Bis[(5RS,11RS)-2,8-dimethyl-5,10-methano-5,6,11,12-tetra­hydro­dibenzo[b,f][1,5]diazo­cine-5-ium dihydrogen phosphate] tris­(phosphoric acid) methanol solvate

In the title compound, 2C₁₇H₁₉N₂⁺·2H₂PO₄⁻·3H₃PO₄·CH₃OH, Tröger base, phospho­ric acid and methanol are included in the crystal structure, the asymmetric unit of which contains three protonated acid units. The structure includes hydro­philic layers of dihydrogen phosphate anions, phospho­ric acid and methanol which are inter­connected by O—H...O hydrogen bonds. These layers alternate with the more hydro­phobic Tröger base. Each Tröger base acts as a proton donor in an N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.130
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N51    -   H51    ...       1.06 Ang.
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O11    -   H11    ...       0.71 Ang.
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O54    -   H54    ...       0.70 Ang.
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O43    -   H43    ...       0.70 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Bis[(5RS,11RS)-2,8-dimethyl-5,10-methano-5,6,11,12- tetrahydrodibenzo[b,f][1,5]diazocine-5-ium dihydrogen phosphate] tris(phosphoric acid) methanol solvate

Crystal data

2C17H19N2^+·2H2O4P^−·3H3O4P·CH4O	Z = 2
Mr = 1022.68	F(000) = 1072
Triclinic, P1	Dx = 1.482 (1) Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1330 (2) Å	Cell parameters from 10003 reflections
b = 10.3690 (2) Å	θ = 1.0–27.5°
c = 22.4040 (6) Å	µ = 0.28 mm^−1
α = 76.9690 (13)°	T = 150 K
β = 88.3810 (14)°	Plate, colourless
γ = 88.3660 (15)°	0.15 × 0.12 × 0.08 mm
V = 2291.84 (9) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	6499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Horizontally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 2.8°
Detector resolution: 9.091 pixels mm^-1	h = −13→13
ω and φ scans to fill the Ewald sphere	k = −13→13
42017 measured reflections	l = −29→29
10505 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0589P)^2 + 0.239P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.38 e Å^−3
10505 reflections	Δρmin = −0.46 e Å^−3
650 parameters

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P5	0.40259 (6)	0.24297 (7)	0.26181 (3)	0.02172 (17)
P3	0.08059 (6)	0.09936 (7)	0.41827 (3)	0.02095 (17)
P2	0.84929 (6)	0.17066 (6)	0.24042 (3)	0.02033 (17)
P4	0.62331 (6)	0.09727 (7)	0.43613 (3)	0.02254 (17)
P1	0.89884 (7)	0.35481 (7)	0.06475 (3)	0.02727 (18)
O21	0.73292 (16)	0.24362 (17)	0.20668 (8)	0.0246 (4)
O33	0.19599 (19)	0.12604 (19)	0.45566 (9)	0.0277 (5)
H33	0.253 (4)	0.071 (4)	0.462 (2)	0.098 (17)*
O31	0.09443 (17)	0.16060 (17)	0.35114 (8)	0.0258 (4)
O32	−0.04398 (18)	0.15178 (17)	0.44781 (9)	0.0247 (4)
H32	−0.120 (5)	0.143 (5)	0.425 (2)	0.112 (17)*
O51	0.47133 (17)	0.29942 (16)	0.30761 (8)	0.0244 (4)
O44	0.53065 (19)	0.22130 (19)	0.42412 (10)	0.0288 (5)
H44	0.508 (4)	0.239 (4)	0.3884 (18)	0.070 (14)*
O23	0.8052 (2)	0.05097 (19)	0.29220 (10)	0.0272 (5)
H23	0.786 (3)	0.071 (3)	0.3218 (14)	0.034 (10)*
O34	0.06914 (19)	−0.05338 (19)	0.42491 (10)	0.0278 (5)
H34	0.064 (3)	−0.087 (3)	0.4601 (15)	0.041 (11)*
O43	0.5522 (2)	−0.0168 (2)	0.41569 (10)	0.0287 (5)
H43	0.498 (3)	−0.036 (3)	0.4357 (15)	0.037 (11)*
O53	0.4949 (2)	0.1722 (2)	0.22296 (10)	0.0319 (5)
H53	0.572 (3)	0.199 (3)	0.2204 (16)	0.054 (11)*
N55	0.5018 (2)	0.7754 (2)	0.23828 (10)	0.0223 (5)
N51	0.5663 (2)	0.5450 (2)	0.26619 (10)	0.0217 (5)
H51	0.528 (3)	0.450 (3)	0.2853 (15)	0.055 (10)*
O41	0.64901 (17)	0.06435 (17)	0.50406 (8)	0.0250 (4)
O24	0.94507 (17)	0.11562 (16)	0.19912 (8)	0.0242 (4)
O52	0.3042 (2)	0.1342 (2)	0.28866 (11)	0.0366 (5)
H52	0.235 (4)	0.150 (4)	0.308 (2)	0.097 (16)*
O14	0.9338 (2)	0.2055 (2)	0.08289 (11)	0.0341 (5)
H14	0.940 (4)	0.178 (3)	0.1187 (16)	0.055 (12)*
C59	0.7329 (2)	0.4753 (3)	0.34504 (13)	0.0248 (6)
H59	0.7356	0.3929	0.3351	0.030*
C4	0.1208 (3)	0.8739 (2)	0.29055 (12)	0.0239 (6)
H4A	0.0626	0.9153	0.3163	0.029*
H4B	0.2010	0.9244	0.2825	0.029*
C62	0.7218 (3)	0.7195 (3)	0.37479 (13)	0.0243 (6)
H62	0.7175	0.8014	0.3853	0.029*
N5	0.0551 (2)	0.8761 (2)	0.23151 (10)	0.0219 (5)
H5	0.015 (3)	0.956 (3)	0.2157 (14)	0.048 (10)*
O22	0.91630 (19)	0.27132 (18)	0.27148 (9)	0.0271 (5)
H22	0.977 (3)	0.233 (3)	0.2972 (16)	0.056 (11)*
O13	1.0076 (2)	0.43759 (19)	0.07753 (9)	0.0377 (5)
C9	0.1422 (3)	0.4986 (3)	0.33545 (13)	0.0271 (6)
H9A	0.1088	0.4260	0.3234	0.032*
C2	0.1030 (2)	0.6256 (2)	0.30604 (12)	0.0214 (6)
O42	0.74826 (17)	0.11911 (19)	0.39687 (8)	0.0289 (5)
C57	0.6616 (2)	0.6870 (2)	0.17183 (12)	0.0219 (6)
N1	0.0106 (2)	0.6434 (2)	0.25698 (10)	0.0239 (5)
C61	0.8074 (2)	0.6221 (3)	0.40607 (13)	0.0244 (6)
C11	0.2800 (3)	0.5853 (3)	0.40246 (13)	0.0283 (7)
O54	0.3314 (2)	0.3609 (2)	0.21879 (12)	0.0379 (6)
H54	0.313 (4)	0.336 (4)	0.1938 (18)	0.064 (15)*
O12	0.7671 (2)	0.3810 (2)	0.09732 (11)	0.0462 (6)
H12	0.753 (4)	0.330 (4)	0.131 (2)	0.087 (16)*
C8	0.0711 (3)	0.6179 (3)	0.20008 (13)	0.0259 (6)
H8A	0.0021	0.6036	0.1733	0.031*
H8B	0.1257	0.5379	0.2098	0.031*
C3	0.1539 (2)	0.7340 (2)	0.32375 (12)	0.0197 (6)
C12	0.2391 (2)	0.7120 (3)	0.37324 (12)	0.0247 (6)
H12A	0.2691	0.7841	0.3869	0.030*
O11	0.8661 (2)	0.3829 (2)	−0.00367 (11)	0.0394 (6)
H11	0.895 (4)	0.438 (4)	−0.0240 (18)	0.061 (14)*
C60	0.8111 (3)	0.4992 (3)	0.39045 (13)	0.0276 (6)
H60A	0.8673	0.4324	0.4110	0.033*
C53	0.6419 (2)	0.6990 (2)	0.32814 (12)	0.0212 (6)
C56	0.5982 (2)	0.7942 (2)	0.18903 (12)	0.0215 (6)
C6	0.1459 (2)	0.8546 (3)	0.18200 (12)	0.0221 (6)
C63	0.6297 (3)	0.9215 (3)	0.15841 (13)	0.0280 (7)
H63A	0.5881	0.9935	0.1700	0.034*
C58	0.6395 (3)	0.5470 (3)	0.20712 (12)	0.0242 (6)
H58A	0.5896	0.5006	0.1825	0.029*
H58B	0.7241	0.5011	0.2155	0.029*
C68	0.8942 (3)	0.6481 (3)	0.45500 (14)	0.0343 (7)
H68A	0.9840	0.6554	0.4400	0.051*
H68B	0.8882	0.5764	0.4905	0.051*
H68C	0.8661	0.7292	0.4658	0.051*
C18	0.3775 (3)	0.5640 (3)	0.45388 (14)	0.0421 (8)
H18A	0.4646	0.5509	0.4380	0.063*
H18B	0.3538	0.4873	0.4847	0.063*
H18C	0.3759	0.6403	0.4715	0.063*
C64	0.7220 (3)	0.9430 (3)	0.11098 (13)	0.0296 (7)
H64A	0.7431	1.0292	0.0916	0.036*
C67	0.4525 (2)	0.6442 (2)	0.25213 (13)	0.0242 (6)
H67A	0.4047	0.6292	0.2175	0.029*
H67B	0.3921	0.6330	0.2872	0.029*
C17	−0.0505 (2)	0.7729 (2)	0.24448 (13)	0.0244 (6)
H17A	−0.1046	0.7840	0.2795	0.029*
H17B	−0.1069	0.7836	0.2094	0.029*
C16	0.2424 (3)	0.7172 (3)	0.11945 (13)	0.0284 (7)
H16A	0.2499	0.6357	0.1087	0.034*
C7	0.1542 (2)	0.7311 (3)	0.16718 (13)	0.0238 (6)
C54	0.5513 (3)	0.8077 (3)	0.29410 (13)	0.0260 (6)
H54A	0.4772	0.8205	0.3207	0.031*
H54B	0.5988	0.8900	0.2832	0.031*
C52	0.6502 (2)	0.5752 (2)	0.31449 (12)	0.0213 (6)
C66	0.7525 (3)	0.7099 (3)	0.12222 (12)	0.0259 (6)
H66A	0.7921	0.6381	0.1097	0.031*
C10	0.2303 (3)	0.4792 (3)	0.38237 (13)	0.0308 (7)
H10A	0.2573	0.3935	0.4010	0.037*
C65	0.7843 (3)	0.8367 (3)	0.09155 (13)	0.0287 (7)
C15	0.3182 (3)	0.8202 (3)	0.08792 (13)	0.0317 (7)
C13	0.2204 (3)	0.9600 (3)	0.15119 (14)	0.0304 (7)
H13A	0.2130	1.0416	0.1618	0.036*
C14	0.3059 (3)	0.9421 (3)	0.10444 (14)	0.0359 (7)
H14A	0.3561	1.0126	0.0836	0.043*
C69	0.8857 (3)	0.8619 (3)	0.04020 (15)	0.0447 (8)
H69A	0.9496	0.7903	0.0463	0.067*
H69B	0.9291	0.9432	0.0397	0.067*
H69C	0.8430	0.8684	0.0019	0.067*
C19	0.4133 (3)	0.8004 (4)	0.03758 (15)	0.0467 (9)
H19A	0.4964	0.7671	0.0550	0.070*
H19B	0.4261	0.8834	0.0090	0.070*
H19C	0.3780	0.7381	0.0168	0.070*
O1S	0.2448 (3)	0.3222 (3)	0.11858 (12)	0.0564 (7)
H1S	0.177 (4)	0.359 (4)	0.106 (2)	0.090 (17)*
C1S	0.3348 (4)	0.3360 (4)	0.06772 (19)	0.0700 (12)
H11S	0.3264	0.4238	0.0425	0.105*
H12S	0.3154	0.2726	0.0441	0.105*
H13S	0.4234	0.3209	0.0822	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P5	0.0179 (3)	0.0206 (4)	0.0274 (4)	−0.0020 (3)	0.0020 (3)	−0.0070 (3)
P3	0.0203 (3)	0.0217 (4)	0.0204 (4)	−0.0008 (3)	0.0011 (3)	−0.0039 (3)
P2	0.0204 (3)	0.0190 (4)	0.0203 (4)	0.0015 (3)	0.0023 (3)	−0.0023 (3)
P4	0.0186 (3)	0.0275 (4)	0.0197 (4)	0.0002 (3)	0.0019 (3)	−0.0020 (3)
P1	0.0333 (4)	0.0260 (4)	0.0200 (4)	−0.0044 (3)	0.0011 (3)	0.0004 (3)
O21	0.0195 (9)	0.0250 (10)	0.0260 (11)	0.0038 (7)	0.0022 (8)	0.0001 (8)
O33	0.0241 (10)	0.0285 (11)	0.0313 (12)	0.0012 (9)	−0.0058 (9)	−0.0082 (9)
O31	0.0224 (9)	0.0304 (10)	0.0226 (11)	−0.0027 (8)	0.0042 (8)	−0.0018 (8)
O32	0.0223 (10)	0.0268 (10)	0.0249 (11)	0.0017 (8)	0.0028 (9)	−0.0065 (8)
O51	0.0281 (10)	0.0213 (10)	0.0233 (11)	−0.0037 (8)	−0.0022 (8)	−0.0032 (8)
O44	0.0296 (11)	0.0308 (11)	0.0246 (13)	0.0063 (8)	0.0004 (9)	−0.0038 (9)
O23	0.0365 (12)	0.0232 (11)	0.0209 (12)	−0.0022 (8)	0.0050 (10)	−0.0032 (9)
O34	0.0345 (12)	0.0236 (11)	0.0252 (13)	−0.0023 (8)	0.0034 (10)	−0.0054 (10)
O43	0.0260 (11)	0.0348 (12)	0.0263 (13)	−0.0057 (9)	0.0080 (10)	−0.0096 (10)
O53	0.0212 (11)	0.0357 (12)	0.0442 (14)	−0.0028 (9)	0.0073 (10)	−0.0210 (10)
N55	0.0200 (11)	0.0196 (11)	0.0270 (14)	0.0005 (9)	0.0022 (10)	−0.0052 (10)
N51	0.0225 (11)	0.0190 (12)	0.0230 (13)	−0.0028 (9)	0.0029 (10)	−0.0033 (10)
O41	0.0206 (9)	0.0325 (11)	0.0197 (11)	0.0008 (8)	0.0014 (8)	−0.0016 (8)
O24	0.0259 (10)	0.0232 (10)	0.0211 (11)	0.0074 (8)	0.0044 (8)	−0.0013 (8)
O52	0.0295 (11)	0.0313 (12)	0.0530 (15)	−0.0121 (9)	0.0185 (11)	−0.0191 (10)
O14	0.0502 (13)	0.0271 (11)	0.0223 (13)	−0.0002 (9)	0.0056 (11)	−0.0004 (10)
C59	0.0246 (14)	0.0201 (14)	0.0300 (17)	0.0004 (11)	0.0038 (12)	−0.0071 (12)
C4	0.0269 (14)	0.0204 (14)	0.0254 (16)	0.0008 (11)	−0.0004 (12)	−0.0078 (12)
C62	0.0263 (14)	0.0211 (14)	0.0268 (16)	−0.0040 (11)	0.0063 (12)	−0.0085 (12)
N5	0.0208 (11)	0.0203 (12)	0.0227 (13)	0.0029 (9)	0.0008 (10)	−0.0017 (10)
O22	0.0311 (11)	0.0234 (10)	0.0270 (12)	−0.0009 (8)	−0.0044 (9)	−0.0052 (9)
O13	0.0545 (13)	0.0355 (12)	0.0203 (11)	−0.0159 (10)	−0.0061 (10)	0.0023 (9)
C9	0.0293 (15)	0.0213 (14)	0.0303 (17)	−0.0043 (12)	0.0055 (13)	−0.0055 (12)
C2	0.0173 (13)	0.0230 (14)	0.0220 (15)	0.0000 (11)	0.0035 (11)	−0.0016 (12)
O42	0.0194 (9)	0.0433 (12)	0.0222 (11)	−0.0010 (8)	0.0038 (8)	−0.0042 (9)
C57	0.0198 (13)	0.0203 (14)	0.0242 (16)	−0.0012 (11)	−0.0026 (12)	−0.0018 (12)
N1	0.0226 (11)	0.0219 (12)	0.0287 (14)	−0.0008 (9)	−0.0031 (10)	−0.0087 (10)
C61	0.0215 (14)	0.0284 (15)	0.0228 (16)	−0.0040 (11)	0.0047 (12)	−0.0049 (12)
C11	0.0202 (14)	0.0358 (17)	0.0248 (17)	0.0031 (12)	0.0025 (12)	0.0013 (13)
O54	0.0452 (13)	0.0316 (12)	0.0382 (15)	0.0090 (10)	−0.0169 (12)	−0.0099 (11)
O12	0.0459 (14)	0.0455 (14)	0.0358 (15)	0.0121 (11)	0.0086 (11)	0.0120 (12)
C8	0.0247 (14)	0.0258 (15)	0.0302 (17)	0.0021 (11)	−0.0040 (12)	−0.0127 (13)
C3	0.0166 (12)	0.0217 (14)	0.0211 (15)	0.0009 (10)	0.0022 (11)	−0.0061 (11)
C12	0.0196 (13)	0.0316 (16)	0.0240 (16)	−0.0004 (11)	0.0039 (12)	−0.0089 (13)
O11	0.0471 (14)	0.0436 (14)	0.0233 (13)	−0.0186 (11)	−0.0057 (11)	0.0038 (11)
C60	0.0269 (15)	0.0267 (15)	0.0273 (17)	−0.0011 (12)	0.0021 (13)	−0.0023 (13)
C53	0.0207 (13)	0.0220 (14)	0.0201 (15)	−0.0030 (11)	0.0082 (11)	−0.0041 (11)
C56	0.0202 (13)	0.0218 (14)	0.0214 (15)	−0.0008 (11)	−0.0039 (11)	−0.0023 (11)
C6	0.0182 (13)	0.0268 (15)	0.0198 (15)	0.0030 (11)	−0.0013 (11)	−0.0026 (12)
C63	0.0305 (15)	0.0219 (15)	0.0306 (17)	0.0020 (12)	−0.0034 (13)	−0.0040 (13)
C58	0.0263 (14)	0.0238 (14)	0.0233 (16)	−0.0013 (11)	0.0003 (12)	−0.0071 (12)
C68	0.0336 (16)	0.0383 (18)	0.0310 (18)	−0.0027 (13)	−0.0007 (14)	−0.0075 (14)
C18	0.0325 (17)	0.056 (2)	0.0316 (19)	0.0044 (15)	−0.0054 (15)	0.0020 (16)
C64	0.0301 (15)	0.0241 (15)	0.0304 (18)	−0.0090 (12)	−0.0010 (13)	0.0038 (13)
C67	0.0202 (13)	0.0254 (15)	0.0265 (16)	−0.0003 (11)	−0.0010 (12)	−0.0050 (12)
C17	0.0166 (13)	0.0282 (15)	0.0281 (17)	0.0010 (11)	−0.0013 (12)	−0.0057 (12)
C16	0.0272 (15)	0.0344 (16)	0.0249 (17)	0.0080 (13)	−0.0065 (13)	−0.0100 (13)
C7	0.0204 (13)	0.0281 (15)	0.0235 (16)	0.0036 (11)	−0.0060 (12)	−0.0073 (12)
C54	0.0259 (14)	0.0246 (15)	0.0275 (17)	0.0006 (11)	0.0037 (12)	−0.0066 (12)
C52	0.0191 (13)	0.0222 (14)	0.0227 (15)	−0.0030 (11)	0.0040 (11)	−0.0052 (12)
C66	0.0230 (14)	0.0314 (16)	0.0236 (16)	0.0019 (12)	−0.0030 (12)	−0.0069 (13)
C10	0.0313 (16)	0.0252 (15)	0.0297 (18)	0.0053 (12)	0.0043 (13)	0.0054 (13)
C65	0.0270 (15)	0.0345 (17)	0.0226 (16)	−0.0057 (12)	−0.0030 (12)	−0.0013 (13)
C15	0.0266 (15)	0.0461 (19)	0.0214 (17)	0.0019 (13)	0.0006 (13)	−0.0063 (14)
C13	0.0291 (15)	0.0269 (16)	0.0328 (18)	0.0033 (12)	−0.0019 (14)	−0.0020 (13)
C14	0.0258 (15)	0.0440 (19)	0.0320 (19)	−0.0028 (13)	0.0020 (14)	0.0036 (15)
C69	0.0380 (18)	0.057 (2)	0.035 (2)	−0.0069 (16)	0.0114 (15)	−0.0028 (17)
C19	0.0358 (18)	0.070 (2)	0.034 (2)	0.0000 (16)	0.0077 (15)	−0.0128 (18)
O1S	0.0526 (16)	0.0709 (18)	0.0459 (17)	0.0024 (14)	−0.0220 (14)	−0.0112 (13)
C1S	0.079 (3)	0.074 (3)	0.059 (3)	0.017 (2)	−0.001 (2)	−0.021 (2)

Geometric parameters (Å, º)

P5—O51	1.4884 (18)	N1—C8	1.473 (3)
P5—O52	1.534 (2)	C61—C60	1.395 (4)
P5—O53	1.541 (2)	C61—C68	1.500 (4)
P5—O54	1.550 (2)	C11—C12	1.387 (4)
P5—H54	1.86 (4)	C11—C10	1.390 (4)
P3—O31	1.4991 (19)	C11—C18	1.513 (4)
P3—O33	1.5245 (19)	O54—H54	0.70 (4)
P3—O32	1.5501 (18)	O12—H12	0.82 (4)
P3—O34	1.564 (2)	C8—C7	1.504 (4)
P2—O21	1.5086 (17)	C8—H8A	0.9700
P2—O24	1.5097 (18)	C8—H8B	0.9700
P2—O22	1.559 (2)	C3—C12	1.399 (4)
P2—O23	1.562 (2)	C12—H12A	0.9300
P4—O41	1.5112 (19)	O11—H11	0.71 (4)
P4—O42	1.5138 (19)	C60—H60A	0.9300
P4—O44	1.5483 (19)	C53—C52	1.385 (3)
P4—O43	1.562 (2)	C53—C54	1.513 (3)
P4—H43	1.91 (3)	C56—C63	1.385 (4)
P1—O13	1.489 (2)	C6—C13	1.385 (4)
P1—O11	1.538 (2)	C6—C7	1.393 (4)
P1—O14	1.543 (2)	C63—C64	1.379 (4)
P1—O12	1.550 (2)	C63—H63A	0.9300
O33—H33	0.79 (4)	C58—H58A	0.9700
O32—H32	0.95 (5)	C58—H58B	0.9700
O44—H44	0.82 (4)	C68—H68A	0.9600
O23—H23	0.76 (3)	C68—H68B	0.9600
O34—H34	0.79 (3)	C68—H68C	0.9600
O43—H43	0.71 (3)	C18—H18A	0.9600
O53—H53	0.83 (3)	C18—H18B	0.9600
N55—C67	1.427 (3)	C18—H18C	0.9600
N55—C56	1.436 (3)	C64—C65	1.402 (4)
N55—C54	1.470 (3)	C64—H64A	0.9300
N51—C52	1.487 (3)	C67—H67A	0.9700
N51—C58	1.495 (3)	C67—H67B	0.9700
N51—C67	1.514 (3)	C17—H17A	0.9700
N51—H51	1.06 (3)	C17—H17B	0.9700
O52—H52	0.85 (4)	C16—C15	1.381 (4)
O14—H14	0.79 (3)	C16—C7	1.403 (4)
C59—C60	1.377 (4)	C16—H16A	0.9300
C59—C52	1.381 (3)	C54—H54A	0.9700
C59—H59	0.9300	C54—H54B	0.9700
C4—N5	1.492 (3)	C66—C65	1.381 (4)
C4—C3	1.507 (3)	C66—H66A	0.9300
C4—H4A	0.9700	C10—H10A	0.9300
C4—H4B	0.9700	C65—C69	1.503 (4)
C62—C61	1.389 (4)	C15—C14	1.397 (4)
C62—C53	1.397 (4)	C15—C19	1.508 (4)
C62—H62	0.9300	C13—C14	1.381 (4)
N5—C6	1.473 (3)	C13—H13A	0.9300
N5—C17	1.511 (3)	C14—H14A	0.9300
N5—H5	0.92 (3)	C69—H69A	0.9600
O22—H22	0.88 (3)	C69—H69B	0.9600
C9—C10	1.375 (4)	C69—H69C	0.9600
C9—C2	1.386 (4)	C19—H19A	0.9600
C9—H9A	0.9300	C19—H19B	0.9600
C2—C3	1.390 (4)	C19—H19C	0.9600
C2—N1	1.441 (3)	O1S—C1S	1.423 (5)
C57—C56	1.391 (4)	O1S—H1S	0.80 (4)
C57—C66	1.406 (4)	C1S—H11S	0.9600
C57—C58	1.508 (4)	C1S—H12S	0.9600
N1—C17	1.435 (3)	C1S—H13S	0.9600
O51—P5—O52	115.30 (12)	C59—C60—C61	121.0 (3)
O51—P5—O53	114.33 (11)	C59—C60—H60A	119.5
O52—P5—O53	101.61 (12)	C61—C60—H60A	119.5
O51—P5—O54	106.31 (12)	C52—C53—C62	116.9 (2)
O52—P5—O54	110.31 (13)	C52—C53—C54	121.9 (2)
O53—P5—O54	108.90 (13)	C62—C53—C54	121.3 (2)
O31—P3—O33	113.69 (11)	C63—C56—C57	119.3 (3)
O31—P3—O32	112.29 (10)	C63—C56—N55	119.4 (2)
O33—P3—O32	105.39 (11)	C57—C56—N55	121.3 (2)
O31—P3—O34	107.11 (12)	C13—C6—C7	122.0 (3)
O33—P3—O34	109.36 (11)	C13—C6—N5	118.1 (2)
O32—P3—O34	108.92 (11)	C7—C6—N5	119.9 (2)
O21—P2—O24	112.93 (10)	C64—C63—C56	120.8 (3)
O21—P2—O22	106.16 (10)	C64—C63—H63A	119.6
O24—P2—O22	111.66 (11)	C56—C63—H63A	119.6
O21—P2—O23	111.84 (11)	N51—C58—C57	111.1 (2)
O24—P2—O23	106.58 (11)	N51—C58—H58A	109.4
O22—P2—O23	107.63 (11)	C57—C58—H58A	109.4
O41—P4—O42	113.26 (10)	N51—C58—H58B	109.4
O41—P4—O44	106.25 (11)	C57—C58—H58B	109.4
O42—P4—O44	111.94 (11)	H58A—C58—H58B	108.0
O41—P4—O43	112.08 (11)	C61—C68—H68A	109.5
O42—P4—O43	104.99 (12)	C61—C68—H68B	109.5
O44—P4—O43	108.32 (11)	H68A—C68—H68B	109.5
O13—P1—O11	112.65 (12)	C61—C68—H68C	109.5
O13—P1—O14	112.21 (12)	H68A—C68—H68C	109.5
O11—P1—O14	105.44 (14)	H68B—C68—H68C	109.5
O13—P1—O12	112.48 (14)	C11—C18—H18A	109.5
O11—P1—O12	104.69 (14)	C11—C18—H18B	109.5
O14—P1—O12	108.85 (13)	H18A—C18—H18B	109.5
P3—O33—H33	116 (3)	C11—C18—H18C	109.5
P3—O32—H32	110 (3)	H18A—C18—H18C	109.5
P4—O44—H44	110 (3)	H18B—C18—H18C	109.5
P2—O23—H23	113 (2)	C63—C64—C65	121.0 (3)
P3—O34—H34	108 (2)	C63—C64—H64A	119.5
P4—O43—H43	109 (3)	C65—C64—H64A	119.5
P5—O53—H53	113 (2)	N55—C67—N51	109.7 (2)
C67—N55—C56	111.7 (2)	N55—C67—H67A	109.7
C67—N55—C54	109.9 (2)	N51—C67—H67A	109.7
C56—N55—C54	112.9 (2)	N55—C67—H67B	109.7
C52—N51—C58	113.4 (2)	N51—C67—H67B	109.7
C52—N51—C67	110.75 (19)	H67A—C67—H67B	108.2
C58—N51—C67	107.2 (2)	N1—C17—N5	109.40 (19)
C52—N51—H51	105.1 (17)	N1—C17—H17A	109.8
C58—N51—H51	111.2 (17)	N5—C17—H17A	109.8
C67—N51—H51	109.1 (17)	N1—C17—H17B	109.8
P5—O52—H52	122 (3)	N5—C17—H17B	109.8
P1—O14—H14	113 (3)	H17A—C17—H17B	108.2
C60—C59—C52	119.1 (2)	C15—C16—C7	122.3 (3)
C60—C59—H59	120.4	C15—C16—H16A	118.8
C52—C59—H59	120.4	C7—C16—H16A	118.8
N5—C4—C3	110.9 (2)	C6—C7—C16	117.1 (3)
N5—C4—H4A	109.5	C6—C7—C8	121.7 (2)
C3—C4—H4A	109.5	C16—C7—C8	121.2 (2)
N5—C4—H4B	109.5	N55—C54—C53	111.4 (2)
C3—C4—H4B	109.5	N55—C54—H54A	109.3
H4A—C4—H4B	108.0	C53—C54—H54A	109.3
C61—C62—C53	122.4 (2)	N55—C54—H54B	109.3
C61—C62—H62	118.8	C53—C54—H54B	109.3
C53—C62—H62	118.8	H54A—C54—H54B	108.0
C6—N5—C4	114.2 (2)	C59—C52—C53	122.4 (2)
C6—N5—C17	110.9 (2)	C59—C52—N51	117.5 (2)
C4—N5—C17	107.5 (2)	C53—C52—N51	120.0 (2)
C6—N5—H5	104 (2)	C65—C66—C57	121.6 (3)
C4—N5—H5	112.0 (19)	C65—C66—H66A	119.2
C17—N5—H5	107.8 (19)	C57—C66—H66A	119.2
P2—O22—H22	112 (2)	C9—C10—C11	121.3 (2)
C10—C9—C2	120.4 (3)	C9—C10—H10A	119.3
C10—C9—H9A	119.8	C11—C10—H10A	119.3
C2—C9—H9A	119.8	C66—C65—C64	117.9 (3)
C9—C2—C3	119.8 (2)	C66—C65—C69	121.8 (3)
C9—C2—N1	119.3 (2)	C64—C65—C69	120.2 (3)
C3—C2—N1	120.9 (2)	C16—C15—C14	118.3 (3)
C56—C57—C66	119.3 (2)	C16—C15—C19	120.6 (3)
C56—C57—C58	121.3 (2)	C14—C15—C19	121.0 (3)
C66—C57—C58	119.3 (2)	C14—C13—C6	119.0 (3)
C17—N1—C2	112.1 (2)	C14—C13—H13A	120.5
C17—N1—C8	109.4 (2)	C6—C13—H13A	120.5
C2—N1—C8	112.6 (2)	C13—C14—C15	121.2 (3)
C62—C61—C60	118.1 (2)	C13—C14—H14A	119.4
C62—C61—C68	121.1 (2)	C15—C14—H14A	119.4
C60—C61—C68	120.8 (2)	C65—C69—H69A	109.5
C12—C11—C10	118.0 (3)	C65—C69—H69B	109.5
C12—C11—C18	120.7 (3)	H69A—C69—H69B	109.5
C10—C11—C18	121.3 (3)	C65—C69—H69C	109.5
P5—O54—H54	105 (3)	H69A—C69—H69C	109.5
P1—O12—H12	115 (3)	H69B—C69—H69C	109.5
N1—C8—C7	111.8 (2)	C15—C19—H19A	109.5
N1—C8—H8A	109.2	C15—C19—H19B	109.5
C7—C8—H8A	109.2	H19A—C19—H19B	109.5
N1—C8—H8B	109.2	C15—C19—H19C	109.5
C7—C8—H8B	109.2	H19A—C19—H19C	109.5
H8A—C8—H8B	107.9	H19B—C19—H19C	109.5
C2—C3—C12	118.9 (2)	C1S—O1S—H1S	108 (3)
C2—C3—C4	121.7 (2)	O1S—C1S—H11S	109.5
C12—C3—C4	119.4 (2)	O1S—C1S—H12S	109.5
C11—C12—C3	121.5 (3)	H11S—C1S—H12S	109.5
C11—C12—H12A	119.2	O1S—C1S—H13S	109.5
C3—C12—H12A	119.2	H11S—C1S—H13S	109.5
P1—O11—H11	119 (3)	H12S—C1S—H13S	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O33—H33···O41^i	0.79 (4)	1.74 (4)	2.506 (3)	162 (5)
O32—H32···O42^ii	0.95 (5)	1.54 (5)	2.490 (2)	172 (5)
O44—H44···O51	0.82 (4)	1.82 (4)	2.634 (3)	172 (4)
O23—H23···O42	0.76 (3)	1.89 (3)	2.642 (3)	177 (3)
O34—H34···O32^iii	0.79 (3)	2.03 (3)	2.811 (3)	174 (3)
O43—H43···O41^i	0.71 (3)	1.96 (3)	2.661 (3)	171 (4)
O53—H53···O21	0.83 (3)	1.71 (4)	2.535 (3)	172 (4)
N51—H51···O51	1.06 (3)	1.65 (3)	2.700 (3)	174 (3)
O52—H52···O31	0.85 (4)	1.71 (5)	2.554 (3)	172 (4)
O14—H14···O24	0.79 (3)	1.77 (4)	2.565 (3)	177 (4)
N5—H5···O24^iv	0.92 (3)	1.74 (3)	2.648 (3)	169 (3)
O22—H22···O31^v	0.88 (3)	1.75 (3)	2.627 (3)	177 (3)
O54—H54···O1S	0.70 (4)	1.88 (4)	2.551 (3)	163 (5)
O12—H12···O21	0.82 (4)	1.75 (4)	2.561 (3)	170 (5)
O11—H11···O13^vi	0.71 (4)	1.84 (4)	2.543 (3)	171 (5)
O1S—H1S···O13^ii	0.80 (4)	1.94 (4)	2.743 (3)	176 (5)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x, −y, −z+1; (iv) x−1, y+1, z; (v) x+1, y, z; (vi) −x+2, −y+1, −z.