catena-Poly[[[(4-amino­benzoato-κN)aqua­(2,2′-diamino-4,4′-bithia­zole-κ²N,N′)nickel(II)]-μ-4-amino­benzoato-κ²N:O] monohydrate]

In the crystal structure of the title compound, {[Ni(C₇H₆NO₂)₂(C₆H₆N₄S₂)(H₂O)]·H₂O}_n, the amino­benzoate anion bridges Ni^II ions through its terminal carboxylate and amino groups to form the polymeric Ni^II complex chain. π–π Stacking is observed between amino­benzoate and diamino­bithia­zole ligands.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.059
• wR factor = 0.217
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT163_ALERT_4_C Missing or Zero su (esd) on z-coordinate for ...         NI
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C11    -   C12    ...       1.53 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6A    ...          ?

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           25.00
           From the CIF: _reflns_number_total               3891
           Count of symmetry unique reflns         2158
           Completeness (_total/calc)            180.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1733
           Fraction of Friedel pairs measured     0.803
           Are heavy atom types Z>Si present        yes

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

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

---

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

catena-Poly[[[(4-aminobenzoato-κN)aqua(2,2'-diamino-4,4'-bithiazole-κ²N,N')- nickel(II)]-µ-4-aminobenzoato-κ²N:O] monohydrate]

Crystal data

[Ni(C7H6NO2)2(C6H6N4S2)(H2O)]·H2O	F(000) = 1168
Mr = 565.27	Dx = 1.618 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 23.383 (3) Å	θ = 5.2–16.6°
b = 9.082 (2) Å	µ = 1.07 mm^−1
c = 10.929 (2) Å	T = 295 K
V = 2320.9 (7) Å^3	Prism, yellow
Z = 4	0.33 × 0.26 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
ω/2θ scans	h = 0→27
Absorption correction: empirical (using intensity measurements) ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.732, Tmax = 0.810	l = −12→12
3891 measured reflections	3 standard reflections every 120 reflections
3891 independent reflections	intensity decay: 1.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.217	w = 1/[σ^2(Fo^2) + (0.1078P)^2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
3891 reflections	Δρmax = 0.77 e Å^−3
316 parameters	Δρmin = −0.52 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1766 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (4)

Special details

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

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

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

	x	y	z	Uiso*/Ueq
Ni	0.42068 (4)	0.64121 (12)	0.5000	0.0234 (3)
S1	0.33028 (12)	1.0928 (4)	0.5843 (3)	0.0442 (7)
S2	0.32505 (11)	0.6448 (3)	0.1302 (3)	0.0407 (7)
N1	0.3782 (3)	0.8445 (8)	0.5259 (8)	0.0260 (19)
N2	0.4074 (3)	0.9404 (11)	0.7155 (8)	0.037 (2)
H2A	0.4298	0.8671	0.7296	0.045*
H2B	0.4046	1.0105	0.7681	0.045*
N3	0.3731 (3)	0.6545 (8)	0.3411 (7)	0.0214 (17)
N4	0.3922 (3)	0.4376 (9)	0.2348 (8)	0.0312 (19)
H4A	0.4115	0.4022	0.2950	0.037*
H4B	0.3881	0.3870	0.1689	0.037*
N5	0.4941 (3)	−0.2617 (9)	0.4081 (8)	0.0295 (19)
H5A	0.5262	−0.3045	0.4363	0.035*
H5B	0.4917	−0.2807	0.3274	0.035*
N6	0.3534 (3)	0.5133 (10)	0.5959 (8)	0.0306 (18)
H6A	0.3576	0.4174	0.5774	0.037*
H6B	0.3583	0.5233	0.6771	0.037*
O1	0.4540 (3)	0.4355 (7)	0.4567 (7)	0.0312 (16)
O2	0.5111 (3)	0.3925 (9)	0.6155 (8)	0.046 (2)
O3	0.1260 (3)	0.7145 (10)	0.3235 (8)	0.049 (2)
O4	0.1179 (2)	0.8499 (8)	0.4894 (8)	0.0381 (16)
O5	0.4673 (3)	0.6481 (7)	0.6604 (6)	0.0275 (15)
H5C	0.4942	0.5971	0.6806	0.041*
H5D	0.4463	0.6327	0.7213	0.041*
C1	0.3771 (4)	0.9453 (11)	0.6121 (9)	0.028 (2)
C2	0.3122 (4)	1.0087 (13)	0.4467 (10)	0.040 (3)
H2	0.2858	1.0455	0.3911	0.048*
C3	0.3418 (4)	0.8828 (11)	0.4319 (11)	0.031 (2)
C4	0.3405 (4)	0.7841 (12)	0.3303 (10)	0.031 (2)
C5	0.3125 (4)	0.7986 (13)	0.2234 (11)	0.041 (3)
H5	0.2897	0.8786	0.2021	0.050*
C6	0.3687 (3)	0.5711 (11)	0.2438 (9)	0.026 (2)
C11	0.4865 (4)	0.3548 (11)	0.5186 (10)	0.029 (2)
C12	0.4935 (3)	0.1944 (11)	0.4787 (10)	0.030 (2)
C13	0.4611 (4)	0.1371 (11)	0.3872 (10)	0.031 (2)
H13	0.4363	0.1977	0.3437	0.038*
C14	0.4650 (4)	−0.0134 (12)	0.3577 (10)	0.031 (2)
H14	0.4446	−0.0500	0.2913	0.038*
C15	0.4983 (4)	−0.1068 (11)	0.4254 (9)	0.029 (2)
C16	0.5323 (4)	−0.0466 (11)	0.5171 (10)	0.032 (2)
H16	0.5564	−0.1072	0.5624	0.038*
C17	0.5304 (4)	0.1026 (12)	0.5414 (9)	0.030 (2)
H17	0.5544	0.1419	0.6009	0.036*
C21	0.1417 (4)	0.7487 (12)	0.4264 (9)	0.029 (2)
C22	0.1934 (4)	0.6732 (10)	0.4820 (10)	0.029 (2)
C23	0.2189 (4)	0.5548 (12)	0.4209 (9)	0.032 (2)
H23	0.2012	0.5142	0.3525	0.039*
C24	0.2704 (4)	0.4978 (13)	0.4620 (10)	0.039 (3)
H24	0.2876	0.4197	0.4211	0.047*
C25	0.2961 (4)	0.5585 (12)	0.5646 (9)	0.031 (2)
C26	0.2697 (4)	0.6674 (13)	0.6276 (10)	0.038 (3)
H26	0.2864	0.7031	0.6989	0.046*
C27	0.2183 (4)	0.7267 (12)	0.5882 (11)	0.035 (2)
H27	0.2008	0.8016	0.6324	0.042*
O1W	0.3927 (3)	0.5971 (10)	0.8529 (8)	0.055 (2)
H1A	0.4089	0.5153	0.8790	0.083*
H1B	0.3679	0.6317	0.9104	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0213 (5)	0.0243 (6)	0.0246 (6)	0.0012 (4)	−0.0019 (5)	−0.0022 (6)
S1	0.0435 (14)	0.0443 (18)	0.0449 (16)	0.0167 (13)	−0.0060 (12)	−0.0128 (14)
S2	0.0420 (14)	0.0494 (18)	0.0308 (14)	0.0087 (12)	−0.0126 (11)	−0.0073 (13)
N1	0.024 (3)	0.017 (4)	0.037 (5)	0.006 (3)	−0.001 (3)	−0.004 (4)
N2	0.046 (5)	0.035 (5)	0.030 (5)	0.009 (4)	−0.009 (4)	−0.007 (4)
N3	0.026 (3)	0.012 (4)	0.026 (4)	0.002 (3)	−0.003 (3)	−0.005 (3)
N4	0.042 (4)	0.025 (5)	0.026 (4)	−0.004 (4)	−0.003 (4)	−0.009 (4)
N5	0.021 (4)	0.030 (5)	0.037 (5)	−0.004 (3)	0.004 (3)	−0.004 (4)
N6	0.031 (4)	0.028 (5)	0.034 (5)	−0.003 (3)	0.000 (3)	0.004 (4)
O1	0.035 (3)	0.018 (4)	0.041 (4)	0.004 (3)	−0.001 (3)	−0.001 (3)
O2	0.051 (4)	0.043 (5)	0.045 (5)	0.011 (4)	−0.024 (4)	−0.019 (4)
O3	0.036 (3)	0.066 (6)	0.045 (5)	0.010 (4)	−0.012 (3)	−0.031 (5)
O4	0.036 (3)	0.045 (4)	0.032 (4)	0.004 (3)	0.002 (4)	−0.011 (4)
O5	0.032 (3)	0.027 (4)	0.023 (4)	0.003 (3)	−0.003 (3)	0.000 (3)
C1	0.023 (4)	0.027 (6)	0.034 (6)	−0.004 (4)	0.002 (4)	−0.006 (4)
C2	0.038 (5)	0.043 (7)	0.041 (6)	0.019 (5)	−0.009 (4)	−0.005 (5)
C3	0.026 (5)	0.024 (6)	0.044 (6)	0.003 (4)	−0.010 (4)	−0.001 (5)
C4	0.024 (5)	0.031 (6)	0.038 (6)	0.008 (4)	0.004 (4)	0.004 (5)
C5	0.042 (6)	0.040 (6)	0.042 (6)	0.020 (5)	−0.020 (5)	−0.013 (5)
C6	0.018 (4)	0.026 (5)	0.034 (6)	0.003 (4)	0.003 (4)	0.003 (5)
C11	0.026 (4)	0.027 (5)	0.034 (7)	−0.004 (4)	0.002 (4)	0.004 (4)
C12	0.022 (4)	0.029 (5)	0.038 (6)	−0.007 (4)	−0.001 (4)	0.005 (4)
C13	0.032 (5)	0.024 (6)	0.038 (6)	0.006 (4)	0.007 (4)	−0.002 (5)
C14	0.022 (4)	0.034 (6)	0.038 (6)	−0.004 (4)	−0.004 (4)	−0.013 (5)
C15	0.020 (4)	0.033 (6)	0.035 (6)	−0.008 (4)	0.010 (4)	−0.011 (5)
C16	0.029 (4)	0.031 (6)	0.035 (6)	−0.002 (4)	−0.004 (4)	0.008 (5)
C17	0.028 (5)	0.034 (6)	0.027 (5)	−0.007 (4)	−0.009 (4)	0.005 (4)
C21	0.027 (4)	0.034 (6)	0.027 (5)	−0.015 (4)	0.001 (4)	0.001 (5)
C22	0.030 (4)	0.024 (5)	0.033 (6)	−0.004 (4)	0.009 (4)	−0.008 (4)
C23	0.038 (5)	0.036 (6)	0.023 (5)	0.004 (5)	0.001 (4)	−0.013 (5)
C24	0.027 (5)	0.043 (7)	0.048 (7)	−0.002 (5)	0.006 (4)	0.002 (5)
C25	0.024 (4)	0.041 (6)	0.030 (6)	−0.006 (4)	0.006 (4)	0.011 (5)
C26	0.024 (5)	0.056 (7)	0.034 (6)	−0.013 (5)	−0.001 (4)	0.002 (5)
C27	0.028 (5)	0.032 (6)	0.044 (6)	0.006 (4)	0.008 (4)	−0.007 (5)
O1W	0.063 (5)	0.060 (6)	0.042 (5)	−0.008 (4)	0.011 (4)	0.006 (4)

Geometric parameters (Å, º)

Ni—O1	2.078 (7)	O5—H5D	0.8398
Ni—O5	2.066 (6)	C2—C3	1.345 (14)
Ni—N1	2.116 (7)	C2—H2	0.9300
Ni—N3	2.066 (7)	C3—C4	1.428 (15)
Ni—N5^i	2.176 (7)	C4—C5	1.346 (15)
Ni—N6	2.218 (8)	C5—H5	0.9300
S1—C2	1.739 (11)	C11—C12	1.529 (14)
S1—C1	1.756 (10)	C12—C13	1.357 (15)
S2—C6	1.741 (10)	C12—C17	1.383 (14)
S2—C5	1.754 (11)	C13—C14	1.408 (14)
N1—C1	1.313 (13)	C13—H13	0.9300
N1—C3	1.379 (13)	C14—C15	1.369 (15)
N2—C1	1.335 (13)	C14—H14	0.9300
N2—H2A	0.8600	C15—C16	1.392 (14)
N2—H2B	0.8600	C16—C17	1.381 (14)
N3—C6	1.309 (13)	C16—H16	0.9300
N3—C4	1.407 (12)	C17—H17	0.9300
N4—C6	1.335 (12)	C21—C22	1.517 (14)
N4—H4A	0.8600	C22—C27	1.387 (15)
N4—H4B	0.8600	C22—C23	1.399 (13)
N5—C15	1.422 (13)	C23—C24	1.387 (13)
N5—H5A	0.9000	C23—H23	0.9300
N5—H5B	0.9000	C24—C25	1.386 (14)
N6—C25	1.442 (12)	C24—H24	0.9300
N6—H6A	0.9000	C25—C26	1.355 (16)
N6—H6B	0.9000	C26—C27	1.385 (14)
O1—C11	1.254 (11)	C26—H26	0.9300
O2—C11	1.254 (13)	C27—H27	0.9300
O3—C21	1.224 (12)	O1W—H1A	0.8816
O4—C21	1.276 (12)	O1W—H1B	0.9118
O5—H5C	0.8112
O5—Ni—N3	174.9 (3)	N1—C3—C4	115.7 (8)
O5—Ni—O1	91.3 (3)	C5—C4—N3	114.7 (9)
N3—Ni—O1	93.6 (3)	C5—C4—C3	128.6 (10)
O5—Ni—N1	96.2 (3)	N3—C4—C3	116.7 (9)
N3—Ni—N1	79.0 (3)	C4—C5—S2	110.1 (8)
O1—Ni—N1	172.2 (3)	C4—C5—H5	124.9
O5—Ni—N5^i	87.9 (3)	S2—C5—H5	124.9
N3—Ni—N5^i	90.8 (3)	N3—C6—N4	123.5 (9)
O1—Ni—N5^i	87.9 (3)	N3—C6—S2	113.8 (7)
N1—Ni—N5^i	94.5 (3)	N4—C6—S2	122.6 (8)
O5—Ni—N6	89.4 (3)	O1—C11—O2	125.1 (10)
N3—Ni—N6	92.6 (3)	O1—C11—C12	117.9 (9)
O1—Ni—N6	84.4 (3)	O2—C11—C12	116.8 (9)
N1—Ni—N6	93.5 (3)	C13—C12—C17	118.8 (9)
N5^i—Ni—N6	171.8 (3)	C13—C12—C11	121.0 (8)
C2—S1—C1	88.0 (5)	C17—C12—C11	120.0 (9)
C6—S2—C5	89.4 (5)	C12—C13—C14	120.4 (10)
C1—N1—C3	110.2 (8)	C12—C13—H13	119.8
C1—N1—Ni	135.5 (7)	C14—C13—H13	119.8
C3—N1—Ni	114.2 (6)	C15—C14—C13	120.9 (9)
C1—N2—H2A	120.0	C15—C14—H14	119.5
C1—N2—H2B	120.0	C13—C14—H14	119.5
H2A—N2—H2B	120.0	C14—C15—C16	118.1 (9)
C6—N3—C4	111.9 (8)	C14—C15—N5	120.1 (8)
C6—N3—Ni	133.7 (6)	C16—C15—N5	121.6 (9)
C4—N3—Ni	114.2 (6)	C17—C16—C15	120.4 (9)
C6—N4—H4A	120.0	C17—C16—H16	119.8
C6—N4—H4B	120.0	C15—C16—H16	119.8
H4A—N4—H4B	120.0	C16—C17—C12	121.1 (9)
C15—N5—Ni^ii	113.2 (5)	C16—C17—H17	119.5
C15—N5—H5A	108.9	C12—C17—H17	119.5
Ni^ii—N5—H5A	108.9	O3—C21—O4	123.3 (10)
C15—N5—H5B	108.9	O3—C21—C22	119.4 (9)
Ni^ii—N5—H5B	108.9	O4—C21—C22	117.2 (9)
H5A—N5—H5B	107.8	C27—C22—C23	119.3 (9)
C25—N6—Ni	113.4 (6)	C27—C22—C21	120.8 (9)
C25—N6—H6A	108.9	C23—C22—C21	119.7 (9)
Ni—N6—H6A	108.9	C24—C23—C22	120.2 (9)
C25—N6—H6B	108.9	C24—C23—H23	119.9
Ni—N6—H6B	108.9	C22—C23—H23	119.9
H6A—N6—H6B	107.7	C25—C24—C23	119.4 (10)
C11—O1—Ni	129.0 (7)	C25—C24—H24	120.3
Ni—O5—H5C	128.5	C23—C24—H24	120.3
Ni—O5—H5D	110.9	C26—C25—C24	120.2 (9)
H5C—O5—H5D	98.2	C26—C25—N6	120.7 (9)
N1—C1—N2	125.0 (9)	C24—C25—N6	118.8 (9)
N1—C1—S1	114.8 (7)	C25—C26—C27	121.4 (10)
N2—C1—S1	120.2 (8)	C25—C26—H26	119.3
C3—C2—S1	110.6 (8)	C27—C26—H26	119.3
C3—C2—H2	124.7	C26—C27—C22	119.3 (10)
S1—C2—H2	124.7	C26—C27—H27	120.4
C2—C3—N1	116.2 (10)	C22—C27—H27	120.4
C2—C3—C4	128.1 (10)	H1A—O1W—H1B	109.9
O5—Ni—N1—C1	−2.3 (9)	N1—C3—C4—N3	4.5 (13)
N3—Ni—N1—C1	179.5 (10)	N3—C4—C5—S2	1.0 (12)
N5^i—Ni—N1—C1	−90.7 (9)	C3—C4—C5—S2	−179.6 (9)
N6—Ni—N1—C1	87.4 (9)	C6—S2—C5—C4	−0.5 (9)
O5—Ni—N1—C3	178.9 (7)	C4—N3—C6—N4	−175.2 (9)
N3—Ni—N1—C3	0.7 (7)	Ni—N3—C6—N4	8.9 (14)
N5^i—Ni—N1—C3	90.6 (7)	C4—N3—C6—S2	0.7 (10)
N6—Ni—N1—C3	−91.3 (7)	Ni—N3—C6—S2	−175.2 (5)
O1—Ni—N3—C6	−4.9 (9)	C5—S2—C6—N3	−0.1 (8)
N1—Ni—N3—C6	177.5 (9)	C5—S2—C6—N4	175.8 (9)
N5^i—Ni—N3—C6	83.1 (9)	Ni—O1—C11—O2	−9.3 (14)
N6—Ni—N3—C6	−89.4 (9)	Ni—O1—C11—C12	166.1 (6)
O1—Ni—N3—C4	179.3 (6)	O1—C11—C12—C13	−6.7 (14)
N1—Ni—N3—C4	1.7 (6)	O2—C11—C12—C13	169.1 (10)
N5^i—Ni—N3—C4	−92.8 (7)	O1—C11—C12—C17	177.6 (9)
N6—Ni—N3—C4	94.7 (6)	O2—C11—C12—C17	−6.6 (13)
O5—Ni—N6—C25	138.5 (7)	C17—C12—C13—C14	0.6 (14)
N3—Ni—N6—C25	−36.7 (7)	C11—C12—C13—C14	−175.2 (9)
O1—Ni—N6—C25	−130.1 (7)	C12—C13—C14—C15	4.3 (15)
N1—Ni—N6—C25	42.4 (7)	C13—C14—C15—C16	−5.7 (14)
O5—Ni—O1—C11	4.5 (8)	C13—C14—C15—N5	169.1 (8)
N3—Ni—O1—C11	−177.1 (8)	Ni^ii—N5—C15—C14	−79.4 (10)
N5^i—Ni—O1—C11	92.3 (8)	Ni^ii—N5—C15—C16	95.2 (8)
N6—Ni—O1—C11	−84.8 (8)	C14—C15—C16—C17	2.4 (14)
C3—N1—C1—N2	179.7 (9)	N5—C15—C16—C17	−172.3 (9)
Ni—N1—C1—N2	0.9 (16)	C15—C16—C17—C12	2.4 (15)
C3—N1—C1—S1	1.0 (11)	C13—C12—C17—C16	−3.9 (14)
Ni—N1—C1—S1	−177.8 (5)	C11—C12—C17—C16	171.9 (9)
C2—S1—C1—N1	−0.2 (8)	O3—C21—C22—C27	168.4 (10)
C2—S1—C1—N2	−179.0 (9)	O4—C21—C22—C27	−9.0 (13)
C1—S1—C2—C3	−0.7 (9)	O3—C21—C22—C23	−6.8 (14)
S1—C2—C3—N1	1.4 (13)	O4—C21—C22—C23	175.7 (9)
S1—C2—C3—C4	−178.1 (9)	C27—C22—C23—C24	−4.0 (15)
C1—N1—C3—C2	−1.5 (13)	C21—C22—C23—C24	171.3 (8)
Ni—N1—C3—C2	177.6 (8)	C22—C23—C24—C25	0.6 (15)
C1—N1—C3—C4	178.0 (8)	C23—C24—C25—C26	3.3 (15)
Ni—N1—C3—C4	−2.9 (11)	C23—C24—C25—N6	−171.0 (9)
C6—N3—C4—C5	−1.1 (13)	Ni—N6—C25—C26	−88.4 (10)
Ni—N3—C4—C5	175.6 (8)	Ni—N6—C25—C24	85.8 (9)
C6—N3—C4—C3	179.4 (8)	C24—C25—C26—C27	−3.7 (16)
Ni—N3—C4—C3	−3.8 (11)	N6—C25—C26—C27	170.5 (9)
C2—C3—C4—C5	5 (2)	C25—C26—C27—C22	0.1 (16)
N1—C3—C4—C5	−174.9 (11)	C23—C22—C27—C26	3.7 (15)
C2—C3—C4—N3	−176.1 (10)	C21—C22—C27—C26	−171.6 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5	0.86	2.30	3.061 (11)	147
N2—H2B···O3^iii	0.86	2.08	2.863 (13)	152
N4—H4A···O1	0.86	2.05	2.823 (11)	149
N4—H4B···O4^iv	0.86	1.99	2.808 (12)	157
N5—H5A···O4^v	0.90	2.26	3.133 (9)	163
N5—H5B···O2^vi	0.90	2.53	3.413 (12)	167
N6—H6B···O1W	0.90	2.19	3.052 (12)	161
O5—H5C···O2	0.81	2.03	2.584 (10)	125
O5—H5D···O1W	0.84	1.93	2.772 (11)	175
O1W—H1A···O4^vii	0.88	2.03	2.707 (12)	133
O1W—H1B···S2^viii	0.91	2.60	3.446 (9)	154

Symmetry codes: (iii) −x+1/2, y+1/2, z+1/2; (iv) −x+1/2, y−1/2, z−1/2; (v) x+1/2, −y+1/2, z; (vi) −x+1, −y, z−1/2; (vii) −x+1/2, y−1/2, z+1/2; (viii) x, y, z+1.