catena-Poly[[[aqua­(di-2-pyridylamine-κ²N,N′)nickel(II)]-μ-4-amino­benzoato-κ³O,O′:N] chloride trihydrate]

The title complex, [Ni(C₇H₆NO₂)(C₁₀H₉N₃)(H₂O)]Cl·3H₂O, has a zigzag polymeric structure. Each Ni ion is bonded to two N atoms from a di-2-pyridylamine (BPA) ligand, two O atoms from a 4-amino­benzoic acid (p-AB) ligand, one water O atom and one amino N atom from another p-AB ligand. This is the first example of an aromatic amino N acting in a bridging role linking adjacent mol­ecules to form a chain structure. Three water mol­ecules and one chloride ion are also in the asymmetric unit. There are several hydrogen bonds stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.035
• wR factor = 0.086
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT417_ALERT_2_C Short Inter D-H..H-D       H18    ..  H20     ..       2.11 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C17 H23 Cl1 N4 Ni1 O6
            Atom count from _chemical_formula_moiety:C17 H19 Cl3 N4 Ni1 O4

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 2003); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999)'; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

catena-Poly[[[aqua(di-2-pyridylamine-κ²N:N')nickel(II)]-µ-4-aminobenzoato- κ³O,O':N] chloride trihydrate]

Crystal data

[Ni(C7H6NO2)(C10H9N3)(H2O)]Cl·3H2O	F(000) = 984.00
Mr = 473.53	Dx = 1.573 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -p_2yn	Cell parameters from 12978 reflections
a = 11.28 (1) Å	θ = 3.3–27.5°
b = 14.51 (1) Å	µ = 1.15 mm^−1
c = 12.22 (2) Å	T = 123 K
β = 90.11 (5)°	Platelet, blue
V = 2000 (4) Å^3	0.10 × 0.10 × 0.05 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2151 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.062
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.899, Tmax = 0.944	k = −18→18
19036 measured reflections	l = −15→15
4570 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0449P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max < 0.001
S = 0.84	Δρmax = 0.37 e Å^−3
4570 reflections	Δρmin = −0.59 e Å^−3
262 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Ni1	−0.00057 (3)	0.11394 (3)	0.18110 (3)	0.01417 (10)
Cl1	0.29202 (6)	−0.09895 (6)	0.22434 (6)	0.02572 (19)
O1	0.03527 (16)	0.13104 (14)	0.01290 (16)	0.0168 (5)
O2	0.17737 (16)	0.14664 (13)	0.13481 (16)	0.0166 (4)
O3	0.03765 (16)	−0.02726 (14)	0.16894 (16)	0.0185 (5)
H16	0.0165	−0.0517	0.1040	0.028*
H17	0.1164	−0.0353	0.1783	0.028*
O4	0.13425 (17)	0.45499 (15)	0.04175 (16)	0.0227 (5)
H18	0.0789	0.4135	0.0219	0.034*
H19	0.1498	0.4490	0.1136	0.034*
O5	0.06732 (18)	0.64091 (14)	0.02870 (18)	0.0254 (5)
H20	0.0976	0.5833	0.0343	0.038*
H21	0.0773	0.6685	0.0952	0.038*
O6	0.12560 (19)	0.72295 (15)	0.23024 (19)	0.0307 (6)
H22	0.1700	0.6853	0.2738	0.046*
H23	0.1631	0.7792	0.2293	0.046*
N1	−0.1758 (2)	0.08599 (16)	0.18011 (19)	0.0151 (5)
N2	−0.1929 (2)	0.07272 (17)	0.3736 (2)	0.0180 (6)
H5	−0.2428	0.0592	0.4242	0.022*
N3	0.0102 (2)	0.10582 (17)	0.34487 (18)	0.0153 (5)
N4	0.4693 (2)	0.23637 (17)	−0.30573 (19)	0.0175 (6)
H14	0.4504	0.2091	−0.3709	0.021*
H15	0.5395	0.1997	−0.2929	0.021*
C1	−0.2318 (3)	0.0852 (2)	0.0817 (2)	0.0188 (7)
H1	−0.1875	0.0988	0.0196	0.023*
C2	−0.3500 (3)	0.0654 (2)	0.0685 (3)	0.0205 (7)
H2	−0.3850	0.0665	−0.0005	0.025*
C3	−0.4161 (3)	0.0435 (2)	0.1613 (3)	0.0210 (7)
H3	−0.4961	0.0285	0.1552	0.025*
C4	−0.3611 (3)	0.0445 (2)	0.2621 (3)	0.0193 (7)
H4	−0.4036	0.0299	0.3249	0.023*
C5	−0.2407 (2)	0.06778 (19)	0.2694 (2)	0.0149 (6)
C6	−0.0816 (2)	0.09489 (19)	0.4131 (2)	0.0162 (6)
C7	−0.0701 (2)	0.1049 (2)	0.5266 (2)	0.0184 (6)
H6	−0.1357	0.0983	0.5719	0.022*
C8	0.0392 (3)	0.1247 (2)	0.5702 (2)	0.0213 (7)
H7	0.0486	0.1320	0.6454	0.026*
C9	0.1359 (3)	0.1336 (2)	0.5001 (3)	0.0223 (7)
H8	0.2112	0.1459	0.5277	0.027*
C10	0.1179 (2)	0.1240 (2)	0.3906 (2)	0.0186 (6)
H9	0.1828	0.1301	0.3443	0.022*
C11	0.3880 (2)	0.20962 (19)	−0.2221 (2)	0.0150 (6)
C12	0.2664 (2)	0.2105 (2)	−0.2419 (2)	0.0169 (6)
H10	0.2381	0.2245	−0.3114	0.020*
C13	0.1873 (3)	0.19043 (19)	−0.1584 (2)	0.0171 (6)
H11	0.1062	0.1910	−0.1724	0.021*
C14	0.2285 (2)	0.16957 (19)	−0.0540 (2)	0.0154 (6)
C15	0.3509 (2)	0.16937 (19)	−0.0339 (2)	0.0161 (6)
H12	0.3794	0.1567	0.0360	0.019*
C16	0.4294 (2)	0.18796 (19)	−0.1178 (2)	0.0170 (6)
H13	0.5106	0.1860	−0.1044	0.020*
C17	0.1447 (2)	0.14819 (19)	0.0357 (2)	0.0163 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01290 (17)	0.01905 (19)	0.01057 (19)	−0.00071 (18)	0.00286 (13)	−0.00025 (17)
Cl1	0.0203 (4)	0.0378 (5)	0.0191 (4)	0.0051 (3)	0.0005 (3)	−0.0005 (3)
O1	0.0145 (10)	0.0237 (12)	0.0122 (11)	−0.0021 (9)	0.0033 (8)	−0.0016 (8)
O2	0.0181 (10)	0.0197 (11)	0.0119 (11)	−0.0026 (9)	0.0032 (8)	−0.0009 (8)
O3	0.0160 (10)	0.0231 (12)	0.0164 (12)	0.0000 (9)	−0.0003 (9)	−0.0039 (9)
O4	0.0183 (11)	0.0331 (13)	0.0166 (12)	−0.0032 (10)	0.0012 (9)	−0.0013 (10)
O5	0.0258 (12)	0.0269 (12)	0.0236 (13)	0.0018 (10)	0.0001 (10)	−0.0002 (9)
O6	0.0270 (12)	0.0370 (14)	0.0280 (14)	0.0025 (11)	−0.0025 (10)	−0.0020 (11)
N1	0.0140 (12)	0.0193 (13)	0.0120 (13)	0.0006 (10)	0.0023 (10)	−0.0008 (10)
N2	0.0141 (12)	0.0293 (15)	0.0107 (13)	−0.0028 (11)	0.0043 (10)	0.0019 (11)
N3	0.0159 (12)	0.0187 (13)	0.0114 (13)	−0.0002 (11)	0.0017 (10)	0.0006 (10)
N4	0.0185 (13)	0.0220 (14)	0.0120 (13)	0.0023 (11)	0.0057 (10)	−0.0001 (10)
C1	0.0198 (15)	0.0249 (16)	0.0117 (15)	0.0013 (13)	0.0024 (12)	−0.0002 (12)
C2	0.0195 (15)	0.0272 (18)	0.0147 (16)	−0.0012 (14)	−0.0057 (12)	−0.0015 (13)
C3	0.0139 (14)	0.0250 (17)	0.0241 (18)	−0.0015 (13)	−0.0022 (12)	−0.0008 (13)
C4	0.0159 (14)	0.0253 (17)	0.0167 (16)	−0.0036 (13)	0.0031 (12)	−0.0008 (13)
C5	0.0160 (14)	0.0173 (15)	0.0115 (15)	−0.0012 (13)	0.0002 (11)	0.0000 (11)
C6	0.0156 (14)	0.0189 (16)	0.0140 (15)	−0.0022 (12)	0.0018 (11)	0.0001 (12)
C7	0.0161 (14)	0.0248 (17)	0.0144 (15)	−0.0001 (14)	0.0041 (11)	0.0017 (13)
C8	0.0238 (15)	0.0264 (18)	0.0136 (16)	0.0003 (15)	0.0015 (12)	−0.0026 (13)
C9	0.0163 (14)	0.0281 (18)	0.0224 (18)	−0.0042 (13)	0.0002 (12)	−0.0030 (13)
C10	0.0147 (13)	0.0243 (17)	0.0169 (16)	−0.0027 (13)	0.0029 (11)	0.0001 (13)
C11	0.0167 (14)	0.0145 (14)	0.0139 (15)	−0.0017 (12)	0.0068 (12)	−0.0020 (11)
C12	0.0203 (15)	0.0203 (16)	0.0100 (15)	−0.0016 (13)	−0.0013 (12)	−0.0003 (12)
C13	0.0149 (14)	0.0193 (16)	0.0172 (16)	−0.0023 (13)	0.0024 (12)	−0.0022 (12)
C14	0.0158 (14)	0.0124 (14)	0.0180 (16)	−0.0015 (12)	0.0055 (12)	−0.0015 (12)
C15	0.0183 (14)	0.0142 (14)	0.0158 (16)	−0.0002 (12)	0.0002 (12)	0.0014 (12)
C16	0.0153 (14)	0.0167 (16)	0.0188 (17)	0.0010 (12)	0.0030 (12)	0.0003 (12)
C17	0.0170 (14)	0.0128 (14)	0.0190 (17)	0.0009 (12)	0.0025 (12)	−0.0006 (12)

Geometric parameters (Å, º)

Ni1—N3	2.007 (3)	C1—C2	1.372 (4)
Ni1—N1	2.016 (3)	C1—H1	0.9300
Ni1—O3	2.099 (3)	C2—C3	1.395 (4)
Ni1—O1	2.109 (3)	C2—H2	0.9300
Ni1—O2	2.139 (3)	C3—C4	1.377 (4)
Ni1—N4^i	2.204 (3)	C3—H3	0.9300
Ni1—C17	2.469 (4)	C4—C5	1.402 (4)
O1—C17	1.288 (4)	C4—H4	0.9300
O2—C17	1.265 (4)	C6—C7	1.401 (4)
O3—H16	0.8999	C7—C8	1.371 (4)
O3—H17	0.9028	C7—H6	0.9300
O4—H18	0.8997	C8—C9	1.394 (4)
O4—H19	0.8989	C8—H7	0.9300
O5—H20	0.9048	C9—C10	1.361 (4)
O5—H21	0.9120	C9—H8	0.9300
O6—H22	0.9118	C10—H9	0.9300
O6—H23	0.9196	C11—C12	1.391 (4)
N1—C5	1.341 (4)	C11—C16	1.393 (4)
N1—C1	1.357 (4)	C12—C13	1.387 (4)
N2—C6	1.381 (4)	C12—H10	0.9300
N2—C5	1.383 (4)	C13—C14	1.390 (4)
N2—H5	0.8600	C13—H11	0.9300
N3—C6	1.339 (4)	C14—C15	1.401 (4)
N3—C10	1.361 (4)	C14—C17	1.481 (4)
N4—C11	1.428 (4)	C15—C16	1.382 (4)
N4—Ni1	2.204 (3)	C15—H12	0.9300
N4—H14	0.9139	C16—H13	0.9300
N4—H15	0.9665
Cl1···O4	3.075 (4)	C5···Cl1	3.542 (5)
Cl1···O6	3.195 (3)	C5···C12	3.222 (5)
Cl1···N4	3.492 (4)	C6···C7	3.445 (5)
O1···O3	2.805 (4)	C6···C8	3.228 (5)
O1···O5	3.542 (4)	C6···C9	3.535 (5)
O1···N4	3.028 (4)	C6···Cl1	3.300 (5)
O2···O6	2.977 (4)	C6···C15	3.564 (5)
O2···N4	2.987 (4)	C6···C16	3.176 (5)
O3···O1	2.805 (4)	C7···O4	3.451 (5)
O3···C8	3.593 (5)	C7···N3	3.502 (5)
O3···C13	3.472 (4)	C7···C6	3.445 (5)
O4···Cl1	3.075 (4)	C7···C7	3.492 (6)
O4···O4	3.450 (5)	C7···C8	3.553 (5)
O4···O5	2.800 (4)	C7···C9	3.555 (5)
O4···N2	2.863 (4)	C7···C10	3.514 (5)
O4···C4	3.417 (6)	C7···C15	3.473 (5)
O4···C7	3.451 (5)	C7···C16	3.484 (5)
O5···O1	3.542 (4)	C8···O3	3.593 (5)
O5···O4	2.800 (4)	C8···N2	3.417 (5)
O5···N4	3.083 (5)	C8···N3	3.546 (5)
O5···C9	3.367 (5)	C8···C6	3.228 (5)
O6···Cl1	3.195 (3)	C8···C7	3.553 (5)
O6···O2	2.977 (4)	C9···O5	3.367 (5)
O6···C10	3.553 (5)	C9···N2	3.428 (5)
N1···N4	3.057 (4)	C9···C6	3.535 (5)
N1···Cl1	3.276 (5)	C9···C7	3.555 (5)
N1···C12	3.171 (5)	C10···O6	3.553 (5)
N2···O4	2.863 (4)	C10···N4	3.556 (5)
N2···C8	3.417 (5)	C10···C7	3.514 (5)
N2···C9	3.428 (5)	C10···C16	3.460 (5)
N2···Cl1	3.489 (5)	Cl1···N1	3.276 (5)
N2···C12	3.477 (5)	Cl1···N2	3.489 (5)
N3···N4	2.973 (4)	Cl1···N3	3.120 (4)
N3···C7	3.502 (5)	Cl1···C5	3.542 (5)
N3···C8	3.546 (5)	Cl1···C6	3.300 (5)
N3···Cl1	3.120 (4)	C12···N1	3.171 (5)
N3···C16	3.161 (5)	C12···N2	3.477 (5)
N4···Cl1	3.492 (4)	C12···C5	3.222 (5)
N4···O1	3.028 (4)	C13···O3	3.472 (4)
N4···O2	2.987 (4)	C15···C2	3.432 (5)
N4···O5	3.083 (5)	C15···C3	3.537 (5)
N4···N1	3.057 (4)	C15···C6	3.564 (5)
N4···N3	2.973 (4)	C15···C7	3.473 (5)
N4···C10	3.556 (5)	C16···N3	3.161 (5)
N4···C17	3.238 (4)	C16···C3	3.404 (5)
C2···C15	3.432 (5)	C16···C6	3.176 (5)
C3···C15	3.537 (5)	C16···C7	3.484 (5)
C3···C16	3.404 (5)	C16···C10	3.460 (5)
C4···O4	3.417 (6)	C17···N4	3.238 (4)
N3—Ni1—N1	92.95 (11)	C3—C2—H2	120.9
N3—Ni1—O3	90.07 (9)	C4—C3—C2	118.9 (3)
N1—Ni1—O3	90.26 (9)	C4—C3—H3	120.6
N3—Ni1—O1	165.08 (8)	C2—C3—H3	120.6
N1—Ni1—O1	101.97 (10)	C3—C4—C5	119.6 (3)
O3—Ni1—O1	90.35 (8)	C3—C4—H4	120.2
N3—Ni1—O2	102.81 (10)	C5—C4—H4	120.2
N1—Ni1—O2	164.24 (9)	N1—C5—N2	121.7 (3)
O3—Ni1—O2	90.29 (8)	N1—C5—C4	121.8 (3)
O1—Ni1—O2	62.27 (8)	N2—C5—C4	116.5 (3)
N3—Ni1—N4^i	89.66 (9)	N3—C6—N2	120.9 (3)
N1—Ni1—N4^i	92.71 (10)	N3—C6—C7	122.2 (3)
O3—Ni1—N4^i	177.02 (8)	N2—C6—C7	116.9 (3)
O1—Ni1—N4^i	89.14 (8)	C8—C7—C6	119.2 (3)
O2—Ni1—N4^i	86.88 (9)	C8—C7—H6	120.4
N3—Ni1—C17	133.63 (11)	C6—C7—H6	120.4
N1—Ni1—C17	133.41 (11)	C7—C8—C9	119.0 (3)
O3—Ni1—C17	90.51 (9)	C7—C8—H7	120.5
O1—Ni1—C17	31.45 (9)	C9—C8—H7	120.5
O2—Ni1—C17	30.83 (9)	C10—C9—C8	118.6 (3)
N4^i—Ni1—C17	87.52 (9)	C10—C9—H8	120.7
C17—O1—Ni1	89.86 (18)	C8—C9—H8	120.7
C17—O2—Ni1	89.15 (18)	C9—C10—N3	123.7 (3)
Ni1—O3—H16	113.00	C9—C10—H9	118.2
Ni1—O3—H17	109.00	N3—C10—H9	118.2
H16—O3—H17	108.7136	C12—C11—C16	119.3 (3)
H18—O4—H19	109.4438	C12—C11—N4	120.5 (3)
H20—O5—H21	106.9693	C16—C11—N4	120.1 (3)
H22—O6—H23	106.7102	C13—C12—C11	120.4 (3)
C5—N1—C1	117.7 (3)	C13—C12—H10	119.8
C5—N1—Ni1	124.8 (2)	C11—C12—H10	119.8
C1—N1—Ni1	117.5 (2)	C12—C13—C14	120.4 (3)
C6—N2—C5	133.3 (3)	C12—C13—H11	119.8
C6—N2—H5	113.4	C14—C13—H11	119.8
C5—N2—H5	113.4	C13—C14—C15	119.2 (3)
C6—N3—C10	117.2 (3)	C13—C14—C17	120.8 (3)
C6—N3—Ni1	125.6 (2)	C15—C14—C17	120.0 (3)
C10—N3—Ni1	116.70 (19)	C16—C15—C14	120.1 (3)
C11—N4—Ni1	114.81 (18)	C16—C15—H12	119.9
C11—N4—H14	111.00	C14—C15—H12	119.9
Ni1—N4—H14	113.5070	C15—C16—C11	120.6 (3)
C11—N4—H15	105.00	C15—C16—H13	119.7
Ni1—N4—H15	115.2997	C11—C16—H13	119.7
H14—N4—H15	95.00	O2—C17—O1	118.7 (3)
N1—C1—C2	123.8 (3)	O2—C17—C14	121.7 (3)
N1—C1—H1	118.1	O1—C17—C14	119.5 (3)
C2—C1—H1	118.1	O2—C17—Ni1	60.02 (16)
C1—C2—C3	118.2 (3)	O1—C17—Ni1	58.69 (16)
C1—C2—H2	120.9	C14—C17—Ni1	178.1 (2)
N3—Ni1—O1—C17	1.2 (4)	C3—C4—C5—N2	176.3 (3)
N1—Ni1—O1—C17	179.25 (16)	C10—N3—C6—N2	−177.4 (3)
O3—Ni1—O1—C17	−90.41 (17)	Ni1—N3—C6—N2	10.9 (4)
O2—Ni1—O1—C17	−0.27 (15)	C10—N3—C6—C7	2.4 (4)
N3—Ni1—O2—C17	−179.34 (17)	Ni1—N3—C6—C7	−169.2 (2)
N1—Ni1—O2—C17	−1.4 (4)	C5—N2—C6—N3	−8.8 (5)
O3—Ni1—O2—C17	90.52 (16)	C5—N2—C6—C7	171.3 (3)
O1—Ni1—O2—C17	0.28 (15)	N3—C6—C7—C8	−1.4 (4)
N3—Ni1—N1—C5	−1.8 (2)	N2—C6—C7—C8	178.4 (3)
O3—Ni1—N1—C5	88.3 (2)	C6—C7—C8—C9	−0.4 (4)
O1—Ni1—N1—C5	178.7 (2)	C7—C8—C9—C10	1.1 (5)
O2—Ni1—N1—C5	−179.8 (3)	C8—C9—C10—N3	−0.1 (5)
C17—Ni1—N1—C5	179.2 (2)	C6—N3—C10—C9	−1.7 (4)
N3—Ni1—N1—C1	178.5 (2)	Ni1—N3—C10—C9	170.7 (2)
O3—Ni1—N1—C1	−91.4 (2)	C16—C11—C12—C13	0.3 (4)
O1—Ni1—N1—C1	−1.0 (2)	N4—C11—C12—C13	−175.7 (3)
O2—Ni1—N1—C1	0.6 (4)	C11—C12—C13—C14	0.2 (4)
C17—Ni1—N1—C1	−0.5 (3)	C12—C13—C14—C15	0.2 (4)
N1—Ni1—N3—C6	−5.9 (2)	C12—C13—C14—C17	179.9 (3)
O3—Ni1—N3—C6	−96.1 (2)	C13—C14—C15—C16	−1.3 (4)
O1—Ni1—N3—C6	172.2 (3)	C17—C14—C15—C16	179.0 (3)
O2—Ni1—N3—C6	173.6 (2)	C14—C15—C16—C11	1.8 (4)
C17—Ni1—N3—C6	173.1 (2)	C12—C11—C16—C15	−1.4 (4)
N1—Ni1—N3—C10	−177.5 (2)	N4—C11—C16—C15	174.6 (3)
O3—Ni1—N3—C10	92.2 (2)	Ni1—O2—C17—O1	−0.5 (3)
O1—Ni1—N3—C10	0.6 (5)	Ni1—O2—C17—C14	179.2 (2)
O2—Ni1—N3—C10	1.9 (2)	Ni1—O1—C17—O2	0.5 (3)
C17—Ni1—N3—C10	1.4 (3)	Ni1—O1—C17—C14	−179.2 (2)
C5—N1—C1—C2	−1.1 (4)	C13—C14—C17—O2	−166.1 (3)
Ni1—N1—C1—C2	178.6 (2)	C15—C14—C17—O2	13.6 (4)
N1—C1—C2—C3	−1.0 (5)	C13—C14—C17—O1	13.6 (4)
C1—C2—C3—C4	1.3 (5)	C15—C14—C17—O1	−166.7 (3)
C2—C3—C4—C5	0.3 (5)	N3—Ni1—C17—O2	0.9 (2)
C1—N1—C5—N2	−175.9 (3)	N1—Ni1—C17—O2	179.46 (14)
Ni1—N1—C5—N2	4.4 (4)	O3—Ni1—C17—O2	−89.70 (16)
C1—N1—C5—C4	2.8 (4)	O1—Ni1—C17—O2	−179.5 (3)
Ni1—N1—C5—C4	−176.9 (2)	N3—Ni1—C17—O1	−179.58 (15)
C6—N2—C5—N1	0.4 (5)	N1—Ni1—C17—O1	−1.0 (2)
C6—N2—C5—C4	−178.3 (3)	O3—Ni1—C17—O1	89.83 (16)
C3—C4—C5—N1	−2.5 (5)	O2—Ni1—C17—O1	179.5 (3)

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O4^i	0.86	2.01	2.863 (4)	172
N4—H15···Cl1^ii	0.97	2.538	3.492 (4)	169
O3—H16···O1^iii	0.90	1.93	2.805 (4)	165
O3—H17···Cl1	0.90	2.26	3.124 (4)	161
O4—H18···O5^iv	0.90	1.93	2.799 (4)	162
O4—H19···Cl1^v	0.90	2.20	3.075 (4)	165
O5—H20···O4	0.91	1.91	2.806 (4)	170
O5—H21···O6	0.91	1.91	2.811 (4)	170
O6—H22···O2^v	0.91	2.13	2.977 (4)	155
O6—H23···Cl1^vi	0.92	2.29	3.195 (3)	167

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