Synthesis and crystal structure of a nickel(II) 2′-de­oxy-6-thio­guanosine nitrate com­plex

The reaction of Ni(NO₃)₂·6H₂O with the thio-modified nucleoside 2′-de­oxy-6-thio­guanosine (d-tG, C₁₀H₁₃N₅O₃S) in methanol in a 1:1.3 stoichiometric ratio deposited the title com­pound, [Ni(d-tG)₃](NO₃)₂·2H₂O, as green crystals. Despite the <1:3 Ni–ligand ratio used in the synthesis, the de­oxy-thio­guanosine binds to form three N⁷,S⁶-coordinated five-membered chelate rings with individual Ni^II ions in mononuclear com­plexes rather than bridge metal centres into more extended oligomeric or polymeric structures.

Computing details

Tris(2'-deoxy-6-thioguanosine)nickel(II) dinitrate dihydrate

Crystal data

[Ni(C10H13N5O3S)3](NO3)2·2H2O	Dx = 1.584 Mg m^−3
Mr = 1068.70	Synchrotron radiation, λ = 0.6889 Å
Trigonal, P3	Cell parameters from 9951 reflections
a = 24.185 (4) Å	θ = 2.5–27.4°
c = 6.6341 (10) Å	µ = 0.61 mm^−1
V = 3360.4 (12) Å^3	T = 150 K
Z = 3	Needle, green
F(000) = 1662	0.10 × 0.01 × 0.01 mm

Data collection

Rigaku Saturn 724+ CCD on kappa diffractometer	Rint = 0.047
Radiation source: Diamond beamline I19	θmax = 27.4°, θmin = 2.5°
wide–frame ω scans	h = −32→32
28605 measured reflections	k = −31→32
10450 independent reflections	l = −6→8
8773 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.1065P)^2 + 0.2709P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.157	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 1.26 e Å^−3
10450 reflections	Δρmin = −0.55 e Å^−3
660 parameters	Extinction correction: SHELXL2019/2 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
94 restraints	Extinction coefficient: 0.015 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 3360 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.031 (8)

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)
Ni1	1.000000	1.000000	0.77356 (18)	0.0240 (3)
N1	0.8453 (2)	0.8104 (2)	0.9900 (7)	0.0256 (9)
H1	0.852758	0.794724	1.099721	0.031*
N2	0.7426 (2)	0.7246 (3)	1.0012 (9)	0.0347 (12)
H2A	0.703580	0.701588	0.953598	0.042*
H2B	0.753626	0.712954	1.112794	0.042*
C2	0.7855 (3)	0.7779 (3)	0.9031 (9)	0.0270 (11)
N3	0.7685 (2)	0.7954 (2)	0.7335 (7)	0.0269 (10)
C4	0.8169 (3)	0.8495 (3)	0.6564 (9)	0.0243 (10)
C5	0.8772 (2)	0.8857 (3)	0.7357 (9)	0.0248 (11)
S6	0.96714 (7)	0.90937 (7)	1.0140 (2)	0.0292 (3)
C6	0.8941 (3)	0.8669 (2)	0.9109 (8)	0.0235 (10)
N7	0.9138 (2)	0.9388 (2)	0.6203 (7)	0.0262 (10)
C8	0.8764 (3)	0.9350 (3)	0.4721 (9)	0.0306 (12)
H8	0.888991	0.965774	0.367335	0.037*
N9	0.8164 (2)	0.8811 (2)	0.4846 (7)	0.0264 (10)
C10	0.7617 (3)	0.8597 (3)	0.3458 (9)	0.0309 (12)
H10	0.741642	0.812797	0.321008	0.037*
O11	0.7864 (2)	0.8935 (2)	0.1644 (6)	0.0350 (10)
C12	0.7397 (3)	0.9067 (3)	0.0727 (10)	0.0341 (13)
H12	0.724597	0.884314	−0.059698	0.041*
C13	0.6851 (3)	0.8857 (4)	0.2198 (11)	0.0422 (16)
H13	0.673181	0.919553	0.236344	0.051*
C14	0.7121 (4)	0.8755 (5)	0.4176 (11)	0.052 (2)
H14A	0.731535	0.914610	0.501232	0.062*
H14B	0.678357	0.839805	0.496635	0.062*
C15	0.7702 (10)	0.9798 (8)	0.049 (4)	0.049 (4)	0.49 (2)
H15A	0.810357	0.996758	−0.029315	0.059*	0.49 (2)
H15B	0.740745	0.989553	−0.026559	0.059*	0.49 (2)
O16	0.7834 (6)	1.0098 (7)	0.245 (3)	0.063 (5)	0.49 (2)
H16	0.810439	1.003703	0.304599	0.095*	0.49 (2)
C15X	0.7719 (13)	0.9717 (10)	−0.041 (4)	0.063 (6)	0.51 (2)
H15C	0.806486	0.974723	−0.128899	0.076*	0.51 (2)
H15D	0.740030	0.974457	−0.128012	0.076*	0.51 (2)
O16X	0.7979 (9)	1.0238 (6)	0.103 (3)	0.088 (6)	0.51 (2)
H16X	0.828273	1.056334	0.049731	0.132*	0.51 (2)
O17	0.6314 (2)	0.8268 (3)	0.1635 (10)	0.0604 (17)
H17	0.612377	0.832828	0.067210	0.091*
Ni2	0.333333	0.666667	0.99733 (18)	0.0221 (3)
N1'	0.3426 (2)	0.4946 (2)	1.1869 (7)	0.0267 (10)
H1'	0.322949	0.475478	1.299169	0.032*
N2'	0.3825 (3)	0.4252 (3)	1.1732 (9)	0.0373 (12)
H2'1	0.405534	0.410652	1.115778	0.045*
H2'2	0.362111	0.408077	1.286442	0.045*
C2'	0.3785 (3)	0.4728 (3)	1.0892 (8)	0.0245 (10)
N3'	0.4101 (2)	0.4981 (2)	0.9164 (8)	0.0284 (10)
C4'	0.4042 (3)	0.5469 (2)	0.8509 (8)	0.0229 (10)
C5'	0.3696 (2)	0.5717 (2)	0.9437 (8)	0.0233 (10)
S6'	0.29406 (7)	0.57376 (7)	1.2332 (2)	0.0288 (3)
C6'	0.3358 (2)	0.5443 (3)	1.1180 (8)	0.0243 (10)
N7'	0.3753 (2)	0.6232 (2)	0.8367 (7)	0.0231 (9)
C8'	0.4111 (2)	0.6289 (3)	0.6806 (8)	0.0229 (10)
H8'	0.422802	0.660708	0.579526	0.027*
N9'	0.4302 (2)	0.5834 (2)	0.6795 (7)	0.0235 (9)
C10'	0.4710 (3)	0.5724 (3)	0.5376 (9)	0.0299 (12)
H10'	0.447782	0.527082	0.490290	0.036*
O11'	0.5282 (2)	0.5855 (2)	0.6330 (7)	0.0347 (10)
C12'	0.5753 (3)	0.6520 (4)	0.5994 (10)	0.0375 (14)
H12'	0.615640	0.654302	0.552046	0.045*
C13'	0.5512 (3)	0.6771 (3)	0.4342 (9)	0.0322 (12)
H13'	0.538225	0.707090	0.491849	0.039*
C14'	0.4927 (3)	0.6175 (3)	0.3554 (9)	0.0287 (11)
H14C	0.503915	0.598885	0.240263	0.034*
H14D	0.459143	0.626969	0.312797	0.034*
C15'	0.5891 (3)	0.6884 (4)	0.7962 (10)	0.0403 (15)
H15E	0.623155	0.733281	0.776044	0.048*
H15F	0.550262	0.688286	0.844021	0.048*
O16'	0.6088 (2)	0.6587 (3)	0.9406 (8)	0.0455 (12)
H16'	0.599697	0.665463	1.056769	0.068*
O17'	0.5976 (2)	0.7081 (3)	0.2833 (7)	0.0426 (11)
H17'	0.611091	0.747575	0.288022	0.064*
Ni3	0.666667	0.333333	0.03478 (18)	0.0300 (3)
N1"	0.7596 (3)	0.5456 (3)	−0.0627 (8)	0.0365 (12)
H1"	0.745559	0.559047	−0.163220	0.044*
N2"	0.8338 (4)	0.6521 (3)	0.0016 (10)	0.0497 (16)
H2"1	0.865319	0.682146	0.072282	0.060*
H2"2	0.819367	0.662330	−0.105503	0.060*
C2"	0.8077 (3)	0.5907 (3)	0.0574 (10)	0.0364 (14)
N3"	0.8309 (3)	0.5767 (3)	0.2219 (8)	0.0333 (11)
C4"	0.8018 (3)	0.5131 (3)	0.2569 (9)	0.0291 (11)
C5"	0.7550 (3)	0.4654 (3)	0.1359 (9)	0.0294 (12)
S6"	0.67602 (8)	0.42332 (9)	−0.1810 (2)	0.0386 (4)
C6"	0.7327 (3)	0.4816 (3)	−0.0337 (9)	0.0314 (12)
N7"	0.7361 (2)	0.4058 (3)	0.2097 (8)	0.0314 (10)
C8"	0.7696 (3)	0.4157 (3)	0.3747 (9)	0.0299 (12)
H8"	0.766162	0.382450	0.459155	0.036*
N9"	0.8102 (2)	0.4797 (2)	0.4127 (8)	0.0298 (10)
C10"	0.8506 (3)	0.5026 (3)	0.5910 (9)	0.0306 (12)
H10"	0.829980	0.471253	0.703238	0.037*
O11"	0.8574 (2)	0.5626 (2)	0.6488 (7)	0.0349 (10)
C12"	0.9220 (3)	0.6046 (3)	0.7177 (10)	0.0371 (14)
H12"	0.919517	0.617680	0.858876	0.044*
C13"	0.9537 (3)	0.5640 (3)	0.7251 (11)	0.0366 (14)
H13"	1.000688	0.589666	0.699604	0.044*
C14"	0.9187 (3)	0.5150 (3)	0.5586 (11)	0.0356 (14)
H14E	0.921299	0.475798	0.578191	0.043*
H14F	0.935175	0.532921	0.423217	0.043*
C15"	0.9528 (4)	0.6639 (3)	0.5904 (12)	0.0442 (16)
H15G	0.928451	0.686583	0.605013	0.053*
H15H	0.996642	0.692550	0.640687	0.053*
O16"	0.9558 (2)	0.6511 (2)	0.3829 (8)	0.0434 (11)
H16"	0.921183	0.642060	0.326703	0.065*
O17"	0.9395 (2)	0.5347 (2)	0.9210 (8)	0.0437 (12)
H17"	0.955572	0.511051	0.931634	0.066*
N21	0.7510 (5)	0.6393 (6)	−0.4683 (17)	0.115 (4)
O22	0.7157 (5)	0.5884 (5)	−0.3777 (16)	0.122 (4)
O23	0.7380 (7)	0.6567 (8)	−0.6306 (17)	0.174 (6)
O24	0.8066 (5)	0.6805 (6)	−0.3892 (13)	0.105 (3)
N25	0.5808 (3)	0.8577 (3)	−0.3187 (9)	0.0393 (13)
O26	0.6205 (3)	0.8864 (4)	−0.1865 (9)	0.0656 (18)
O27	0.5422 (4)	0.7993 (3)	−0.3014 (13)	0.084 (2)
O28	0.5764 (3)	0.8877 (3)	−0.4633 (8)	0.0462 (12)
O29	0.9229 (19)	0.7988 (18)	1.472 (6)	0.087 (12)	0.23 (2)
O30	0.9665 (5)	0.4436 (5)	0.9981 (19)	0.083 (5)	0.66 (2)
O29X	0.8735 (4)	0.7704 (6)	1.3376 (15)	0.096 (5)	0.77 (2)
O30X	0.9248 (9)	0.3925 (9)	1.105 (5)	0.087 (9)	0.34 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0240 (4)	0.0240 (4)	0.0238 (6)	0.01202 (18)	0.000	0.000
N1	0.028 (2)	0.026 (2)	0.022 (2)	0.0135 (19)	−0.0019 (18)	0.0049 (17)
N2	0.025 (2)	0.037 (3)	0.037 (3)	0.012 (2)	0.002 (2)	0.014 (2)
C2	0.026 (2)	0.032 (3)	0.024 (3)	0.016 (2)	−0.003 (2)	0.004 (2)
N3	0.022 (2)	0.034 (2)	0.025 (2)	0.0140 (19)	−0.0006 (18)	0.0047 (19)
C4	0.024 (2)	0.032 (3)	0.022 (3)	0.018 (2)	−0.002 (2)	0.001 (2)
C5	0.022 (2)	0.029 (3)	0.025 (3)	0.014 (2)	−0.001 (2)	0.006 (2)
S6	0.0281 (7)	0.0293 (7)	0.0280 (7)	0.0127 (6)	−0.0099 (6)	0.0001 (6)
C6	0.023 (2)	0.024 (2)	0.022 (3)	0.011 (2)	−0.0024 (19)	0.001 (2)
N7	0.023 (2)	0.030 (2)	0.023 (2)	0.0116 (19)	0.0005 (18)	0.0056 (18)
C8	0.033 (3)	0.039 (3)	0.023 (3)	0.020 (3)	0.003 (2)	0.007 (2)
N9	0.025 (2)	0.033 (2)	0.024 (2)	0.017 (2)	0.0002 (18)	0.0062 (19)
C10	0.023 (2)	0.051 (3)	0.020 (3)	0.019 (3)	−0.003 (2)	0.005 (2)
O11	0.036 (2)	0.063 (3)	0.022 (2)	0.036 (2)	0.0011 (17)	0.008 (2)
C12	0.031 (3)	0.049 (4)	0.029 (3)	0.025 (3)	−0.008 (2)	0.005 (3)
C13	0.038 (3)	0.071 (5)	0.034 (4)	0.040 (3)	0.002 (3)	0.005 (3)
C14	0.042 (4)	0.102 (6)	0.028 (4)	0.048 (4)	0.003 (3)	0.009 (4)
C15	0.035 (6)	0.051 (7)	0.070 (12)	0.028 (5)	0.001 (9)	0.013 (8)
O16	0.049 (7)	0.059 (8)	0.075 (10)	0.022 (6)	−0.012 (6)	−0.011 (7)
C15X	0.055 (8)	0.064 (9)	0.060 (12)	0.022 (7)	−0.013 (10)	0.019 (9)
O16X	0.086 (9)	0.051 (7)	0.100 (12)	0.014 (7)	−0.004 (9)	0.031 (8)
O17	0.030 (2)	0.078 (4)	0.058 (4)	0.016 (2)	−0.002 (2)	0.035 (3)
Ni2	0.0228 (4)	0.0228 (4)	0.0209 (6)	0.01138 (18)	0.000	0.000
N1'	0.030 (2)	0.026 (2)	0.023 (2)	0.0126 (19)	0.0046 (18)	0.0067 (18)
N2'	0.051 (3)	0.035 (3)	0.034 (3)	0.027 (3)	0.009 (2)	0.011 (2)
C2'	0.026 (2)	0.025 (2)	0.021 (3)	0.012 (2)	0.000 (2)	0.001 (2)
N3'	0.037 (2)	0.027 (2)	0.026 (2)	0.019 (2)	0.002 (2)	0.0038 (19)
C4'	0.025 (2)	0.024 (2)	0.020 (2)	0.011 (2)	0.0020 (19)	0.0005 (19)
C5'	0.024 (2)	0.024 (2)	0.022 (3)	0.012 (2)	0.001 (2)	0.000 (2)
S6'	0.0326 (7)	0.0327 (7)	0.0242 (7)	0.0187 (6)	0.0094 (6)	0.0047 (6)
C6'	0.022 (2)	0.026 (3)	0.022 (3)	0.010 (2)	0.001 (2)	0.001 (2)
N7'	0.024 (2)	0.027 (2)	0.023 (2)	0.0165 (18)	0.0029 (17)	0.0036 (17)
C8'	0.024 (2)	0.026 (2)	0.022 (3)	0.014 (2)	0.002 (2)	0.005 (2)
N9'	0.024 (2)	0.025 (2)	0.023 (2)	0.0134 (18)	0.0044 (18)	0.0016 (17)
C10'	0.028 (3)	0.038 (3)	0.022 (3)	0.016 (2)	0.002 (2)	−0.005 (2)
O11'	0.026 (2)	0.048 (3)	0.034 (2)	0.0211 (19)	0.0043 (17)	0.0077 (19)
C12'	0.023 (3)	0.052 (4)	0.031 (3)	0.014 (3)	0.003 (2)	0.004 (3)
C13'	0.027 (3)	0.039 (3)	0.024 (3)	0.012 (2)	0.006 (2)	0.000 (2)
C14'	0.029 (3)	0.039 (3)	0.019 (3)	0.018 (2)	0.003 (2)	0.003 (2)
C15'	0.032 (3)	0.047 (4)	0.035 (4)	0.014 (3)	0.001 (3)	0.001 (3)
O16'	0.039 (3)	0.057 (3)	0.032 (3)	0.017 (2)	−0.004 (2)	0.002 (2)
O17'	0.033 (2)	0.055 (3)	0.033 (2)	0.017 (2)	0.0086 (19)	0.012 (2)
Ni3	0.0354 (4)	0.0354 (4)	0.0191 (6)	0.0177 (2)	0.000	0.000
N1"	0.047 (3)	0.051 (3)	0.023 (3)	0.034 (3)	−0.003 (2)	0.003 (2)
N2"	0.079 (5)	0.046 (3)	0.037 (3)	0.041 (3)	−0.014 (3)	0.003 (3)
C2"	0.049 (4)	0.042 (3)	0.029 (3)	0.031 (3)	−0.004 (3)	0.005 (3)
N3"	0.048 (3)	0.037 (3)	0.022 (2)	0.027 (2)	−0.004 (2)	0.004 (2)
C4"	0.031 (3)	0.037 (3)	0.022 (3)	0.019 (2)	0.000 (2)	0.003 (2)
C5"	0.029 (3)	0.039 (3)	0.021 (3)	0.018 (2)	0.001 (2)	0.000 (2)
S6"	0.0439 (9)	0.0497 (9)	0.0234 (8)	0.0243 (7)	−0.0068 (6)	−0.0001 (6)
C6"	0.031 (3)	0.046 (3)	0.024 (3)	0.024 (3)	0.001 (2)	0.002 (2)
N7"	0.033 (2)	0.037 (3)	0.022 (2)	0.016 (2)	−0.0030 (19)	0.000 (2)
C8"	0.030 (3)	0.036 (3)	0.023 (3)	0.017 (2)	0.000 (2)	0.005 (2)
N9"	0.028 (2)	0.037 (3)	0.024 (2)	0.016 (2)	−0.0014 (19)	0.006 (2)
C10"	0.031 (3)	0.040 (3)	0.025 (3)	0.021 (2)	−0.003 (2)	0.002 (2)
O11"	0.032 (2)	0.042 (2)	0.031 (2)	0.0188 (19)	−0.0054 (17)	−0.0028 (18)
C12"	0.034 (3)	0.046 (4)	0.031 (3)	0.020 (3)	−0.001 (2)	0.001 (3)
C13"	0.034 (3)	0.035 (3)	0.041 (4)	0.017 (3)	−0.008 (3)	0.000 (3)
C14"	0.032 (3)	0.033 (3)	0.046 (4)	0.019 (3)	−0.002 (3)	0.003 (3)
C15"	0.058 (4)	0.026 (3)	0.043 (4)	0.016 (3)	−0.005 (3)	−0.004 (3)
O16"	0.047 (3)	0.035 (2)	0.039 (3)	0.014 (2)	0.000 (2)	0.004 (2)
O17"	0.040 (2)	0.045 (3)	0.042 (3)	0.019 (2)	−0.007 (2)	0.010 (2)
N21	0.088 (7)	0.156 (10)	0.085 (7)	0.049 (7)	0.003 (5)	0.060 (7)
O22	0.110 (6)	0.119 (7)	0.101 (7)	0.031 (5)	−0.039 (5)	0.067 (6)
O23	0.221 (14)	0.278 (17)	0.089 (7)	0.176 (14)	0.021 (8)	0.102 (9)
O24	0.125 (6)	0.175 (9)	0.065 (5)	0.112 (6)	0.016 (5)	0.032 (5)
N25	0.045 (3)	0.047 (3)	0.035 (3)	0.030 (3)	0.003 (2)	0.004 (2)
O26	0.062 (4)	0.120 (6)	0.036 (3)	0.062 (4)	−0.010 (3)	0.005 (3)
O27	0.110 (6)	0.048 (3)	0.095 (6)	0.039 (4)	0.037 (5)	0.013 (4)
O28	0.056 (3)	0.056 (3)	0.031 (3)	0.031 (3)	−0.005 (2)	0.003 (2)
O29	0.09 (2)	0.08 (2)	0.10 (3)	0.048 (18)	−0.002 (19)	−0.001 (19)
O30	0.090 (7)	0.077 (7)	0.117 (9)	0.070 (6)	0.070 (7)	0.067 (6)
O29X	0.052 (5)	0.144 (10)	0.078 (7)	0.037 (5)	−0.004 (4)	0.079 (7)
O30X	0.041 (9)	0.046 (10)	0.17 (2)	0.021 (8)	0.035 (12)	0.028 (12)

Geometric parameters (Å, º)

Ni1—S6	2.4975 (17)	C8'—N9'	1.390 (7)
Ni1—S6^i	2.4975 (17)	N9'—C10'	1.481 (7)
Ni1—S6^ii	2.4975 (17)	C10'—H10'	1.000
Ni1—N7	2.118 (5)	C10'—O11'	1.406 (7)
Ni1—N7^ii	2.118 (5)	C10'—C14'	1.533 (8)
Ni1—N7^i	2.118 (5)	O11'—C12'	1.451 (8)
N1—H1	0.880	C12'—H12'	1.000
N1—C2	1.381 (7)	C12'—C13'	1.503 (9)
N1—C6	1.386 (7)	C12'—C15'	1.515 (10)
N2—H2A	0.880	C13'—H13'	1.000
N2—H2B	0.880	C13'—C14'	1.520 (9)
N2—C2	1.350 (8)	C13'—O17'	1.408 (7)
C2—N3	1.338 (7)	C14'—H14C	0.990
N3—C4	1.346 (7)	C14'—H14D	0.990
C4—C5	1.376 (7)	C15'—H15E	0.990
C4—N9	1.377 (7)	C15'—H15F	0.990
C5—C6	1.383 (8)	C15'—O16'	1.416 (9)
C5—N7	1.372 (7)	O16'—H16'	0.840
S6—C6	1.682 (5)	O17'—H17'	0.840
N7—C8	1.307 (7)	Ni3—S6"	2.5189 (19)
C8—H8	0.950	Ni3—S6"^v	2.5189 (19)
C8—N9	1.385 (8)	Ni3—S6"^vi	2.5189 (19)
N9—C10	1.476 (7)	Ni3—N7"	2.073 (5)
C10—H10	1.000	Ni3—N7"^v	2.073 (5)
C10—O11	1.409 (7)	Ni3—N7"^vi	2.073 (5)
C10—C14	1.507 (9)	N1"—H1"	0.880
O11—C12	1.450 (6)	N1"—C2"	1.382 (9)
C12—H12	1.000	N1"—C6"	1.361 (9)
C12—C13	1.512 (9)	N2"—H2"1	0.880
C12—C15	1.546 (17)	N2"—H2"2	0.880
C12—C15X	1.557 (18)	N2"—C2"	1.343 (9)
C13—H13	1.000	C2"—N3"	1.345 (8)
C13—C14	1.540 (10)	N3"—C4"	1.354 (8)
C13—O17	1.416 (10)	C4"—C5"	1.397 (9)
C14—H14A	0.990	C4"—N9"	1.388 (8)
C14—H14B	0.990	C5"—C6"	1.384 (8)
C15—H15A	0.990	C5"—N7"	1.368 (8)
C15—H15B	0.990	S6"—C6"	1.700 (7)
C15—O16	1.45 (3)	N7"—C8"	1.309 (8)
O16—H16	0.840	C8"—H8"	0.950
C15X—H15C	0.990	C8"—N9"	1.378 (8)
C15X—H15D	0.990	N9"—C10"	1.456 (8)
C15X—O16X	1.45 (3)	C10"—H10"	1.000
O16X—H16X	0.840	C10"—O11"	1.429 (8)
O17—H17	0.840	C10"—C14"	1.535 (8)
Ni2—S6'	2.5030 (16)	O11"—C12"	1.446 (8)
Ni2—S6'^iii	2.5030 (16)	C12"—H12"	1.000
Ni2—S6'^iv	2.5030 (16)	C12"—C13"	1.520 (9)
Ni2—N7'	2.083 (5)	C12"—C15"	1.503 (10)
Ni2—N7'^iii	2.083 (5)	C13"—H13"	1.000
Ni2—N7'^iv	2.083 (5)	C13"—C14"	1.529 (10)
N1'—H1'	0.880	C13"—O17"	1.437 (9)
N1'—C2'	1.382 (7)	C14"—H14E	0.990
N1'—C6'	1.370 (7)	C14"—H14F	0.990
N2'—H2'1	0.880	C15"—H15G	0.990
N2'—H2'2	0.880	C15"—H15H	0.990
N2'—C2'	1.326 (8)	C15"—O16"	1.421 (9)
C2'—N3'	1.343 (7)	O16"—H16"	0.840
N3'—C4'	1.331 (7)	O17"—H17"	0.840
C4'—C5'	1.392 (7)	N21—O22	1.246 (12)
C4'—N9'	1.382 (7)	N21—O23	1.253 (11)
C5'—C6'	1.380 (8)	N21—O24	1.318 (13)
C5'—N7'	1.378 (7)	N25—O26	1.227 (9)
S6'—C6'	1.683 (6)	N25—O27	1.251 (9)
N7'—C8'	1.313 (7)	N25—O28	1.238 (8)
C8'—H8'	0.950
S6^i—Ni1—S6^ii	83.59 (6)	C5'—N7'—C8'	105.3 (4)
S6—Ni1—S6^i	83.59 (6)	N7'—C8'—H8'	123.7
S6—Ni1—S6^ii	83.59 (6)	N7'—C8'—N9'	112.5 (5)
S6—Ni1—N7	85.61 (13)	H8'—C8'—N9'	123.7
S6^i—Ni1—N7	168.37 (14)	C4'—N9'—C8'	106.0 (4)
S6^i—Ni1—N7^ii	90.95 (14)	C4'—N9'—C10'	122.7 (5)
S6^i—Ni1—N7^i	85.61 (13)	C8'—N9'—C10'	131.3 (5)
S6^ii—Ni1—N7	90.95 (14)	N9'—C10'—H10'	109.7
S6^ii—Ni1—N7^ii	85.61 (13)	N9'—C10'—O11'	110.0 (5)
S6^ii—Ni1—N7^i	168.38 (14)	N9'—C10'—C14'	113.4 (5)
S6—Ni1—N7^ii	168.38 (14)	H10'—C10'—O11'	109.7
S6—Ni1—N7^i	90.95 (14)	H10'—C10'—C14'	109.7
N7—Ni1—N7^ii	98.88 (17)	O11'—C10'—C14'	104.2 (5)
N7—Ni1—N7^i	98.88 (17)	C10'—O11'—C12'	108.6 (5)
N7^ii—Ni1—N7^i	98.88 (18)	O11'—C12'—H12'	108.2
H1—N1—C2	118.8	O11'—C12'—C13'	108.1 (5)
H1—N1—C6	118.8	O11'—C12'—C15'	109.5 (5)
C2—N1—C6	122.4 (5)	H12'—C12'—C13'	108.2
H2A—N2—H2B	120.0	H12'—C12'—C15'	108.2
H2A—N2—C2	120.0	C13'—C12'—C15'	114.3 (6)
H2B—N2—C2	120.0	C12'—C13'—H13'	109.8
N1—C2—N2	115.4 (5)	C12'—C13'—C14'	103.5 (5)
N1—C2—N3	124.9 (5)	C12'—C13'—O17'	111.5 (5)
N2—C2—N3	119.8 (5)	H13'—C13'—C14'	109.8
C2—N3—C4	111.8 (5)	H13'—C13'—O17'	109.8
N3—C4—C5	127.2 (5)	C14'—C13'—O17'	112.1 (5)
N3—C4—N9	127.6 (5)	C10'—C14'—C13'	103.2 (5)
C5—C4—N9	105.3 (5)	C10'—C14'—H14C	111.1
C4—C5—C6	120.4 (5)	C10'—C14'—H14D	111.1
C4—C5—N7	111.4 (5)	C13'—C14'—H14C	111.1
C6—C5—N7	128.2 (5)	C13'—C14'—H14D	111.1
Ni1—S6—C6	93.02 (19)	H14C—C14'—H14D	109.1
N1—C6—C5	113.3 (5)	C12'—C15'—H15E	110.0
N1—C6—S6	124.4 (4)	C12'—C15'—H15F	110.0
C5—C6—S6	122.3 (4)	C12'—C15'—O16'	108.7 (6)
Ni1—N7—C5	109.6 (4)	H15E—C15'—H15F	108.3
Ni1—N7—C8	144.6 (4)	H15E—C15'—O16'	110.0
C5—N7—C8	104.7 (5)	H15F—C15'—O16'	110.0
N7—C8—H8	123.7	C15'—O16'—H16'	109.5
N7—C8—N9	112.6 (5)	C13'—O17'—H17'	109.5
H8—C8—N9	123.7	S6"^v—Ni3—S6"^vi	90.88 (6)
C4—N9—C8	106.0 (5)	S6"—Ni3—S6"^v	90.88 (6)
C4—N9—C10	125.2 (5)	S6"—Ni3—S6"^vi	90.88 (6)
C8—N9—C10	128.7 (5)	S6"—Ni3—N7"	84.43 (15)
N9—C10—H10	110.0	S6"^v—Ni3—N7"^v	84.43 (15)
N9—C10—O11	106.5 (5)	S6"^v—Ni3—N7"	93.31 (15)
N9—C10—C14	113.6 (5)	S6"^v—Ni3—N7"^vi	173.76 (15)
H10—C10—O11	110.0	S6"^vi—Ni3—N7"^v	93.31 (15)
H10—C10—C14	110.0	S6"^vi—Ni3—N7"	173.76 (15)
O11—C10—C14	106.4 (5)	S6"^vi—Ni3—N7"^vi	84.43 (15)
C10—O11—C12	109.6 (4)	S6"—Ni3—N7"^v	173.76 (15)
O11—C12—H12	111.3	S6"—Ni3—N7"^vi	93.31 (15)
O11—C12—C13	107.5 (5)	N7"—Ni3—N7"^v	91.7 (2)
O11—C12—C15	108.4 (10)	N7"^v—Ni3—N7"^vi	91.7 (2)
O11—C12—C15X	112.0 (11)	N7"—Ni3—N7"^vi	91.7 (2)
H12—C12—C13	111.3	H1"—N1"—C2"	118.3
H12—C12—C15	111.3	H1"—N1"—C6"	118.3
C13—C12—C15	106.7 (10)	C2"—N1"—C6"	123.4 (5)
C13—C12—C15X	124.4 (14)	H2"1—N2"—H2"2	120.0
C12—C13—H13	110.9	H2"1—N2"—C2"	120.0
C12—C13—C14	103.6 (5)	H2"2—N2"—C2"	120.0
C12—C13—O17	112.1 (6)	N1"—C2"—N2"	117.3 (6)
H13—C13—C14	110.9	N1"—C2"—N3"	124.1 (6)
H13—C13—O17	110.9	N2"—C2"—N3"	118.6 (6)
C14—C13—O17	108.2 (7)	C2"—N3"—C4"	112.4 (6)
C10—C14—C13	103.1 (5)	N3"—C4"—C5"	125.8 (5)
C10—C14—H14A	111.1	N3"—C4"—N9"	130.2 (6)
C10—C14—H14B	111.1	C5"—C4"—N9"	104.0 (5)
C13—C14—H14A	111.1	C4"—C5"—C6"	120.2 (6)
C13—C14—H14B	111.1	C4"—C5"—N7"	111.6 (5)
H14A—C14—H14B	109.1	C6"—C5"—N7"	128.1 (6)
C12—C15—H15A	109.7	Ni3—S6"—C6"	94.4 (2)
C12—C15—H15B	109.7	N1"—C6"—C5"	113.8 (6)
C12—C15—O16	109.9 (15)	N1"—C6"—S6"	126.2 (5)
H15A—C15—H15B	108.2	C5"—C6"—S6"	120.0 (5)
H15A—C15—O16	109.7	Ni3—N7"—C5"	113.1 (4)
H15B—C15—O16	109.7	Ni3—N7"—C8"	142.0 (4)
C15—O16—H16	109.5	C5"—N7"—C8"	104.9 (5)
C12—C15X—H15C	109.7	N7"—C8"—H8"	123.6
C12—C15X—H15D	109.7	N7"—C8"—N9"	112.7 (5)
C12—C15X—O16X	109.6 (16)	H8"—C8"—N9"	123.6
H15C—C15X—H15D	108.2	C4"—N9"—C8"	106.7 (5)
H15C—C15X—O16X	109.7	C4"—N9"—C10"	130.4 (5)
H15D—C15X—O16X	109.7	C8"—N9"—C10"	122.8 (5)
C15X—O16X—H16X	109.5	N9"—C10"—H10"	109.3
C13—O17—H17	109.5	N9"—C10"—O11"	108.7 (5)
S6'—Ni2—S6'^iii	85.05 (6)	N9"—C10"—C14"	114.3 (5)
S6'^iii—Ni2—S6'^iv	85.05 (6)	H10"—C10"—O11"	109.3
S6'—Ni2—S6'^iv	85.05 (6)	H10"—C10"—C14"	109.3
S6'—Ni2—N7'	85.90 (13)	O11"—C10"—C14"	105.7 (5)
S6'^iii—Ni2—N7'^iii	85.91 (13)	C10"—O11"—C12"	109.5 (5)
S6'^iii—Ni2—N7'^iv	92.52 (13)	O11"—C12"—H12"	107.7
S6'^iii—Ni2—N7'	170.81 (14)	O11"—C12"—C13"	105.9 (5)
S6'—Ni2—N7'^iii	92.52 (13)	O11"—C12"—C15"	109.8 (6)
S6'—Ni2—N7'^iv	170.80 (14)	H12"—C12"—C13"	107.7
S6'^iv—Ni2—N7'^iii	170.81 (14)	H12"—C12"—C15"	107.7
S6'^iv—Ni2—N7'^iv	85.90 (13)	C13"—C12"—C15"	117.8 (6)
S6'^iv—Ni2—N7'	92.52 (13)	C12"—C13"—H13"	112.1
N7'^iii—Ni2—N7'^iv	96.16 (17)	C12"—C13"—C14"	102.4 (5)
N7'—Ni2—N7'^iii	96.15 (17)	C12"—C13"—O17"	105.9 (6)
N7'—Ni2—N7'^iv	96.15 (18)	H13"—C13"—C14"	112.1
H1'—N1'—C2'	118.3	H13"—C13"—O17"	112.1
H1'—N1'—C6'	118.3	C14"—C13"—O17"	111.7 (5)
C2'—N1'—C6'	123.5 (5)	C10"—C14"—C13"	100.1 (5)
H2'1—N2'—H2'2	120.0	C10"—C14"—H14E	111.8
H2'1—N2'—C2'	120.0	C10"—C14"—H14F	111.8
H2'2—N2'—C2'	120.0	C13"—C14"—H14E	111.8
N1'—C2'—N2'	117.8 (5)	C13"—C14"—H14F	111.8
N1'—C2'—N3'	123.3 (5)	H14E—C14"—H14F	109.5
N2'—C2'—N3'	118.9 (5)	C12"—C15"—H15G	109.0
C2'—N3'—C4'	113.2 (5)	C12"—C15"—H15H	109.0
N3'—C4'—C5'	126.3 (5)	C12"—C15"—O16"	113.0 (5)
N3'—C4'—N9'	128.1 (5)	H15G—C15"—H15H	107.8
C5'—C4'—N9'	105.6 (4)	H15G—C15"—O16"	109.0
C4'—C5'—C6'	120.2 (5)	H15H—C15"—O16"	109.0
C4'—C5'—N7'	110.6 (5)	C15"—O16"—H16"	109.5
C6'—C5'—N7'	129.3 (5)	C13"—O17"—H17"	109.5
Ni2—S6'—C6'	93.3 (2)	O22—N21—O23	125.8 (12)
N1'—C6'—C5'	113.6 (5)	O22—N21—O24	119.4 (9)
N1'—C6'—S6'	125.4 (4)	O23—N21—O24	114.8 (11)
C5'—C6'—S6'	120.9 (4)	O26—N25—O27	120.3 (7)
Ni2—N7'—C5'	109.8 (3)	O26—N25—O28	119.7 (7)
Ni2—N7'—C8'	144.4 (4)	O27—N25—O28	119.9 (7)
C6—N1—C2—N2	−178.2 (5)	Ni2—N7'—C8'—N9'	169.6 (5)
C6—N1—C2—N3	2.1 (9)	C5'—N7'—C8'—N9'	−0.4 (6)
N1—C2—N3—C4	−0.4 (8)	N3'—C4'—N9'—C8'	−178.8 (5)
N2—C2—N3—C4	179.9 (6)	N3'—C4'—N9'—C10'	−0.2 (9)
C2—N3—C4—C5	−1.6 (8)	C5'—C4'—N9'—C8'	1.2 (6)
C2—N3—C4—N9	−179.8 (6)	C5'—C4'—N9'—C10'	179.8 (5)
N3—C4—C5—C6	1.9 (9)	N7'—C8'—N9'—C4'	−0.5 (6)
N3—C4—C5—N7	−178.1 (5)	N7'—C8'—N9'—C10'	−178.9 (5)
N9—C4—C5—C6	−179.5 (5)	C4'—N9'—C10'—O11'	−65.4 (7)
N9—C4—C5—N7	0.4 (6)	C4'—N9'—C10'—C14'	178.3 (5)
C4—C5—C6—N1	−0.1 (8)	C8'—N9'—C10'—O11'	112.7 (6)
C4—C5—C6—S6	179.9 (4)	C8'—N9'—C10'—C14'	−3.5 (8)
N7—C5—C6—N1	179.9 (5)	N9'—C10'—O11'—C12'	−90.9 (6)
N7—C5—C6—S6	−0.1 (9)	C14'—C10'—O11'—C12'	30.9 (6)
C2—N1—C6—C5	−1.6 (8)	C10'—O11'—C12'—C13'	−14.3 (7)
C2—N1—C6—S6	178.3 (4)	C10'—O11'—C12'—C15'	110.9 (6)
Ni1—S6—C6—N1	−172.5 (5)	O11'—C12'—C13'—C14'	−8.7 (6)
Ni1—S6—C6—C5	7.4 (5)	O11'—C12'—C13'—O17'	−129.5 (5)
C4—C5—N7—Ni1	170.9 (4)	C15'—C12'—C13'—C14'	−131.0 (5)
C4—C5—N7—C8	−0.1 (7)	C15'—C12'—C13'—O17'	108.3 (6)
C6—C5—N7—Ni1	−9.2 (8)	C12'—C13'—C14'—C10'	26.2 (6)
C6—C5—N7—C8	179.8 (6)	O17'—C13'—C14'—C10'	146.5 (5)
Ni1—N7—C8—N9	−165.5 (5)	N9'—C10'—C14'—C13'	84.1 (6)
C5—N7—C8—N9	−0.2 (7)	O11'—C10'—C14'—C13'	−35.5 (6)
N3—C4—N9—C8	178.0 (6)	O11'—C12'—C15'—O16'	56.1 (7)
N3—C4—N9—C10	−2.4 (9)	C13'—C12'—C15'—O16'	177.6 (5)
C5—C4—N9—C8	−0.5 (6)	C6"—N1"—C2"—N2"	174.3 (6)
C5—C4—N9—C10	179.1 (5)	C6"—N1"—C2"—N3"	−3.9 (10)
N7—C8—N9—C4	0.5 (7)	N1"—C2"—N3"—C4"	0.2 (9)
N7—C8—N9—C10	−179.1 (5)	N2"—C2"—N3"—C4"	−178.0 (6)
C4—N9—C10—O11	−162.6 (5)	C2"—N3"—C4"—C5"	2.8 (9)
C4—N9—C10—C14	80.6 (8)	C2"—N3"—C4"—N9"	−177.6 (6)
C8—N9—C10—O11	17.0 (8)	N3"—C4"—C5"—C6"	−2.3 (10)
C8—N9—C10—C14	−99.9 (8)	N3"—C4"—C5"—N7"	178.6 (6)
N9—C10—O11—C12	−145.9 (5)	N9"—C4"—C5"—C6"	178.0 (5)
C14—C10—O11—C12	−24.3 (7)	N9"—C4"—C5"—N7"	−1.1 (7)
C10—O11—C12—C13	6.5 (7)	C2"—N1"—C6"—C5"	4.1 (9)
C10—O11—C12—C15	121.5 (11)	C2"—N1"—C6"—S6"	−176.9 (5)
C10—O11—C12—C15X	146.5 (14)	C4"—C5"—C6"—N1"	−1.3 (8)
O11—C12—C13—C14	13.3 (8)	C4"—C5"—C6"—S6"	179.7 (5)
O11—C12—C13—O17	−103.1 (6)	N7"—C5"—C6"—N1"	177.6 (6)
C15—C12—C13—C14	−102.8 (11)	N7"—C5"—C6"—S6"	−1.4 (9)
C15—C12—C13—O17	140.7 (11)	Ni3—S6"—C6"—N1"	−178.1 (5)
C15X—C12—C13—C14	−120.4 (13)	Ni3—S6"—C6"—C5"	0.8 (5)
C15X—C12—C13—O17	123.2 (12)	C4"—C5"—N7"—Ni3	−179.9 (4)
N9—C10—C14—C13	148.6 (6)	C4"—C5"—N7"—C8"	0.9 (7)
O11—C10—C14—C13	31.7 (8)	C6"—C5"—N7"—Ni3	1.1 (8)
C12—C13—C14—C10	−26.7 (8)	C6"—C5"—N7"—C8"	−178.1 (6)
O17—C13—C14—C10	92.4 (7)	Ni3—N7"—C8"—N9"	−179.1 (5)
O11—C12—C15—O16	−65.1 (15)	C5"—N7"—C8"—N9"	−0.4 (7)
C13—C12—C15—O16	50.4 (15)	N7"—C8"—N9"—C4"	−0.3 (7)
O11—C12—C15X—O16X	−73 (2)	N7"—C8"—N9"—C10"	177.8 (5)
C13—C12—C15X—O16X	59 (2)	N3"—C4"—N9"—C8"	−178.9 (6)
C6'—N1'—C2'—N2'	178.6 (5)	N3"—C4"—N9"—C10"	3.2 (11)
C6'—N1'—C2'—N3'	−0.4 (9)	C5"—C4"—N9"—C8"	0.8 (6)
N1'—C2'—N3'—C4'	1.1 (8)	C5"—C4"—N9"—C10"	−177.1 (6)
N2'—C2'—N3'—C4'	−177.9 (5)	C4"—N9"—C10"—O11"	30.2 (8)
C2'—N3'—C4'—C5'	0.0 (8)	C4"—N9"—C10"—C14"	−87.6 (8)
C2'—N3'—C4'—N9'	−180.0 (5)	C8"—N9"—C10"—O11"	−147.4 (5)
N3'—C4'—C5'—C6'	−1.9 (9)	C8"—N9"—C10"—C14"	94.8 (7)
N3'—C4'—C5'—N7'	178.5 (5)	N9"—C10"—O11"—C12"	−141.7 (5)
N9'—C4'—C5'—C6'	178.1 (5)	C14"—C10"—O11"—C12"	−18.6 (6)
N9'—C4'—C5'—N7'	−1.5 (6)	C10"—O11"—C12"—C13"	−7.1 (7)
C2'—N1'—C6'—C5'	−1.4 (8)	C10"—O11"—C12"—C15"	121.0 (6)
C2'—N1'—C6'—S6'	−178.6 (4)	O11"—C12"—C13"—C14"	29.7 (6)
C4'—C5'—C6'—N1'	2.4 (8)	O11"—C12"—C13"—O17"	−87.4 (6)
C4'—C5'—C6'—S6'	179.7 (4)	C15"—C12"—C13"—C14"	−93.4 (7)
N7'—C5'—C6'—N1'	−178.1 (5)	C15"—C12"—C13"—O17"	149.4 (6)
N7'—C5'—C6'—S6'	−0.7 (8)	C12"—C13"—C14"—C10"	−39.2 (6)
Ni2—S6'—C6'—N1'	171.8 (5)	O17"—C13"—C14"—C10"	73.7 (6)
Ni2—S6'—C6'—C5'	−5.3 (5)	N9"—C10"—C14"—C13"	155.5 (5)
C4'—C5'—N7'—Ni2	−172.7 (4)	O11"—C10"—C14"—C13"	36.0 (6)
C4'—C5'—N7'—C8'	1.2 (6)	O11"—C12"—C15"—O16"	−59.7 (8)
C6'—C5'—N7'—Ni2	7.8 (7)	C13"—C12"—C15"—O16"	61.4 (9)
C6'—C5'—N7'—C8'	−178.4 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O29X	0.88	1.84	2.716 (8)	174
N2—H2A···O16′	0.88	1.99	2.831 (7)	159
N2—H2B···O23^vii	0.88	2.09	2.914 (10)	155
O16—H16···O29^viii	0.84	2.02	2.51 (4)	116
O17—H17···O26	0.84	2.07	2.813 (8)	147
N1′—H1′···O28^ix	0.88	1.94	2.758 (7)	153
N2′—H2′1···O17"^vi	0.88	2.00	2.835 (8)	159
N2′—H2′2···O16"^x	0.88	2.44	2.952 (8)	117
N2′—H2′2···O28^ix	0.88	2.21	2.953 (8)	142
O16′—H16′···O17′^xi	0.84	1.84	2.646 (8)	161
O17′—H17′···O17	0.84	1.91	2.683 (8)	152
N1"—H1"···O22	0.88	1.89	2.767 (9)	180
N2"—H2"1···O16X^i	0.88	2.49	3.296 (16)	152
N2"—H2"2···O24	0.88	1.99	2.842 (10)	162
O16"—H16"···N3"	0.84	2.07	2.841 (8)	152
O17"—H17"···O30	0.84	1.83	2.641 (10)	162

Symmetry codes: (i) −y+2, x−y+1, z; (vi) −y+1, x−y, z; (vii) x, y, z+2; (viii) −x+y+1, −x+2, z−1; (ix) −x+y, −x+1, z+2; (x) −y+1, x−y, z+1; (xi) x, y, z+1.