(R)-Methyl {[(2-carb-oxy-bicyclo-[2.2.2]octan-1-yl)-ammonio]-methyl}-phos-phon-ate dichloro-methane 0.25-solvate.

The carb-oxy-lic acid mol-ecule of the title compound, C(11)H(20)NO(5)P·0.25CH(2)Cl(2), exists as a zwitterion with the H atom of the phospho-nate group being transferred to the imine N atom. In the asymmetric unit, there are two crystallographically independent acid mol-ecules adopting the same absolute configuration and differing slightly in their geometrical parameters. In each mol-ecule, the imino and carboxyl groups are connected via an intra-molecular N-H⋯O hydrogen bond. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds induce the formation of layers parallel to the ab plane. The dichloro-methane solvent mol-ecule, with a site occupancy of 0.5, is located between the layers.

Related literature

For general background of the use of amino­phospho­nic acid derivatives in organic synthesis and as biologically active compounds, see: Kafarski & Lejczak (2001 ▶); Orsini et al. (2010 ▶); Troev (2006 ▶); Naydenova et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C11H20NO5P·0.25CH2Cl2

M = 298.48

Orthorhombic,

a = 9.3520 (2) Å

b = 12.7553 (3) Å

c = 24.1148 (8) Å

V = 2876.60 (13) Å3

Z = 8

Cu Kα radiation

μ = 2.70 mm−1

T = 290 K

0.32 × 0.24 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.151, T max = 0.582

11759 measured reflections

4532 independent reflections

3305 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.205

S = 1.02

4532 reflections

356 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 1914 Friedel paris

Flack parameter: 0.04 (4)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029503/is2751sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029503/is2751Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029503/is2751Isup3.cml

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

C11H20NO5P·0.25CH2Cl2	F(000) = 1268
Mr = 298.48	Dx = 1.378 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5494 reflections
a = 9.3520 (2) Å	θ = 3.5–62.6°
b = 12.7553 (3) Å	µ = 2.70 mm−1
c = 24.1148 (8) Å	T = 290 K
V = 2876.60 (13) Å3	Prism, colorless
Z = 8	0.32 × 0.24 × 0.20 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	4532 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3305 reflections with I > 2σ(I)
mirror	Rint = 0.088
Detector resolution: 10.3974 pixels mm-1	θmax = 62.6°, θmin = 3.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
Tmin = 0.151, Tmax = 0.582	l = −27→26
11759 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)] = 0.070	H-atom parameters constrained
wR(F2) = 0.205	w = 1/[σ2(Fo2) + (0.1029P)2 + 1.5603P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4532 reflections	Δρmax = 0.36 e Å−3
356 parameters	Δρmin = −0.34 e Å−3
0 restraints	Absolute structure: Flack (1983), 1914 Friedel paris
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (4)

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	Occ. (<1)
C1	−0.1337 (7)	0.3754 (5)	0.3764 (3)	0.0544 (16)
H1	−0.2314	0.3609	0.3639	0.065*
C2	−0.1299 (10)	0.3581 (7)	0.4400 (3)	0.088 (3)
H2A	−0.1011	0.4225	0.4582	0.106*
H2B	−0.2247	0.3397	0.4531	0.106*
C3	−0.0267 (9)	0.2721 (6)	0.4544 (3)	0.078 (2)
H3	−0.0215	0.2620	0.4946	0.094*
C4	0.1183 (8)	0.3043 (10)	0.4311 (4)	0.104 (3)
H4A	0.1903	0.2549	0.4436	0.124*
H4B	0.1435	0.3729	0.4455	0.124*
C5	0.1193 (6)	0.3083 (5)	0.3675 (3)	0.0546 (15)
H5A	0.1567	0.3751	0.3549	0.066*
H5B	0.1791	0.2528	0.3528	0.066*
C6	−0.0345 (6)	0.2944 (4)	0.3481 (2)	0.0427 (12)
C7	−0.0851 (7)	0.1847 (5)	0.3641 (3)	0.0623 (18)
H7A	−0.1841	0.1754	0.3531	0.075*
H7B	−0.0279	0.1324	0.3451	0.075*
C8	−0.0712 (12)	0.1713 (6)	0.4255 (4)	0.102 (3)
H8A	−0.0008	0.1173	0.4331	0.123*
H8B	−0.1620	0.1480	0.4405	0.123*
C9	−0.0977 (7)	0.4880 (5)	0.3593 (3)	0.0566 (16)
C10	0.0450 (6)	0.2480 (5)	0.2480 (2)	0.0478 (14)
H10A	0.0197	0.1743	0.2499	0.057*
H10B	0.1438	0.2551	0.2596	0.057*
C11	0.2109 (7)	0.4460 (6)	0.1910 (4)	0.093 (3)
H11A	0.2119	0.5114	0.2107	0.139*
H11B	0.2574	0.4546	0.1558	0.139*
H11C	0.2604	0.3938	0.2123	0.139*
C12	−0.098 (2)	0.3952 (18)	0.5960 (10)	0.134 (9)	0.50
H12A	−0.0840	0.3587	0.6309	0.161*	0.50
H12B	−0.1257	0.3432	0.5688	0.161*	0.50
C21	0.5079 (6)	0.5691 (5)	0.4133 (3)	0.0538 (16)
H21	0.5952	0.5949	0.3954	0.065*
C22	0.5372 (7)	0.5643 (7)	0.4775 (3)	0.072 (2)
H22A	0.5465	0.4918	0.4891	0.086*
H22B	0.6261	0.6001	0.4859	0.086*
C23	0.4134 (8)	0.6165 (6)	0.5092 (3)	0.0646 (18)
H23	0.4219	0.6029	0.5490	0.078*
C24	0.2722 (7)	0.5731 (6)	0.4870 (3)	0.0608 (17)
H24A	0.2734	0.4971	0.4888	0.073*
H24B	0.1937	0.5981	0.5097	0.073*
C25	0.2507 (6)	0.6079 (5)	0.4276 (3)	0.0523 (16)
H25A	0.1764	0.6608	0.4260	0.063*
H25B	0.2205	0.5487	0.4052	0.063*
C26	0.3902 (5)	0.6526 (4)	0.4044 (2)	0.0422 (13)
C27	0.4266 (8)	0.7527 (5)	0.4352 (3)	0.0643 (18)
H27A	0.3602	0.8078	0.4249	0.077*
H27B	0.5224	0.7754	0.4255	0.077*
C28	0.4176 (10)	0.7321 (6)	0.4980 (3)	0.082 (2)
H28A	0.4999	0.7628	0.5163	0.098*
H28B	0.3322	0.7649	0.5128	0.098*
C29	0.4765 (7)	0.4605 (5)	0.3898 (3)	0.0581 (16)
C30	0.4830 (6)	0.7393 (5)	0.3151 (2)	0.0523 (15)
H30A	0.5762	0.7141	0.3268	0.063*
H30B	0.4748	0.8120	0.3265	0.063*
C31	0.6373 (13)	0.5596 (10)	0.2371 (8)	0.196 (8)
H31A	0.6546	0.5112	0.2073	0.293*
H31B	0.6415	0.5231	0.2719	0.293*
H31C	0.7087	0.6136	0.2365	0.293*
N1	−0.0493 (5)	0.3092 (4)	0.28655 (19)	0.0476 (11)
H1A	−0.1406	0.2946	0.2775	0.057*
H1B	−0.0353	0.3777	0.2793	0.057*
N21	0.3695 (4)	0.6765 (4)	0.3434 (2)	0.0475 (12)
H21A	0.3609	0.6151	0.3253	0.057*
H21B	0.2860	0.7108	0.3396	0.057*
O1	−0.0342 (6)	0.5114 (3)	0.3167 (2)	0.0776 (15)
O2	−0.1409 (5)	0.5589 (3)	0.3936 (2)	0.0646 (13)
H2	−0.1349	0.6168	0.3790	0.097*
O3	0.0658 (5)	0.4134 (3)	0.1823 (2)	0.0641 (13)
O4	0.1387 (5)	0.2392 (3)	0.14410 (18)	0.0602 (12)
O5	−0.1266 (4)	0.2891 (4)	0.16076 (19)	0.0639 (12)
O21	0.4858 (7)	0.3804 (4)	0.4138 (3)	0.100 (2)
O22	0.4354 (6)	0.4666 (4)	0.3379 (2)	0.0729 (14)
H22	0.4600	0.4135	0.3213	0.109*
O23	0.4943 (7)	0.6072 (5)	0.2303 (2)	0.107 (2)
O24	0.3242 (5)	0.7561 (7)	0.2252 (2)	0.128 (3)
O25	0.5913 (4)	0.7934 (4)	0.21767 (19)	0.0665 (13)
P1	0.02660 (16)	0.29346 (12)	0.17764 (7)	0.0495 (4)
P21	0.47115 (16)	0.73176 (16)	0.24091 (7)	0.0615 (5)
Cl1	−0.2400 (7)	0.4823 (5)	0.6043 (3)	0.139 (2)	0.50
Cl2	0.0552 (7)	0.4434 (7)	0.5772 (3)	0.159 (3)	0.50

	U11	U22	U33	U12	U13	U23
C1	0.049 (4)	0.055 (4)	0.059 (4)	0.001 (3)	0.004 (3)	0.002 (3)
C2	0.110 (7)	0.090 (6)	0.065 (6)	0.019 (5)	0.022 (5)	0.010 (4)
C3	0.097 (6)	0.087 (5)	0.050 (4)	−0.016 (5)	−0.004 (4)	0.016 (4)
C4	0.062 (5)	0.172 (10)	0.077 (6)	−0.024 (6)	−0.017 (4)	0.001 (6)
C5	0.044 (3)	0.062 (4)	0.058 (4)	−0.004 (3)	−0.012 (3)	−0.005 (3)
C6	0.042 (3)	0.042 (3)	0.044 (3)	0.002 (3)	−0.004 (2)	−0.004 (2)
C7	0.058 (4)	0.046 (3)	0.083 (5)	−0.014 (3)	−0.006 (3)	0.007 (3)
C8	0.164 (9)	0.064 (5)	0.080 (6)	−0.025 (6)	0.006 (6)	0.021 (4)
C9	0.058 (4)	0.052 (4)	0.059 (4)	0.002 (3)	0.008 (3)	0.002 (3)
C10	0.038 (3)	0.055 (3)	0.051 (4)	0.006 (3)	−0.001 (2)	−0.007 (3)
C11	0.044 (4)	0.065 (4)	0.170 (9)	−0.025 (4)	−0.034 (5)	0.014 (5)
C12	0.131 (18)	0.131 (18)	0.14 (2)	−0.060 (16)	0.064 (15)	−0.039 (15)
C21	0.030 (3)	0.076 (4)	0.055 (4)	0.013 (3)	−0.004 (3)	0.005 (3)
C22	0.047 (4)	0.106 (6)	0.063 (5)	0.012 (4)	−0.007 (3)	0.013 (4)
C23	0.074 (5)	0.078 (4)	0.042 (4)	0.000 (4)	−0.008 (3)	0.001 (3)
C24	0.048 (4)	0.073 (4)	0.062 (5)	−0.002 (3)	0.004 (3)	0.006 (4)
C25	0.036 (3)	0.065 (4)	0.055 (4)	0.002 (3)	0.007 (3)	0.001 (3)
C26	0.029 (3)	0.051 (3)	0.047 (4)	0.002 (2)	0.000 (2)	0.006 (3)
C27	0.071 (4)	0.056 (4)	0.066 (5)	−0.011 (3)	−0.014 (3)	−0.008 (3)
C28	0.101 (6)	0.079 (5)	0.066 (5)	−0.010 (4)	0.000 (4)	−0.017 (4)
C29	0.052 (3)	0.072 (4)	0.051 (4)	0.009 (3)	−0.004 (3)	0.004 (3)
C30	0.034 (3)	0.064 (4)	0.059 (4)	−0.012 (3)	−0.003 (3)	0.020 (3)
C31	0.118 (10)	0.106 (8)	0.36 (2)	0.020 (8)	0.138 (13)	0.024 (11)
N1	0.035 (2)	0.049 (3)	0.059 (3)	0.000 (2)	−0.013 (2)	−0.004 (2)
N21	0.023 (2)	0.069 (3)	0.051 (3)	0.001 (2)	−0.0021 (19)	0.007 (2)
O1	0.113 (4)	0.047 (2)	0.073 (3)	0.015 (3)	0.032 (3)	0.001 (2)
O2	0.066 (3)	0.053 (2)	0.076 (3)	0.004 (2)	0.024 (2)	−0.005 (2)
O3	0.054 (3)	0.036 (2)	0.102 (4)	−0.0116 (18)	−0.023 (2)	0.013 (2)
O4	0.061 (3)	0.062 (2)	0.058 (3)	−0.009 (2)	0.017 (2)	−0.003 (2)
O5	0.044 (2)	0.081 (3)	0.067 (3)	−0.018 (2)	−0.019 (2)	0.008 (2)
O21	0.142 (6)	0.057 (3)	0.102 (4)	0.026 (3)	−0.012 (4)	0.014 (3)
O22	0.080 (3)	0.059 (3)	0.080 (4)	0.005 (3)	−0.008 (3)	−0.008 (2)
O23	0.115 (5)	0.105 (4)	0.101 (5)	−0.058 (4)	0.028 (4)	−0.022 (3)
O24	0.030 (2)	0.279 (10)	0.073 (4)	0.000 (4)	−0.013 (2)	0.060 (5)
O25	0.042 (2)	0.086 (3)	0.071 (3)	−0.007 (2)	0.007 (2)	0.030 (2)
P1	0.0394 (7)	0.0521 (8)	0.0569 (10)	−0.0083 (7)	−0.0040 (7)	0.0004 (7)
P21	0.0294 (7)	0.0956 (13)	0.0596 (11)	−0.0111 (9)	−0.0006 (7)	0.0131 (9)
Cl1	0.115 (4)	0.117 (4)	0.185 (7)	−0.017 (4)	−0.031 (4)	0.044 (4)
Cl2	0.107 (4)	0.199 (7)	0.171 (6)	−0.050 (5)	0.002 (4)	−0.003 (5)

C1—C9	1.532 (9)	C22—C23	1.539 (10)
C1—C6	1.546 (8)	C22—H22A	0.9700
C1—C2	1.550 (10)	C22—H22B	0.9700
C1—H1	0.9800	C23—C28	1.500 (10)
C2—C3	1.502 (11)	C23—C24	1.528 (9)
C2—H2A	0.9700	C23—H23	0.9800
C2—H2B	0.9700	C24—C25	1.515 (9)
C3—C8	1.521 (11)	C24—H24A	0.9700
C3—C4	1.524 (11)	C24—H24B	0.9700
C3—H3	0.9800	C25—C26	1.529 (7)
C4—C5	1.533 (10)	C25—H25A	0.9700
C4—H4A	0.9700	C25—H25B	0.9700
C4—H4B	0.9700	C26—N21	1.515 (7)
C5—C6	1.523 (7)	C26—C27	1.516 (8)
C5—H5A	0.9700	C27—C28	1.537 (10)
C5—H5B	0.9700	C27—H27A	0.9700
C6—N1	1.503 (7)	C27—H27B	0.9700
C6—C7	1.527 (8)	C28—H28A	0.9700
C7—C8	1.495 (10)	C28—H28B	0.9700
C7—H7A	0.9700	C29—O21	1.177 (8)
C7—H7B	0.9700	C29—O22	1.313 (7)
C8—H8A	0.9700	C30—N21	1.495 (7)
C8—H8B	0.9700	C30—P21	1.795 (6)
C9—O1	1.223 (7)	C30—H30A	0.9700
C9—O2	1.291 (7)	C30—H30B	0.9700
C10—N1	1.501 (7)	C31—O23	1.478 (13)
C10—P1	1.802 (6)	C31—H31A	0.9600
C10—H10A	0.9700	C31—H31B	0.9600
C10—H10B	0.9700	C31—H31C	0.9600
C11—O3	1.434 (7)	N1—H1A	0.9000
C11—H11A	0.9600	N1—H1B	0.9000
C11—H11B	0.9600	N21—H21A	0.9000
C11—H11C	0.9600	N21—H21B	0.9000
C12—Cl2	1.622 (19)	O2—H2	0.8200
C12—Cl1	1.74 (2)	O3—P1	1.578 (4)
C12—H12A	0.9700	O4—P1	1.494 (4)
C12—H12B	0.9700	O5—P1	1.491 (4)
C21—C29	1.525 (9)	O22—H22	0.8200
C21—C26	1.547 (8)	O23—P21	1.624 (7)
C21—C22	1.572 (9)	O24—P21	1.459 (5)
C21—H21	0.9800	O25—P21	1.481 (4)
C9—C1—C6	112.1 (5)	H22A—C22—H22B	108.2
C9—C1—C2	113.2 (6)	C28—C23—C24	108.5 (6)
C6—C1—C2	109.1 (5)	C28—C23—C22	108.5 (7)
C9—C1—H1	107.4	C24—C23—C22	108.6 (6)
C6—C1—H1	107.4	C28—C23—H23	110.4
C2—C1—H1	107.4	C24—C23—H23	110.4
C3—C2—C1	110.3 (6)	C22—C23—H23	110.4
C3—C2—H2A	109.6	C25—C24—C23	109.8 (5)
C1—C2—H2A	109.6	C25—C24—H24A	109.7
C3—C2—H2B	109.6	C23—C24—H24A	109.7
C1—C2—H2B	109.6	C25—C24—H24B	109.7
H2A—C2—H2B	108.1	C23—C24—H24B	109.7
C2—C3—C8	109.6 (7)	H24A—C24—H24B	108.2
C2—C3—C4	106.8 (7)	C24—C25—C26	110.0 (5)
C8—C3—C4	107.6 (8)	C24—C25—H25A	109.7
C2—C3—H3	110.9	C26—C25—H25A	109.7
C8—C3—H3	110.9	C24—C25—H25B	109.7
C4—C3—H3	110.9	C26—C25—H25B	109.7
C3—C4—C5	112.5 (6)	H25A—C25—H25B	108.2
C3—C4—H4A	109.1	N21—C26—C27	109.6 (5)
C5—C4—H4A	109.1	N21—C26—C25	108.7 (4)
C3—C4—H4B	109.1	C27—C26—C25	109.1 (5)
C5—C4—H4B	109.1	N21—C26—C21	111.3 (5)
H4A—C4—H4B	107.8	C27—C26—C21	110.6 (5)
C6—C5—C4	107.4 (5)	C25—C26—C21	107.4 (5)
C6—C5—H5A	110.2	C26—C27—C28	109.0 (6)
C4—C5—H5A	110.2	C26—C27—H27A	109.9
C6—C5—H5B	110.2	C28—C27—H27A	109.9
C4—C5—H5B	110.2	C26—C27—H27B	109.9
H5A—C5—H5B	108.5	C28—C27—H27B	109.9
N1—C6—C5	112.1 (5)	H27A—C27—H27B	108.3
N1—C6—C7	109.6 (5)	C23—C28—C27	110.3 (6)
C5—C6—C7	108.8 (5)	C23—C28—H28A	109.6
N1—C6—C1	107.2 (4)	C27—C28—H28A	109.6
C5—C6—C1	110.7 (5)	C23—C28—H28B	109.6
C7—C6—C1	108.3 (5)	C27—C28—H28B	109.6
C8—C7—C6	109.1 (6)	H28A—C28—H28B	108.1
C8—C7—H7A	109.9	O21—C29—O22	122.9 (7)
C6—C7—H7A	109.9	O21—C29—C21	126.2 (6)
C8—C7—H7B	109.9	O22—C29—C21	110.9 (5)
C6—C7—H7B	109.9	N21—C30—P21	112.5 (4)
H7A—C7—H7B	108.3	N21—C30—H30A	109.1
C7—C8—C3	112.4 (6)	P21—C30—H30A	109.1
C7—C8—H8A	109.1	N21—C30—H30B	109.1
C3—C8—H8A	109.1	P21—C30—H30B	109.1
C7—C8—H8B	109.1	H30A—C30—H30B	107.8
C3—C8—H8B	109.1	O23—C31—H31A	109.5
H8A—C8—H8B	107.9	O23—C31—H31B	109.5
O1—C9—O2	121.3 (6)	H31A—C31—H31B	109.5
O1—C9—C1	124.1 (6)	O23—C31—H31C	109.5
O2—C9—C1	114.6 (6)	H31A—C31—H31C	109.5
N1—C10—P1	111.1 (4)	H31B—C31—H31C	109.5
N1—C10—H10A	109.4	C10—N1—C6	119.5 (4)
P1—C10—H10A	109.4	C10—N1—H1A	107.5
N1—C10—H10B	109.4	C6—N1—H1A	107.5
P1—C10—H10B	109.4	C10—N1—H1B	107.5
H10A—C10—H10B	108.0	C6—N1—H1B	107.5
O3—C11—H11A	109.5	H1A—N1—H1B	107.0
O3—C11—H11B	109.5	C30—N21—C26	117.4 (4)
H11A—C11—H11B	109.5	C30—N21—H21A	107.9
O3—C11—H11C	109.5	C26—N21—H21A	107.9
H11A—C11—H11C	109.5	C30—N21—H21B	107.9
H11B—C11—H11C	109.5	C26—N21—H21B	107.9
Cl2—C12—Cl1	117.6 (14)	H21A—N21—H21B	107.2
Cl2—C12—H12A	107.9	C9—O2—H2	109.5
Cl1—C12—H12A	107.9	C11—O3—P1	120.8 (4)
Cl2—C12—H12B	107.9	C29—O22—H22	109.5
Cl1—C12—H12B	107.9	C31—O23—P21	120.3 (6)
H12A—C12—H12B	107.2	O5—P1—O4	120.6 (3)
C29—C21—C26	115.9 (5)	O5—P1—O3	106.2 (3)
C29—C21—C22	111.3 (5)	O4—P1—O3	108.9 (3)
C26—C21—C22	106.7 (5)	O5—P1—C10	109.7 (3)
C29—C21—H21	107.5	O4—P1—C10	107.1 (3)
C26—C21—H21	107.5	O3—P1—C10	102.9 (3)
C22—C21—H21	107.5	O24—P21—O25	120.2 (3)
C23—C22—C21	109.9 (5)	O24—P21—O23	107.0 (4)
C23—C22—H22A	109.7	O25—P21—O23	111.0 (3)
C21—C22—H22A	109.7	O24—P21—C30	107.8 (3)
C23—C22—H22B	109.7	O25—P21—C30	107.6 (3)
C21—C22—H22B	109.7	O23—P21—C30	101.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O24i	0.90	1.79	2.673 (6)	168.
N1—H1B···O1	0.90	1.93	2.683 (6)	140.
N21—H21A···O22	0.90	2.04	2.750 (7)	135.
N21—H21B···O5ii	0.90	1.79	2.690 (6)	173.
O2—H2···O4ii	0.82	1.66	2.474 (6)	172.
O22—H22···O25iii	0.82	1.86	2.596 (6)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O24i	0.90	1.79	2.673 (6)	168
N1—H1B⋯O1	0.90	1.93	2.683 (6)	140
N21—H21A⋯O22	0.90	2.04	2.750 (7)	135
N21—H21B⋯O5ii	0.90	1.79	2.690 (6)	173
O2—H2⋯O4ii	0.82	1.66	2.474 (6)	172
O22—H22⋯O25iii	0.82	1.86	2.596 (6)	149

Symmetry codes: (i) ; (ii) ; (iii) .