(2,6-Bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thia-diazol-5-yl)diazen-yl]-1H-pyrazol-1-yl}-4-oxo-1,4-dihydro-1,3,5-triazin-1-ido)methanol(phenol)sodium phenol tetra-solvate.

The title compound, [Na(C(23)H(28)N(17)OS(2))(CH(3)OH)(C(6)H(5)OH)]·4C(6)H(5)OH, is a five-coordinate Na(I) complex. The Na(+) cation is bound to three N atoms of the triazinide ligand, two from each pyrazole ring and one from the central deprotonated triazine ring system. O atoms from a methanol and a phenol mol-ecule complete the five-coordinate NaN(3)O(2) coordination environment. The asymmetric unit also includes three complete and two half phenol mol-ecules, four of which are hydrogen bonded to the N atoms of the thia-diazole ring. Two of the phenol solvent mol-ecules are disordered over two discrete inversion centres. The triazinide ligand is essentially planar (mean deviation from the least-squares plane = 0.0524 Å), with the methyl groups of the tert-butyl substituents on the pyrazole rings located above and below the plane. The planarity of this system is further assisted by the formation of four intra-molecular N-H⋯N hydrogen bonds between the N-H bonds of both amino groups on the pyrazole rings and the N atoms of the triazine ring and also from each of the adjacent diazene (-N=N-) bonds. The highly polar mol-ecules are stacked along the a axis through the central Na atom sandwiched by two kinds of alternating inter-molecular hydrogen bonds: O(carbon-yl)⋯H-O(methanol)/Na/O-H(phenol)⋯O(carbon-yl). These inter-actions form two polymer chains per mol-ecule.

Related literature

For details of azo pigments, see: Herbst & Hunger (2004 ▶). For the synthesis of the title compound, see: Nagata & Tateishi (2009 ▶). For the structures of other azo complexes with five-coordinate Na+, see: Mizuguchi et al. (2007 ▶); Sato, Shibata et al. (2008 ▶); Sato, Uta et al. (2008 ▶). For the structure of a related ligand, see: Shibata & Mizuguchi (2010 ▶).

Experimental

Crystal data

[Na(C23H28N17OS2)(CH4O)(C6H6O)]·4C6H6O

M = 1148.30

Triclinic,

a = 8.38964 (15) Å

b = 18.8780 (3) Å

c = 20.4060 (4) Å

α = 114.103 (1)°

β = 96.580 (1)°

γ = 95.650 (1)°

V = 2892.83 (9) Å3

Z = 2

Cu Kα radiation

μ = 1.46 mm−1

T = 93 K

0.50 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.345, T max = 0.748

32979 measured reflections

10340 independent reflections

7267 reflections with I > 2σ(I 2)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.196

S = 0.99

10340 reflections

819 parameters

156 restraints

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.47 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2006 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001086X/sj2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001086X/sj2750Isup2.hkl

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

[Na(C23H28N17OS2)(CH4O)(C6H6O)]·4C6H6O	Z = 2
Mr = 1148.30	F(000) = 1208.00
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 8.38964 (15) Å	Cell parameters from 26974 reflections
b = 18.8780 (3) Å	θ = 4.2–68.2°
c = 20.4060 (4) Å	µ = 1.46 mm−1
α = 114.103 (1)°	T = 93 K
β = 96.580 (1)°	Needle, yellow
γ = 95.650 (1)°	0.50 × 0.30 × 0.20 mm
V = 2892.83 (9) Å3

Rigaku R-AXIS RAPID diffractometer	7267 reflections with F2 > 2σ(F2)
ω scans	Rint = 0.054
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	θmax = 68.2°
Tmin = 0.345, Tmax = 0.748	h = −9→9
32979 measured reflections	k = −20→22
10340 independent reflections	l = −24→24

Refinement on F2	156 restraints
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.196	w = 1/[σ2(Fo2) + (0.101P)2 + 2.2948P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
10340 reflections	Δρmax = 0.66 e Å−3
819 parameters	Δρmin = −0.47 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	1.47119 (10)	0.92371 (4)	0.62076 (4)	0.0412 (2)
S2	−0.01553 (10)	0.09004 (5)	0.26699 (4)	0.0442 (2)
Na1	0.70228 (15)	0.50735 (7)	0.35073 (6)	0.0382 (3)
O1	0.8097 (3)	0.48489 (11)	0.65787 (10)	0.0342 (5)
O2	0.8888 (3)	0.45383 (13)	0.26640 (11)	0.0428 (5)
H2O	0.9806	0.4741	0.2926	0.051*
O3	1.8364 (3)	1.11563 (15)	0.72119 (14)	0.0583 (7)
H3O	1.7553	1.0805	0.7099	0.070*
O4	−0.3653 (3)	−0.08841 (19)	0.18027 (15)	0.0843 (11)
H4O	−0.2885	−0.0683	0.2158	0.101*
O6	1.2701 (9)	1.3726 (4)	0.9187 (4)	0.104 (2)	0.50
H6O	1.2690	1.3365	0.9328	0.124*	0.50
O7	0.3015 (6)	0.1073 (2)	0.5196 (2)	0.0435 (11)	0.50
H7O	0.2190	0.0895	0.4867	0.052*	0.50
O8	0.4989 (3)	0.57323 (15)	0.32562 (14)	0.0543 (7)
H8O	0.4084	0.5590	0.3341	0.065*
N1	1.5988 (3)	0.98531 (15)	0.69533 (16)	0.0435 (7)
N2	1.4734 (3)	0.89848 (15)	0.73354 (15)	0.0423 (6)
N3	1.2860 (3)	0.80306 (14)	0.63605 (14)	0.0389 (6)
N4	1.2247 (3)	0.78470 (14)	0.56894 (14)	0.0367 (6)
N5	0.9211 (3)	0.62032 (14)	0.45304 (13)	0.0359 (6)
N6	0.9431 (3)	0.61113 (13)	0.51868 (13)	0.0318 (6)
N7	0.7394 (3)	0.50109 (14)	0.46751 (13)	0.0322 (6)
N8	0.6688 (3)	0.43844 (14)	0.54359 (13)	0.0329 (6)
N9	0.8837 (3)	0.54727 (14)	0.58893 (13)	0.0321 (6)
N10	0.5377 (3)	0.39052 (14)	0.42586 (13)	0.0333 (6)
N11	0.5108 (3)	0.39071 (15)	0.35605 (13)	0.0349 (6)
N12	0.2410 (3)	0.22050 (14)	0.33247 (13)	0.0354 (6)
N13	0.2218 (3)	0.19251 (14)	0.38056 (13)	0.0356 (6)
N14	−0.1125 (4)	0.01872 (16)	0.28168 (16)	0.0488 (7)
N15	0.0696 (3)	0.08488 (14)	0.38837 (14)	0.0373 (6)
N16	1.1016 (3)	0.67754 (15)	0.63825 (13)	0.0378 (6)
H16N	1.0588	0.6422	0.6517	0.045*
H16M	1.1748	0.7174	0.6692	0.045*
N17	0.4406 (3)	0.31137 (15)	0.48461 (13)	0.0369 (6)
H17N	0.5025	0.3423	0.5266	0.044*
H17M	0.3762	0.2695	0.4805	0.044*
C1	1.6865 (5)	1.0074 (2)	0.8222 (2)	0.0545 (9)
H1A	1.7624	1.0501	0.8219	0.082*
H1B	1.7478	0.9715	0.8344	0.082*
H1C	1.6169	1.0293	0.8586	0.082*
C2	1.5832 (4)	0.96327 (19)	0.74835 (19)	0.0444 (8)
C3	1.4027 (4)	0.87033 (17)	0.66531 (18)	0.0386 (7)
C4	1.1104 (4)	0.71951 (16)	0.53837 (16)	0.0345 (7)
C5	1.0559 (4)	0.67071 (16)	0.57146 (16)	0.0320 (7)
C6	1.0198 (4)	0.68461 (16)	0.46545 (17)	0.0361 (7)
C7	0.8499 (4)	0.54981 (16)	0.52534 (16)	0.0310 (6)
C8	0.7878 (4)	0.49012 (16)	0.59835 (16)	0.0314 (6)
C9	0.6561 (4)	0.44673 (17)	0.48198 (15)	0.0310 (6)
C10	0.4443 (4)	0.32788 (17)	0.42756 (16)	0.0333 (7)
C11	0.3520 (4)	0.28622 (17)	0.35716 (16)	0.0349 (7)
C12	0.3997 (4)	0.32902 (18)	0.31600 (16)	0.0353 (7)
C13	0.1050 (4)	0.12619 (17)	0.35169 (16)	0.0346 (7)
C14	−0.0544 (4)	0.02450 (18)	0.34631 (18)	0.0400 (7)
C15	−0.1193 (5)	−0.0316 (2)	0.3746 (2)	0.0545 (9)
H15A	−0.2214	−0.0631	0.3432	0.082*
H15B	−0.1393	−0.0023	0.4243	0.082*
H15C	−0.0401	−0.0663	0.3750	0.082*
C16	1.0319 (5)	0.71468 (17)	0.40775 (17)	0.0436 (8)
C17	1.2056 (5)	0.7151 (2)	0.3907 (2)	0.0552 (10)
H17A	1.2826	0.7492	0.4351	0.083*
H17B	1.2140	0.7348	0.3534	0.083*
H17C	1.2310	0.6615	0.3727	0.083*
C18	0.9917 (6)	0.79872 (19)	0.4363 (2)	0.0580 (10)
H18A	0.8826	0.7986	0.4490	0.087*
H18B	0.9957	0.8179	0.3984	0.087*
H18C	1.0713	0.8332	0.4796	0.087*
C19	0.9102 (5)	0.6628 (2)	0.33927 (19)	0.0579 (11)
H19A	0.9341	0.6090	0.3205	0.087*
H19B	0.9181	0.6830	0.3023	0.087*
H19C	0.8000	0.6631	0.3508	0.087*
C20	0.3341 (4)	0.30941 (19)	0.23735 (16)	0.0389 (7)
C21	0.3634 (6)	0.2270 (2)	0.18819 (19)	0.0658 (12)
H21A	0.4805	0.2268	0.1893	0.099*
H21B	0.3097	0.2122	0.1381	0.099*
H21C	0.3189	0.1893	0.2057	0.099*
C22	0.4140 (5)	0.3709 (2)	0.21546 (19)	0.0547 (10)
H22A	0.3912	0.4229	0.2468	0.082*
H22B	0.3703	0.3579	0.1646	0.082*
H22C	0.5317	0.3714	0.2210	0.082*
C23	0.1522 (4)	0.3110 (2)	0.22894 (17)	0.0441 (8)
H23A	0.0976	0.2701	0.2403	0.066*
H23B	0.1101	0.3013	0.1787	0.066*
H23C	0.1317	0.3625	0.2624	0.066*
C24	0.9025 (5)	0.43178 (19)	0.19536 (13)	0.0392 (13)	0.786 (6)
C25	0.8044 (4)	0.36536 (19)	0.14096 (16)	0.0517 (13)	0.786 (6)
H25	0.7270	0.3347	0.1533	0.062*	0.786 (6)
C26	0.8195 (4)	0.34377 (19)	0.06846 (14)	0.0626 (15)	0.786 (6)
H26	0.7525	0.2984	0.0313	0.075*	0.786 (6)
C27	0.9327 (5)	0.3886 (2)	0.05035 (16)	0.0588 (15)	0.786 (6)
H27	0.9431	0.3739	0.0008	0.071*	0.786 (6)
C28	1.0308 (5)	0.4550 (2)	0.1048 (2)	0.0534 (15)	0.786 (6)
H28	1.1081	0.4857	0.0924	0.064*	0.786 (6)
C29	1.0156 (5)	0.47662 (17)	0.1773 (2)	0.0456 (14)	0.786 (6)
H29	1.0827	0.5220	0.2144	0.055*	0.786 (6)
C24A	0.9176 (15)	0.4523 (8)	0.1933 (5)	0.033 (4)	0.214 (6)
C25A	0.7821 (11)	0.4243 (8)	0.1384 (5)	0.045 (4)	0.214 (6)
H25A	0.6774	0.4145	0.1493	0.054*	0.214 (6)
C26A	0.7998 (12)	0.4108 (7)	0.0676 (5)	0.050 (4)	0.214 (6)
H26A	0.7072	0.3917	0.0300	0.060*	0.214 (6)
C27A	0.9531 (15)	0.4252 (7)	0.0516 (6)	0.044 (4)	0.214 (6)
H27A	0.9652	0.4160	0.0032	0.053*	0.214 (6)
C28A	1.0885 (11)	0.4532 (8)	0.1065 (8)	0.037 (4)	0.214 (6)
H28A	1.1933	0.4631	0.0956	0.044*	0.214 (6)
C29A	1.0708 (12)	0.4667 (8)	0.1773 (7)	0.032 (4)	0.214 (6)
H29A	1.1634	0.4858	0.2148	0.039*	0.214 (6)
C30	1.7987 (5)	1.1878 (2)	0.7660 (2)	0.0549 (10)
C31	1.9181 (6)	1.2527 (2)	0.7902 (2)	0.0623 (11)
H31	2.0216	1.2477	0.7756	0.075*
C32	1.8840 (7)	1.3265 (2)	0.8368 (2)	0.0718 (14)
H32	1.9667	1.3712	0.8550	0.086*
C33	1.7335 (8)	1.3350 (3)	0.8566 (3)	0.0808 (15)
H33	1.7113	1.3853	0.8871	0.097*
C34	1.6159 (7)	1.2702 (3)	0.8321 (3)	0.0838 (15)
H34	1.5117	1.2755	0.8458	0.101*
C35	1.6479 (6)	1.1958 (3)	0.7868 (3)	0.0762 (13)
H35	1.5659	1.1510	0.7703	0.091*
C36	−0.3128 (4)	−0.1420 (2)	0.1217 (2)	0.0550 (10)
C37	−0.4253 (5)	−0.1824 (3)	0.0581 (2)	0.0708 (13)
H37	−0.5345	−0.1729	0.0567	0.085*
C38	−0.3786 (5)	−0.2362 (2)	−0.0028 (2)	0.0577 (10)
H38	−0.4548	−0.2624	−0.0467	0.069*
C39	−0.2229 (5)	−0.2522 (2)	−0.00060 (18)	0.0497 (9)
H39	−0.1909	−0.2896	−0.0426	0.060*
C40	−0.1127 (5)	−0.2129 (2)	0.06386 (18)	0.0479 (8)
H40	−0.0050	−0.2242	0.0661	0.057*
C41	−0.1577 (4)	−0.15748 (19)	0.12469 (18)	0.0435 (8)
H41	−0.0810	−0.1303	0.1684	0.052*
O5	1.2733 (5)	0.8315 (3)	0.8091 (3)	0.0608 (12)	0.750 (5)
H5O	1.3243	0.8554	0.7891	0.073*	0.750 (5)
C42	1.2431 (6)	0.8841 (2)	0.87364 (18)	0.0589 (16)	0.750 (5)
C43	1.1592 (6)	0.85495 (18)	0.9146 (2)	0.0800 (19)	0.750 (5)
H43	1.1281	0.7998	0.8978	0.096*	0.750 (5)
C44	1.1207 (7)	0.9064 (3)	0.9800 (2)	0.107 (2)	0.750 (5)
H44	1.0633	0.8864	1.0080	0.128*	0.750 (5)
C45	1.1662 (7)	0.9870 (2)	1.0046 (2)	0.115 (3)	0.750 (5)
H45	1.1399	1.0221	1.0493	0.138*	0.750 (5)
C46	1.2501 (7)	1.01619 (17)	0.9636 (2)	0.103 (2)	0.750 (5)
H46	1.2812	1.0713	0.9804	0.123*	0.750 (5)
C47	1.2886 (5)	0.9648 (2)	0.8982 (2)	0.0742 (17)	0.750 (5)
H47	1.3460	0.9847	0.8702	0.089*	0.750 (5)
O5A	1.2908 (14)	0.7925 (7)	0.7733 (6)	0.046 (3)	0.250 (5)
H5OA	1.3261	0.8288	0.7624	0.055*	0.250 (5)
C42A	1.2674 (13)	0.8238 (6)	0.8441 (4)	0.042 (3)	0.250 (5)
C43A	1.2089 (12)	0.7696 (5)	0.8690 (4)	0.044 (3)	0.250 (5)
H43A	1.1923	0.7149	0.8380	0.053*	0.250 (5)
C44A	1.1747 (12)	0.7953 (6)	0.9394 (5)	0.059 (4)	0.250 (5)
H44A	1.1347	0.7583	0.9564	0.070*	0.250 (5)
C45A	1.1989 (14)	0.8753 (7)	0.9848 (4)	0.072 (4)	0.250 (5)
H45A	1.1755	0.8929	1.0329	0.086*	0.250 (5)
C46A	1.2575 (14)	0.9295 (5)	0.9598 (5)	0.073 (4)	0.250 (5)
H46A	1.2741	0.9841	0.9909	0.088*	0.250 (5)
C47A	1.2917 (14)	0.9038 (5)	0.8895 (6)	0.059 (4)	0.250 (5)
H47A	1.3317	0.9408	0.8724	0.071*	0.250 (5)
C48	1.3808 (7)	1.4337 (3)	0.9641 (5)	0.107 (2)
C49	1.3945 (9)	1.4900 (4)	0.9377 (4)	0.123 (2)
H49	1.3234	1.4847	0.8957	0.148*
C50	1.4826 (9)	1.4444 (4)	1.0249 (4)	0.119 (2)
H50	1.4705	1.4057	1.0433	0.143*
C51	0.3909 (5)	0.0526 (2)	0.5112 (2)	0.0512 (9)
C52	0.3499 (5)	−0.0221 (2)	0.4556 (2)	0.0505 (9)
H52	0.2458	−0.0376	0.4256	0.061*
C53	0.4588 (5)	−0.0747 (2)	0.4431 (2)	0.0511 (9)
H53	0.4315	−0.1254	0.4036	0.061*
C54	0.4742 (6)	0.5906 (4)	0.2625 (3)	0.0928 (18)
H54A	0.5798	0.6023	0.2497	0.139*
H54B	0.4180	0.6363	0.2738	0.139*
H54C	0.4083	0.5451	0.2213	0.139*

	U11	U22	U33	U12	U13	U23
S1	0.0477 (5)	0.0303 (4)	0.0446 (5)	0.0054 (3)	0.0105 (4)	0.0144 (3)
S2	0.0453 (5)	0.0398 (4)	0.0356 (4)	0.0109 (4)	−0.0028 (3)	0.0058 (3)
Na1	0.0423 (7)	0.0411 (7)	0.0361 (7)	0.0094 (5)	0.0071 (5)	0.0206 (5)
O1	0.0411 (12)	0.0334 (11)	0.0301 (11)	0.0062 (9)	0.0051 (9)	0.0157 (9)
O2	0.0402 (13)	0.0472 (13)	0.0325 (12)	0.0089 (10)	0.0005 (9)	0.0094 (10)
O3	0.0552 (16)	0.0481 (14)	0.0577 (16)	−0.0048 (12)	0.0098 (13)	0.0116 (12)
O4	0.0449 (16)	0.095 (2)	0.0560 (17)	0.0093 (15)	0.0047 (13)	−0.0235 (16)
O6	0.094 (5)	0.077 (5)	0.149 (7)	−0.007 (4)	−0.009 (5)	0.070 (5)
O7	0.047 (3)	0.040 (2)	0.037 (2)	0.008 (2)	−0.005 (2)	0.012 (2)
O8	0.0424 (14)	0.0757 (17)	0.0714 (17)	0.0151 (12)	0.0148 (12)	0.0550 (15)
N1	0.0406 (16)	0.0363 (14)	0.0507 (17)	0.0072 (12)	0.0099 (13)	0.0147 (13)
N2	0.0465 (17)	0.0359 (14)	0.0449 (16)	0.0109 (12)	0.0066 (13)	0.0169 (13)
N3	0.0461 (17)	0.0299 (13)	0.0410 (15)	0.0116 (12)	0.0108 (12)	0.0134 (12)
N4	0.0473 (16)	0.0243 (12)	0.0393 (15)	0.0108 (11)	0.0133 (12)	0.0119 (11)
N5	0.0536 (17)	0.0288 (13)	0.0306 (13)	0.0106 (12)	0.0109 (12)	0.0159 (11)
N6	0.0426 (15)	0.0285 (12)	0.0279 (13)	0.0064 (11)	0.0068 (11)	0.0152 (10)
N7	0.0392 (15)	0.0299 (13)	0.0307 (13)	0.0095 (11)	0.0081 (11)	0.0146 (11)
N8	0.0370 (14)	0.0331 (13)	0.0288 (13)	0.0060 (11)	0.0048 (11)	0.0135 (11)
N9	0.0390 (15)	0.0301 (13)	0.0301 (13)	0.0061 (11)	0.0059 (11)	0.0157 (11)
N10	0.0374 (15)	0.0373 (14)	0.0267 (13)	0.0049 (11)	0.0024 (10)	0.0162 (11)
N11	0.0380 (15)	0.0417 (14)	0.0291 (13)	0.0112 (12)	0.0061 (11)	0.0179 (12)
N12	0.0389 (15)	0.0342 (13)	0.0340 (14)	0.0131 (11)	0.0088 (11)	0.0132 (11)
N13	0.0374 (15)	0.0336 (13)	0.0321 (13)	0.0069 (11)	0.0039 (11)	0.0106 (11)
N14	0.0481 (18)	0.0370 (15)	0.0480 (17)	0.0084 (13)	0.0013 (14)	0.0062 (13)
N15	0.0391 (15)	0.0313 (13)	0.0366 (14)	0.0071 (11)	0.0075 (11)	0.0091 (11)
N16	0.0476 (16)	0.0338 (14)	0.0327 (14)	0.0035 (12)	0.0073 (12)	0.0153 (11)
N17	0.0428 (16)	0.0368 (14)	0.0310 (13)	−0.0010 (12)	0.0028 (11)	0.0168 (11)
C1	0.047 (2)	0.058 (2)	0.049 (2)	0.0053 (18)	0.0004 (17)	0.0158 (18)
C2	0.0398 (19)	0.0398 (18)	0.052 (2)	0.0141 (15)	0.0100 (16)	0.0152 (16)
C3	0.0414 (19)	0.0273 (15)	0.0457 (19)	0.0118 (13)	0.0092 (15)	0.0123 (14)
C4	0.051 (2)	0.0229 (14)	0.0346 (16)	0.0120 (13)	0.0141 (14)	0.0138 (12)
C5	0.0391 (17)	0.0250 (14)	0.0326 (16)	0.0099 (12)	0.0100 (13)	0.0109 (12)
C6	0.053 (2)	0.0245 (14)	0.0361 (17)	0.0128 (13)	0.0157 (14)	0.0141 (13)
C7	0.0378 (17)	0.0276 (14)	0.0322 (15)	0.0124 (13)	0.0100 (13)	0.0149 (12)
C8	0.0374 (17)	0.0283 (14)	0.0305 (15)	0.0098 (12)	0.0073 (12)	0.0131 (12)
C9	0.0305 (16)	0.0340 (15)	0.0302 (15)	0.0090 (13)	0.0054 (12)	0.0143 (13)
C10	0.0339 (17)	0.0366 (16)	0.0323 (16)	0.0091 (13)	0.0071 (13)	0.0164 (13)
C11	0.0414 (18)	0.0320 (15)	0.0290 (15)	0.0101 (13)	0.0057 (13)	0.0099 (13)
C12	0.0385 (18)	0.0393 (17)	0.0312 (16)	0.0139 (14)	0.0084 (13)	0.0156 (14)
C13	0.0305 (16)	0.0301 (15)	0.0334 (16)	0.0066 (12)	0.0041 (12)	0.0038 (13)
C14	0.0339 (18)	0.0309 (16)	0.0451 (19)	0.0074 (13)	0.0027 (14)	0.0066 (14)
C15	0.049 (2)	0.0377 (19)	0.069 (3)	0.0014 (16)	0.0086 (18)	0.0158 (18)
C16	0.074 (3)	0.0260 (15)	0.0331 (17)	0.0057 (15)	0.0109 (16)	0.0148 (13)
C17	0.085 (3)	0.0392 (19)	0.050 (2)	0.0057 (19)	0.026 (2)	0.0244 (17)
C18	0.096 (3)	0.0300 (17)	0.049 (2)	0.0127 (18)	0.004 (2)	0.0191 (16)
C19	0.097 (3)	0.0339 (18)	0.043 (2)	−0.0061 (19)	0.003 (2)	0.0219 (16)
C20	0.046 (2)	0.0450 (18)	0.0281 (16)	0.0178 (15)	0.0068 (14)	0.0154 (14)
C21	0.107 (4)	0.065 (3)	0.0338 (19)	0.051 (2)	0.019 (2)	0.0190 (18)
C22	0.056 (2)	0.078 (3)	0.0365 (19)	0.001 (2)	0.0018 (16)	0.0340 (19)
C23	0.048 (2)	0.0476 (19)	0.0347 (17)	0.0154 (16)	0.0007 (15)	0.0153 (15)
C24	0.043 (3)	0.038 (2)	0.034 (2)	0.014 (2)	0.0033 (19)	0.0117 (19)
C25	0.043 (3)	0.049 (3)	0.046 (2)	0.005 (2)	0.003 (2)	0.005 (2)
C26	0.058 (3)	0.063 (3)	0.040 (2)	0.013 (2)	0.001 (2)	−0.003 (2)
C27	0.073 (4)	0.060 (3)	0.037 (2)	0.025 (3)	0.008 (2)	0.011 (2)
C28	0.070 (4)	0.050 (3)	0.047 (3)	0.021 (3)	0.017 (3)	0.022 (2)
C29	0.069 (4)	0.036 (2)	0.033 (2)	0.017 (2)	0.008 (2)	0.0136 (19)
C24A	0.044 (7)	0.036 (6)	0.023 (6)	0.006 (6)	0.001 (6)	0.018 (5)
C25A	0.048 (7)	0.055 (7)	0.031 (6)	0.007 (6)	0.002 (5)	0.020 (5)
C26A	0.050 (7)	0.053 (7)	0.038 (6)	0.002 (6)	0.000 (6)	0.014 (5)
C27A	0.049 (7)	0.042 (7)	0.034 (7)	0.005 (6)	0.002 (6)	0.010 (6)
C28A	0.045 (7)	0.035 (6)	0.033 (6)	0.017 (5)	0.007 (6)	0.014 (5)
C29A	0.041 (7)	0.028 (6)	0.033 (6)	0.008 (6)	0.002 (6)	0.017 (5)
C30	0.074 (3)	0.043 (2)	0.043 (2)	−0.0019 (19)	0.0022 (19)	0.0182 (17)
C31	0.081 (3)	0.057 (2)	0.051 (2)	−0.007 (2)	−0.009 (2)	0.034 (2)
C32	0.111 (4)	0.041 (2)	0.054 (2)	−0.005 (2)	−0.024 (3)	0.0244 (19)
C33	0.116 (5)	0.056 (3)	0.060 (3)	0.016 (3)	−0.001 (3)	0.017 (2)
C34	0.103 (4)	0.062 (3)	0.085 (3)	0.024 (3)	0.029 (3)	0.024 (3)
C35	0.091 (4)	0.055 (3)	0.077 (3)	0.010 (2)	0.032 (3)	0.017 (2)
C36	0.043 (2)	0.055 (2)	0.042 (2)	−0.0004 (17)	0.0077 (16)	−0.0020 (17)
C37	0.041 (2)	0.077 (3)	0.054 (2)	0.003 (2)	0.0028 (18)	−0.009 (2)
C38	0.057 (2)	0.057 (2)	0.038 (2)	−0.0003 (19)	0.0006 (17)	0.0023 (17)
C39	0.064 (2)	0.048 (2)	0.0321 (18)	0.0109 (18)	0.0094 (16)	0.0104 (15)
C40	0.054 (2)	0.0462 (19)	0.0423 (19)	0.0122 (17)	0.0094 (16)	0.0168 (16)
C41	0.046 (2)	0.0422 (18)	0.0353 (17)	0.0000 (15)	0.0030 (14)	0.0121 (15)
O5	0.056 (2)	0.053 (2)	0.078 (4)	0.009 (2)	0.005 (2)	0.034 (2)
C42	0.074 (4)	0.050 (3)	0.055 (3)	−0.005 (3)	−0.014 (3)	0.035 (3)
C43	0.113 (5)	0.061 (3)	0.061 (3)	−0.020 (3)	−0.009 (3)	0.035 (3)
C44	0.178 (6)	0.082 (4)	0.055 (3)	−0.026 (4)	0.010 (4)	0.036 (3)
C45	0.204 (6)	0.080 (4)	0.047 (3)	−0.029 (4)	0.015 (4)	0.025 (3)
C46	0.177 (6)	0.065 (4)	0.053 (3)	−0.027 (4)	0.003 (4)	0.026 (3)
C47	0.107 (4)	0.056 (3)	0.056 (3)	−0.013 (3)	−0.004 (3)	0.029 (3)
O5A	0.058 (6)	0.052 (6)	0.027 (5)	0.000 (5)	0.003 (4)	0.021 (4)
C42A	0.046 (6)	0.062 (6)	0.020 (5)	0.012 (5)	0.003 (4)	0.020 (5)
C43A	0.037 (6)	0.072 (7)	0.028 (5)	0.004 (5)	0.001 (4)	0.029 (5)
C44A	0.041 (6)	0.088 (8)	0.043 (6)	0.002 (6)	0.006 (5)	0.026 (5)
C45A	0.050 (7)	0.101 (9)	0.045 (7)	0.000 (7)	0.015 (6)	0.013 (6)
C46A	0.054 (7)	0.091 (8)	0.048 (7)	0.007 (6)	0.004 (6)	0.005 (6)
C47A	0.047 (7)	0.073 (8)	0.037 (6)	0.015 (6)	0.012 (6)	0.001 (6)
C48	0.068 (4)	0.067 (3)	0.183 (7)	0.011 (3)	0.005 (4)	0.054 (4)
C49	0.112 (5)	0.085 (4)	0.164 (7)	0.006 (4)	0.012 (5)	0.050 (5)
C50	0.126 (6)	0.072 (4)	0.157 (7)	−0.009 (4)	0.018 (5)	0.055 (4)
C51	0.052 (2)	0.054 (2)	0.062 (2)	0.0115 (17)	0.0103 (18)	0.0383 (19)
C52	0.047 (2)	0.054 (2)	0.060 (2)	0.0032 (17)	0.0028 (17)	0.0355 (19)
C53	0.061 (2)	0.045 (2)	0.052 (2)	0.0049 (17)	0.0048 (18)	0.0283 (17)
C54	0.071 (3)	0.150 (5)	0.115 (4)	0.032 (3)	0.027 (3)	0.108 (4)

S1—N1	1.659 (3)	C22—H22C	0.9800
S1—C3	1.711 (3)	C23—H23A	0.9800
S2—N14	1.654 (3)	C23—H23B	0.9800
S2—C13	1.725 (3)	C23—H23C	0.9800
Na1—O8	2.336 (3)	C24—C25	1.3900
Na1—N7	2.420 (3)	C24—C29	1.3900
Na1—O2	2.437 (2)	C25—C26	1.3900
Na1—N11	2.642 (3)	C25—H25	0.9500
Na1—N5	2.644 (3)	C26—C27	1.3900
O1—C8	1.253 (3)	C26—H26	0.9500
O2—C24	1.357 (3)	C27—C28	1.3900
O2—C24A	1.528 (10)	C27—H27	0.9500
O2—H2O	0.8400	C28—C29	1.3900
O3—C30	1.388 (4)	C28—H28	0.9500
O3—H3O	0.8400	C29—H29	0.9500
O4—C36	1.367 (4)	C24A—C25A	1.3900
O4—H4O	0.8400	C24A—C29A	1.3900
O6—C48	1.330 (9)	C25A—C26A	1.3900
O6—H6O	0.8400	C25A—H25A	0.9500
O7—C51	1.301 (5)	C26A—C27A	1.3900
O7—H7O	0.8400	C26A—H26A	0.9500
O8—C54	1.452 (5)	C27A—C28A	1.3900
O8—H8O	0.8400	C27A—H27A	0.9500
N1—C2	1.323 (4)	C28A—C29A	1.3900
N2—C3	1.310 (4)	C28A—H28A	0.9500
N2—C2	1.360 (4)	C29A—H29A	0.9500
N3—N4	1.295 (4)	C30—C31	1.378 (5)
N3—C3	1.389 (4)	C30—C35	1.382 (6)
N4—C4	1.351 (4)	C31—C32	1.410 (6)
N5—C6	1.314 (4)	C31—H31	0.9500
N5—N6	1.413 (3)	C32—C33	1.374 (7)
N6—C5	1.374 (4)	C32—H32	0.9500
N6—C7	1.394 (4)	C33—C34	1.367 (7)
N7—C9	1.335 (4)	C33—H33	0.9500
N7—C7	1.339 (4)	C34—C35	1.403 (6)
N8—C9	1.323 (4)	C34—H34	0.9500
N8—C8	1.363 (4)	C35—H35	0.9500
N9—C7	1.317 (4)	C36—C41	1.361 (5)
N9—C8	1.372 (4)	C36—C37	1.388 (5)
N10—C10	1.368 (4)	C37—C38	1.374 (5)
N10—C9	1.401 (4)	C37—H37	0.9500
N10—N11	1.418 (3)	C38—C39	1.369 (5)
N11—C12	1.314 (4)	C38—H38	0.9500
N12—N13	1.308 (3)	C39—C40	1.387 (5)
N12—C11	1.347 (4)	C39—H39	0.9500
N13—C13	1.378 (4)	C40—C41	1.379 (4)
N14—C14	1.309 (4)	C40—H40	0.9500
N15—C13	1.318 (4)	C41—H41	0.9500
N15—C14	1.372 (4)	O5—C42	1.358 (5)
N16—C5	1.322 (4)	O5—H5O	0.8400
N16—H16N	0.8800	C42—C43	1.3900
N16—H16M	0.8800	C42—C47	1.3900
N17—C10	1.325 (4)	C43—C44	1.3900
N17—H17N	0.8800	C43—H43	0.9500
N17—H17M	0.8800	C44—C45	1.3900
C1—C2	1.500 (5)	C44—H44	0.9500
C1—H1A	0.9800	C45—C46	1.3900
C1—H1B	0.9800	C45—H45	0.9500
C1—H1C	0.9800	C46—C47	1.3900
C4—C5	1.418 (4)	C46—H46	0.9500
C4—C6	1.438 (4)	C47—H47	0.9500
C6—C16	1.510 (4)	O5A—C42A	1.365 (12)
C10—C11	1.408 (4)	O5A—H5OA	0.8400
C11—C12	1.444 (4)	C42A—C43A	1.3900
C12—C20	1.513 (4)	C42A—C47A	1.3900
C14—C15	1.486 (5)	C43A—C44A	1.3900
C15—H15A	0.9800	C43A—H43A	0.9500
C15—H15B	0.9800	C44A—C45A	1.3900
C15—H15C	0.9800	C44A—H44A	0.9500
C16—C19	1.520 (5)	C45A—C46A	1.3900
C16—C17	1.537 (5)	C45A—H45A	0.9500
C16—C18	1.538 (4)	C46A—C47A	1.3900
C17—H17A	0.9800	C46A—H46A	0.9500
C17—H17B	0.9800	C47A—H47A	0.9500
C17—H17C	0.9800	C48—C50	1.353 (9)
C18—H18A	0.9800	C48—C49	1.374 (9)
C18—H18B	0.9800	C49—C50i	1.405 (8)
C18—H18C	0.9800	C49—H49	0.9500
C19—H19A	0.9800	C50—C49i	1.405 (8)
C19—H19B	0.9800	C50—H50	0.9500
C19—H19C	0.9800	C51—C52	1.380 (5)
C20—C23	1.521 (4)	C51—C53ii	1.394 (5)
C20—C22	1.528 (5)	C52—C53	1.382 (5)
C20—C21	1.531 (4)	C52—H52	0.9500
C21—H21A	0.9800	C53—C51ii	1.394 (5)
C21—H21B	0.9800	C53—H53	0.9500
C21—H21C	0.9800	C54—H54A	0.9800
C22—H22A	0.9800	C54—H54B	0.9800
C22—H22B	0.9800	C54—H54C	0.9800
N1—S1—C3	90.98 (15)	H22A—C22—H22B	109.5
N14—S2—C13	90.84 (15)	C20—C22—H22C	109.5
O8—Na1—N7	118.62 (9)	H22A—C22—H22C	109.5
O8—Na1—O2	121.65 (9)	H22B—C22—H22C	109.5
N7—Na1—O2	119.57 (9)	C20—C23—H23A	109.5
O8—Na1—N11	97.59 (9)	C20—C23—H23B	109.5
N7—Na1—N11	65.51 (8)	H23A—C23—H23B	109.5
O2—Na1—N11	109.37 (9)	C20—C23—H23C	109.5
O8—Na1—N5	104.19 (9)	H23A—C23—H23C	109.5
N7—Na1—N5	65.04 (8)	H23B—C23—H23C	109.5
O2—Na1—N5	96.00 (9)	O2—C24—C25	120.7 (3)
N11—Na1—N5	130.53 (8)	O2—C24—C29	119.3 (3)
C24—O2—C24A	15.1 (6)	C25—C24—C29	120.0
C24—O2—Na1	140.8 (2)	C24—C25—C26	120.0
C24A—O2—Na1	136.1 (5)	C24—C25—H25	120.0
C24—O2—H2O	109.5	C26—C25—H25	120.0
C24A—O2—H2O	102.3	C27—C26—C25	120.0
Na1—O2—H2O	103.0	C27—C26—H26	120.0
C30—O3—H3O	109.5	C25—C26—H26	120.0
C36—O4—H4O	109.5	C26—C27—C28	120.0
C48—O6—H6O	109.5	C26—C27—H27	120.0
C51—O7—H7O	109.5	C28—C27—H27	120.0
C54—O8—Na1	125.3 (2)	C29—C28—C27	120.0
C54—O8—H8O	109.5	C29—C28—H28	120.0
Na1—O8—H8O	113.0	C27—C28—H28	120.0
C2—N1—S1	109.0 (2)	C28—C29—C24	120.0
C3—N2—C2	108.6 (3)	C28—C29—H29	120.0
N4—N3—C3	112.2 (3)	C24—C29—H29	120.0
N3—N4—C4	114.1 (3)	C25A—C24A—C29A	120.0
C6—N5—N6	105.8 (2)	C25A—C24A—O2	115.8 (8)
C6—N5—Na1	142.0 (2)	C29A—C24A—O2	123.6 (7)
N6—N5—Na1	112.22 (17)	C24A—C25A—C26A	120.0
C5—N6—C7	127.7 (2)	C24A—C25A—H25A	120.0
C5—N6—N5	111.5 (2)	C26A—C25A—H25A	120.0
C7—N6—N5	120.7 (2)	C27A—C26A—C25A	120.0
C9—N7—C7	111.0 (2)	C27A—C26A—H26A	120.0
C9—N7—Na1	124.4 (2)	C25A—C26A—H26A	120.0
C7—N7—Na1	124.62 (19)	C28A—C27A—C26A	120.0
C9—N8—C8	115.5 (3)	C28A—C27A—H27A	120.0
C7—N9—C8	115.9 (3)	C26A—C27A—H27A	120.0
C10—N10—C9	127.2 (2)	C27A—C28A—C29A	120.0
C10—N10—N11	111.7 (2)	C27A—C28A—H28A	120.0
C9—N10—N11	120.9 (2)	C29A—C28A—H28A	120.0
C12—N11—N10	105.4 (2)	C28A—C29A—C24A	120.0
C12—N11—Na1	142.8 (2)	C28A—C29A—H29A	120.0
N10—N11—Na1	111.76 (17)	C24A—C29A—H29A	120.0
N13—N12—C11	114.4 (3)	C31—C30—C35	120.1 (4)
N12—N13—C13	111.0 (2)	C31—C30—O3	117.6 (4)
C14—N14—S2	110.1 (2)	C35—C30—O3	122.3 (4)
C13—N15—C14	108.6 (3)	C30—C31—C32	118.8 (5)
C5—N16—H16N	120.0	C30—C31—H31	120.6
C5—N16—H16M	120.0	C32—C31—H31	120.6
H16N—N16—H16M	120.0	C33—C32—C31	121.3 (4)
C10—N17—H17N	120.0	C33—C32—H32	119.3
C10—N17—H17M	120.0	C31—C32—H32	119.3
H17N—N17—H17M	120.0	C34—C33—C32	119.2 (5)
C2—C1—H1A	109.5	C34—C33—H33	120.4
C2—C1—H1B	109.5	C32—C33—H33	120.4
H1A—C1—H1B	109.5	C33—C34—C35	120.5 (5)
C2—C1—H1C	109.5	C33—C34—H34	119.8
H1A—C1—H1C	109.5	C35—C34—H34	119.8
H1B—C1—H1C	109.5	C30—C35—C34	120.0 (5)
N1—C2—N2	118.1 (3)	C30—C35—H35	120.0
N1—C2—C1	120.9 (3)	C34—C35—H35	120.0
N2—C2—C1	120.9 (3)	C41—C36—O4	122.4 (3)
N2—C3—N3	120.1 (3)	C41—C36—C37	120.2 (3)
N2—C3—S1	113.2 (2)	O4—C36—C37	117.4 (3)
N3—C3—S1	126.7 (3)	C38—C37—C36	119.9 (4)
N4—C4—C5	127.1 (3)	C38—C37—H37	120.1
N4—C4—C6	127.4 (3)	C36—C37—H37	120.1
C5—C4—C6	105.5 (3)	C39—C38—C37	120.5 (4)
N16—C5—N6	125.1 (3)	C39—C38—H38	119.8
N16—C5—C4	129.2 (3)	C37—C38—H38	119.8
N6—C5—C4	105.7 (2)	C38—C39—C40	119.0 (3)
N5—C6—C4	111.5 (3)	C38—C39—H39	120.5
N5—C6—C16	121.9 (3)	C40—C39—H39	120.5
C4—C6—C16	126.5 (3)	C41—C40—C39	120.8 (3)
N9—C7—N7	128.1 (3)	C41—C40—H40	119.6
N9—C7—N6	114.7 (3)	C39—C40—H40	119.6
N7—C7—N6	117.2 (2)	C36—C41—C40	119.5 (3)
O1—C8—N8	119.3 (3)	C36—C41—H41	120.2
O1—C8—N9	119.8 (3)	C40—C41—H41	120.2
N8—C8—N9	120.9 (3)	C42—O5—H5O	109.5
N8—C9—N7	128.5 (3)	O5—C42—C43	117.6 (3)
N8—C9—N10	114.1 (3)	O5—C42—C47	122.4 (3)
N7—C9—N10	117.4 (3)	C43—C42—C47	120.0
N17—C10—N10	126.4 (3)	C42—C43—C44	120.0
N17—C10—C11	127.6 (3)	C42—C43—H43	120.0
N10—C10—C11	105.9 (3)	C44—C43—H43	120.0
N12—C11—C10	127.9 (3)	C43—C44—C45	120.0
N12—C11—C12	126.4 (3)	C43—C44—H44	120.0
C10—C11—C12	105.7 (3)	C45—C44—H44	120.0
N11—C12—C11	111.3 (3)	C46—C45—C44	120.0
N11—C12—C20	121.8 (3)	C46—C45—H45	120.0
C11—C12—C20	126.9 (3)	C44—C45—H45	120.0
N15—C13—N13	122.4 (3)	C45—C46—C47	120.0
N15—C13—S2	112.6 (2)	C45—C46—H46	120.0
N13—C13—S2	125.0 (2)	C47—C46—H46	120.0
N14—C14—N15	117.9 (3)	C46—C47—C42	120.0
N14—C14—C15	122.0 (3)	C46—C47—H47	120.0
N15—C14—C15	120.1 (3)	C42—C47—H47	120.0
C14—C15—H15A	109.5	C42A—O5A—H5OA	109.5
C14—C15—H15B	109.5	O5A—C42A—C43A	115.2 (8)
H15A—C15—H15B	109.5	O5A—C42A—C47A	124.7 (8)
C14—C15—H15C	109.5	C43A—C42A—C47A	120.0
H15A—C15—H15C	109.5	C42A—C43A—C44A	120.0
H15B—C15—H15C	109.5	C42A—C43A—H43A	120.0
C6—C16—C19	110.0 (3)	C44A—C43A—H43A	120.0
C6—C16—C17	109.3 (3)	C43A—C44A—C45A	120.0
C19—C16—C17	110.3 (3)	C43A—C44A—H44A	120.0
C6—C16—C18	109.1 (3)	C45A—C44A—H44A	120.0
C19—C16—C18	108.6 (3)	C44A—C45A—C46A	120.0
C17—C16—C18	109.7 (3)	C44A—C45A—H45A	120.0
C16—C17—H17A	109.5	C46A—C45A—H45A	120.0
C16—C17—H17B	109.5	C47A—C46A—C45A	120.0
H17A—C17—H17B	109.5	C47A—C46A—H46A	120.0
C16—C17—H17C	109.5	C45A—C46A—H46A	120.0
H17A—C17—H17C	109.5	C46A—C47A—C42A	120.0
H17B—C17—H17C	109.5	C46A—C47A—H47A	120.0
C16—C18—H18A	109.5	C42A—C47A—H47A	120.0
C16—C18—H18B	109.5	O6—C48—C50	130.8 (7)
H18A—C18—H18B	109.5	O6—C48—C49	109.8 (8)
C16—C18—H18C	109.5	C50—C48—C49	119.1 (6)
H18A—C18—H18C	109.5	C48—C49—C50i	117.7 (7)
H18B—C18—H18C	109.5	C48—C49—H49	121.1
C16—C19—H19A	109.5	C50i—C49—H49	121.1
C16—C19—H19B	109.5	C48—C50—C49i	123.2 (7)
H19A—C19—H19B	109.5	C48—C50—H50	118.4
C16—C19—H19C	109.5	C49i—C50—H50	118.4
H19A—C19—H19C	109.5	O7—C51—C52	122.9 (4)
H19B—C19—H19C	109.5	O7—C51—C53ii	116.9 (4)
C12—C20—C23	109.1 (2)	C52—C51—C53ii	119.9 (3)
C12—C20—C22	110.1 (3)	C51—C52—C53	120.6 (4)
C23—C20—C22	108.0 (3)	C51—C52—H52	119.7
C12—C20—C21	109.8 (3)	C53—C52—H52	119.7
C23—C20—C21	108.8 (3)	C52—C53—C51ii	119.5 (4)
C22—C20—C21	111.0 (3)	C52—C53—H53	120.3
C20—C21—H21A	109.5	C51ii—C53—H53	120.3
C20—C21—H21B	109.5	O8—C54—H54A	109.5
H21A—C21—H21B	109.5	O8—C54—H54B	109.5
C20—C21—H21C	109.5	H54A—C54—H54B	109.5
H21A—C21—H21C	109.5	O8—C54—H54C	109.5
H21B—C21—H21C	109.5	H54A—C54—H54C	109.5
C20—C22—H22A	109.5	H54B—C54—H54C	109.5
C20—C22—H22B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1iii	0.84	1.84	2.682 (2)	175
O3—H3O···N1	0.84	2.01	2.835 (3)	166
O4—H4O···N14	0.84	1.99	2.757 (3)	152
O5—H5O···N2	0.84	2.10	2.926 (6)	170
O5A—H5OA···N2	0.84	2.02	2.831 (14)	162
O7—H7O···N15	0.84	2.21	2.975 (5)	152
O8—H8O···O1iv	0.84	1.99	2.822 (3)	173
N16—H16M···N3	0.88	2.16	2.719 (4)	121
N16—H16N···N9	0.88	2.05	2.660 (3)	126
N17—H17M···N13	0.88	2.13	2.705 (2)	122
N17—H17N···N8	0.88	2.06	2.661 (3)	125

Na1—O8	2.336 (3)
Na1—N7	2.420 (3)
Na1—O2	2.437 (2)
Na1—N11	2.642 (3)
Na1—N5	2.644 (3)
N3—N4	1.295 (4)
N12—N13	1.308 (3)

N7—Na1—N11	65.51 (8)
N7—Na1—N5	65.04 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.84	1.84	2.682 (2)	175
O3—H3O⋯N1	0.84	2.01	2.835 (3)	166
O4—H4O⋯N14	0.84	1.99	2.757 (3)	152
O5—H5O⋯N2	0.84	2.10	2.926 (6)	170
O5A—H5OA⋯N2	0.84	2.02	2.831 (14)	162
O7—H7O⋯N15	0.84	2.21	2.975 (5)	152
O8—H8O⋯O1ii	0.84	1.99	2.822 (3)	173
N16—H16M⋯N3	0.88	2.16	2.719 (4)	121
N16—H16N⋯N9	0.88	2.05	2.660 (3)	126
N17—H17M⋯N13	0.88	2.13	2.705 (2)	122
N17—H17N⋯N8	0.88	2.06	2.661 (3)	125

Symmetry codes: (i) ; (ii) .