3-[4-(2-Amino-2-oxoeth-yl)phen-oxy]-2-hy-droxy-N-isopropyl-propanaminium 1,1'-binaphthyl-2,2'-diyl phosphate.

In the title salt, C(14)H(23)N(2)O(3) (+)·C(20)H(12)O(4)P(-), the dihedral angle between the two naphthyl ring systems in the anion is 57.77 (6)°. In the crystal, an O-H⋯O hydrogen bond links the components. The ammonium group engages in N-H⋯O hydrogen bonds, generating a layer structure.

Related literature

For the uses of BINOL-phospho­ric acid, see: Jacques et al. (1971 ▶); Sewgobind et al., (2008 ▶). For a clinical pharmacological study of atenolol [systematic name: 3-(4-(2-amino-2-oxoeth­yl)phen­oxy)-2-hy­droxy-N-isopropyl­propan-1-amine], see: Agon et al. (1991 ▶). For the stereoselective features of atenolol, see: Stoschitzky et al. (1993 ▶).

Experimental

Crystal data

C14H23N2O3 +·C20H12O4P−

M = 614.61

Orthorhombic,

a = 9.8646 (14) Å

b = 26.145 (4) Å

c = 11.9306 (16) Å

V = 3077.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 273 K

0.39 × 0.38 × 0.35 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.947, T max = 0.952

14697 measured reflections

5261 independent reflections

3982 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.088

S = 1.06

5261 reflections

421 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2855 Friedel pairs

Flack parameter: 0.03 (10)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049494/ng5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049494/ng5070Isup2.hkl

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

C14H23N2O3+·C20H12O4P−	Dx = 1.327 Mg m−3
Mr = 614.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 4710 reflections
a = 9.8646 (14) Å	θ = 2.6–22.7°
b = 26.145 (4) Å	µ = 0.14 mm−1
c = 11.9306 (16) Å	T = 273 K
V = 3077.1 (7) Å3	Plate, colorless
Z = 4	0.39 × 0.38 × 0.35 mm
F(000) = 1296

Bruker SMART diffractometer	5261 independent reflections
Radiation source: fine-focus sealed tube	3982 reflections with I > 2σ(I)
graphite	Rint = 0.035
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.947, Tmax = 0.952	k = −19→31
14697 measured reflections	l = −14→14

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.2334P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
5261 reflections	Δρmax = 0.28 e Å−3
421 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 2855 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (10)

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)
N1	1.0356 (2)	0.73553 (9)	0.9249 (2)	0.0503 (6)
H1A	1.0214	0.7081	0.9628	0.060*
H1B	0.9688	0.7550	0.9070	0.060*
N2	0.7574 (2)	0.84866 (8)	0.09975 (18)	0.0425 (6)
H2A	0.7757	0.8256	0.0458	0.051*
H2B	0.6727	0.8425	0.1243	0.051*
O1	0.85501 (19)	0.60766 (7)	0.23253 (15)	0.0414 (5)
O2	0.79646 (19)	0.59375 (7)	0.03175 (14)	0.0428 (5)
O3	0.72831 (19)	0.67462 (7)	0.11765 (19)	0.0537 (5)
O4	0.97968 (19)	0.65639 (8)	0.08968 (18)	0.0565 (6)
O5	1.2588 (2)	0.72090 (7)	0.91795 (17)	0.0487 (5)
O6	0.9002 (2)	0.79899 (8)	0.41140 (16)	0.0508 (5)
O7	0.7363 (2)	0.76326 (8)	0.2308 (2)	0.0639 (6)
H7A	0.7331	0.7348	0.2019	0.096*
P1	0.84174 (7)	0.63871 (3)	0.11563 (7)	0.04164 (19)
C1	0.7172 (3)	0.53332 (10)	0.2126 (2)	0.0354 (6)
C2	0.7427 (3)	0.57925 (10)	0.2645 (2)	0.0363 (6)
C3	0.6600 (3)	0.59822 (11)	0.3496 (2)	0.0427 (7)
H3	0.6821	0.6288	0.3849	0.051*
C4	0.5485 (3)	0.57245 (11)	0.3810 (3)	0.0468 (7)
H4	0.4960	0.5849	0.4397	0.056*
C5	0.5094 (3)	0.52674 (10)	0.3266 (2)	0.0396 (7)
C6	0.3886 (3)	0.50032 (12)	0.3525 (3)	0.0515 (8)
H6	0.3353	0.5116	0.4118	0.062*
C7	0.3484 (3)	0.45894 (12)	0.2931 (3)	0.0532 (8)
H7	0.2684	0.4422	0.3118	0.064*
C8	0.4272 (3)	0.44137 (11)	0.2032 (3)	0.0499 (8)
H8	0.3978	0.4137	0.1606	0.060*
C9	0.5465 (3)	0.46459 (11)	0.1783 (2)	0.0425 (7)
H9	0.5986	0.4519	0.1196	0.051*
C10	0.5938 (3)	0.50747 (10)	0.2389 (2)	0.0349 (6)
C11	0.8142 (3)	0.51381 (9)	0.1265 (2)	0.0352 (6)
C12	0.8525 (3)	0.54511 (10)	0.0395 (2)	0.0384 (6)
C13	0.9387 (3)	0.52908 (12)	−0.0454 (2)	0.0464 (8)
H13	0.9626	0.5515	−0.1026	0.056*
C14	0.9877 (3)	0.48104 (13)	−0.0448 (3)	0.0568 (9)
H14	1.0420	0.4701	−0.1038	0.068*
C15	0.9584 (3)	0.44693 (11)	0.0438 (3)	0.0501 (8)
C16	1.0124 (4)	0.39660 (14)	0.0491 (4)	0.0739 (11)
H16	1.0673	0.3851	−0.0090	0.089*
C17	0.9863 (4)	0.36521 (13)	0.1357 (4)	0.0715 (11)
H17	1.0225	0.3324	0.1366	0.086*
C18	0.9060 (4)	0.38159 (12)	0.2232 (3)	0.0611 (9)
H18	0.8897	0.3599	0.2835	0.073*
C19	0.8500 (3)	0.42961 (11)	0.2220 (3)	0.0479 (8)
H19	0.7961	0.4400	0.2817	0.058*
C20	0.8726 (3)	0.46360 (10)	0.1314 (2)	0.0396 (7)
C21	1.1587 (3)	0.74762 (11)	0.8944 (2)	0.0396 (7)
C22	1.1765 (3)	0.79671 (11)	0.8281 (3)	0.0499 (8)
H22A	1.1437	0.8251	0.8729	0.060*
H22B	1.2724	0.8021	0.8148	0.060*
C23	1.1032 (3)	0.79705 (10)	0.7164 (2)	0.0419 (7)
C24	1.1619 (3)	0.77574 (10)	0.6244 (3)	0.0510 (7)
H24	1.2475	0.7612	0.6319	0.061*
C25	1.1003 (3)	0.77459 (11)	0.5198 (3)	0.0499 (8)
H25	1.1425	0.7593	0.4587	0.060*
C26	0.9733 (3)	0.79712 (10)	0.5096 (2)	0.0414 (7)
C27	0.9134 (3)	0.81967 (10)	0.6010 (2)	0.0442 (7)
H27	0.8295	0.8355	0.5936	0.053*
C28	0.9773 (3)	0.81891 (11)	0.7032 (2)	0.0460 (7)
H28	0.9345	0.8335	0.7649	0.055*
C29	0.9557 (3)	0.77359 (12)	0.3161 (2)	0.0495 (8)
H29A	0.9613	0.7371	0.3302	0.059*
H29B	1.0463	0.7863	0.3011	0.059*
C30	0.8654 (3)	0.78359 (11)	0.2172 (3)	0.0476 (8)
H30	0.9066	0.7675	0.1513	0.057*
C31	0.8528 (3)	0.83978 (11)	0.1944 (3)	0.0524 (8)
H31A	0.8197	0.8571	0.2610	0.063*
H31B	0.9411	0.8538	0.1760	0.063*
C32	0.7597 (4)	0.90039 (13)	0.0483 (3)	0.0705 (11)
H32	0.6919	0.9007	−0.0117	0.085*
C33	0.702 (3)	0.9354 (9)	0.150 (2)	0.071 (5)	0.52 (5)
H33A	0.6246	0.9189	0.1829	0.106*	0.52 (5)
H33B	0.6755	0.9682	0.1211	0.106*	0.52 (5)
H33C	0.7711	0.9397	0.2055	0.106*	0.52 (5)
C34	0.885 (4)	0.9195 (11)	0.002 (3)	0.084 (6)	0.52 (5)
H34A	0.9543	0.9183	0.0582	0.127*	0.52 (5)
H34B	0.8723	0.9542	−0.0222	0.127*	0.52 (5)
H34C	0.9109	0.8987	−0.0608	0.127*	0.52 (5)
C33'	0.736 (3)	0.9449 (9)	0.112 (3)	0.071 (5)	0.48 (5)
H33D	0.6466	0.9438	0.1426	0.106*	0.48 (5)
H33E	0.7454	0.9744	0.0644	0.106*	0.48 (5)
H33F	0.8015	0.9468	0.1714	0.106*	0.48 (5)
C34'	0.905 (4)	0.9000 (11)	−0.014 (3)	0.084 (6)	0.48 (5)
H34D	0.9755	0.9062	0.0400	0.127*	0.48 (5)
H34E	0.9069	0.9262	−0.0702	0.127*	0.48 (5)
H34F	0.9193	0.8672	−0.0485	0.127*	0.48 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0371 (16)	0.0527 (16)	0.0611 (16)	0.0033 (12)	−0.0007 (13)	0.0174 (13)
N2	0.0456 (14)	0.0460 (13)	0.0359 (13)	−0.0060 (10)	−0.0034 (11)	−0.0012 (11)
O1	0.0418 (12)	0.0404 (11)	0.0420 (10)	−0.0062 (9)	−0.0069 (9)	−0.0006 (9)
O2	0.0485 (12)	0.0423 (11)	0.0376 (11)	−0.0027 (9)	−0.0046 (9)	0.0038 (9)
O3	0.0509 (12)	0.0416 (11)	0.0686 (13)	0.0055 (9)	−0.0095 (12)	0.0013 (11)
O4	0.0455 (13)	0.0587 (13)	0.0654 (14)	−0.0107 (10)	−0.0040 (11)	0.0149 (11)
O5	0.0364 (12)	0.0554 (12)	0.0542 (12)	0.0032 (10)	0.0005 (10)	0.0106 (10)
O6	0.0526 (13)	0.0634 (13)	0.0364 (11)	0.0136 (10)	−0.0030 (10)	0.0002 (10)
O7	0.0598 (16)	0.0606 (15)	0.0712 (16)	−0.0103 (12)	0.0109 (12)	−0.0049 (12)
P1	0.0403 (4)	0.0378 (4)	0.0469 (4)	−0.0062 (3)	−0.0050 (4)	0.0061 (4)
C1	0.0380 (17)	0.0374 (16)	0.0307 (14)	0.0030 (13)	−0.0012 (12)	0.0042 (12)
C2	0.0399 (17)	0.0367 (16)	0.0323 (15)	0.0015 (14)	−0.0047 (13)	0.0032 (12)
C3	0.053 (2)	0.0409 (16)	0.0345 (15)	0.0052 (15)	−0.0024 (15)	−0.0028 (13)
C4	0.055 (2)	0.0487 (18)	0.0364 (15)	0.0123 (16)	0.0069 (14)	0.0003 (14)
C5	0.0403 (18)	0.0439 (16)	0.0348 (15)	0.0077 (14)	0.0027 (13)	0.0064 (14)
C6	0.047 (2)	0.059 (2)	0.0478 (18)	0.0068 (16)	0.0154 (15)	0.0117 (16)
C7	0.046 (2)	0.053 (2)	0.061 (2)	−0.0061 (16)	0.0108 (17)	0.0140 (17)
C8	0.050 (2)	0.0425 (18)	0.0577 (19)	−0.0066 (14)	0.0051 (17)	0.0035 (15)
C9	0.0440 (19)	0.0417 (17)	0.0418 (16)	0.0002 (14)	0.0054 (14)	−0.0025 (13)
C10	0.0350 (16)	0.0351 (15)	0.0347 (14)	0.0017 (13)	0.0036 (13)	0.0068 (12)
C11	0.0339 (15)	0.0376 (14)	0.0340 (14)	−0.0049 (11)	−0.0004 (13)	−0.0043 (13)
C12	0.0338 (16)	0.0404 (16)	0.0410 (16)	−0.0062 (13)	−0.0027 (13)	−0.0013 (13)
C13	0.0397 (18)	0.059 (2)	0.0403 (17)	−0.0098 (15)	0.0072 (14)	0.0009 (15)
C14	0.045 (2)	0.069 (2)	0.055 (2)	0.0013 (17)	0.0150 (16)	−0.0134 (19)
C15	0.0414 (19)	0.0492 (19)	0.060 (2)	0.0005 (14)	0.0068 (16)	−0.0107 (16)
C16	0.067 (3)	0.058 (2)	0.096 (3)	0.0145 (19)	0.019 (2)	−0.020 (2)
C17	0.071 (3)	0.045 (2)	0.099 (3)	0.0164 (18)	0.001 (2)	−0.006 (2)
C18	0.064 (2)	0.0431 (19)	0.076 (2)	0.0054 (17)	−0.010 (2)	−0.0019 (18)
C19	0.049 (2)	0.0415 (17)	0.0533 (19)	0.0032 (15)	−0.0030 (15)	−0.0024 (15)
C20	0.0361 (17)	0.0376 (16)	0.0450 (16)	−0.0025 (12)	−0.0051 (13)	−0.0069 (15)
C21	0.0391 (18)	0.0433 (17)	0.0363 (15)	−0.0004 (14)	−0.0080 (14)	0.0009 (13)
C22	0.055 (2)	0.0433 (17)	0.0517 (18)	−0.0073 (15)	−0.0076 (15)	0.0095 (15)
C23	0.0463 (19)	0.0354 (15)	0.0441 (18)	−0.0014 (14)	−0.0002 (15)	0.0104 (13)
C24	0.0445 (17)	0.0519 (18)	0.0565 (19)	0.0140 (14)	−0.0032 (17)	0.0130 (18)
C25	0.053 (2)	0.0537 (19)	0.0425 (17)	0.0178 (16)	0.0052 (16)	0.0058 (15)
C26	0.0480 (19)	0.0389 (17)	0.0374 (16)	0.0036 (14)	0.0005 (14)	0.0060 (13)
C27	0.0429 (16)	0.0456 (17)	0.0442 (17)	0.0067 (12)	0.0010 (16)	0.0032 (15)
C28	0.053 (2)	0.0443 (18)	0.0410 (17)	−0.0002 (15)	0.0060 (15)	0.0037 (14)
C29	0.051 (2)	0.0525 (18)	0.0446 (18)	0.0074 (16)	0.0003 (15)	−0.0046 (15)
C30	0.046 (2)	0.0487 (18)	0.0479 (18)	−0.0063 (14)	0.0026 (15)	−0.0040 (15)
C31	0.060 (2)	0.0522 (19)	0.0454 (18)	−0.0136 (16)	−0.0161 (16)	0.0047 (15)
C32	0.080 (3)	0.063 (2)	0.068 (2)	−0.017 (2)	−0.036 (2)	0.013 (2)
C33	0.081 (12)	0.046 (8)	0.085 (13)	−0.006 (6)	−0.030 (9)	−0.003 (7)
C34	0.107 (13)	0.069 (12)	0.077 (10)	−0.037 (13)	−0.007 (9)	0.022 (12)
C33'	0.081 (13)	0.046 (9)	0.085 (14)	−0.006 (6)	−0.030 (10)	−0.003 (7)
C34'	0.107 (13)	0.069 (13)	0.077 (11)	−0.037 (14)	−0.007 (9)	0.022 (12)

N1—C21	1.306 (3)	C16—H16	0.9300
N1—H1A	0.8600	C17—C18	1.378 (5)
N1—H1B	0.8600	C17—H17	0.9300
N2—C32	1.485 (4)	C18—C19	1.372 (4)
N2—C31	1.488 (4)	C18—H18	0.9300
N2—H2A	0.9000	C19—C20	1.417 (4)
N2—H2B	0.9000	C19—H19	0.9300
O1—C2	1.388 (3)	C21—C22	1.518 (4)
O1—P1	1.6189 (19)	C22—C23	1.516 (4)
O2—C12	1.390 (3)	C22—H22A	0.9700
O2—P1	1.6071 (19)	C22—H22B	0.9700
O3—P1	1.4608 (19)	C23—C24	1.361 (4)
O4—P1	1.470 (2)	C23—C28	1.377 (4)
O5—C21	1.242 (3)	C24—C25	1.388 (4)
O6—C26	1.376 (3)	C24—H24	0.9300
O6—C29	1.426 (3)	C25—C26	1.390 (4)
O7—C30	1.389 (3)	C25—H25	0.9300
O7—H7A	0.8200	C26—C27	1.373 (4)
C1—C2	1.374 (4)	C27—C28	1.373 (4)
C1—C10	1.428 (4)	C27—H27	0.9300
C1—C11	1.494 (4)	C28—H28	0.9300
C2—C3	1.394 (4)	C29—C30	1.502 (4)
C3—C4	1.343 (4)	C29—H29A	0.9700
C3—H3	0.9300	C29—H29B	0.9700
C4—C5	1.414 (4)	C30—C31	1.499 (4)
C4—H4	0.9300	C30—H30	0.9800
C5—C6	1.412 (4)	C31—H31A	0.9700
C5—C10	1.428 (4)	C31—H31B	0.9700
C6—C7	1.353 (4)	C32—C33'	1.41 (3)
C6—H6	0.9300	C32—C34	1.44 (3)
C7—C8	1.402 (4)	C32—C34'	1.62 (4)
C7—H7	0.9300	C32—C33	1.62 (3)
C8—C9	1.356 (4)	C32—H32	0.9800
C8—H8	0.9300	C33—H33A	0.9600
C9—C10	1.413 (4)	C33—H33B	0.9600
C9—H9	0.9300	C33—H33C	0.9600
C11—C12	1.374 (4)	C34—H34A	0.9600
C11—C20	1.435 (3)	C34—H34B	0.9600
C12—C13	1.388 (4)	C34—H34C	0.9600
C13—C14	1.346 (4)	C33'—H33D	0.9600
C13—H13	0.9300	C33'—H33E	0.9600
C14—C15	1.412 (4)	C33'—H33F	0.9600
C14—H14	0.9300	C34'—H34D	0.9600
C15—C20	1.413 (4)	C34'—H34E	0.9600
C15—C16	1.421 (5)	C34'—H34F	0.9600
C16—C17	1.344 (5)
C21—N1—H1A	120.0	O5—C21—N1	122.7 (3)
C21—N1—H1B	120.0	O5—C21—C22	120.1 (3)
H1A—N1—H1B	120.0	N1—C21—C22	117.2 (3)
C32—N2—C31	116.5 (2)	C23—C22—C21	114.1 (2)
C32—N2—H2A	108.2	C23—C22—H22A	108.7
C31—N2—H2A	108.2	C21—C22—H22A	108.7
C32—N2—H2B	108.2	C23—C22—H22B	108.7
C31—N2—H2B	108.2	C21—C22—H22B	108.7
H2A—N2—H2B	107.3	H22A—C22—H22B	107.6
C2—O1—P1	116.13 (16)	C24—C23—C28	117.5 (3)
C12—O2—P1	121.14 (16)	C24—C23—C22	120.3 (3)
C26—O6—C29	117.5 (2)	C28—C23—C22	122.2 (3)
C30—O7—H7A	109.5	C23—C24—C25	123.2 (3)
O3—P1—O4	120.69 (12)	C23—C24—H24	118.4
O3—P1—O2	105.51 (11)	C25—C24—H24	118.4
O4—P1—O2	110.86 (12)	C24—C25—C26	117.7 (3)
O3—P1—O1	111.71 (12)	C24—C25—H25	121.1
O4—P1—O1	105.32 (11)	C26—C25—H25	121.1
O2—P1—O1	101.09 (9)	C27—C26—O6	115.8 (2)
C2—C1—C10	118.1 (2)	C27—C26—C25	120.0 (3)
C2—C1—C11	119.4 (2)	O6—C26—C25	124.2 (3)
C10—C1—C11	122.4 (2)	C28—C27—C26	120.2 (3)
C1—C2—O1	119.3 (2)	C28—C27—H27	119.9
C1—C2—C3	122.2 (3)	C26—C27—H27	119.9
O1—C2—C3	118.5 (2)	C27—C28—C23	121.4 (3)
C4—C3—C2	120.2 (3)	C27—C28—H28	119.3
C4—C3—H3	119.9	C23—C28—H28	119.3
C2—C3—H3	119.9	O6—C29—C30	108.5 (2)
C3—C4—C5	121.3 (3)	O6—C29—H29A	110.0
C3—C4—H4	119.4	C30—C29—H29A	110.0
C5—C4—H4	119.4	O6—C29—H29B	110.0
C6—C5—C4	122.9 (3)	C30—C29—H29B	110.0
C6—C5—C10	118.6 (3)	H29A—C29—H29B	108.4
C4—C5—C10	118.4 (3)	O7—C30—C31	108.7 (2)
C7—C6—C5	121.6 (3)	O7—C30—C29	112.7 (3)
C7—C6—H6	119.2	C31—C30—C29	111.2 (2)
C5—C6—H6	119.2	O7—C30—H30	108.0
C6—C7—C8	120.0 (3)	C31—C30—H30	108.0
C6—C7—H7	120.0	C29—C30—H30	108.0
C8—C7—H7	120.0	N2—C31—C30	110.0 (2)
C9—C8—C7	120.1 (3)	N2—C31—H31A	109.7
C9—C8—H8	119.9	C30—C31—H31A	109.7
C7—C8—H8	119.9	N2—C31—H31B	109.7
C8—C9—C10	121.9 (3)	C30—C31—H31B	109.7
C8—C9—H9	119.0	H31A—C31—H31B	108.2
C10—C9—H9	119.0	C33'—C32—C34	93.4 (11)
C9—C10—C1	123.0 (2)	C33'—C32—N2	121.9 (13)
C9—C10—C5	117.5 (3)	C34—C32—N2	119.1 (13)
C1—C10—C5	119.4 (2)	C33'—C32—C34'	113.4 (12)
C12—C11—C20	117.7 (2)	C34—C32—C34'	20.9 (11)
C12—C11—C1	119.5 (2)	N2—C32—C34'	101.3 (12)
C20—C11—C1	122.8 (2)	C33'—C32—C33	22.2 (9)
C11—C12—C13	122.7 (3)	C34—C32—C33	113.1 (12)
C11—C12—O2	119.1 (2)	N2—C32—C33	101.6 (10)
C13—C12—O2	118.1 (2)	C34'—C32—C33	131.3 (12)
C14—C13—C12	119.9 (3)	C33'—C32—H32	105.9
C14—C13—H13	120.1	C34—C32—H32	107.5
C12—C13—H13	120.1	N2—C32—H32	107.5
C13—C14—C15	121.3 (3)	C34'—C32—H32	105.7
C13—C14—H14	119.3	C33—C32—H32	107.5
C15—C14—H14	119.3	C32—C33—H33A	109.5
C14—C15—C20	118.8 (3)	C32—C33—H33B	109.5
C14—C15—C16	122.7 (3)	C32—C33—H33C	109.5
C20—C15—C16	118.5 (3)	C32—C34—H34A	109.5
C17—C16—C15	121.9 (3)	C32—C34—H34B	109.5
C17—C16—H16	119.1	C32—C34—H34C	109.5
C15—C16—H16	119.1	C32—C33'—H33D	109.5
C16—C17—C18	120.1 (3)	C32—C33'—H33E	109.5
C16—C17—H17	119.9	H33D—C33'—H33E	109.5
C18—C17—H17	119.9	C32—C33'—H33F	109.5
C19—C18—C17	120.5 (3)	H33D—C33'—H33F	109.5
C19—C18—H18	119.7	H33E—C33'—H33F	109.5
C17—C18—H18	119.7	C32—C34'—H34D	109.5
C18—C19—C20	121.2 (3)	C32—C34'—H34E	109.5
C18—C19—H19	119.4	H34D—C34'—H34E	109.5
C20—C19—H19	119.4	C32—C34'—H34F	109.5
C15—C20—C19	117.7 (2)	H34D—C34'—H34F	109.5
C15—C20—C11	119.5 (3)	H34E—C34'—H34F	109.5
C19—C20—C11	122.8 (3)
C12—O2—P1—O3	−155.99 (19)	C12—C13—C14—C15	−3.0 (4)
C12—O2—P1—O4	71.7 (2)	C13—C14—C15—C20	1.8 (4)
C12—O2—P1—O1	−39.5 (2)	C13—C14—C15—C16	−177.7 (3)
C2—O1—P1—O3	58.6 (2)	C14—C15—C16—C17	178.1 (3)
C2—O1—P1—O4	−168.71 (18)	C20—C15—C16—C17	−1.4 (5)
C2—O1—P1—O2	−53.25 (19)	C15—C16—C17—C18	−0.5 (6)
C10—C1—C2—O1	−173.7 (2)	C16—C17—C18—C19	1.2 (5)
C11—C1—C2—O1	2.7 (4)	C17—C18—C19—C20	0.1 (5)
C10—C1—C2—C3	7.1 (4)	C14—C15—C20—C19	−177.0 (3)
C11—C1—C2—C3	−176.5 (2)	C16—C15—C20—C19	2.5 (4)
P1—O1—C2—C1	76.7 (3)	C14—C15—C20—C11	2.1 (4)
P1—O1—C2—C3	−104.1 (2)	C16—C15—C20—C11	−178.5 (3)
C1—C2—C3—C4	−2.4 (4)	C18—C19—C20—C15	−1.9 (4)
O1—C2—C3—C4	178.4 (2)	C18—C19—C20—C11	179.1 (3)
C2—C3—C4—C5	−2.2 (4)	C12—C11—C20—C15	−4.5 (4)
C3—C4—C5—C6	−175.9 (3)	C1—C11—C20—C15	176.8 (2)
C3—C4—C5—C10	1.9 (4)	C12—C11—C20—C19	174.5 (3)
C4—C5—C6—C7	174.7 (3)	C1—C11—C20—C19	−4.2 (4)
C10—C5—C6—C7	−3.1 (4)	O5—C21—C22—C23	118.5 (3)
C5—C6—C7—C8	−0.1 (5)	N1—C21—C22—C23	−61.8 (4)
C6—C7—C8—C9	2.5 (5)	C21—C22—C23—C24	−84.0 (4)
C7—C8—C9—C10	−1.6 (4)	C21—C22—C23—C28	96.6 (3)
C8—C9—C10—C1	−178.4 (3)	C28—C23—C24—C25	−0.9 (4)
C8—C9—C10—C5	−1.6 (4)	C22—C23—C24—C25	179.8 (3)
C2—C1—C10—C9	169.6 (2)	C23—C24—C25—C26	1.0 (5)
C11—C1—C10—C9	−6.7 (4)	C29—O6—C26—C27	−176.7 (3)
C2—C1—C10—C5	−7.2 (4)	C29—O6—C26—C25	3.7 (4)
C11—C1—C10—C5	176.5 (2)	C24—C25—C26—C27	0.3 (4)
C6—C5—C10—C9	3.9 (4)	C24—C25—C26—O6	179.9 (3)
C4—C5—C10—C9	−174.0 (3)	O6—C26—C27—C28	178.7 (2)
C6—C5—C10—C1	−179.2 (2)	C25—C26—C27—C28	−1.6 (4)
C4—C5—C10—C1	2.9 (4)	C26—C27—C28—C23	1.8 (4)
C2—C1—C11—C12	−51.5 (3)	C24—C23—C28—C27	−0.5 (4)
C10—C1—C11—C12	124.7 (3)	C22—C23—C28—C27	178.8 (3)
C2—C1—C11—C20	127.1 (3)	C26—O6—C29—C30	−176.0 (2)
C10—C1—C11—C20	−56.7 (4)	O6—C29—C30—O7	−63.6 (3)
C20—C11—C12—C13	3.4 (4)	O6—C29—C30—C31	58.7 (3)
C1—C11—C12—C13	−177.9 (2)	C32—N2—C31—C30	−165.2 (3)
C20—C11—C12—O2	179.2 (2)	O7—C30—C31—N2	−52.6 (3)
C1—C11—C12—O2	−2.0 (4)	C29—C30—C31—N2	−177.2 (2)
P1—O2—C12—C11	73.7 (3)	C31—N2—C32—C33'	−57.1 (15)
P1—O2—C12—C13	−110.2 (2)	C31—N2—C32—C34	58.1 (17)
C11—C12—C13—C14	0.4 (4)	C31—N2—C32—C34'	69.9 (13)
O2—C12—C13—C14	−175.5 (3)	C31—N2—C32—C33	−66.8 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O3	0.82	1.87	2.683 (3)	172.
N2—H2B···O4i	0.90	1.95	2.746 (3)	147.
N2—H2A···O5ii	0.90	1.96	2.831 (3)	163.
N1—H1B···O5i	0.86	2.17	2.960 (3)	153.
N1—H1A···O4iii	0.86	2.07	2.907 (3)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O3	0.82	1.87	2.683 (3)	172
N2—H2B⋯O4i	0.90	1.95	2.746 (3)	147
N2—H2A⋯O5ii	0.90	1.96	2.831 (3)	163
N1—H1B⋯O5i	0.86	2.17	2.960 (3)	153
N1—H1A⋯O4iii	0.86	2.07	2.907 (3)	164

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