
N2—C11—C10	110.3 (2)	H28A—C28—H28B	108.0
N2—C11—H11A	109.6	O8—C29—C30	111.6 (2)
C10—C11—H11A	109.6	O8—C29—H29A	109.3
N2—C11—H11B	109.6	C30—C29—H29A	109.3
C10—C11—H11B	109.6	O8—C29—H29B	109.3
H11A—C11—H11B	108.1	C30—C29—H29B	109.3
N3—C12—C13	109.3 (2)	H29A—C29—H29B	108.0
N3—C12—H12A	109.8	N6—C30—C29	110.6 (2)
C13—C12—H12A	109.8	N6—C30—H30A	109.5
N3—C12—H12B	109.8	C29—C30—H30A	109.5
C13—C12—H12B	109.8	N6—C30—H30B	109.5
H12A—C12—H12B	108.3	C29—C30—H30B	109.5
O4—C13—C12	110.0 (2)	H30A—C30—H30B	108.1
O2—P1—N1—C7	169.2 (2)	P1—N2—C8—C9	119.3 (2)
N2—P1—N1—C7	48.5 (2)	C10—O3—C9—C8	−61.2 (3)
N3—P1—N1—C7	−64.9 (2)	N2—C8—C9—O3	56.1 (3)
O2—P1—N2—C8	165.5 (2)	C9—O3—C10—C11	61.6 (3)
N3—P1—N2—C8	37.6 (2)	C8—N2—C11—C10	52.5 (3)
N1—P1—N2—C8	−77.6 (2)	P1—N2—C11—C10	−119.2 (2)
O2—P1—N2—C11	−24.1 (2)	O3—C10—C11—N2	−57.0 (3)
N3—P1—N2—C11	−152.0 (2)	C15—N3—C12—C13	56.9 (3)
N1—P1—N2—C11	92.9 (2)	P1—N3—C12—C13	−160.6 (2)
O2—P1—N3—C15	76.8 (2)	C14—O4—C13—C12	61.5 (3)
N2—P1—N3—C15	−159.7 (2)	N3—C12—C13—O4	−60.0 (3)
N1—P1—N3—C15	−40.6 (2)	C13—O4—C14—C15	−59.7 (3)
O2—P1—N3—C12	−61.2 (2)	C12—N3—C15—C14	−54.3 (3)
N2—P1—N3—C12	62.3 (2)	P1—N3—C15—C14	165.87 (19)
N1—P1—N3—C12	−178.56 (19)	O4—C14—C15—N3	56.1 (3)
O6—P2—N4—C22	178.2 (2)	C21—C16—C17—C18	0.9 (4)
N5—P2—N4—C22	58.0 (3)	C16—C17—C18—F2	179.5 (2)
N6—P2—N4—C22	−54.5 (2)	C16—C17—C18—C19	−0.8 (4)
O6—P2—N5—C26	−25.8 (2)	F2—C18—C19—C20	179.2 (2)
N6—P2—N5—C26	−155.8 (2)	C17—C18—C19—C20	−0.5 (4)
N4—P2—N5—C26	90.6 (2)	C18—C19—C20—C21	1.6 (4)
O6—P2—N5—C23	171.3 (2)	C19—C20—C21—C16	−1.5 (4)
N6—P2—N5—C23	41.3 (2)	C19—C20—C21—C22	179.3 (2)
N4—P2—N5—C23	−72.3 (2)	C17—C16—C21—C20	0.2 (4)
O6—P2—N6—C30	79.2 (2)	C17—C16—C21—C22	179.3 (2)
N5—P2—N6—C30	−156.6 (2)	P2—N4—C22—O5	11.3 (4)
N4—P2—N6—C30	−37.8 (2)	P2—N4—C22—C21	−169.64 (19)
O6—P2—N6—C27	−81.7 (2)	C20—C21—C22—O5	22.0 (4)
N5—P2—N6—C27	42.5 (2)	C16—C21—C22—O5	−157.1 (3)
N4—P2—N6—C27	161.3 (2)	C20—C21—C22—N4	−157.1 (2)
C6—C1—C2—C3	0.5 (4)	C16—C21—C22—N4	23.8 (4)
C1—C2—C3—F1	−178.6 (2)	C26—N5—C23—C24	−52.1 (3)
C1—C2—C3—C4	1.1 (4)	P2—N5—C23—C24	112.1 (2)
F1—C3—C4—C5	177.7 (2)	C25—O7—C24—C23	−61.5 (3)
C2—C3—C4—C5	−2.0 (4)	N5—C23—C24—O7	55.9 (3)
C3—C4—C5—C6	1.3 (4)	C24—O7—C25—C26	61.8 (3)
C4—C5—C6—C1	0.2 (4)	C23—N5—C26—C25	52.7 (3)
C4—C5—C6—C7	−176.9 (2)	P2—N5—C26—C25	−112.2 (2)
C2—C1—C6—C5	−1.2 (4)	O7—C25—C26—N5	−57.1 (3)
C2—C1—C6—C7	175.8 (3)	C30—N6—C27—C28	−53.3 (3)
P1—N1—C7—O1	22.8 (4)	P2—N6—C27—C28	109.8 (3)
P1—N1—C7—C6	−156.19 (19)	C29—O8—C28—C27	−59.2 (3)
C5—C6—C7—O1	11.5 (4)	N6—C27—C28—O8	56.7 (3)
C1—C6—C7—O1	−165.6 (3)	C28—O8—C29—C30	58.9 (3)
C5—C6—C7—N1	−169.6 (2)	C27—N6—C30—C29	52.9 (3)
C1—C6—C7—N1	13.4 (4)	P2—N6—C30—C29	−110.0 (3)
C11—N2—C8—C9	−51.9 (3)	O8—C29—C30—N6	−56.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O2i	0.85 (2)	2.01 (2)	2.855 (3)	176 (3)
N1—H1N···O6ii	0.87 (2)	2.04 (2)	2.870 (3)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O2i	0.85 (2)	2.01 (2)	2.855 (3)	176 (3)
N1—H1N⋯O6ii	0.87 (2)	2.04 (2)	2.870 (3)	159 (3)

Symmetry codes: (i) ; (ii) .