(−)-(2R,3R)-O,O′-Dibenzoyl-(2R,3R)-tartaric acid–hexa­methyl­phospho­ramide (1/2)

Zhang, Y.-J.; Shu, Z.; Feng, W.-J.; Li, M.-C.; Jin, Z.-M.

doi:10.1107/S1600536807008380

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(−)-(2R,3R)-O,O′-Dibenzoyl-(2R,3R)-tartaric acid–hexamethylphosphoramide (1/2)

Y.-J. Zhang, Z. Shu, W.-J. Feng, M.-C. Li and Z.-M. Jin

In the title compound, C₁₈H₁₄O₈·2C₆H₁₈N₃OP, one acid and two phosphoramide molecules are linked together by strong O—H

O hydrogen bonds. There are two crystallographically independent amide–acid assemblies in the asymmetric unit. Three of the four symmetry-independent phosphoramide molecules adopt propeller-like conformations. The crystal structure is additionally stabilized by C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008380/gk2052sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008380/gk2052Isup2.hkl Contains datablock I

CCDC reference: 642993

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.098
Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.66 mm
PLAT213_ALERT_2_C Atom C59     has ADP max/min Ratio .............       3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.89 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P4     -   N12     ..       5.18 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N12
PLAT731_ALERT_1_C Bond    Calc     0.81(3), Rep   0.815(10) ......       3.00 su-Ra
              O13  -H13O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.81(3), Rep   0.815(10) ......       3.00 su-Ra
              O13  -H13O    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.68(3), Rep   1.684(13) ......       2.31 su-Ra
              H3O  -O19     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C18 H14 O8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C6 H18 N3 O P
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              C6 H18 N3 O P

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total              17538
           Count of symmetry unique reflns         9591
           Completeness (_total/calc)            182.86%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      7947
           Fraction of Friedel pairs measured     0.829
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          R

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(-)-(2R,3R)-O,O'-Dibenzoyl-(2R,3R)-tartaric acid–hexamethylphosphoramide (1/2) top

Crystal data top

C₁₈H₁₄O₈·2C₆H₁₈N₃OP	F(000) = 3056
M_r = 716.70	D_x = 1.242 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 72558 reflections
a = 12.2940 (2) Å	θ = 3.0–27.5°
b = 19.1370 (3) Å	µ = 0.17 mm⁻¹
c = 32.5842 (6) Å	T = 153 K
V = 7666.1 (2) Å³	Block, colorless
Z = 8	0.66 × 0.60 × 0.43 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	17538 independent reflections
Radiation source: fine-focus sealed tube	16986 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: empirical (using intensity measurements) (SHELXTL; Bruker, 1998)	h = −15→15
T_min = 0.896, T_max = 0.930	k = −24→24
75480 measured reflections	l = −42→41

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0611P)² + 1.9189P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.65 e Å⁻³
17538 reflections	Δρ_min = −0.35 e Å⁻³
905 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.00144 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 7969 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (4)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1	0.13863 (4)	0.26509 (2)	0.667800 (14)	0.02901 (9)
P2	0.71607 (3)	0.03102 (2)	0.616460 (12)	0.02503 (8)
P3	−0.20907 (3)	−0.12980 (2)	0.478180 (12)	0.02244 (8)
P4	−0.54515 (4)	−0.04960 (3)	0.836700 (16)	0.03801 (11)
O1	0.20609 (9)	−0.03026 (5)	0.58923 (3)	0.0237 (2)
O2	0.18329 (11)	−0.14392 (6)	0.60546 (4)	0.0324 (3)
O3	0.04013 (9)	−0.06667 (7)	0.54276 (4)	0.0311 (3)
O4	0.14125 (11)	−0.08164 (7)	0.48638 (4)	0.0368 (3)
O5	0.45881 (10)	−0.02727 (7)	0.55845 (5)	0.0372 (3)
O6	0.41509 (11)	0.08578 (6)	0.56581 (4)	0.0347 (3)
O7	0.22425 (9)	0.06768 (6)	0.52593 (4)	0.0263 (2)
O8	0.33128 (10)	0.11084 (7)	0.47587 (4)	0.0370 (3)
O9	−0.28699 (9)	0.19469 (6)	0.78833 (3)	0.0251 (2)
O10	−0.43071 (11)	0.18114 (8)	0.74633 (4)	0.0416 (3)
O11	−0.07661 (10)	0.15476 (6)	0.71719 (4)	0.0311 (3)
O12	−0.15101 (12)	0.25775 (7)	0.73419 (5)	0.0423 (3)
O13	−0.31018 (11)	0.02309 (7)	0.78817 (4)	0.0358 (3)
O14	−0.22739 (14)	0.03867 (7)	0.84878 (4)	0.0433 (3)
O15	−0.09648 (9)	0.13906 (6)	0.81715 (3)	0.0266 (2)
O16	0.01587 (13)	0.04707 (8)	0.82515 (4)	0.0483 (4)
O17	0.06665 (11)	0.20278 (7)	0.67135 (4)	0.0368 (3)
O18	0.64841 (10)	−0.00655 (7)	0.58574 (4)	0.0356 (3)
O19	−0.12337 (10)	−0.11772 (8)	0.50950 (4)	0.0394 (3)
O20	−0.43284 (13)	−0.06244 (9)	0.82249 (7)	0.0623 (5)
N1	0.09442 (16)	0.31830 (9)	0.63265 (6)	0.0465 (4)
N2	0.14431 (15)	0.30533 (9)	0.71213 (5)	0.0414 (4)
N3	0.26349 (14)	0.24666 (11)	0.65334 (6)	0.0480 (4)
N4	0.78128 (12)	−0.02690 (7)	0.64458 (4)	0.0289 (3)
N5	0.79852 (14)	0.08470 (8)	0.59218 (4)	0.0360 (3)
N6	0.65271 (13)	0.07917 (9)	0.65082 (5)	0.0371 (3)
N7	−0.30990 (11)	−0.17658 (7)	0.49573 (5)	0.0295 (3)
N8	−0.15703 (11)	−0.16987 (7)	0.43845 (4)	0.0278 (3)
N9	−0.26322 (13)	−0.05615 (7)	0.46299 (4)	0.0316 (3)
N10	−0.58744 (15)	0.03168 (10)	0.83515 (6)	0.0480 (4)
N11	−0.5503 (2)	−0.06998 (12)	0.88550 (7)	0.0683 (6)
N12	−0.6314 (2)	−0.09688 (14)	0.81113 (9)	0.0795 (8)
C1	0.15722 (15)	0.01362 (9)	0.66674 (6)	0.0323 (3)
H1	0.1754	0.0464	0.6468	0.039*
C2	0.13258 (17)	0.03498 (10)	0.70651 (6)	0.0403 (4)
H2	0.1340	0.0822	0.7132	0.048*
C3	0.10596 (17)	−0.01397 (11)	0.73617 (6)	0.0411 (4)
H3	0.0901	0.0005	0.7628	0.049*
C4	0.10284 (16)	−0.08405 (11)	0.72644 (6)	0.0369 (4)
H4	0.0845	−0.1166	0.7465	0.044*
C5	0.12703 (14)	−0.10627 (9)	0.68687 (5)	0.0314 (3)
H5	0.1249	−0.1536	0.6804	0.038*
C6	0.15447 (12)	−0.05739 (8)	0.65700 (5)	0.0258 (3)
C7	0.18147 (12)	−0.08318 (8)	0.61532 (5)	0.0244 (3)
C8	0.23168 (12)	−0.05067 (8)	0.54795 (5)	0.0230 (3)
H8	0.2783	−0.0922	0.5489	0.028*
C9	0.13058 (12)	−0.06770 (8)	0.52232 (5)	0.0239 (3)
C10	0.29524 (12)	0.00866 (8)	0.52880 (5)	0.0245 (3)
H10	0.3177	−0.0051	0.5011	0.029*
C11	0.39667 (12)	0.02795 (8)	0.55371 (5)	0.0244 (3)
C12	0.25391 (13)	0.11687 (9)	0.49818 (5)	0.0276 (3)
C13	0.17936 (13)	0.17758 (9)	0.49866 (5)	0.0301 (3)
C14	0.09099 (17)	0.18145 (11)	0.52494 (7)	0.0453 (5)
H14	0.0767	0.1451	0.5431	0.054*
C15	0.0240 (2)	0.23953 (14)	0.52412 (10)	0.0668 (8)
H15	−0.0342	0.2426	0.5423	0.080*
C16	0.0431 (2)	0.29322 (12)	0.49640 (9)	0.0579 (6)
H16	−0.0032	0.3316	0.4955	0.070*
C17	0.1300 (2)	0.28926 (11)	0.47059 (7)	0.0505 (5)
H17	0.1434	0.3255	0.4522	0.061*
C18	0.19858 (17)	0.23194 (11)	0.47139 (6)	0.0419 (4)
H18	0.2577	0.2298	0.4536	0.050*
C19	−0.39103 (14)	0.30002 (9)	0.83090 (5)	0.0297 (3)
H19	−0.3155	0.2981	0.8324	0.036*
C20	−0.44879 (16)	0.34634 (10)	0.85567 (5)	0.0358 (4)
H20	−0.4115	0.3762	0.8732	0.043*
C21	−0.56111 (17)	0.34828 (11)	0.85433 (6)	0.0404 (4)
H21	−0.5994	0.3788	0.8712	0.048*
C22	−0.61614 (17)	0.30442 (14)	0.82768 (7)	0.0538 (6)
H22	−0.6917	0.3054	0.8268	0.065*
C23	−0.55983 (16)	0.25921 (12)	0.80239 (7)	0.0443 (5)
H23	−0.5975	0.2304	0.7843	0.053*
C24	−0.44692 (13)	0.25671 (8)	0.80397 (5)	0.0260 (3)
C25	−0.38985 (13)	0.20736 (8)	0.77597 (5)	0.0255 (3)
C26	−0.22253 (12)	0.15071 (8)	0.76234 (4)	0.0218 (3)
H26	−0.2709	0.1248	0.7439	0.026*
C27	−0.14554 (13)	0.19533 (8)	0.73655 (5)	0.0242 (3)
C28	−0.16136 (12)	0.09907 (8)	0.78918 (4)	0.0232 (3)
H28	−0.1133	0.0708	0.7718	0.028*
C29	−0.23749 (14)	0.05049 (8)	0.81288 (5)	0.0278 (3)
C30	−0.01169 (14)	0.10517 (9)	0.83458 (5)	0.0313 (3)
C31	0.04182 (14)	0.14950 (10)	0.86644 (5)	0.0322 (4)
C32	0.00569 (14)	0.21662 (9)	0.87538 (5)	0.0296 (3)
H32	−0.0520	0.2358	0.8607	0.036*
C33	0.05573 (16)	0.25512 (10)	0.90620 (6)	0.0373 (4)
H33	0.0318	0.3001	0.9122	0.045*
C34	0.14132 (18)	0.22625 (14)	0.92800 (7)	0.0505 (5)
H34	0.1751	0.2521	0.9485	0.061*
C35	0.1771 (2)	0.15907 (15)	0.91945 (8)	0.0632 (7)
H35	0.2341	0.1398	0.9344	0.076*
C36	0.1276 (2)	0.12051 (13)	0.88839 (7)	0.0560 (6)
H36	0.1517	0.0756	0.8824	0.067*
C37	−0.0223 (2)	0.33556 (17)	0.63343 (11)	0.0722 (8)
H37A	−0.0515	0.3322	0.6062	0.087*
H37B	−0.0317	0.3823	0.6435	0.087*
H37C	−0.0597	0.3035	0.6511	0.087*
C38	0.1606 (3)	0.36685 (16)	0.60916 (9)	0.0790 (9)
H38A	0.1529	0.4130	0.6203	0.095*
H38B	0.1371	0.3668	0.5811	0.095*
H38C	0.2355	0.3528	0.6106	0.095*
C39	0.1845 (3)	0.37679 (13)	0.71519 (9)	0.0651 (7)
H39A	0.2530	0.3770	0.7293	0.078*
H39B	0.1330	0.4047	0.7301	0.078*
H39C	0.1939	0.3958	0.6882	0.078*
C40	0.13351 (18)	0.26933 (14)	0.75089 (7)	0.0493 (5)
H40A	0.0862	0.2955	0.7686	0.059*
H40B	0.2038	0.2649	0.7635	0.059*
H40C	0.1034	0.2237	0.7463	0.059*
C41	0.3505 (2)	0.23795 (19)	0.68172 (9)	0.0696 (8)
H41A	0.4170	0.2541	0.6695	0.083*
H41B	0.3574	0.1894	0.6887	0.083*
H41C	0.3357	0.2645	0.7061	0.083*
C42	0.2781 (2)	0.20833 (19)	0.61509 (10)	0.0779 (10)
H42A	0.2694	0.1592	0.6201	0.094*
H42B	0.3496	0.2171	0.6045	0.094*
H42C	0.2247	0.2235	0.5955	0.094*
C43	0.83819 (15)	−0.08261 (10)	0.62267 (6)	0.0354 (4)
H43A	0.8392	−0.1240	0.6393	0.042*
H43B	0.9115	−0.0682	0.6170	0.042*
H43C	0.8013	−0.0922	0.5973	0.042*
C44	0.8304 (2)	−0.01129 (13)	0.68409 (6)	0.0531 (6)
H44A	0.9044	0.0033	0.6801	0.064*
H44B	0.8289	−0.0523	0.7010	0.064*
H44C	0.7904	0.0255	0.6972	0.064*
C45	0.8866 (2)	0.11865 (16)	0.61478 (7)	0.0657 (8)
H45A	0.9071	0.1610	0.6010	0.079*
H45B	0.9482	0.0878	0.6161	0.079*
H45C	0.8625	0.1294	0.6421	0.079*
C46	0.82486 (19)	0.07248 (11)	0.54911 (6)	0.0438 (5)
H46A	0.8913	0.0463	0.5472	0.053*
H46B	0.8336	0.1165	0.5354	0.053*
H46C	0.7670	0.0466	0.5364	0.053*
C47	0.5724 (2)	0.04252 (15)	0.67619 (8)	0.0599 (7)
H47A	0.5038	0.0413	0.6621	0.072*
H47B	0.5640	0.0666	0.7018	0.072*
H47C	0.5967	−0.0044	0.6812	0.072*
C48	0.6199 (3)	0.15073 (13)	0.64077 (7)	0.0600 (7)
H48A	0.6006	0.1750	0.6655	0.072*
H48B	0.5584	0.1496	0.6226	0.072*
H48C	0.6791	0.1745	0.6276	0.072*
C49	−0.33702 (16)	−0.24654 (9)	0.48281 (6)	0.0359 (4)
H49A	−0.4091	−0.2470	0.4715	0.043*
H49B	−0.3340	−0.2775	0.5060	0.043*
H49C	−0.2860	−0.2618	0.4624	0.043*
C50	−0.37046 (17)	−0.15222 (11)	0.53123 (7)	0.0464 (5)
H50A	−0.3604	−0.1842	0.5536	0.056*
H50B	−0.4464	−0.1495	0.5245	0.056*
H50C	−0.3446	−0.1068	0.5391	0.056*
C51	−0.06732 (18)	−0.21887 (13)	0.44291 (8)	0.0506 (5)
H51A	−0.0156	−0.2114	0.4213	0.061*
H51B	−0.0946	−0.2658	0.4414	0.061*
H51C	−0.0326	−0.2117	0.4690	0.061*
C52	−0.21689 (16)	−0.17701 (9)	0.40016 (5)	0.0331 (3)
H52A	−0.2461	−0.2234	0.3982	0.040*
H52B	−0.1688	−0.1686	0.3775	0.040*
H52C	−0.2753	−0.1437	0.3996	0.040*
C53	−0.1895 (2)	−0.00054 (10)	0.44965 (6)	0.0462 (5)
H53A	−0.2146	0.0435	0.4601	0.055*
H53B	−0.1877	0.0010	0.4202	0.055*
H53C	−0.1177	−0.0097	0.4599	0.055*
C54	−0.37541 (18)	−0.04687 (12)	0.44964 (7)	0.0491 (5)
H54A	−0.3769	−0.0383	0.4206	0.059*
H54B	−0.4069	−0.0078	0.4638	0.059*
H54C	−0.4163	−0.0884	0.4557	0.059*
C55	−0.5286 (2)	0.08434 (12)	0.85847 (9)	0.0582 (6)
H55A	−0.5795	0.1156	0.8712	0.070*
H55B	−0.4819	0.1102	0.8404	0.070*
H55C	−0.4855	0.0620	0.8792	0.070*
C56	−0.6496 (3)	0.05830 (18)	0.80108 (10)	0.0785 (9)
H56A	−0.6010	0.0744	0.7801	0.094*
H56B	−0.6942	0.0964	0.8102	0.094*
H56C	−0.6949	0.0218	0.7903	0.094*
C57	−0.6298 (4)	−0.0437 (2)	0.91505 (10)	0.0934 (11)
H57A	−0.5990	−0.0449	0.9421	0.112*
H57B	−0.6938	−0.0724	0.9143	0.112*
H57C	−0.6487	0.0036	0.9082	0.112*
C58	−0.4941 (4)	−0.13183 (18)	0.89993 (11)	0.0847 (10)
H58A	−0.5437	−0.1706	0.9003	0.102*
H58B	−0.4670	−0.1237	0.9271	0.102*
H58C	−0.4345	−0.1422	0.8819	0.102*
C59	−0.6148 (4)	−0.1272 (3)	0.77356 (16)	0.154 (3)
H59A	−0.5419	−0.1180	0.7646	0.185*	0.50
H59B	−0.6654	−0.1082	0.7541	0.185*	0.50
H59C	−0.6256	−0.1768	0.7757	0.185*	0.50
H59D	−0.6800	−0.1507	0.7650	0.185*	0.50
H59E	−0.5565	−0.1604	0.7755	0.185*	0.50
H59F	−0.5963	−0.0919	0.7539	0.185*	0.50
C60	−0.7433 (3)	−0.1080 (2)	0.82836 (13)	0.1027 (14)
H60A	−0.7559	−0.1571	0.8320	0.123*
H60B	−0.7963	−0.0893	0.8097	0.123*
H60C	−0.7492	−0.0846	0.8543	0.123*
H3O	−0.0120 (18)	−0.0784 (17)	0.5287 (9)	0.076 (10)*
H5O	0.5180 (15)	−0.0169 (17)	0.5680 (10)	0.082 (10)*
H11O	−0.038 (2)	0.1788 (13)	0.7022 (7)	0.060 (8)*
H13O	−0.341 (3)	−0.0103 (13)	0.7983 (10)	0.093 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.02788 (19)	0.02493 (19)	0.0342 (2)	−0.00459 (15)	0.00849 (16)	−0.00191 (16)
P2	0.02070 (17)	0.02834 (19)	0.02606 (18)	0.00089 (14)	−0.00294 (14)	−0.00823 (15)
P3	0.02010 (16)	0.02318 (17)	0.02405 (16)	−0.00374 (14)	−0.00453 (14)	0.00116 (14)
P4	0.0329 (2)	0.0340 (2)	0.0472 (3)	−0.01166 (18)	0.0121 (2)	−0.0117 (2)
O1	0.0240 (5)	0.0201 (5)	0.0269 (5)	−0.0011 (4)	−0.0028 (4)	−0.0017 (4)
O2	0.0425 (7)	0.0214 (5)	0.0334 (6)	−0.0005 (5)	−0.0018 (5)	−0.0017 (4)
O3	0.0187 (5)	0.0453 (7)	0.0293 (6)	−0.0034 (5)	−0.0032 (4)	−0.0058 (5)
O4	0.0306 (6)	0.0492 (7)	0.0306 (6)	−0.0063 (5)	0.0016 (5)	−0.0102 (5)
O5	0.0203 (5)	0.0271 (6)	0.0643 (9)	0.0015 (5)	−0.0135 (5)	−0.0075 (6)
O6	0.0345 (6)	0.0261 (6)	0.0436 (7)	−0.0006 (5)	−0.0067 (5)	−0.0070 (5)
O7	0.0200 (5)	0.0244 (5)	0.0346 (6)	0.0023 (4)	0.0019 (4)	0.0055 (4)
O8	0.0308 (6)	0.0430 (7)	0.0374 (6)	0.0005 (5)	0.0074 (5)	0.0071 (6)
O9	0.0229 (5)	0.0288 (5)	0.0237 (5)	0.0060 (4)	−0.0009 (4)	−0.0064 (4)
O10	0.0338 (7)	0.0541 (8)	0.0369 (6)	0.0146 (6)	−0.0122 (5)	−0.0212 (6)
O11	0.0362 (6)	0.0232 (6)	0.0340 (6)	−0.0034 (5)	0.0140 (5)	−0.0020 (5)
O12	0.0451 (8)	0.0238 (6)	0.0581 (8)	0.0041 (5)	0.0113 (6)	0.0055 (6)
O13	0.0359 (7)	0.0327 (6)	0.0386 (7)	−0.0085 (5)	0.0041 (5)	0.0033 (5)
O14	0.0661 (9)	0.0390 (7)	0.0248 (6)	−0.0044 (7)	0.0084 (6)	0.0014 (5)
O15	0.0284 (5)	0.0254 (5)	0.0261 (5)	0.0038 (4)	−0.0066 (4)	−0.0037 (4)
O16	0.0600 (9)	0.0449 (8)	0.0400 (7)	0.0277 (7)	−0.0174 (6)	−0.0161 (6)
O17	0.0414 (7)	0.0291 (6)	0.0400 (6)	−0.0110 (5)	0.0133 (6)	−0.0039 (5)
O18	0.0221 (5)	0.0439 (7)	0.0407 (7)	0.0030 (5)	−0.0090 (5)	−0.0177 (6)
O19	0.0287 (6)	0.0560 (8)	0.0336 (6)	−0.0135 (6)	−0.0117 (5)	0.0037 (6)
O20	0.0418 (8)	0.0420 (8)	0.1029 (14)	−0.0042 (7)	0.0335 (9)	0.0149 (9)
N1	0.0526 (10)	0.0365 (9)	0.0503 (10)	0.0030 (8)	0.0080 (8)	0.0101 (8)
N2	0.0431 (9)	0.0391 (9)	0.0420 (8)	−0.0114 (7)	0.0096 (7)	−0.0117 (7)
N3	0.0324 (8)	0.0579 (11)	0.0537 (10)	−0.0014 (7)	0.0114 (7)	−0.0184 (9)
N4	0.0276 (6)	0.0314 (7)	0.0275 (6)	−0.0011 (6)	−0.0014 (5)	−0.0027 (5)
N5	0.0446 (9)	0.0392 (8)	0.0243 (6)	−0.0091 (7)	−0.0040 (6)	−0.0002 (6)
N6	0.0353 (8)	0.0373 (8)	0.0385 (8)	0.0043 (6)	0.0035 (6)	−0.0139 (6)
N7	0.0267 (7)	0.0247 (7)	0.0370 (7)	−0.0078 (5)	0.0064 (6)	−0.0068 (5)
N8	0.0217 (6)	0.0309 (7)	0.0309 (7)	0.0038 (5)	−0.0012 (5)	0.0007 (5)
N9	0.0403 (8)	0.0224 (6)	0.0321 (7)	0.0004 (6)	−0.0010 (6)	0.0020 (5)
N10	0.0457 (9)	0.0409 (9)	0.0573 (10)	−0.0014 (8)	−0.0091 (8)	−0.0124 (8)
N11	0.0947 (18)	0.0500 (11)	0.0600 (12)	0.0092 (12)	0.0309 (13)	0.0055 (10)
N12	0.0653 (14)	0.0755 (16)	0.0976 (18)	−0.0112 (13)	−0.0007 (14)	−0.0527 (15)
C1	0.0368 (9)	0.0246 (8)	0.0353 (8)	0.0025 (6)	−0.0048 (7)	−0.0018 (6)
C2	0.0451 (10)	0.0321 (9)	0.0436 (10)	0.0073 (8)	−0.0022 (8)	−0.0122 (8)
C3	0.0412 (10)	0.0486 (11)	0.0336 (9)	0.0114 (8)	−0.0017 (8)	−0.0071 (8)
C4	0.0355 (9)	0.0421 (10)	0.0333 (9)	0.0071 (7)	0.0025 (7)	0.0046 (7)
C5	0.0309 (8)	0.0273 (8)	0.0360 (8)	0.0008 (6)	−0.0013 (7)	0.0014 (7)
C6	0.0212 (7)	0.0252 (7)	0.0311 (7)	0.0027 (5)	−0.0038 (6)	−0.0022 (6)
C7	0.0217 (7)	0.0215 (7)	0.0299 (7)	−0.0001 (5)	−0.0049 (6)	0.0005 (6)
C8	0.0189 (7)	0.0217 (7)	0.0284 (7)	0.0000 (5)	−0.0019 (5)	−0.0023 (5)
C9	0.0206 (6)	0.0208 (7)	0.0303 (7)	−0.0013 (5)	−0.0022 (6)	−0.0028 (6)
C10	0.0189 (6)	0.0232 (7)	0.0313 (7)	−0.0004 (5)	−0.0005 (6)	−0.0004 (6)
C11	0.0194 (6)	0.0248 (7)	0.0289 (7)	−0.0016 (5)	0.0003 (5)	−0.0003 (6)
C12	0.0238 (7)	0.0300 (8)	0.0291 (7)	−0.0032 (6)	−0.0030 (6)	0.0034 (6)
C13	0.0257 (7)	0.0295 (8)	0.0351 (8)	−0.0004 (6)	−0.0037 (6)	0.0066 (7)
C14	0.0374 (10)	0.0389 (10)	0.0596 (12)	0.0111 (8)	0.0136 (9)	0.0212 (9)
C15	0.0548 (14)	0.0528 (13)	0.0929 (19)	0.0251 (11)	0.0299 (14)	0.0312 (14)
C16	0.0501 (12)	0.0417 (11)	0.0820 (17)	0.0159 (10)	−0.0002 (12)	0.0245 (12)
C17	0.0560 (13)	0.0367 (10)	0.0587 (13)	0.0014 (9)	−0.0055 (10)	0.0215 (9)
C18	0.0393 (10)	0.0402 (10)	0.0462 (10)	−0.0023 (8)	0.0012 (8)	0.0159 (8)
C19	0.0294 (8)	0.0294 (8)	0.0302 (7)	0.0041 (6)	0.0001 (6)	−0.0033 (6)
C20	0.0416 (10)	0.0343 (9)	0.0315 (8)	0.0082 (7)	−0.0023 (7)	−0.0090 (7)
C21	0.0417 (10)	0.0435 (10)	0.0359 (9)	0.0213 (8)	−0.0006 (8)	−0.0076 (8)
C22	0.0304 (9)	0.0699 (15)	0.0612 (13)	0.0212 (10)	−0.0080 (9)	−0.0266 (12)
C23	0.0294 (9)	0.0550 (12)	0.0484 (10)	0.0138 (8)	−0.0093 (8)	−0.0202 (9)
C24	0.0269 (7)	0.0268 (7)	0.0243 (7)	0.0079 (6)	−0.0013 (6)	−0.0004 (6)
C25	0.0258 (7)	0.0262 (7)	0.0244 (7)	0.0037 (6)	−0.0020 (6)	−0.0003 (6)
C26	0.0225 (7)	0.0222 (7)	0.0209 (6)	0.0018 (5)	0.0008 (5)	−0.0040 (5)
C27	0.0244 (7)	0.0234 (7)	0.0247 (7)	−0.0001 (6)	−0.0014 (6)	0.0003 (5)
C28	0.0256 (7)	0.0232 (7)	0.0209 (6)	0.0019 (6)	0.0004 (5)	−0.0028 (5)
C29	0.0345 (8)	0.0203 (7)	0.0286 (7)	0.0035 (6)	0.0095 (6)	−0.0016 (6)
C30	0.0332 (8)	0.0370 (9)	0.0237 (7)	0.0112 (7)	−0.0051 (6)	−0.0038 (7)
C31	0.0311 (8)	0.0398 (9)	0.0258 (7)	0.0074 (7)	−0.0061 (6)	−0.0022 (7)
C32	0.0273 (7)	0.0344 (8)	0.0271 (7)	−0.0026 (6)	0.0003 (6)	0.0001 (6)
C33	0.0354 (9)	0.0396 (10)	0.0370 (9)	−0.0073 (8)	0.0016 (7)	−0.0063 (7)
C34	0.0422 (11)	0.0671 (14)	0.0421 (10)	−0.0035 (10)	−0.0113 (9)	−0.0188 (10)
C35	0.0577 (14)	0.0752 (17)	0.0568 (13)	0.0211 (12)	−0.0363 (12)	−0.0183 (12)
C36	0.0574 (13)	0.0598 (14)	0.0508 (12)	0.0276 (11)	−0.0276 (11)	−0.0175 (11)
C37	0.0632 (17)	0.0674 (17)	0.086 (2)	0.0261 (14)	−0.0074 (15)	0.0074 (15)
C38	0.114 (3)	0.0542 (15)	0.0683 (17)	−0.0291 (17)	0.0071 (17)	0.0264 (13)
C39	0.0793 (18)	0.0484 (13)	0.0677 (15)	−0.0224 (12)	0.0152 (14)	−0.0251 (12)
C40	0.0396 (10)	0.0691 (14)	0.0393 (10)	−0.0070 (10)	−0.0029 (8)	−0.0105 (10)
C41	0.0370 (12)	0.102 (2)	0.0692 (16)	0.0155 (13)	0.0081 (11)	0.0011 (15)
C42	0.0491 (14)	0.105 (2)	0.0797 (19)	−0.0085 (15)	0.0266 (14)	−0.0491 (18)
C43	0.0295 (8)	0.0336 (9)	0.0430 (9)	0.0061 (7)	0.0027 (7)	−0.0018 (7)
C44	0.0734 (16)	0.0507 (12)	0.0352 (10)	0.0100 (11)	−0.0203 (10)	−0.0047 (9)
C45	0.0709 (16)	0.0863 (19)	0.0398 (11)	−0.0500 (15)	−0.0100 (11)	0.0096 (12)
C46	0.0595 (13)	0.0409 (10)	0.0311 (9)	0.0036 (9)	0.0073 (8)	−0.0007 (8)
C47	0.0445 (12)	0.0691 (16)	0.0661 (15)	−0.0117 (11)	0.0272 (11)	−0.0328 (13)
C48	0.0840 (18)	0.0503 (13)	0.0457 (11)	0.0329 (13)	−0.0053 (11)	−0.0173 (10)
C49	0.0465 (10)	0.0273 (8)	0.0338 (8)	−0.0138 (7)	0.0003 (7)	−0.0024 (7)
C50	0.0383 (10)	0.0419 (10)	0.0590 (12)	−0.0150 (8)	0.0227 (9)	−0.0192 (9)
C51	0.0379 (10)	0.0566 (13)	0.0572 (12)	0.0230 (9)	−0.0054 (9)	−0.0052 (10)
C52	0.0414 (9)	0.0329 (8)	0.0251 (7)	0.0022 (7)	0.0013 (7)	0.0002 (6)
C53	0.0785 (15)	0.0289 (9)	0.0312 (8)	−0.0160 (9)	−0.0009 (9)	0.0054 (7)
C54	0.0475 (12)	0.0496 (12)	0.0503 (11)	0.0241 (10)	−0.0042 (9)	0.0054 (9)
C55	0.0678 (16)	0.0325 (10)	0.0743 (16)	−0.0046 (10)	−0.0118 (13)	−0.0131 (10)
C56	0.085 (2)	0.0708 (18)	0.0794 (19)	−0.0204 (16)	−0.0305 (17)	0.0194 (16)
C57	0.119 (3)	0.098 (3)	0.0636 (18)	0.002 (2)	0.0351 (19)	−0.0108 (18)
C58	0.111 (3)	0.0671 (19)	0.0764 (19)	−0.0034 (19)	0.0025 (19)	0.0194 (16)
C59	0.096 (3)	0.210 (6)	0.156 (4)	−0.002 (3)	−0.008 (3)	−0.146 (5)
C60	0.082 (2)	0.131 (3)	0.095 (2)	−0.063 (2)	0.0126 (19)	−0.025 (2)

Geometric parameters (Å, º) top

P1—O17	1.4894 (13)	C21—H21	0.9300
P1—N1	1.6261 (18)	C22—C23	1.381 (3)
P1—N2	1.6384 (16)	C22—H22	0.9300
P1—N3	1.6440 (17)	C23—C24	1.390 (2)
P2—O18	1.4869 (12)	C23—H23	0.9300
P2—N5	1.6458 (16)	C24—C25	1.489 (2)
P2—N6	1.6460 (15)	C26—C28	1.519 (2)
P2—N4	1.6465 (15)	C26—C27	1.527 (2)
P3—O19	1.4849 (12)	C26—H26	0.9800
P3—N7	1.6325 (14)	C28—C29	1.529 (2)
P3—N8	1.6350 (14)	C28—H28	0.9800
P3—N9	1.6354 (15)	C30—C31	1.493 (2)
P4—O20	1.4769 (16)	C31—C36	1.389 (3)
P4—N12	1.624 (2)	C31—C32	1.390 (2)
P4—N11	1.638 (2)	C32—C33	1.389 (2)
P4—N10	1.641 (2)	C32—H32	0.9300
O1—C7	1.3564 (19)	C33—C34	1.385 (3)
O1—C8	1.4355 (18)	C33—H33	0.9300
O2—C7	1.206 (2)	C34—C35	1.387 (4)
O3—C9	1.2963 (19)	C34—H34	0.9300
O3—H3O	0.819 (10)	C35—C36	1.393 (3)
O4—C9	1.208 (2)	C35—H35	0.9300
O5—C11	1.313 (2)	C36—H36	0.9300
O5—H5O	0.817 (10)	C37—H37A	0.9600
O6—C11	1.196 (2)	C37—H37B	0.9600
O7—C12	1.3552 (19)	C37—H37C	0.9600
O7—C10	1.4304 (18)	C38—H38A	0.9600
O8—C12	1.203 (2)	C38—H38B	0.9600
O9—C25	1.3491 (19)	C38—H38C	0.9600
O9—C26	1.4330 (17)	C39—H39A	0.9600
O10—C25	1.199 (2)	C39—H39B	0.9600
O11—C27	1.3111 (19)	C39—H39C	0.9600
O11—H11O	0.822 (10)	C40—H40A	0.9600
O12—C27	1.199 (2)	C40—H40B	0.9600
O13—C29	1.312 (2)	C40—H40C	0.9600
O13—H13O	0.815 (10)	C41—H41A	0.9600
O14—C29	1.198 (2)	C41—H41B	0.9600
O15—C30	1.3527 (19)	C41—H41C	0.9600
O15—C28	1.4327 (18)	C42—H42A	0.9600
O16—C30	1.202 (2)	C42—H42B	0.9600
N1—C38	1.453 (3)	C42—H42C	0.9600
N1—C37	1.472 (3)	C43—H43A	0.9600
N2—C40	1.445 (3)	C43—H43B	0.9600
N2—C39	1.457 (3)	C43—H43C	0.9600
N3—C41	1.423 (3)	C44—H44A	0.9600
N3—C42	1.457 (3)	C44—H44B	0.9600
N4—C44	1.453 (2)	C44—H44C	0.9600
N4—C43	1.461 (2)	C45—H45A	0.9600
N5—C46	1.459 (2)	C45—H45B	0.9600
N5—C45	1.462 (3)	C45—H45C	0.9600
N6—C48	1.465 (3)	C46—H46A	0.9600
N6—C47	1.467 (3)	C46—H46B	0.9600
N7—C49	1.443 (2)	C46—H46C	0.9600
N7—C50	1.452 (2)	C47—H47A	0.9600
N8—C51	1.455 (2)	C47—H47B	0.9600
N8—C52	1.455 (2)	C47—H47C	0.9600
N9—C54	1.457 (3)	C48—H48A	0.9600
N9—C53	1.464 (2)	C48—H48B	0.9600
N10—C56	1.441 (3)	C48—H48C	0.9600
N10—C55	1.455 (3)	C49—H49A	0.9600
N11—C58	1.449 (4)	C49—H49B	0.9600
N11—C57	1.461 (4)	C49—H49C	0.9600
N12—C59	1.370 (4)	C50—H50A	0.9600
N12—C60	1.501 (4)	C50—H50B	0.9600
C1—C2	1.392 (3)	C50—H50C	0.9600
C1—C6	1.396 (2)	C51—H51A	0.9600
C1—H1	0.9300	C51—H51B	0.9600
C2—C3	1.385 (3)	C51—H51C	0.9600
C2—H2	0.9300	C52—H52A	0.9600
C3—C4	1.379 (3)	C52—H52B	0.9600
C3—H3	0.9300	C52—H52C	0.9600
C4—C5	1.390 (3)	C53—H53A	0.9600
C4—H4	0.9300	C53—H53B	0.9600
C5—C6	1.391 (2)	C53—H53C	0.9600
C5—H5	0.9300	C54—H54A	0.9600
C6—C7	1.483 (2)	C54—H54B	0.9600
C8—C10	1.513 (2)	C54—H54C	0.9600
C8—C9	1.532 (2)	C55—H55A	0.9600
C8—H8	0.9800	C55—H55B	0.9600
C10—C11	1.533 (2)	C55—H55C	0.9600
C10—H10	0.9800	C56—H56A	0.9600
C12—C13	1.480 (2)	C56—H56B	0.9600
C13—C14	1.385 (3)	C56—H56C	0.9600
C13—C18	1.388 (2)	C57—H57A	0.9600
C14—C15	1.383 (3)	C57—H57B	0.9600
C14—H14	0.9300	C57—H57C	0.9600
C15—C16	1.388 (3)	C58—H58A	0.9600
C15—H15	0.9300	C58—H58B	0.9600
C16—C17	1.362 (4)	C58—H58C	0.9600
C16—H16	0.9300	C59—H59A	0.9600
C17—C18	1.384 (3)	C59—H59B	0.9600
C17—H17	0.9300	C59—H59C	0.9600
C18—H18	0.9300	C59—H59D	0.9600
C19—C24	1.389 (2)	C59—H59E	0.9600
C19—C20	1.393 (2)	C59—H59F	0.9600
C19—H19	0.9300	C60—H60A	0.9600
C20—C21	1.382 (3)	C60—H60B	0.9600
C20—H20	0.9300	C60—H60C	0.9600
C21—C22	1.384 (3)

O17—P1—N1	110.94 (9)	C33—C32—H32	120.0
O17—P1—N2	109.46 (8)	C31—C32—H32	120.0
N1—P1—N2	109.93 (10)	C34—C33—C32	119.72 (18)
O17—P1—N3	113.91 (9)	C34—C33—H33	120.1
N1—P1—N3	104.16 (10)	C32—C33—H33	120.1
N2—P1—N3	108.28 (10)	C33—C34—C35	120.53 (19)
O18—P2—N5	108.83 (8)	C33—C34—H34	119.7
O18—P2—N6	117.64 (8)	C35—C34—H34	119.7
N5—P2—N6	105.61 (9)	C34—C35—C36	119.9 (2)
O18—P2—N4	108.75 (8)	C34—C35—H35	120.1
N5—P2—N4	112.82 (8)	C36—C35—H35	120.1
N6—P2—N4	103.22 (8)	C31—C36—C35	119.6 (2)
O19—P3—N7	112.54 (8)	C31—C36—H36	120.2
O19—P3—N8	109.85 (8)	C35—C36—H36	120.2
N7—P3—N8	108.50 (7)	N1—C37—H37A	109.5
O19—P3—N9	111.26 (8)	N1—C37—H37B	109.5
N7—P3—N9	105.64 (8)	H37A—C37—H37B	109.5
N8—P3—N9	108.90 (7)	N1—C37—H37C	109.5
O20—P4—N12	110.90 (13)	H37A—C37—H37C	109.5
O20—P4—N11	107.49 (13)	H37B—C37—H37C	109.5
N12—P4—N11	109.89 (16)	N1—C38—H38A	109.5
O20—P4—N10	116.38 (10)	N1—C38—H38B	109.5
N12—P4—N10	107.79 (13)	H38A—C38—H38B	109.5
N11—P4—N10	104.08 (11)	N1—C38—H38C	109.5
C7—O1—C8	115.66 (11)	H38A—C38—H38C	109.5
C9—O3—H3O	112 (2)	H38B—C38—H38C	109.5
C11—O5—H5O	112 (2)	N2—C39—H39A	109.5
C12—O7—C10	115.34 (12)	N2—C39—H39B	109.5
C25—O9—C26	116.58 (11)	H39A—C39—H39B	109.5
C27—O11—H11O	109 (2)	N2—C39—H39C	109.5
C29—O13—H13O	113 (3)	H39A—C39—H39C	109.5
C30—O15—C28	116.11 (12)	H39B—C39—H39C	109.5
C38—N1—C37	114.3 (2)	N2—C40—H40A	109.5
C38—N1—P1	125.8 (2)	N2—C40—H40B	109.5
C37—N1—P1	117.00 (18)	H40A—C40—H40B	109.5
C40—N2—C39	114.76 (19)	N2—C40—H40C	109.5
C40—N2—P1	122.86 (14)	H40A—C40—H40C	109.5
C39—N2—P1	121.05 (16)	H40B—C40—H40C	109.5
C41—N3—C42	113.9 (2)	N3—C41—H41A	109.5
C41—N3—P1	122.70 (16)	N3—C41—H41B	109.5
C42—N3—P1	117.89 (17)	H41A—C41—H41B	109.5
C44—N4—C43	112.57 (16)	N3—C41—H41C	109.5
C44—N4—P2	123.85 (13)	H41A—C41—H41C	109.5
C43—N4—P2	116.90 (12)	H41B—C41—H41C	109.5
C46—N5—C45	113.02 (18)	N3—C42—H42A	109.5
C46—N5—P2	119.93 (14)	N3—C42—H42B	109.5
C45—N5—P2	119.44 (13)	H42A—C42—H42B	109.5
C48—N6—C47	112.8 (2)	N3—C42—H42C	109.5
C48—N6—P2	120.12 (15)	H42A—C42—H42C	109.5
C47—N6—P2	115.75 (14)	H42B—C42—H42C	109.5
C49—N7—C50	114.32 (14)	N4—C43—H43A	109.5
C49—N7—P3	125.61 (12)	N4—C43—H43B	109.5
C50—N7—P3	119.48 (11)	H43A—C43—H43B	109.5
C51—N8—C52	114.11 (15)	N4—C43—H43C	109.5
C51—N8—P3	121.32 (13)	H43A—C43—H43C	109.5
C52—N8—P3	121.67 (11)	H43B—C43—H43C	109.5
C54—N9—C53	114.14 (17)	N4—C44—H44A	109.5
C54—N9—P3	125.50 (14)	N4—C44—H44B	109.5
C53—N9—P3	117.66 (14)	H44A—C44—H44B	109.5
C56—N10—C55	114.9 (2)	N4—C44—H44C	109.5
C56—N10—P4	121.80 (19)	H44A—C44—H44C	109.5
C55—N10—P4	118.88 (16)	H44B—C44—H44C	109.5
C58—N11—C57	112.7 (3)	N5—C45—H45A	109.5
C58—N11—P4	119.4 (2)	N5—C45—H45B	109.5
C57—N11—P4	125.7 (2)	H45A—C45—H45B	109.5
C59—N12—C60	114.2 (3)	N5—C45—H45C	109.5
C59—N12—P4	126.7 (3)	H45A—C45—H45C	109.5
C60—N12—P4	119.0 (2)	H45B—C45—H45C	109.5
C2—C1—C6	119.49 (17)	N5—C46—H46A	109.5
C2—C1—H1	120.3	N5—C46—H46B	109.5
C6—C1—H1	120.3	H46A—C46—H46B	109.5
C3—C2—C1	120.15 (18)	N5—C46—H46C	109.5
C3—C2—H2	119.9	H46A—C46—H46C	109.5
C1—C2—H2	119.9	H46B—C46—H46C	109.5
C4—C3—C2	120.27 (18)	N6—C47—H47A	109.5
C4—C3—H3	119.9	N6—C47—H47B	109.5
C2—C3—H3	119.9	H47A—C47—H47B	109.5
C3—C4—C5	120.33 (18)	N6—C47—H47C	109.5
C3—C4—H4	119.8	H47A—C47—H47C	109.5
C5—C4—H4	119.8	H47B—C47—H47C	109.5
C4—C5—C6	119.68 (16)	N6—C48—H48A	109.5
C4—C5—H5	120.2	N6—C48—H48B	109.5
C6—C5—H5	120.2	H48A—C48—H48B	109.5
C5—C6—C1	120.09 (16)	N6—C48—H48C	109.5
C5—C6—C7	118.11 (14)	H48A—C48—H48C	109.5
C1—C6—C7	121.80 (15)	H48B—C48—H48C	109.5
O2—C7—O1	123.26 (15)	N7—C49—H49A	109.5
O2—C7—C6	124.68 (15)	N7—C49—H49B	109.5
O1—C7—C6	112.06 (13)	H49A—C49—H49B	109.5
O1—C8—C10	107.18 (12)	N7—C49—H49C	109.5
O1—C8—C9	113.00 (12)	H49A—C49—H49C	109.5
C10—C8—C9	110.72 (13)	H49B—C49—H49C	109.5
O1—C8—H8	108.6	N7—C50—H50A	109.5
C10—C8—H8	108.6	N7—C50—H50B	109.5
C9—C8—H8	108.6	H50A—C50—H50B	109.5
O4—C9—O3	126.47 (14)	N7—C50—H50C	109.5
O4—C9—C8	119.15 (14)	H50A—C50—H50C	109.5
O3—C9—C8	114.36 (13)	H50B—C50—H50C	109.5
O7—C10—C8	107.72 (12)	N8—C51—H51A	109.5
O7—C10—C11	109.92 (12)	N8—C51—H51B	109.5
C8—C10—C11	112.49 (13)	H51A—C51—H51B	109.5
O7—C10—H10	108.9	N8—C51—H51C	109.5
C8—C10—H10	108.9	H51A—C51—H51C	109.5
C11—C10—H10	108.9	H51B—C51—H51C	109.5
O6—C11—O5	126.55 (15)	N8—C52—H52A	109.5
O6—C11—C10	123.45 (14)	N8—C52—H52B	109.5
O5—C11—C10	109.98 (13)	H52A—C52—H52B	109.5
O8—C12—O7	123.33 (15)	N8—C52—H52C	109.5
O8—C12—C13	124.86 (15)	H52A—C52—H52C	109.5
O7—C12—C13	111.82 (13)	H52B—C52—H52C	109.5
C14—C13—C18	119.28 (17)	N9—C53—H53A	109.5
C14—C13—C12	122.29 (15)	N9—C53—H53B	109.5
C18—C13—C12	118.43 (16)	H53A—C53—H53B	109.5
C15—C14—C13	119.85 (19)	N9—C53—H53C	109.5
C15—C14—H14	120.1	H53A—C53—H53C	109.5
C13—C14—H14	120.1	H53B—C53—H53C	109.5
C14—C15—C16	120.5 (2)	N9—C54—H54A	109.5
C14—C15—H15	119.8	N9—C54—H54B	109.5
C16—C15—H15	119.8	H54A—C54—H54B	109.5
C17—C16—C15	119.5 (2)	N9—C54—H54C	109.5
C17—C16—H16	120.2	H54A—C54—H54C	109.5
C15—C16—H16	120.2	H54B—C54—H54C	109.5
C16—C17—C18	120.70 (19)	N10—C55—H55A	109.5
C16—C17—H17	119.7	N10—C55—H55B	109.5
C18—C17—H17	119.7	H55A—C55—H55B	109.5
C17—C18—C13	120.16 (19)	N10—C55—H55C	109.5
C17—C18—H18	119.9	H55A—C55—H55C	109.5
C13—C18—H18	119.9	H55B—C55—H55C	109.5
C24—C19—C20	119.57 (16)	N10—C56—H56A	109.5
C24—C19—H19	120.2	N10—C56—H56B	109.5
C20—C19—H19	120.2	H56A—C56—H56B	109.5
C21—C20—C19	120.53 (17)	N10—C56—H56C	109.5
C21—C20—H20	119.7	H56A—C56—H56C	109.5
C19—C20—H20	119.7	H56B—C56—H56C	109.5
C20—C21—C22	119.46 (17)	N11—C57—H57A	109.5
C20—C21—H21	120.3	N11—C57—H57B	109.5
C22—C21—H21	120.3	H57A—C57—H57B	109.5
C23—C22—C21	120.61 (19)	N11—C57—H57C	109.5
C23—C22—H22	119.7	H57A—C57—H57C	109.5
C21—C22—H22	119.7	H57B—C57—H57C	109.5
C22—C23—C24	120.01 (18)	N11—C58—H58A	109.5
C22—C23—H23	120.0	N11—C58—H58B	109.5
C24—C23—H23	120.0	H58A—C58—H58B	109.5
C19—C24—C23	119.80 (15)	N11—C58—H58C	109.5
C19—C24—C25	122.18 (14)	H58A—C58—H58C	109.5
C23—C24—C25	118.02 (15)	H58B—C58—H58C	109.5
O10—C25—O9	123.92 (15)	N12—C59—H59A	109.5
O10—C25—C24	124.18 (15)	N12—C59—H59B	109.5
O9—C25—C24	111.89 (13)	H59A—C59—H59B	109.5
O9—C26—C28	108.40 (11)	N12—C59—H59C	109.5
O9—C26—C27	109.85 (12)	H59A—C59—H59C	109.5
C28—C26—C27	111.95 (12)	H59B—C59—H59C	109.5
O9—C26—H26	108.9	N12—C59—H59D	109.5
C28—C26—H26	108.9	H59A—C59—H59D	141.1
C27—C26—H26	108.9	H59B—C59—H59D	56.3
O12—C27—O11	126.54 (15)	H59C—C59—H59D	56.3
O12—C27—C26	123.90 (15)	N12—C59—H59E	109.5
O11—C27—C26	109.53 (12)	H59A—C59—H59E	56.3
O15—C28—C26	107.12 (12)	H59B—C59—H59E	141.1
O15—C28—C29	110.14 (12)	H59C—C59—H59E	56.3
C26—C28—C29	112.55 (13)	H59D—C59—H59E	109.5
O15—C28—H28	109.0	N12—C59—H59F	109.5
C26—C28—H28	109.0	H59A—C59—H59F	56.3
C29—C28—H28	109.0	H59B—C59—H59F	56.3
O14—C29—O13	126.46 (16)	H59C—C59—H59F	141.1
O14—C29—C28	123.00 (16)	H59D—C59—H59F	109.5
O13—C29—C28	110.49 (13)	H59E—C59—H59F	109.5
O16—C30—O15	123.59 (16)	N12—C60—H60A	109.5
O16—C30—C31	125.37 (16)	N12—C60—H60B	109.5
O15—C30—C31	111.04 (14)	H60A—C60—H60B	109.5
C36—C31—C32	120.23 (17)	N12—C60—H60C	109.5
C36—C31—C30	117.73 (17)	H60A—C60—H60C	109.5
C32—C31—C30	122.00 (15)	H60B—C60—H60C	109.5
C33—C32—C31	120.01 (17)

O17—P1—N1—C38	−153.2 (2)	C8—O1—C7—O2	1.9 (2)
N2—P1—N1—C38	85.5 (2)	C8—O1—C7—C6	−179.10 (12)
N3—P1—N1—C38	−30.3 (2)	C5—C6—C7—O2	−1.4 (2)
O17—P1—N1—C37	47.4 (2)	C1—C6—C7—O2	177.92 (16)
N2—P1—N1—C37	−73.8 (2)	C5—C6—C7—O1	179.69 (14)
N3—P1—N1—C37	170.4 (2)	C1—C6—C7—O1	−1.0 (2)
O17—P1—N2—C40	30.1 (2)	C7—O1—C8—C10	−159.40 (12)
N1—P1—N2—C40	152.22 (17)	C7—O1—C8—C9	78.36 (15)
N3—P1—N2—C40	−94.59 (19)	O1—C8—C9—O4	175.77 (14)
O17—P1—N2—C39	−163.7 (2)	C10—C8—C9—O4	55.52 (19)
N1—P1—N2—C39	−41.6 (2)	O1—C8—C9—O3	−5.49 (18)
N3—P1—N2—C39	71.6 (2)	C10—C8—C9—O3	−125.73 (14)
O17—P1—N3—C41	−96.2 (2)	C12—O7—C10—C8	−159.26 (13)
N1—P1—N3—C41	142.8 (2)	C12—O7—C10—C11	77.86 (16)
N2—P1—N3—C41	25.8 (3)	O1—C8—C10—O7	−65.51 (14)
O17—P1—N3—C42	55.9 (2)	C9—C8—C10—O7	58.14 (16)
N1—P1—N3—C42	−65.1 (2)	O1—C8—C10—C11	55.79 (15)
N2—P1—N3—C42	177.9 (2)	C9—C8—C10—C11	179.44 (12)
O18—P2—N4—C44	−162.32 (17)	O7—C10—C11—O6	−5.2 (2)
N5—P2—N4—C44	76.83 (19)	C8—C10—C11—O6	−125.27 (17)
N6—P2—N4—C44	−36.66 (19)	O7—C10—C11—O5	176.26 (13)
O18—P2—N4—C43	48.53 (14)	C8—C10—C11—O5	56.23 (17)
N5—P2—N4—C43	−72.31 (14)	C10—O7—C12—O8	3.4 (2)
N6—P2—N4—C43	174.19 (13)	C10—O7—C12—C13	−177.13 (13)
O18—P2—N5—C46	−21.74 (18)	O8—C12—C13—C14	179.61 (19)
N6—P2—N5—C46	−148.90 (16)	O7—C12—C13—C14	0.1 (2)
N4—P2—N5—C46	99.06 (16)	O8—C12—C13—C18	0.4 (3)
O18—P2—N5—C45	−169.23 (19)	O7—C12—C13—C18	−179.11 (16)
N6—P2—N5—C45	63.6 (2)	C18—C13—C14—C15	−0.8 (4)
N4—P2—N5—C45	−48.4 (2)	C12—C13—C14—C15	179.9 (2)
O18—P2—N6—C48	−83.6 (2)	C13—C14—C15—C16	1.7 (5)
N5—P2—N6—C48	38.0 (2)	C14—C15—C16—C17	−1.7 (5)
N4—P2—N6—C48	156.67 (18)	C15—C16—C17—C18	0.8 (4)
O18—P2—N6—C47	57.39 (19)	C16—C17—C18—C13	0.0 (4)
N5—P2—N6—C47	179.02 (17)	C14—C13—C18—C17	0.0 (3)
N4—P2—N6—C47	−62.34 (18)	C12—C13—C18—C17	179.30 (19)
O19—P3—N7—C49	−112.37 (16)	C24—C19—C20—C21	1.6 (3)
N8—P3—N7—C49	9.40 (17)	C19—C20—C21—C22	−0.9 (3)
N9—P3—N7—C49	126.03 (15)	C20—C21—C22—C23	−0.3 (4)
O19—P3—N7—C50	58.31 (18)	C21—C22—C23—C24	0.9 (4)
N8—P3—N7—C50	−179.91 (15)	C20—C19—C24—C23	−0.9 (3)
N9—P3—N7—C50	−63.28 (17)	C20—C19—C24—C25	178.46 (16)
O19—P3—N8—C51	31.83 (18)	C22—C23—C24—C19	−0.3 (3)
N7—P3—N8—C51	−91.57 (17)	C22—C23—C24—C25	−179.7 (2)
N9—P3—N8—C51	153.91 (16)	C26—O9—C25—O10	4.3 (2)
O19—P3—N8—C52	−168.55 (13)	C26—O9—C25—C24	−176.76 (12)
N7—P3—N8—C52	68.04 (15)	C19—C24—C25—O10	−162.27 (18)
N9—P3—N8—C52	−46.47 (15)	C23—C24—C25—O10	17.1 (3)
O19—P3—N9—C54	−148.55 (16)	C19—C24—C25—O9	18.8 (2)
N7—P3—N9—C54	−26.13 (18)	C23—C24—C25—O9	−161.82 (17)
N8—P3—N9—C54	90.23 (17)	C25—O9—C26—C28	−136.12 (13)
O19—P3—N9—C53	51.23 (15)	C25—O9—C26—C27	101.26 (15)
N7—P3—N9—C53	173.65 (13)	O9—C26—C27—O12	−10.5 (2)
N8—P3—N9—C53	−69.98 (14)	C28—C26—C27—O12	−130.94 (17)
O20—P4—N10—C56	95.9 (2)	O9—C26—C27—O11	171.22 (12)
N12—P4—N10—C56	−29.3 (3)	C28—C26—C27—O11	50.73 (16)
N11—P4—N10—C56	−146.0 (2)	C30—O15—C28—C26	−159.86 (13)
O20—P4—N10—C55	−59.3 (2)	C30—O15—C28—C29	77.43 (16)
N12—P4—N10—C55	175.4 (2)	O9—C26—C28—O15	−58.43 (15)
N11—P4—N10—C55	58.8 (2)	C27—C26—C28—O15	62.90 (15)
O20—P4—N11—C58	−41.0 (3)	O9—C26—C28—C29	62.77 (15)
N12—P4—N11—C58	79.8 (3)	C27—C26—C28—C29	−175.90 (12)
N10—P4—N11—C58	−165.0 (3)	O15—C28—C29—O14	−13.5 (2)
O20—P4—N11—C57	157.1 (3)	C26—C28—C29—O14	−132.94 (17)
N12—P4—N11—C57	−82.1 (3)	O15—C28—C29—O13	168.71 (13)
N10—P4—N11—C57	33.1 (3)	C26—C28—C29—O13	49.25 (17)
O20—P4—N12—C59	−20.2 (5)	C28—O15—C30—O16	6.6 (3)
N11—P4—N12—C59	−138.9 (5)	C28—O15—C30—C31	−173.64 (13)
N10—P4—N12—C59	108.2 (5)	O16—C30—C31—C36	−3.0 (3)
O20—P4—N12—C60	162.1 (3)	O15—C30—C31—C36	177.21 (19)
N11—P4—N12—C60	43.4 (4)	O16—C30—C31—C32	179.41 (19)
N10—P4—N12—C60	−69.4 (4)	O15—C30—C31—C32	−0.4 (2)
C6—C1—C2—C3	0.2 (3)	C36—C31—C32—C33	0.4 (3)
C1—C2—C3—C4	−0.5 (3)	C30—C31—C32—C33	177.90 (17)
C2—C3—C4—C5	0.4 (3)	C31—C32—C33—C34	−0.2 (3)
C3—C4—C5—C6	0.0 (3)	C32—C33—C34—C35	−0.3 (4)
C4—C5—C6—C1	−0.3 (3)	C33—C34—C35—C36	0.7 (4)
C4—C5—C6—C7	179.04 (15)	C32—C31—C36—C35	0.1 (4)
C2—C1—C6—C5	0.1 (3)	C30—C31—C36—C35	−177.6 (2)
C2—C1—C6—C7	−179.12 (16)	C34—C35—C36—C31	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O19	0.82 (1)	1.68 (1)	2.4839 (16)	165 (3)
O5—H5O···O18	0.82 (1)	1.72 (1)	2.5262 (16)	172 (4)
O11—H11O···O17	0.82 (1)	1.70 (1)	2.4854 (16)	160 (3)
O13—H13O···O20	0.82 (1)	1.70 (2)	2.4908 (19)	164 (4)
C3—H3···O16	0.93	2.40	3.316 (2)	168
C16—H16···O8ⁱ	0.93	2.49	3.312 (2)	147
C35—H35···O4ⁱⁱ	0.93	2.54	3.455 (2)	168
C50—H50C···O18ⁱⁱⁱ	0.96	2.45	3.314 (2)	150

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

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