Supra­molecular architecture in aza­heterocyclic phospho­nates. III. Structures of an ethyl phos­phonamidate and an ethyl phos­phonate

The novel crystal structures of ethyl (S)-P-(4-oxo-4H-benzo[4,5]thia­zolo[3,2-a]pyrimidin-3-yl)-N-[(R)-1-phenyl­eth­yl]phospho­namidate, C₂₀H₂₀N₃O₃PS, I, and diethyl (4-isopropyl-2-oxo-3,4-di­hydro-2H-benzo[4,5]thia­zolo[3,2-a]pyrimidin-3-yl)phospho­nate, C₁₈H₂₅N₂O₄PS, II, were characterized by X-ray diffraction analysis. The crystal packing of I is dominated by two infinite stacks composed of symmetry-independent mol­ecules linked by distinctively different hydrogen-bond systems. The structure of II shows a ladder packing topology similar to those observed in related phospho­rylated aza­heterocycles. Structural studies are supplemented by calculations on the inter­actions stabilizing the mol­ecular assemblies using the PIXEL method. Additionally, fingerprint plots derived from the Hirshfeld surfaces were generated for each structure to characterize the crystal packing arrangements in detail. The aromaticities of the heterocyclic moieties have been investigated using HOMA and HOMHED parametrization and compared with structures reported previously.

Computing details

Data collection: APEX2 (Bruker, 2014) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (I); CrysAlis PRO (Rigaku OD, 2017) for (II). For both structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b). Molecular graphics: Mercury (Macrae et al., 2008) for (I). Software used to prepare material for publication: publCIF (Westrip, 2010) for (I); SHELXL2018 (Sheldrick, 2015b) for (II).

Ethyl (S)-P-(4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)-N-[(R)-1-phenylethyl]phosphonamidate (I)

Crystal data

C20H20N3O3PS	F(000) = 864
Mr = 413.42	Dx = 1.427 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 16.4417 (7) Å	Cell parameters from 11973 reflections
b = 5.1623 (2) Å	θ = 2.9–70.3°
c = 23.7712 (9) Å	µ = 2.51 mm^−1
β = 107.430 (4)°	T = 100 K
V = 1924.99 (14) Å^3	Needle, colourless
Z = 4	0.1 × 0.07 × 0.03 mm

Data collection

Bruker SMART APEXII diffractometer	6183 reflections with I > 2σ(I)
Radiation source: sealed X-ray microsource	Rint = 0.045
ω scans	θmax = 67.1°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	h = −19→19
Tmin = 0.460, Tmax = 1.000	k = −6→6
20421 measured reflections	l = −28→27
6723 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.1069P)^2 + 0.7717P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.43 e Å^−3
6723 reflections	Δρmin = −0.40 e Å^−3
554 parameters	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower.
194 restraints	Absolute structure parameter: −0.01 (3)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1A	0.44382 (8)	−0.1508 (2)	0.12851 (6)	0.0281 (3)
P1B	0.14833 (8)	0.7025 (3)	0.43466 (6)	0.0299 (3)
S1A	0.83195 (8)	0.0044 (3)	0.16721 (6)	0.0385 (3)
S1B	0.38153 (9)	0.4374 (3)	0.68539 (6)	0.0382 (3)
O1A	0.5962 (2)	−0.4448 (7)	0.21073 (15)	0.0307 (8)
O2A	0.4312 (2)	−0.0789 (7)	0.19040 (16)	0.0322 (8)
O4B	0.1202 (2)	0.4504 (7)	0.40532 (16)	0.0346 (8)
O2B	0.0808 (2)	0.8659 (8)	0.45502 (15)	0.0338 (8)
O1B	0.3121 (3)	0.3723 (8)	0.47081 (16)	0.0407 (9)
O4A	0.4198 (2)	−0.4181 (7)	0.10780 (18)	0.0361 (9)
N2A	0.7019 (3)	−0.2062 (8)	0.18928 (18)	0.0282 (9)
N3A	0.3895 (3)	0.0603 (9)	0.08194 (19)	0.0305 (9)
H3A	0.400 (3)	0.227 (13)	0.092 (2)	0.024 (13)*
N2B	0.3385 (3)	0.4177 (9)	0.57113 (18)	0.0313 (9)
N3B	0.1813 (3)	0.8973 (9)	0.39288 (19)	0.0326 (10)
H3B	0.189 (5)	1.065 (19)	0.401 (3)	0.06 (2)*
NA	0.6693 (3)	0.1535 (9)	0.1229 (2)	0.0338 (10)
N1B	0.2658 (3)	0.7365 (10)	0.6118 (2)	0.0381 (11)
C10A	0.6144 (3)	−0.2642 (11)	0.1832 (2)	0.0295 (10)
C34A	0.2243 (8)	0.304 (3)	0.0207 (7)	0.046 (3)	0.544 (18)
H34A	0.265022	0.422217	0.041385	0.055*	0.544 (18)
C35A	0.1378 (8)	0.369 (4)	0.0064 (7)	0.058 (4)	0.544 (18)
H35A	0.119572	0.526504	0.017169	0.070*	0.544 (18)
C37A	0.1035 (9)	−0.054 (4)	−0.0394 (9)	0.067 (5)	0.544 (18)
H37A	0.064599	−0.180527	−0.058389	0.080*	0.544 (18)
C38A	0.1902 (8)	−0.108 (3)	−0.0246 (8)	0.055 (4)	0.544 (18)
H38A	0.207334	−0.268702	−0.034818	0.066*	0.544 (18)
C31A	0.3456 (3)	0.0046 (10)	0.0194 (2)	0.0314 (11)
H31A	0.351942	−0.180884	0.012930	0.038*
C1A	0.5561 (3)	−0.0909 (10)	0.1441 (2)	0.0276 (10)
C10B	0.2927 (3)	0.4749 (11)	0.5112 (2)	0.0322 (11)
C9A	0.7735 (3)	−0.3405 (10)	0.2259 (2)	0.0301 (11)
C3A	0.7229 (3)	−0.0085 (10)	0.1574 (2)	0.0327 (11)
C5A	0.9286 (3)	−0.3446 (11)	0.2516 (2)	0.0353 (12)
H5A	0.979111	−0.282752	0.246682	0.042*
C21B	0.0007 (3)	0.9464 (11)	0.4135 (2)	0.0360 (12)
H21C	0.001251	0.911311	0.373483	0.043*
H21D	−0.007395	1.131011	0.417178	0.043*
C33B	0.1688 (3)	0.8696 (10)	0.2863 (2)	0.0305 (11)
C9B	0.4019 (3)	0.2264 (11)	0.5904 (2)	0.0336 (11)
C8B	0.4346 (4)	0.0596 (12)	0.5562 (3)	0.0384 (13)
H8B	0.415717	0.069019	0.515218	0.046*
C7B	0.4953 (4)	−0.1191 (13)	0.5844 (3)	0.0447 (14)
H7B	0.518045	−0.230201	0.562282	0.054*
C2A	0.5864 (3)	0.1096 (11)	0.1179 (2)	0.0324 (11)
H2A	0.546597	0.224226	0.094801	0.039*
C38B	0.1737 (4)	0.7088 (12)	0.2405 (2)	0.0360 (12)
H38B	0.209280	0.564893	0.249048	0.043*
C32A	0.3866 (4)	0.1530 (11)	−0.0207 (2)	0.0371 (12)
H32A	0.356093	0.117443	−0.061165	0.056*
H32B	0.444871	0.099547	−0.012741	0.056*
H32C	0.384560	0.335450	−0.013376	0.056*
C6A	0.9290 (3)	−0.5385 (12)	0.2924 (2)	0.0370 (12)
H6A	0.980684	−0.607020	0.315167	0.044*
C2B	0.2168 (4)	0.7849 (11)	0.5555 (2)	0.0344 (12)
H2B	0.174948	0.911643	0.550031	0.041*
C5B	0.4917 (4)	0.0313 (13)	0.6805 (3)	0.0402 (13)
H5B	0.511057	0.022578	0.721437	0.048*
C1B	0.2246 (3)	0.6602 (10)	0.5062 (2)	0.0321 (11)
C4A	0.8495 (3)	−0.2457 (11)	0.2183 (2)	0.0333 (11)
C31B	0.2222 (3)	0.8089 (11)	0.3492 (2)	0.0310 (11)
H31B	0.227859	0.620117	0.352713	0.037*
C8A	0.7744 (3)	−0.5344 (11)	0.2668 (2)	0.0331 (11)
H8A	0.724159	−0.596657	0.272152	0.040*
C34B	0.1155 (4)	1.0857 (11)	0.2725 (2)	0.0354 (12)
H34B	0.111368	1.196882	0.302269	0.043*
C4B	0.4312 (3)	0.2103 (11)	0.6525 (2)	0.0344 (11)
C22B	−0.0704 (4)	0.7994 (12)	0.4263 (3)	0.0422 (13)
H22D	−0.123471	0.843290	0.397591	0.063*
H22E	−0.072959	0.844050	0.464960	0.063*
H22F	−0.060355	0.616786	0.424628	0.063*
C7A	0.8534 (4)	−0.6311 (12)	0.2994 (3)	0.0392 (13)
H7A	0.855656	−0.761767	0.326776	0.047*
C35B	0.0686 (4)	1.1353 (12)	0.2144 (3)	0.0388 (12)
H35B	0.033493	1.280259	0.205581	0.047*
C21A	0.3449 (4)	−0.0840 (11)	0.1948 (3)	0.0371 (12)
H21A	0.343394	−0.188111	0.228452	0.045*
H21B	0.306883	−0.162334	0.159610	0.045*
C22A	0.3151 (4)	0.1883 (12)	0.2018 (3)	0.0395 (13)
H22A	0.257809	0.182695	0.204072	0.059*
H22B	0.316682	0.291077	0.168459	0.059*
H22C	0.351874	0.263802	0.237189	0.059*
C3B	0.3211 (4)	0.5505 (11)	0.6170 (2)	0.0349 (12)
C32B	0.3119 (3)	0.9220 (14)	0.3623 (3)	0.0425 (13)
H32D	0.337800	0.859328	0.333678	0.064*
H32E	0.345608	0.870061	0.401001	0.064*
H32F	0.308510	1.107574	0.360309	0.064*
C37B	0.1267 (4)	0.7574 (13)	0.1824 (3)	0.0432 (14)
H37B	0.130777	0.647343	0.152366	0.052*
C36B	0.0736 (4)	0.9725 (13)	0.1697 (3)	0.0436 (14)
H36B	0.041484	1.006508	0.130976	0.052*
C6B	0.5234 (4)	−0.1360 (13)	0.6464 (3)	0.0445 (14)
H6B	0.563476	−0.260463	0.664639	0.053*
C33A	0.2507 (3)	0.0631 (11)	0.0041 (2)	0.0351 (11)
C34D	0.2113 (10)	0.180 (5)	0.0400 (7)	0.052 (4)	0.456 (18)
H34D	0.244254	0.235478	0.077098	0.063*	0.456 (18)
C35D	0.1238 (10)	0.221 (4)	0.0238 (7)	0.052 (4)	0.456 (18)
H35D	0.099702	0.291365	0.051179	0.063*	0.456 (18)
C36A	0.0758 (4)	0.1659 (18)	−0.0275 (3)	0.0617 (19)
H36A	0.017579	0.200476	−0.039793	0.074*
C37D	0.1111 (10)	0.043 (3)	−0.0701 (9)	0.050 (4)	0.456 (18)
H37D	0.076739	−0.000039	−0.107722	0.060*	0.456 (18)
C38D	0.1985 (9)	−0.008 (3)	−0.0525 (8)	0.047 (4)	0.456 (18)
H38D	0.222602	−0.090570	−0.078405	0.056*	0.456 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1A	0.0325 (6)	0.0188 (6)	0.0293 (6)	−0.0004 (5)	0.0038 (5)	−0.0002 (5)
P1B	0.0356 (6)	0.0230 (6)	0.0282 (6)	−0.0003 (5)	0.0051 (5)	0.0018 (5)
S1A	0.0345 (6)	0.0355 (7)	0.0418 (7)	−0.0020 (5)	0.0056 (5)	0.0100 (6)
S1B	0.0467 (7)	0.0362 (7)	0.0281 (6)	0.0104 (6)	0.0058 (5)	0.0011 (6)
O1A	0.0352 (18)	0.0245 (18)	0.0297 (18)	−0.0012 (14)	0.0054 (14)	0.0029 (15)
O2A	0.0352 (18)	0.0267 (18)	0.0330 (19)	0.0012 (15)	0.0075 (14)	0.0009 (16)
O4B	0.0396 (19)	0.0248 (18)	0.0348 (19)	−0.0027 (16)	0.0042 (15)	0.0000 (16)
O2B	0.0351 (18)	0.033 (2)	0.0295 (18)	0.0041 (16)	0.0043 (14)	0.0006 (17)
O1B	0.051 (2)	0.039 (2)	0.0299 (19)	0.0128 (19)	0.0091 (16)	0.0017 (18)
O4A	0.040 (2)	0.0189 (18)	0.042 (2)	−0.0008 (15)	0.0019 (17)	0.0009 (16)
N2A	0.036 (2)	0.023 (2)	0.024 (2)	−0.0014 (17)	0.0057 (17)	0.0018 (17)
N3A	0.038 (2)	0.020 (2)	0.025 (2)	0.0007 (18)	−0.0017 (18)	−0.0017 (18)
N2B	0.039 (2)	0.025 (2)	0.027 (2)	0.0054 (18)	0.0066 (17)	0.0005 (18)
N3B	0.048 (3)	0.019 (2)	0.031 (2)	−0.0027 (19)	0.0116 (19)	0.0002 (18)
NA	0.034 (2)	0.030 (2)	0.034 (2)	−0.0018 (19)	0.0045 (18)	0.004 (2)
N1B	0.044 (2)	0.035 (2)	0.031 (2)	0.009 (2)	0.0056 (19)	0.000 (2)
C10A	0.035 (2)	0.024 (2)	0.027 (2)	0.000 (2)	0.006 (2)	−0.002 (2)
C34A	0.039 (5)	0.036 (6)	0.052 (8)	0.003 (5)	−0.001 (5)	0.002 (6)
C35A	0.048 (6)	0.056 (8)	0.067 (9)	0.010 (6)	0.012 (6)	0.007 (7)
C37A	0.042 (6)	0.079 (9)	0.069 (10)	−0.016 (6)	0.000 (6)	−0.026 (9)
C38A	0.048 (6)	0.053 (8)	0.057 (8)	−0.012 (5)	0.006 (6)	−0.008 (7)
C31A	0.039 (3)	0.024 (3)	0.026 (2)	−0.001 (2)	0.002 (2)	−0.003 (2)
C1A	0.033 (2)	0.023 (2)	0.023 (2)	−0.003 (2)	0.0023 (18)	−0.001 (2)
C10B	0.036 (3)	0.031 (3)	0.028 (3)	0.004 (2)	0.008 (2)	0.003 (2)
C9A	0.035 (3)	0.026 (3)	0.028 (2)	0.001 (2)	0.007 (2)	−0.004 (2)
C3A	0.039 (3)	0.024 (2)	0.031 (3)	−0.005 (2)	0.004 (2)	0.001 (2)
C5A	0.036 (3)	0.034 (3)	0.033 (3)	−0.001 (2)	0.006 (2)	0.002 (2)
C21B	0.039 (3)	0.027 (3)	0.035 (3)	0.006 (2)	0.002 (2)	0.006 (2)
C33B	0.036 (2)	0.024 (3)	0.031 (3)	−0.004 (2)	0.009 (2)	0.002 (2)
C9B	0.034 (3)	0.029 (3)	0.036 (3)	0.004 (2)	0.008 (2)	0.002 (2)
C8B	0.045 (3)	0.037 (3)	0.033 (3)	0.005 (3)	0.012 (2)	−0.002 (3)
C7B	0.053 (3)	0.038 (3)	0.041 (3)	0.011 (3)	0.012 (3)	−0.006 (3)
C2A	0.038 (3)	0.027 (3)	0.029 (2)	0.001 (2)	0.005 (2)	0.000 (2)
C38B	0.043 (3)	0.029 (3)	0.036 (3)	−0.004 (2)	0.012 (2)	−0.003 (2)
C32A	0.046 (3)	0.034 (3)	0.029 (3)	−0.001 (2)	0.006 (2)	0.000 (2)
C6A	0.036 (3)	0.034 (3)	0.037 (3)	0.009 (2)	0.005 (2)	0.004 (3)
C2B	0.038 (3)	0.029 (3)	0.034 (3)	0.008 (2)	0.007 (2)	−0.002 (2)
C5B	0.040 (3)	0.042 (3)	0.034 (3)	0.006 (3)	0.005 (2)	0.003 (3)
C1B	0.037 (3)	0.026 (3)	0.031 (3)	0.002 (2)	0.008 (2)	0.002 (2)
C4A	0.040 (3)	0.031 (3)	0.027 (2)	−0.002 (2)	0.007 (2)	−0.001 (2)
C31B	0.036 (3)	0.026 (3)	0.029 (2)	0.000 (2)	0.007 (2)	−0.001 (2)
C8A	0.034 (3)	0.030 (3)	0.033 (3)	0.003 (2)	0.007 (2)	0.008 (2)
C34B	0.042 (3)	0.025 (3)	0.037 (3)	−0.002 (2)	0.009 (2)	−0.002 (2)
C4B	0.042 (3)	0.028 (3)	0.031 (3)	0.001 (2)	0.008 (2)	−0.001 (2)
C22B	0.040 (3)	0.037 (3)	0.049 (3)	0.002 (2)	0.012 (3)	0.005 (3)
C7A	0.042 (3)	0.039 (3)	0.035 (3)	0.004 (3)	0.008 (2)	0.006 (3)
C35B	0.040 (3)	0.031 (3)	0.039 (3)	−0.003 (2)	0.003 (2)	0.002 (2)
C21A	0.042 (3)	0.031 (3)	0.040 (3)	0.000 (2)	0.015 (2)	0.002 (2)
C22A	0.044 (3)	0.031 (3)	0.044 (3)	0.000 (2)	0.014 (2)	−0.003 (3)
C3B	0.042 (3)	0.030 (3)	0.030 (3)	0.001 (2)	0.007 (2)	−0.003 (2)
C32B	0.039 (3)	0.047 (3)	0.039 (3)	−0.002 (3)	0.008 (2)	0.002 (3)
C37B	0.057 (4)	0.038 (3)	0.034 (3)	−0.007 (3)	0.012 (3)	−0.003 (3)
C36B	0.050 (3)	0.042 (3)	0.033 (3)	−0.013 (3)	0.003 (2)	0.002 (3)
C6B	0.043 (3)	0.042 (3)	0.046 (3)	0.012 (3)	0.008 (3)	0.005 (3)
C33A	0.038 (3)	0.033 (3)	0.031 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C34D	0.042 (6)	0.075 (12)	0.036 (7)	0.009 (7)	0.007 (5)	−0.002 (8)
C35D	0.043 (6)	0.071 (11)	0.043 (6)	0.023 (7)	0.012 (5)	0.017 (7)
C36A	0.038 (3)	0.078 (5)	0.062 (4)	0.009 (3)	0.005 (3)	0.019 (4)
C37D	0.044 (6)	0.042 (8)	0.052 (8)	0.001 (6)	−0.002 (6)	0.001 (7)
C38D	0.040 (6)	0.042 (9)	0.048 (8)	−0.004 (6)	−0.003 (5)	−0.015 (7)

Geometric parameters (Å, º)

P1A—O4A	1.479 (4)	C33B—C31B	1.523 (7)
P1A—O2A	1.590 (4)	C9B—C8B	1.397 (8)
P1A—N3A	1.618 (4)	C9B—C4B	1.411 (7)
P1A—C1A	1.798 (5)	C8B—C7B	1.377 (8)
P1B—O4B	1.483 (4)	C8B—H8B	0.9300
P1B—O2B	1.581 (4)	C7B—C6B	1.408 (9)
P1B—N3B	1.617 (5)	C7B—H7B	0.9300
P1B—C1B	1.798 (5)	C2A—H2A	0.9300
S1A—C4A	1.737 (6)	C38B—C37B	1.389 (8)
S1A—C3A	1.739 (5)	C38B—H38B	0.9300
S1B—C3B	1.733 (6)	C32A—H32A	0.9600
S1B—C4B	1.743 (6)	C32A—H32B	0.9600
O1A—C10A	1.227 (6)	C32A—H32C	0.9600
O2A—C21A	1.455 (6)	C6A—C7A	1.388 (8)
O2B—C21B	1.450 (6)	C6A—H6A	0.9300
O1B—C10B	1.220 (6)	C2B—C1B	1.377 (8)
N2A—C3A	1.376 (7)	C2B—H2B	0.9300
N2A—C9A	1.418 (7)	C5B—C4B	1.375 (8)
N2A—C10A	1.434 (7)	C5B—C6B	1.388 (9)
N3A—C31A	1.474 (6)	C5B—H5B	0.9300
N3A—H3A	0.90 (7)	C31B—C32B	1.529 (7)
N2B—C3B	1.388 (7)	C31B—H31B	0.9800
N2B—C9B	1.410 (7)	C8A—C7A	1.391 (8)
N2B—C10B	1.429 (6)	C8A—H8A	0.9300
N3B—C31B	1.469 (7)	C34B—C35B	1.389 (8)
N3B—H3B	0.89 (9)	C34B—H34B	0.9300
NA—C3A	1.309 (7)	C22B—H22D	0.9600
NA—C2A	1.351 (7)	C22B—H22E	0.9600
N1B—C3B	1.302 (8)	C22B—H22F	0.9600
N1B—C2B	1.362 (7)	C7A—H7A	0.9300
C10A—C1A	1.432 (7)	C35B—C36B	1.377 (9)
C34A—C35A	1.399 (17)	C35B—H35B	0.9300
C34A—C33A	1.413 (14)	C21A—C22A	1.514 (8)
C34A—H34A	0.9300	C21A—H21A	0.9700
C35A—C36A	1.515 (18)	C21A—H21B	0.9700
C35A—H35A	0.9300	C22A—H22A	0.9600
C37A—C36A	1.29 (2)	C22A—H22B	0.9600
C37A—C38A	1.39 (2)	C22A—H22C	0.9600
C37A—H37A	0.9300	C32B—H32D	0.9600
C38A—C33A	1.354 (14)	C32B—H32E	0.9600
C38A—H38A	0.9300	C32B—H32F	0.9600
C31A—C33A	1.522 (7)	C37B—C36B	1.388 (9)
C31A—C32A	1.527 (7)	C37B—H37B	0.9300
C31A—H31A	0.9800	C36B—H36B	0.9300
C1A—C2A	1.376 (7)	C6B—H6B	0.9300
C10B—C1B	1.450 (7)	C33A—C34D	1.360 (15)
C9A—C8A	1.393 (7)	C33A—C38D	1.411 (14)
C9A—C4A	1.403 (8)	C34D—C35D	1.39 (2)
C5A—C6A	1.391 (8)	C34D—H34D	0.9300
C5A—C4A	1.400 (8)	C35D—C36A	1.272 (18)
C5A—H5A	0.9300	C35D—H35D	0.9300
C21B—C22B	1.501 (8)	C36A—C37D	1.46 (2)
C21B—H21C	0.9700	C36A—H36A	0.9300
C21B—H21D	0.9700	C37D—C38D	1.40 (2)
C33B—C38B	1.390 (8)	C37D—H37D	0.9300
C33B—C34B	1.395 (8)	C38D—H38D	0.9300
O4A—P1A—O2A	115.5 (2)	H32B—C32A—H32C	109.5
O4A—P1A—N3A	111.3 (2)	C7A—C6A—C5A	120.9 (5)
O2A—P1A—N3A	106.1 (2)	C7A—C6A—H6A	119.5
O4A—P1A—C1A	112.6 (2)	C5A—C6A—H6A	119.5
O2A—P1A—C1A	100.3 (2)	N1B—C2B—C1B	124.9 (5)
N3A—P1A—C1A	110.3 (2)	N1B—C2B—H2B	117.6
O4B—P1B—O2B	117.6 (2)	C1B—C2B—H2B	117.6
O4B—P1B—N3B	111.8 (2)	C4B—C5B—C6B	118.6 (5)
O2B—P1B—N3B	104.5 (2)	C4B—C5B—H5B	120.7
O4B—P1B—C1B	111.7 (2)	C6B—C5B—H5B	120.7
O2B—P1B—C1B	97.5 (2)	C2B—C1B—C10B	120.4 (5)
N3B—P1B—C1B	112.9 (2)	C2B—C1B—P1B	122.1 (4)
C4A—S1A—C3A	90.8 (3)	C10B—C1B—P1B	117.4 (4)
C3B—S1B—C4B	91.1 (3)	C5A—C4A—C9A	120.8 (5)
C21A—O2A—P1A	117.6 (3)	C5A—C4A—S1A	126.8 (4)
C21B—O2B—P1B	121.5 (3)	C9A—C4A—S1A	112.4 (4)
C3A—N2A—C9A	113.7 (4)	N3B—C31B—C33B	112.3 (4)
C3A—N2A—C10A	120.6 (4)	N3B—C31B—C32B	110.8 (5)
C9A—N2A—C10A	125.7 (4)	C33B—C31B—C32B	111.0 (4)
C31A—N3A—P1A	124.2 (4)	N3B—C31B—H31B	107.5
C31A—N3A—H3A	118 (4)	C33B—C31B—H31B	107.5
P1A—N3A—H3A	116 (4)	C32B—C31B—H31B	107.5
C3B—N2B—C9B	113.4 (4)	C7A—C8A—C9A	117.4 (5)
C3B—N2B—C10B	120.7 (4)	C7A—C8A—H8A	121.3
C9B—N2B—C10B	125.9 (4)	C9A—C8A—H8A	121.3
C31B—N3B—P1B	123.3 (4)	C35B—C34B—C33B	120.3 (5)
C31B—N3B—H3B	113 (5)	C35B—C34B—H34B	119.9
P1B—N3B—H3B	122 (5)	C33B—C34B—H34B	119.9
C3A—NA—C2A	114.8 (5)	C5B—C4B—C9B	121.2 (5)
C3B—N1B—C2B	114.8 (5)	C5B—C4B—S1B	127.1 (4)
O1A—C10A—C1A	126.7 (5)	C9B—C4B—S1B	111.8 (4)
O1A—C10A—N2A	120.2 (4)	C21B—C22B—H22D	109.5
C1A—C10A—N2A	113.0 (4)	C21B—C22B—H22E	109.5
C35A—C34A—C33A	121.2 (12)	H22D—C22B—H22E	109.5
C35A—C34A—H34A	119.4	C21B—C22B—H22F	109.5
C33A—C34A—H34A	119.4	H22D—C22B—H22F	109.5
C34A—C35A—C36A	116.0 (12)	H22E—C22B—H22F	109.5
C34A—C35A—H35A	122.0	C6A—C7A—C8A	122.0 (6)
C36A—C35A—H35A	122.0	C6A—C7A—H7A	119.0
C36A—C37A—C38A	121.7 (13)	C8A—C7A—H7A	119.0
C36A—C37A—H37A	119.1	C36B—C35B—C34B	120.7 (6)
C38A—C37A—H37A	119.1	C36B—C35B—H35B	119.6
C33A—C38A—C37A	122.7 (14)	C34B—C35B—H35B	119.6
C33A—C38A—H38A	118.7	O2A—C21A—C22A	110.2 (5)
C37A—C38A—H38A	118.7	O2A—C21A—H21A	109.6
N3A—C31A—C33A	111.0 (4)	C22A—C21A—H21A	109.6
N3A—C31A—C32A	111.0 (4)	O2A—C21A—H21B	109.6
C33A—C31A—C32A	111.3 (4)	C22A—C21A—H21B	109.6
N3A—C31A—H31A	107.8	H21A—C21A—H21B	108.1
C33A—C31A—H31A	107.8	C21A—C22A—H22A	109.5
C32A—C31A—H31A	107.8	C21A—C22A—H22B	109.5
C2A—C1A—C10A	120.1 (5)	H22A—C22A—H22B	109.5
C2A—C1A—P1A	121.7 (4)	C21A—C22A—H22C	109.5
C10A—C1A—P1A	118.2 (4)	H22A—C22A—H22C	109.5
O1B—C10B—N2B	120.7 (5)	H22B—C22A—H22C	109.5
O1B—C10B—C1B	126.9 (5)	N1B—C3B—N2B	126.2 (5)
N2B—C10B—C1B	112.4 (5)	N1B—C3B—S1B	121.7 (4)
C8A—C9A—C4A	121.1 (5)	N2B—C3B—S1B	112.0 (4)
C8A—C9A—N2A	127.8 (5)	C31B—C32B—H32D	109.5
C4A—C9A—N2A	111.0 (5)	C31B—C32B—H32E	109.5
NA—C3A—N2A	125.9 (5)	H32D—C32B—H32E	109.5
NA—C3A—S1A	122.2 (4)	C31B—C32B—H32F	109.5
N2A—C3A—S1A	111.9 (4)	H32D—C32B—H32F	109.5
C6A—C5A—C4A	117.8 (5)	H32E—C32B—H32F	109.5
C6A—C5A—H5A	121.1	C36B—C37B—C38B	119.1 (6)
C4A—C5A—H5A	121.1	C36B—C37B—H37B	120.4
O2B—C21B—C22B	108.7 (4)	C38B—C37B—H37B	120.4
O2B—C21B—H21C	110.0	C35B—C36B—C37B	120.0 (5)
C22B—C21B—H21C	110.0	C35B—C36B—H36B	120.0
O2B—C21B—H21D	110.0	C37B—C36B—H36B	120.0
C22B—C21B—H21D	110.0	C5B—C6B—C7B	120.6 (6)
H21C—C21B—H21D	108.3	C5B—C6B—H6B	119.7
C38B—C33B—C34B	118.2 (5)	C7B—C6B—H6B	119.7
C38B—C33B—C31B	119.6 (5)	C34D—C33A—C38D	116.5 (10)
C34B—C33B—C31B	122.2 (5)	C38A—C33A—C34A	118.4 (9)
C8B—C9B—N2B	128.2 (5)	C38A—C33A—C31A	122.4 (8)
C8B—C9B—C4B	120.1 (5)	C34D—C33A—C31A	125.9 (8)
N2B—C9B—C4B	111.6 (5)	C38D—C33A—C31A	117.6 (8)
C7B—C8B—C9B	118.5 (5)	C34A—C33A—C31A	119.2 (7)
C7B—C8B—H8B	120.7	C33A—C34D—C35D	122.9 (13)
C9B—C8B—H8B	120.7	C33A—C34D—H34D	118.6
C8B—C7B—C6B	121.0 (6)	C35D—C34D—H34D	118.6
C8B—C7B—H7B	119.5	C36A—C35D—C34D	121.7 (13)
C6B—C7B—H7B	119.5	C36A—C35D—H35D	119.1
NA—C2A—C1A	125.4 (5)	C34D—C35D—H35D	119.1
NA—C2A—H2A	117.3	C35D—C36A—C37D	120.2 (10)
C1A—C2A—H2A	117.3	C37A—C36A—C35A	120.0 (9)
C37B—C38B—C33B	121.7 (6)	C37A—C36A—H36A	120.0
C37B—C38B—H38B	119.1	C35A—C36A—H36A	120.0
C33B—C38B—H38B	119.1	C38D—C37D—C36A	117.6 (13)
C31A—C32A—H32A	109.5	C38D—C37D—H37D	121.2
C31A—C32A—H32B	109.5	C36A—C37D—H37D	121.2
H32A—C32A—H32B	109.5	C37D—C38D—C33A	121.0 (14)
C31A—C32A—H32C	109.5	C37D—C38D—H38D	119.5
H32A—C32A—H32C	109.5	C33A—C38D—H38D	119.5
O4A—P1A—O2A—C21A	−63.2 (4)	N3B—P1B—C1B—C2B	101.7 (5)
N3A—P1A—O2A—C21A	60.6 (4)	O4B—P1B—C1B—C10B	44.8 (5)
C1A—P1A—O2A—C21A	175.5 (4)	O2B—P1B—C1B—C10B	168.5 (4)
O4B—P1B—O2B—C21B	−57.8 (5)	N3B—P1B—C1B—C10B	−82.2 (5)
N3B—P1B—O2B—C21B	66.8 (4)	C6A—C5A—C4A—C9A	−0.2 (8)
C1B—P1B—O2B—C21B	−177.1 (4)	C6A—C5A—C4A—S1A	177.1 (4)
O4A—P1A—N3A—C31A	−20.2 (5)	C8A—C9A—C4A—C5A	0.3 (8)
O2A—P1A—N3A—C31A	−146.6 (4)	N2A—C9A—C4A—C5A	177.9 (5)
C1A—P1A—N3A—C31A	105.6 (4)	C8A—C9A—C4A—S1A	−177.3 (4)
O4B—P1B—N3B—C31B	−31.0 (5)	N2A—C9A—C4A—S1A	0.3 (6)
O2B—P1B—N3B—C31B	−159.3 (4)	C3A—S1A—C4A—C5A	−175.6 (5)
C1B—P1B—N3B—C31B	95.9 (4)	C3A—S1A—C4A—C9A	1.8 (4)
C3A—N2A—C10A—O1A	178.2 (5)	P1B—N3B—C31B—C33B	114.7 (5)
C9A—N2A—C10A—O1A	−0.5 (8)	P1B—N3B—C31B—C32B	−120.6 (5)
C3A—N2A—C10A—C1A	−2.8 (6)	C38B—C33B—C31B—N3B	−150.2 (5)
C9A—N2A—C10A—C1A	178.5 (4)	C34B—C33B—C31B—N3B	31.0 (7)
C33A—C34A—C35A—C36A	0 (2)	C38B—C33B—C31B—C32B	85.2 (6)
C36A—C37A—C38A—C33A	1 (3)	C34B—C33B—C31B—C32B	−93.7 (6)
P1A—N3A—C31A—C33A	122.2 (5)	C4A—C9A—C8A—C7A	−0.5 (8)
P1A—N3A—C31A—C32A	−113.5 (5)	N2A—C9A—C8A—C7A	−177.6 (5)
O1A—C10A—C1A—C2A	177.6 (5)	C38B—C33B—C34B—C35B	0.4 (8)
N2A—C10A—C1A—C2A	−1.3 (7)	C31B—C33B—C34B—C35B	179.2 (5)
O1A—C10A—C1A—P1A	−4.7 (7)	C6B—C5B—C4B—C9B	−0.5 (9)
N2A—C10A—C1A—P1A	176.3 (3)	C6B—C5B—C4B—S1B	179.4 (5)
O4A—P1A—C1A—C2A	124.6 (4)	C8B—C9B—C4B—C5B	−0.2 (9)
O2A—P1A—C1A—C2A	−112.1 (4)	N2B—C9B—C4B—C5B	178.3 (5)
N3A—P1A—C1A—C2A	−0.4 (5)	C8B—C9B—C4B—S1B	179.9 (5)
O4A—P1A—C1A—C10A	−53.0 (4)	N2B—C9B—C4B—S1B	−1.5 (6)
O2A—P1A—C1A—C10A	70.3 (4)	C3B—S1B—C4B—C5B	−179.1 (6)
N3A—P1A—C1A—C10A	−178.1 (4)	C3B—S1B—C4B—C9B	0.7 (5)
C3B—N2B—C10B—O1B	174.5 (5)	C5A—C6A—C7A—C8A	−0.5 (9)
C9B—N2B—C10B—O1B	−7.0 (8)	C9A—C8A—C7A—C6A	0.6 (9)
C3B—N2B—C10B—C1B	−5.5 (7)	C33B—C34B—C35B—C36B	0.3 (8)
C9B—N2B—C10B—C1B	173.0 (5)	P1A—O2A—C21A—C22A	−110.7 (5)
C3A—N2A—C9A—C8A	174.4 (5)	C2B—N1B—C3B—N2B	5.8 (9)
C10A—N2A—C9A—C8A	−6.8 (8)	C2B—N1B—C3B—S1B	−173.2 (4)
C3A—N2A—C9A—C4A	−3.0 (6)	C9B—N2B—C3B—N1B	179.7 (6)
C10A—N2A—C9A—C4A	175.8 (5)	C10B—N2B—C3B—N1B	−1.6 (9)
C2A—NA—C3A—N2A	−2.5 (8)	C9B—N2B—C3B—S1B	−1.2 (6)
C2A—NA—C3A—S1A	177.0 (4)	C10B—N2B—C3B—S1B	177.5 (4)
C9A—N2A—C3A—NA	−176.1 (5)	C4B—S1B—C3B—N1B	179.4 (5)
C10A—N2A—C3A—NA	5.1 (8)	C4B—S1B—C3B—N2B	0.3 (4)
C9A—N2A—C3A—S1A	4.4 (5)	C33B—C38B—C37B—C36B	0.1 (9)
C10A—N2A—C3A—S1A	−174.5 (4)	C34B—C35B—C36B—C37B	−0.7 (9)
C4A—S1A—C3A—NA	176.9 (5)	C38B—C37B—C36B—C35B	0.5 (9)
C4A—S1A—C3A—N2A	−3.5 (4)	C4B—C5B—C6B—C7B	1.3 (10)
P1B—O2B—C21B—C22B	110.8 (5)	C8B—C7B—C6B—C5B	−1.4 (10)
C3B—N2B—C9B—C8B	−179.9 (6)	C37A—C38A—C33A—C34A	1 (2)
C10B—N2B—C9B—C8B	1.6 (9)	C37A—C38A—C33A—C31A	−179.0 (13)
C3B—N2B—C9B—C4B	1.7 (7)	C35A—C34A—C33A—C38A	−1.8 (18)
C10B—N2B—C9B—C4B	−176.8 (5)	C35A—C34A—C33A—C31A	178.6 (11)
N2B—C9B—C8B—C7B	−178.2 (6)	N3A—C31A—C33A—C38A	−130.1 (11)
C4B—C9B—C8B—C7B	0.1 (9)	C32A—C31A—C33A—C38A	105.7 (11)
C9B—C8B—C7B—C6B	0.7 (10)	N3A—C31A—C33A—C34D	7.6 (15)
C3A—NA—C2A—C1A	−2.1 (8)	C32A—C31A—C33A—C34D	−116.6 (14)
C10A—C1A—C2A—NA	4.0 (8)	N3A—C31A—C33A—C38D	−172.9 (10)
P1A—C1A—C2A—NA	−173.5 (4)	C32A—C31A—C33A—C38D	62.9 (11)
C34B—C33B—C38B—C37B	−0.6 (8)	N3A—C31A—C33A—C34A	49.5 (10)
C31B—C33B—C38B—C37B	−179.5 (5)	C32A—C31A—C33A—C34A	−74.6 (10)
C4A—C5A—C6A—C7A	0.3 (8)	C38D—C33A—C34D—C35D	2 (3)
C3B—N1B—C2B—C1B	−2.5 (9)	C31A—C33A—C34D—C35D	−178.2 (15)
N1B—C2B—C1B—C10B	−4.7 (9)	C33A—C34D—C35D—C36A	−5 (3)
N1B—C2B—C1B—P1B	171.2 (5)	C34D—C35D—C36A—C37D	3 (3)
O1B—C10B—C1B—C2B	−171.7 (6)	C38A—C37A—C36A—C35A	−3 (2)
N2B—C10B—C1B—C2B	8.3 (8)	C34A—C35A—C36A—C37A	3 (2)
O1B—C10B—C1B—P1B	12.1 (8)	C35D—C36A—C37D—C38D	0 (2)
N2B—C10B—C1B—P1B	−167.9 (4)	C36A—C37D—C38D—C33A	−2 (2)
O4B—P1B—C1B—C2B	−131.2 (5)	C34D—C33A—C38D—C37D	1 (2)
O2B—P1B—C1B—C2B	−7.5 (5)	C31A—C33A—C38D—C37D	−178.9 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O4A^i	0.90 (7)	1.88 (7)	2.774 (6)	175 (5)
N3B—H3B···O4B^i	0.89 (9)	2.31 (9)	3.070 (6)	144 (7)
N3B—H3B···O1B^i	0.89 (9)	2.71 (8)	3.419 (6)	137 (6)

Symmetry code: (i) x, y+1, z.

Diethyl (4-isopropyl-2-oxo-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidin-3-yl)phosphonate (II)

Crystal data

C18H25N2O4PS	Z = 2
Mr = 396.43	F(000) = 420
Triclinic, P1	Dx = 1.369 Mg m^−3
a = 9.6275 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.0903 (5) Å	Cell parameters from 10170 reflections
c = 11.8585 (6) Å	θ = 4.3–79.0°
α = 65.779 (5)°	µ = 2.51 mm^−1
β = 67.462 (5)°	T = 100 K
γ = 74.329 (4)°	Prism, colourless
V = 961.59 (9) Å^3	0.18 × 0.08 × 0.07 mm

Data collection

XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer	3490 independent reflections
Radiation source: micro-focus sealed X-ray tube	3290 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
ω scans	θmax = 68.0°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2017)	h = −11→10
Tmin = 0.390, Tmax = 1.000	k = −12→12
14969 measured reflections	l = −14→14

Refinement

Refinement on F^2	417 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.1232P)^2 + 0.414P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3490 reflections	Δρmax = 0.92 e Å^−3
260 parameters	Δρmin = −0.56 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.81925 (19)	0.65340 (18)	0.49949 (16)	0.0341 (4)
C21A	0.8125 (12)	0.5799 (9)	0.4168 (8)	0.038 (2)	0.614 (13)
H21A	0.749241	0.643824	0.360433	0.046*	0.614 (13)
H21B	0.915504	0.555336	0.361139	0.046*	0.614 (13)
C22A	0.7441 (8)	0.4455 (7)	0.5083 (5)	0.0456 (18)	0.614 (13)
H22A	0.745785	0.386210	0.459705	0.068*	0.614 (13)
H22B	0.638963	0.472092	0.556694	0.068*	0.614 (13)
H22C	0.802158	0.388792	0.569318	0.068*	0.614 (13)
C21B	0.8263 (18)	0.5421 (17)	0.4452 (17)	0.046 (4)	0.386 (13)
H21C	0.874911	0.578575	0.349805	0.056*	0.386 (13)
H21D	0.888905	0.450743	0.482802	0.056*	0.386 (13)
C22B	0.6726 (12)	0.5108 (11)	0.4749 (10)	0.052 (3)	0.386 (13)
H22E	0.679401	0.435875	0.439681	0.078*	0.386 (13)
H22F	0.611691	0.600628	0.435319	0.078*	0.386 (13)
H22G	0.624471	0.474962	0.569346	0.078*	0.386 (13)
S1	0.71009 (5)	0.44044 (5)	0.85469 (5)	0.0251 (2)
P1	0.80758 (6)	0.82491 (6)	0.43848 (5)	0.0266 (2)
O3	0.96784 (17)	0.85037 (19)	0.33184 (15)	0.0354 (4)
O1	1.04350 (16)	0.82467 (17)	0.60324 (15)	0.0307 (4)
O4	0.67918 (18)	0.9035 (2)	0.38820 (16)	0.0354 (4)
N1	0.62591 (19)	0.71244 (18)	0.74315 (16)	0.0216 (4)
N2	0.88572 (19)	0.6535 (2)	0.73848 (17)	0.0249 (4)
C2	0.6406 (2)	0.8699 (2)	0.6706 (2)	0.0221 (4)
H2	0.563554	0.914590	0.623145	0.026*
C3	0.4988 (2)	0.6432 (2)	0.77999 (19)	0.0221 (4)
C1	0.8007 (2)	0.8747 (2)	0.5708 (2)	0.0232 (4)
H1	0.821173	0.978773	0.532883	0.028*
C9	0.7492 (2)	0.6204 (2)	0.77049 (19)	0.0220 (4)
C4	0.3606 (2)	0.7071 (2)	0.7571 (2)	0.0245 (4)
H4	0.342393	0.809319	0.711720	0.029*
C5	0.2497 (2)	0.6174 (2)	0.8024 (2)	0.0262 (5)
H5	0.154463	0.659825	0.787797	0.031*
C24	0.6142 (2)	0.9507 (2)	0.7640 (2)	0.0254 (5)
H24	0.690428	0.904223	0.812131	0.030*
C10	0.9200 (2)	0.7830 (2)	0.6388 (2)	0.0243 (5)
C6	0.2738 (2)	0.4666 (2)	0.8689 (2)	0.0256 (5)
C8	0.5256 (2)	0.4927 (2)	0.8445 (2)	0.0231 (4)
C7	0.4130 (2)	0.4035 (2)	0.8896 (2)	0.0245 (4)
H7	0.431645	0.301067	0.933926	0.029*
C26	0.4555 (2)	0.9407 (2)	0.8627 (2)	0.0265 (5)
H26A	0.379613	0.992857	0.817445	0.040*
H26B	0.445254	0.985378	0.925456	0.040*
H26C	0.439759	0.837546	0.908709	0.040*
C31	0.9868 (3)	0.9814 (3)	0.2162 (2)	0.0332 (5)
H31A	1.012657	1.059338	0.232184	0.040*
H31B	0.891546	1.018221	0.193032	0.040*
C25	0.6362 (3)	1.1120 (3)	0.6869 (2)	0.0330 (5)
H25A	0.743580	1.118905	0.636806	0.049*
H25B	0.603876	1.165980	0.747086	0.049*
H25C	0.575235	1.154410	0.627303	0.049*
C32	1.1119 (3)	0.9411 (3)	0.1086 (2)	0.0386 (6)
H32A	1.130507	1.028589	0.030145	0.058*
H32B	1.083035	0.867402	0.090844	0.058*
H32C	1.204467	0.900938	0.134132	0.058*
C61	0.1499 (3)	0.3724 (3)	0.9188 (2)	0.0326 (5)
H61A	0.069036	0.427771	0.879902	0.049*
H61B	0.108379	0.344307	1.013667	0.049*
H61C	0.192056	0.283986	0.895234	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0387 (10)	0.0351 (9)	0.0294 (9)	−0.0025 (7)	−0.0061 (7)	−0.0175 (7)
C21A	0.057 (4)	0.031 (3)	0.028 (3)	−0.003 (3)	−0.010 (2)	−0.015 (3)
C22A	0.064 (4)	0.041 (3)	0.039 (3)	−0.016 (3)	−0.013 (2)	−0.019 (2)
C21B	0.056 (5)	0.050 (8)	0.041 (8)	0.008 (5)	−0.016 (5)	−0.031 (7)
C22B	0.069 (6)	0.041 (5)	0.058 (5)	−0.006 (4)	−0.028 (4)	−0.021 (4)
S1	0.0200 (3)	0.0230 (3)	0.0276 (3)	0.0021 (2)	−0.0077 (2)	−0.0070 (2)
P1	0.0187 (3)	0.0346 (4)	0.0221 (3)	0.0017 (2)	−0.0042 (2)	−0.0107 (3)
O3	0.0211 (8)	0.0465 (10)	0.0248 (8)	0.0036 (7)	−0.0027 (6)	−0.0082 (7)
O1	0.0169 (7)	0.0355 (9)	0.0354 (9)	−0.0041 (6)	−0.0068 (6)	−0.0090 (7)
O4	0.0218 (8)	0.0525 (10)	0.0311 (9)	0.0042 (7)	−0.0106 (7)	−0.0171 (8)
N1	0.0160 (8)	0.0223 (9)	0.0227 (9)	0.0004 (7)	−0.0038 (7)	−0.0081 (7)
N2	0.0165 (8)	0.0293 (9)	0.0261 (9)	0.0017 (7)	−0.0058 (7)	−0.0106 (7)
C2	0.0165 (10)	0.0221 (10)	0.0247 (10)	0.0002 (7)	−0.0047 (8)	−0.0086 (8)
C3	0.0172 (9)	0.0260 (10)	0.0215 (10)	−0.0020 (8)	−0.0029 (7)	−0.0099 (8)
C1	0.0160 (10)	0.0251 (10)	0.0247 (10)	−0.0011 (8)	−0.0045 (8)	−0.0078 (8)
C9	0.0178 (10)	0.0252 (10)	0.0208 (10)	0.0027 (8)	−0.0053 (8)	−0.0098 (8)
C4	0.0206 (10)	0.0247 (10)	0.0257 (10)	−0.0008 (8)	−0.0071 (8)	−0.0077 (8)
C5	0.0186 (10)	0.0322 (11)	0.0270 (11)	−0.0011 (8)	−0.0068 (8)	−0.0111 (9)
C24	0.0181 (10)	0.0288 (11)	0.0297 (11)	0.0002 (8)	−0.0063 (8)	−0.0136 (9)
C10	0.0158 (10)	0.0284 (10)	0.0270 (11)	0.0019 (8)	−0.0044 (8)	−0.0131 (9)
C6	0.0240 (10)	0.0286 (11)	0.0252 (11)	−0.0048 (8)	−0.0062 (8)	−0.0108 (8)
C8	0.0202 (10)	0.0243 (10)	0.0230 (10)	0.0013 (8)	−0.0061 (8)	−0.0096 (8)
C7	0.0244 (10)	0.0230 (10)	0.0240 (10)	−0.0034 (8)	−0.0062 (8)	−0.0073 (8)
C26	0.0206 (10)	0.0322 (11)	0.0273 (11)	0.0004 (8)	−0.0063 (8)	−0.0143 (9)
C31	0.0318 (12)	0.0325 (12)	0.0285 (12)	−0.0013 (9)	−0.0033 (9)	−0.0115 (9)
C25	0.0281 (12)	0.0296 (12)	0.0410 (13)	−0.0033 (9)	−0.0047 (10)	−0.0180 (10)
C32	0.0333 (13)	0.0401 (13)	0.0301 (12)	0.0013 (10)	−0.0022 (10)	−0.0114 (10)
C61	0.0285 (12)	0.0338 (12)	0.0357 (13)	−0.0095 (9)	−0.0097 (10)	−0.0090 (10)

Geometric parameters (Å, º)

O2—C21A	1.479 (8)	C3—C4	1.389 (3)
O2—C21B	1.482 (12)	C3—C8	1.394 (3)
O2—P1	1.5688 (17)	C1—C10	1.533 (3)
C21A—C22A	1.476 (8)	C1—H1	1.0000
C21A—H21A	0.9900	C4—C5	1.390 (3)
C21A—H21B	0.9900	C4—H4	0.9500
C22A—H22A	0.9800	C5—C6	1.398 (3)
C22A—H22B	0.9800	C5—H5	0.9500
C22A—H22C	0.9800	C24—C26	1.526 (3)
C21B—C22B	1.476 (13)	C24—C25	1.532 (3)
C21B—H21C	0.9900	C24—H24	1.0000
C21B—H21D	0.9900	C6—C7	1.388 (3)
C22B—H22E	0.9800	C6—C61	1.512 (3)
C22B—H22F	0.9800	C8—C7	1.399 (3)
C22B—H22G	0.9800	C7—H7	0.9500
S1—C9	1.740 (2)	C26—H26A	0.9800
S1—C8	1.748 (2)	C26—H26B	0.9800
P1—O4	1.4697 (16)	C26—H26C	0.9800
P1—O3	1.5804 (16)	C31—C32	1.493 (3)
P1—C1	1.807 (2)	C31—H31A	0.9900
O3—C31	1.453 (3)	C31—H31B	0.9900
O1—C10	1.228 (3)	C25—H25A	0.9800
N1—C9	1.352 (3)	C25—H25B	0.9800
N1—C3	1.407 (3)	C25—H25C	0.9800
N1—C2	1.480 (3)	C32—H32A	0.9800
N2—C9	1.317 (3)	C32—H32B	0.9800
N2—C10	1.372 (3)	C32—H32C	0.9800
C2—C24	1.541 (3)	C61—H61A	0.9800
C2—C1	1.541 (3)	C61—H61B	0.9800
C2—H2	1.0000	C61—H61C	0.9800
C21A—O2—P1	115.3 (4)	N1—C9—S1	111.46 (15)
C21B—O2—P1	131.3 (7)	C3—C4—C5	118.11 (19)
C22A—C21A—O2	105.3 (6)	C3—C4—H4	120.9
C22A—C21A—H21A	110.7	C5—C4—H4	120.9
O2—C21A—H21A	110.7	C4—C5—C6	122.10 (19)
C22A—C21A—H21B	110.7	C4—C5—H5	118.9
O2—C21A—H21B	110.7	C6—C5—H5	118.9
H21A—C21A—H21B	108.8	C26—C24—C25	109.65 (17)
C21A—C22A—H22A	109.5	C26—C24—C2	111.37 (17)
C21A—C22A—H22B	109.5	C25—C24—C2	110.02 (18)
H22A—C22A—H22B	109.5	C26—C24—H24	108.6
C21A—C22A—H22C	109.5	C25—C24—H24	108.6
H22A—C22A—H22C	109.5	C2—C24—H24	108.6
H22B—C22A—H22C	109.5	O1—C10—N2	121.32 (19)
C22B—C21B—O2	110.5 (10)	O1—C10—C1	120.34 (19)
C22B—C21B—H21C	109.5	N2—C10—C1	118.33 (17)
O2—C21B—H21C	109.5	C7—C6—C5	119.32 (19)
C22B—C21B—H21D	109.5	C7—C6—C61	119.89 (19)
O2—C21B—H21D	109.5	C5—C6—C61	120.80 (19)
H21C—C21B—H21D	108.1	C3—C8—C7	120.78 (19)
C21B—C22B—H22E	109.5	C3—C8—S1	111.11 (15)
C21B—C22B—H22F	109.5	C7—C8—S1	128.10 (16)
H22E—C22B—H22F	109.5	C6—C7—C8	119.11 (19)
C21B—C22B—H22G	109.5	C6—C7—H7	120.4
H22E—C22B—H22G	109.5	C8—C7—H7	120.4
H22F—C22B—H22G	109.5	C24—C26—H26A	109.5
C9—S1—C8	90.98 (10)	C24—C26—H26B	109.5
O4—P1—O2	117.09 (10)	H26A—C26—H26B	109.5
O4—P1—O3	113.67 (9)	C24—C26—H26C	109.5
O2—P1—O3	102.87 (9)	H26A—C26—H26C	109.5
O4—P1—C1	111.61 (10)	H26B—C26—H26C	109.5
O2—P1—C1	102.45 (9)	O3—C31—C32	107.61 (19)
O3—P1—C1	108.10 (10)	O3—C31—H31A	110.2
C31—O3—P1	121.17 (14)	C32—C31—H31A	110.2
C9—N1—C3	114.59 (17)	O3—C31—H31B	110.2
C9—N1—C2	118.28 (17)	C32—C31—H31B	110.2
C3—N1—C2	126.95 (16)	H31A—C31—H31B	108.5
C9—N2—C10	116.44 (17)	C24—C25—H25A	109.5
N1—C2—C24	110.70 (16)	C24—C25—H25B	109.5
N1—C2—C1	105.68 (15)	H25A—C25—H25B	109.5
C24—C2—C1	113.08 (17)	C24—C25—H25C	109.5
N1—C2—H2	109.1	H25A—C25—H25C	109.5
C24—C2—H2	109.1	H25B—C25—H25C	109.5
C1—C2—H2	109.1	C31—C32—H32A	109.5
C4—C3—C8	120.57 (19)	C31—C32—H32B	109.5
C4—C3—N1	127.69 (19)	H32A—C32—H32B	109.5
C8—C3—N1	111.73 (18)	C31—C32—H32C	109.5
C10—C1—C2	110.37 (16)	H32A—C32—H32C	109.5
C10—C1—P1	114.24 (14)	H32B—C32—H32C	109.5
C2—C1—P1	110.61 (14)	C6—C61—H61A	109.5
C10—C1—H1	107.1	C6—C61—H61B	109.5
C2—C1—H1	107.1	H61A—C61—H61B	109.5
P1—C1—H1	107.1	C6—C61—H61C	109.5
N2—C9—N1	127.49 (19)	H61A—C61—H61C	109.5
N2—C9—S1	121.03 (15)	H61B—C61—H61C	109.5
P1—O2—C21A—C22A	−150.4 (6)	C2—N1—C9—N2	−0.9 (3)
P1—O2—C21B—C22B	−91.5 (14)	C3—N1—C9—S1	−4.0 (2)
C21A—O2—P1—O4	52.1 (5)	C2—N1—C9—S1	−179.46 (13)
C21B—O2—P1—O4	56.3 (8)	C8—S1—C9—N2	−175.96 (18)
C21A—O2—P1—O3	−73.3 (5)	C8—S1—C9—N1	2.70 (16)
C21B—O2—P1—O3	−69.1 (8)	C8—C3—C4—C5	1.2 (3)
C21A—O2—P1—C1	174.5 (5)	N1—C3—C4—C5	179.97 (19)
C21B—O2—P1—C1	178.8 (8)	C3—C4—C5—C6	−0.3 (3)
O4—P1—O3—C31	24.8 (2)	N1—C2—C24—C26	−60.5 (2)
O2—P1—O3—C31	152.35 (18)	C1—C2—C24—C26	−178.90 (16)
C1—P1—O3—C31	−99.75 (18)	N1—C2—C24—C25	177.67 (16)
C9—N1—C2—C24	−85.6 (2)	C1—C2—C24—C25	59.3 (2)
C3—N1—C2—C24	99.6 (2)	C9—N2—C10—O1	178.75 (19)
C9—N1—C2—C1	37.2 (2)	C9—N2—C10—C1	−2.0 (3)
C3—N1—C2—C1	−137.62 (19)	C2—C1—C10—O1	−142.2 (2)
C9—N1—C3—C4	−175.4 (2)	P1—C1—C10—O1	92.5 (2)
C2—N1—C3—C4	−0.4 (3)	C2—C1—C10—N2	38.6 (2)
C9—N1—C3—C8	3.4 (2)	P1—C1—C10—N2	−86.8 (2)
C2—N1—C3—C8	178.42 (18)	C4—C5—C6—C7	−0.6 (3)
N1—C2—C1—C10	−52.7 (2)	C4—C5—C6—C61	179.0 (2)
C24—C2—C1—C10	68.6 (2)	C4—C3—C8—C7	−1.2 (3)
N1—C2—C1—P1	74.73 (17)	N1—C3—C8—C7	179.82 (18)
C24—C2—C1—P1	−164.02 (14)	C4—C3—C8—S1	177.69 (16)
O4—P1—C1—C10	172.81 (14)	N1—C3—C8—S1	−1.2 (2)
O2—P1—C1—C10	46.72 (17)	C9—S1—C8—C3	−0.79 (16)
O3—P1—C1—C10	−61.47 (17)	C9—S1—C8—C7	178.1 (2)
O4—P1—C1—C2	47.56 (17)	C5—C6—C7—C8	0.6 (3)
O2—P1—C1—C2	−78.54 (15)	C61—C6—C7—C8	−179.03 (19)
O3—P1—C1—C2	173.28 (13)	C3—C8—C7—C6	0.3 (3)
C10—N2—C9—N1	−19.3 (3)	S1—C8—C7—C6	−178.41 (16)
C10—N2—C9—S1	159.17 (15)	P1—O3—C31—C32	−149.12 (18)
C3—N1—C9—N2	174.55 (19)