Poly[[(μ₃-adamantane-1,3-di­carboxyl­ato)aqua­[μ-N-(pyridin-3-yl)isonicotinamide]­nickel(II)] monohydrate], a layered coordination polymer with (4,4) topology

The title com­pound, {[Ni(C₁₂H₁₄O₄)(C₁₁H₉N₃O)(H₂O)]·H₂O}_n, contains octa­hedrally coordinated Ni^II ions ligated by adamantane-1,3-di­carboxyl­ate (adc) and N-(pyridin-3-yl)isonicotinamide (3-pina) ligands forming coordination polymer layers with a (4,4) grid topology. These diperiodic layer motifs aggregate in an AAA pattern mediated by supra­molecular C—H...O inter­actions to form the full triperiodic crystal structure of the title com­pound.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.115
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.15 Do !
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.14 Report
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range       10.0 Ratio
PLAT245_ALERT_2_C U(iso) H7B       Smaller than U(eq) C7        by      0.011 Ang   2
PLAT245_ALERT_2_C U(iso) H19       Smaller than U(eq) C19       by      0.018 Ang   2
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          5 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          2 Report
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       1.99 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Ni2       (II)      .       1.98 Info
PLAT804_ALERT_5_G Number of ARU-Code Packing Problem(s) in PLATON           1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          7 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         22 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        2.9 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXTL (Sheldrick, 2015); molecular graphics: CrystalMakerX (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[(µ₃-adamantane-1,3-dicarboxylato)aqua[µ-N-(pyridin-3-yl)isonicotinamide]nickel(II)] monohydrate]

Crystal data

[Ni(C12H14O4)(C11H9N3O)(H2O)]·H2O	Z = 2
Mr = 516.18	F(000) = 540
Triclinic, P1	Dx = 1.521 Mg m^−3
a = 10.718 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.933 (3) Å	Cell parameters from 6384 reflections
c = 11.586 (3) Å	θ = 2.2–25.4°
α = 113.462 (4)°	µ = 0.91 mm^−1
β = 109.626 (4)°	T = 173 K
γ = 96.053 (4)°	Block, green
V = 1127.2 (6) Å^3	0.35 × 0.31 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	3363 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.5°, θmin = 2.1°
Detector resolution: 836.6 pixels mm^-1	h = −12→12
φ and ω scans	k = −13→13
12251 measured reflections	l = −14→13
4169 independent reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.5423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
4169 reflections	Δρmax = 0.82 e Å^−3
339 parameters	Δρmin = −0.38 e Å^−3
7 restraints

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
Ni1	1.000000	0.000000	0.000000	0.01704 (15)
Ni2	0.500000	0.500000	0.500000	0.01567 (15)
O1	0.8747 (2)	0.02292 (19)	0.0998 (2)	0.0207 (4)
O2	0.9879 (2)	0.2140 (2)	0.3019 (2)	0.0278 (5)
O3	0.44548 (19)	0.28855 (18)	0.3693 (2)	0.0194 (4)
O4	0.64885 (19)	0.39367 (18)	0.54244 (19)	0.0185 (4)
O5	1.2822 (2)	0.3913 (2)	−0.0396 (2)	0.0257 (5)
O6	0.8399 (2)	−0.1579 (2)	−0.1770 (2)	0.0323 (5)
H6A	0.7521 (16)	−0.180 (3)	−0.228 (3)	0.049*
H6B	0.880 (3)	−0.185 (4)	−0.231 (3)	0.049*
N1	0.9443 (2)	0.1585 (2)	−0.0536 (2)	0.0196 (5)
N2	1.4116 (2)	0.4695 (2)	−0.3776 (2)	0.0188 (5)
N3	1.0701 (2)	0.3768 (2)	−0.1866 (2)	0.0205 (5)
H3	1.027254	0.396693	−0.253463	0.043 (11)*
C1	0.8886 (3)	0.1069 (3)	0.2187 (3)	0.0186 (6)
C2	0.7255 (3)	0.1976 (3)	0.3250 (3)	0.0173 (6)
H2A	0.684592	0.228008	0.254351	0.021*
H2B	0.804113	0.275068	0.404075	0.013 (7)*
C3	0.7765 (3)	0.0702 (3)	0.2634 (3)	0.0180 (6)
C4	0.6536 (3)	−0.0489 (3)	0.1424 (3)	0.0214 (6)
H4A	0.611146	−0.021060	0.069887	0.026*
H4B	0.685396	−0.130982	0.101700	0.012 (7)*
C5	0.8406 (3)	0.0254 (3)	0.3757 (3)	0.0231 (7)
H5A	0.874709	−0.055787	0.337929	0.028*
H5B	0.919763	0.102021	0.455123	0.017 (7)*
C6	0.5469 (3)	−0.0859 (3)	0.1919 (3)	0.0253 (7)
H6	0.467734	−0.164142	0.111628	0.021 (8)*
C7	0.4942 (3)	0.0395 (3)	0.2508 (3)	0.0218 (6)
H7A	0.423551	0.015057	0.281145	0.026*
H7B	0.451510	0.067798	0.178771	0.011 (7)*
C8	0.6825 (3)	0.1151 (3)	0.4850 (3)	0.0238 (7)
H8A	0.761453	0.192252	0.564112	0.029*
H8B	0.614538	0.092712	0.519184	0.033 (9)*
C9	0.7322 (3)	−0.0122 (3)	0.4243 (3)	0.0274 (7)
H9	0.774107	−0.041601	0.496624	0.030 (9)*
C10	0.6096 (4)	−0.1307 (3)	0.3019 (4)	0.0316 (8)
H10A	0.640577	−0.213959	0.263009	0.038*
H10B	0.539579	−0.154594	0.333230	0.027 (8)*
C11	0.6161 (3)	0.1596 (3)	0.3742 (3)	0.0175 (6)
C12	0.5672 (3)	0.2864 (3)	0.4325 (3)	0.0170 (6)
C14	0.8279 (3)	0.1933 (3)	−0.0554 (3)	0.0240 (7)
H14	0.770731	0.149260	−0.027780	0.030 (9)*
C15	1.0241 (3)	0.2222 (3)	−0.0922 (3)	0.0204 (6)
H15	1.108039	0.199666	−0.089106	0.039 (10)*
C16	0.7881 (3)	0.2911 (3)	−0.0962 (3)	0.0239 (7)
H16	0.705149	0.313949	−0.095664	0.028 (8)*
C17	0.9894 (3)	0.3197 (3)	−0.1365 (3)	0.0188 (6)
C18	0.8696 (3)	0.3553 (3)	−0.1376 (3)	0.0220 (6)
H18	0.843662	0.422547	−0.166249	0.022 (8)*
C19	1.2793 (3)	0.3958 (3)	−0.4378 (3)	0.0204 (6)
H19	1.233694	0.352711	−0.535775	0.002 (6)*
C20	1.2063 (3)	0.3793 (3)	−0.3659 (3)	0.0204 (6)
H20	1.112088	0.327124	−0.413126	0.016 (7)*
C21	1.2716 (3)	0.4397 (3)	−0.2230 (3)	0.0173 (6)
C22	1.4077 (3)	0.5186 (3)	−0.1589 (3)	0.0193 (6)
H22	1.455078	0.562638	−0.061051	0.015 (7)*
C23	1.4739 (3)	0.5327 (3)	−0.2388 (3)	0.0211 (6)
H23	1.566465	0.588835	−0.194019	0.034 (9)*
C24	1.2087 (3)	0.4033 (3)	−0.1390 (3)	0.0193 (6)
O1W	0.9387 (2)	0.5047 (2)	−0.3366 (3)	0.0396 (6)
H1WA	0.8521 (19)	0.483 (4)	−0.370 (4)	0.059*
H1WB	0.969 (4)	0.590 (2)	−0.312 (4)	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0171 (3)	0.0182 (3)	0.0183 (3)	0.0030 (2)	0.0112 (2)	0.0079 (2)
Ni2	0.0158 (3)	0.0161 (3)	0.0184 (3)	0.0053 (2)	0.0106 (2)	0.0079 (2)
O1	0.0223 (11)	0.0220 (10)	0.0215 (11)	0.0055 (8)	0.0152 (9)	0.0086 (9)
O2	0.0206 (11)	0.0250 (11)	0.0283 (12)	−0.0013 (9)	0.0137 (10)	0.0024 (9)
O3	0.0157 (11)	0.0188 (9)	0.0242 (11)	0.0059 (8)	0.0093 (9)	0.0094 (9)
O4	0.0179 (11)	0.0182 (9)	0.0207 (11)	0.0059 (8)	0.0093 (9)	0.0088 (9)
O5	0.0213 (11)	0.0356 (12)	0.0254 (11)	0.0057 (9)	0.0089 (10)	0.0201 (10)
O6	0.0156 (11)	0.0406 (13)	0.0269 (13)	0.0016 (10)	0.0110 (10)	0.0024 (10)
N1	0.0183 (13)	0.0221 (12)	0.0204 (13)	0.0038 (10)	0.0103 (11)	0.0103 (10)
N2	0.0178 (13)	0.0207 (12)	0.0214 (13)	0.0054 (10)	0.0103 (11)	0.0111 (10)
N3	0.0198 (13)	0.0272 (12)	0.0234 (13)	0.0070 (10)	0.0108 (11)	0.0183 (11)
C1	0.0200 (16)	0.0212 (14)	0.0218 (15)	0.0103 (12)	0.0125 (13)	0.0125 (13)
C2	0.0170 (15)	0.0172 (13)	0.0210 (15)	0.0037 (11)	0.0122 (13)	0.0086 (12)
C3	0.0189 (15)	0.0208 (13)	0.0200 (15)	0.0066 (12)	0.0139 (13)	0.0095 (12)
C4	0.0186 (15)	0.0212 (14)	0.0249 (16)	0.0066 (12)	0.0135 (13)	0.0072 (13)
C5	0.0232 (17)	0.0285 (15)	0.0283 (17)	0.0144 (13)	0.0153 (14)	0.0176 (14)
C6	0.0229 (17)	0.0165 (14)	0.0337 (18)	0.0006 (12)	0.0186 (15)	0.0047 (13)
C7	0.0180 (15)	0.0176 (13)	0.0326 (17)	0.0039 (12)	0.0171 (14)	0.0092 (13)
C8	0.0305 (18)	0.0300 (15)	0.0277 (17)	0.0146 (14)	0.0215 (15)	0.0197 (14)
C9	0.0336 (19)	0.0363 (17)	0.0376 (19)	0.0212 (15)	0.0267 (16)	0.0280 (16)
C10	0.042 (2)	0.0187 (14)	0.052 (2)	0.0130 (14)	0.0340 (18)	0.0201 (15)
C11	0.0170 (15)	0.0180 (13)	0.0211 (15)	0.0065 (11)	0.0124 (13)	0.0084 (12)
C12	0.0187 (16)	0.0182 (13)	0.0186 (15)	0.0047 (12)	0.0121 (13)	0.0092 (12)
C14	0.0224 (16)	0.0247 (15)	0.0284 (17)	0.0039 (13)	0.0149 (14)	0.0124 (13)
C15	0.0186 (15)	0.0215 (14)	0.0227 (15)	0.0047 (12)	0.0107 (13)	0.0102 (12)
C16	0.0178 (16)	0.0277 (15)	0.0296 (17)	0.0075 (12)	0.0140 (14)	0.0127 (14)
C17	0.0182 (15)	0.0199 (13)	0.0198 (15)	0.0029 (11)	0.0106 (13)	0.0090 (12)
C18	0.0223 (16)	0.0222 (14)	0.0240 (16)	0.0052 (12)	0.0120 (13)	0.0114 (13)
C19	0.0223 (16)	0.0219 (14)	0.0161 (15)	0.0045 (12)	0.0078 (13)	0.0085 (12)
C20	0.0141 (15)	0.0241 (14)	0.0233 (16)	0.0028 (12)	0.0080 (13)	0.0114 (13)
C21	0.0195 (15)	0.0170 (13)	0.0223 (15)	0.0084 (11)	0.0130 (13)	0.0112 (12)
C22	0.0180 (15)	0.0226 (14)	0.0181 (15)	0.0039 (12)	0.0069 (13)	0.0109 (12)
C23	0.0179 (16)	0.0234 (14)	0.0234 (16)	0.0032 (12)	0.0096 (13)	0.0118 (13)
C24	0.0199 (16)	0.0190 (13)	0.0206 (15)	0.0055 (12)	0.0098 (13)	0.0092 (12)
O1W	0.0216 (12)	0.0367 (13)	0.0624 (18)	0.0055 (11)	0.0071 (13)	0.0337 (14)

Geometric parameters (Å, º)

Ni1—O1^i	2.0216 (19)	C5—H5B	0.9900
Ni1—O1	2.0216 (19)	C5—C9	1.536 (4)
Ni1—O6^i	2.079 (2)	C6—H6	1.0000
Ni1—O6	2.079 (2)	C6—C7	1.531 (4)
Ni1—N1	2.138 (2)	C6—C10	1.519 (4)
Ni1—N1^i	2.138 (2)	C7—H7A	0.9900
Ni2—O3	2.0766 (18)	C7—H7B	0.9900
Ni2—O3^ii	2.0766 (18)	C7—C11	1.537 (4)
Ni2—O4	2.1113 (18)	C8—H8A	0.9900
Ni2—O4^ii	2.1113 (18)	C8—H8B	0.9900
Ni2—N2^iii	2.058 (2)	C8—C9	1.531 (4)
Ni2—N2^iv	2.058 (2)	C8—C11	1.533 (4)
O1—C1	1.260 (3)	C9—H9	1.0000
O2—C1	1.258 (3)	C9—C10	1.530 (5)
O3—C12	1.272 (3)	C10—H10A	0.9900
O4—C12	1.269 (3)	C10—H10B	0.9900
O5—C24	1.224 (3)	C11—C12	1.515 (3)
O6—H6A	0.871 (14)	C14—H14	0.9500
O6—H6B	0.849 (18)	C14—C16	1.382 (4)
N1—C14	1.337 (4)	C15—H15	0.9500
N1—C15	1.340 (4)	C15—C17	1.389 (4)
N2—C19	1.339 (4)	C16—H16	0.9500
N2—C23	1.344 (4)	C16—C18	1.382 (4)
N3—H3	0.8800	C17—C18	1.378 (4)
N3—C17	1.410 (3)	C18—H18	0.9500
N3—C24	1.351 (4)	C19—H19	0.9500
C1—C3	1.534 (4)	C19—C20	1.366 (4)
C2—H2A	0.9900	C20—H20	0.9500
C2—H2B	0.9900	C20—C21	1.386 (4)
C2—C3	1.542 (4)	C21—C22	1.385 (4)
C2—C11	1.551 (4)	C21—C24	1.500 (4)
C3—C4	1.530 (4)	C22—H22	0.9500
C3—C5	1.544 (4)	C22—C23	1.384 (4)
C4—H4A	0.9900	C23—H23	0.9500
C4—H4B	0.9900	O1W—H1WA	0.840 (18)
C4—C6	1.526 (4)	O1W—H1WB	0.842 (18)
C5—H5A	0.9900
O1^i—Ni1—O1	180.0	C7—C6—H6	109.0
O1—Ni1—O6^i	90.58 (8)	C10—C6—C4	110.4 (2)
O1—Ni1—O6	89.42 (8)	C10—C6—H6	109.0
O1^i—Ni1—O6^i	89.42 (8)	C10—C6—C7	109.6 (3)
O1^i—Ni1—O6	90.58 (8)	C6—C7—H7A	109.9
O1—Ni1—N1	90.06 (8)	C6—C7—H7B	109.9
O1—Ni1—N1^i	89.94 (8)	C6—C7—C11	108.9 (2)
O1^i—Ni1—N1^i	90.06 (8)	H7A—C7—H7B	108.3
O1^i—Ni1—N1	89.94 (8)	C11—C7—H7A	109.9
O6^i—Ni1—O6	180.0	C11—C7—H7B	109.9
O6—Ni1—N1	93.49 (9)	H8A—C8—H8B	108.2
O6^i—Ni1—N1	86.51 (9)	C9—C8—H8A	109.7
O6^i—Ni1—N1^i	93.49 (9)	C9—C8—H8B	109.7
O6—Ni1—N1^i	86.51 (9)	C9—C8—C11	109.9 (2)
N1—Ni1—N1^i	180.0	C11—C8—H8A	109.7
O3^ii—Ni2—O3	180.0	C11—C8—H8B	109.7
O3—Ni2—O4^ii	116.95 (7)	C5—C9—H9	109.5
O3—Ni2—O4	63.05 (7)	C8—C9—C5	109.1 (2)
O3^ii—Ni2—O4	116.95 (7)	C8—C9—H9	109.5
O3^ii—Ni2—O4^ii	63.05 (7)	C10—C9—C5	109.9 (3)
O4—Ni2—O4^ii	180.0	C10—C9—C8	109.3 (3)
N2^iii—Ni2—O3^ii	92.34 (8)	C10—C9—H9	109.5
N2^iii—Ni2—O3	87.67 (8)	C6—C10—C9	109.3 (2)
N2^iv—Ni2—O3	92.33 (8)	C6—C10—H10A	109.8
N2^iv—Ni2—O3^ii	87.66 (8)	C6—C10—H10B	109.8
N2^iv—Ni2—O4	94.86 (8)	C9—C10—H10A	109.8
N2^iii—Ni2—O4	85.14 (8)	C9—C10—H10B	109.8
N2^iii—Ni2—O4^ii	94.86 (8)	H10A—C10—H10B	108.3
N2^iv—Ni2—O4^ii	85.14 (8)	C7—C11—C2	109.4 (2)
N2^iii—Ni2—N2^iv	180.0	C8—C11—C2	108.7 (2)
C1—O1—Ni1	133.44 (18)	C8—C11—C7	109.7 (2)
C12—O3—Ni2	89.28 (15)	C12—C11—C2	108.2 (2)
C12—O4—Ni2	87.83 (15)	C12—C11—C7	110.0 (2)
Ni1—O6—H6A	143 (2)	C12—C11—C8	110.8 (2)
Ni1—O6—H6B	101 (2)	O3—C12—Ni2	59.03 (13)
H6A—O6—H6B	107 (3)	O3—C12—C11	120.5 (2)
C14—N1—Ni1	121.94 (19)	O4—C12—Ni2	60.60 (13)
C14—N1—C15	118.1 (2)	O4—C12—O3	119.1 (2)
C15—N1—Ni1	119.93 (18)	O4—C12—C11	120.4 (2)
C19—N2—Ni2^v	118.35 (19)	C11—C12—Ni2	170.38 (19)
C19—N2—C23	117.7 (2)	N1—C14—H14	118.9
C23—N2—Ni2^v	123.49 (19)	N1—C14—C16	122.2 (3)
C17—N3—H3	117.7	C16—C14—H14	118.9
C24—N3—H3	117.7	N1—C15—H15	118.6
C24—N3—C17	124.6 (2)	N1—C15—C17	122.8 (3)
O1—C1—C3	116.0 (2)	C17—C15—H15	118.6
O2—C1—O1	124.8 (3)	C14—C16—H16	120.2
O2—C1—C3	119.1 (2)	C18—C16—C14	119.6 (3)
H2A—C2—H2B	108.2	C18—C16—H16	120.2
C3—C2—H2A	109.7	C15—C17—N3	121.4 (2)
C3—C2—H2B	109.7	C18—C17—N3	119.7 (2)
C3—C2—C11	109.7 (2)	C18—C17—C15	118.8 (3)
C11—C2—H2A	109.7	C16—C18—H18	120.8
C11—C2—H2B	109.7	C17—C18—C16	118.5 (3)
C1—C3—C2	110.6 (2)	C17—C18—H18	120.8
C1—C3—C5	107.9 (2)	N2—C19—H19	118.2
C2—C3—C5	108.7 (2)	N2—C19—C20	123.5 (3)
C4—C3—C1	111.7 (2)	C20—C19—H19	118.2
C4—C3—C2	109.0 (2)	C19—C20—H20	120.5
C4—C3—C5	108.9 (2)	C19—C20—C21	119.0 (3)
C3—C4—H4A	109.6	C21—C20—H20	120.5
C3—C4—H4B	109.6	C20—C21—C24	122.1 (2)
H4A—C4—H4B	108.1	C22—C21—C20	118.1 (3)
C6—C4—C3	110.1 (2)	C22—C21—C24	119.0 (2)
C6—C4—H4A	109.6	C21—C22—H22	120.3
C6—C4—H4B	109.6	C23—C22—C21	119.4 (3)
C3—C5—H5A	109.7	C23—C22—H22	120.3
C3—C5—H5B	109.7	N2—C23—C22	122.1 (3)
H5A—C5—H5B	108.2	N2—C23—H23	118.9
C9—C5—C3	109.9 (2)	C22—C23—H23	118.9
C9—C5—H5A	109.7	O5—C24—N3	124.6 (3)
C9—C5—H5B	109.7	O5—C24—C21	119.4 (3)
C4—C6—H6	109.0	N3—C24—C21	115.8 (2)
C4—C6—C7	109.8 (2)	H1WA—O1W—H1WB	109 (3)
Ni1—O1—C1—O2	9.4 (4)	C5—C9—C10—C6	−59.2 (3)
Ni1—O1—C1—C3	−168.59 (17)	C6—C7—C11—C2	59.9 (3)
Ni1—N1—C14—C16	−176.9 (2)	C6—C7—C11—C8	−59.2 (3)
Ni1—N1—C15—C17	175.9 (2)	C6—C7—C11—C12	178.7 (2)
Ni2—O3—C12—O4	8.7 (2)	C7—C6—C10—C9	−61.6 (3)
Ni2—O3—C12—C11	−168.8 (2)	C7—C11—C12—O3	−8.7 (3)
Ni2—O4—C12—O3	−8.5 (2)	C7—C11—C12—O4	173.8 (2)
Ni2—O4—C12—C11	169.0 (2)	C8—C9—C10—C6	60.4 (3)
Ni2^v—N2—C19—C20	−173.9 (2)	C8—C11—C12—O3	−130.2 (3)
Ni2^v—N2—C23—C22	174.8 (2)	C8—C11—C12—O4	52.3 (3)
O1—C1—C3—C2	−132.5 (2)	C9—C8—C11—C2	−60.7 (3)
O1—C1—C3—C4	−10.9 (3)	C9—C8—C11—C7	58.8 (3)
O1—C1—C3—C5	108.7 (3)	C9—C8—C11—C12	−179.5 (2)
O2—C1—C3—C2	49.3 (3)	C10—C6—C7—C11	60.8 (3)
O2—C1—C3—C4	170.9 (2)	C11—C2—C3—C1	−178.0 (2)
O2—C1—C3—C5	−69.5 (3)	C11—C2—C3—C4	58.8 (3)
N1—C14—C16—C18	0.4 (4)	C11—C2—C3—C5	−59.7 (3)
N1—C15—C17—N3	−175.0 (2)	C11—C8—C9—C5	61.0 (3)
N1—C15—C17—C18	1.7 (4)	C11—C8—C9—C10	−59.2 (3)
N2—C19—C20—C21	−0.9 (4)	C14—N1—C15—C17	−1.5 (4)
N3—C17—C18—C16	175.9 (3)	C14—C16—C18—C17	−0.2 (4)
C1—C3—C4—C6	177.9 (2)	C15—N1—C14—C16	0.4 (4)
C1—C3—C5—C9	179.9 (2)	C15—C17—C18—C16	−0.8 (4)
C2—C3—C4—C6	−59.6 (3)	C17—N3—C24—O5	−6.1 (4)
C2—C3—C5—C9	59.9 (3)	C17—N3—C24—C21	169.4 (2)
C2—C11—C12—O3	110.7 (3)	C19—N2—C23—C22	2.8 (4)
C2—C11—C12—O4	−66.8 (3)	C19—C20—C21—C22	2.2 (4)
C3—C2—C11—C7	−59.5 (3)	C19—C20—C21—C24	−167.4 (2)
C3—C2—C11—C8	60.3 (3)	C20—C21—C22—C23	−1.0 (4)
C3—C2—C11—C12	−179.3 (2)	C20—C21—C24—O5	140.1 (3)
C3—C4—C6—C7	61.0 (3)	C20—C21—C24—N3	−35.7 (4)
C3—C4—C6—C10	−60.0 (3)	C21—C22—C23—N2	−1.6 (4)
C3—C5—C9—C8	−60.5 (3)	C22—C21—C24—O5	−29.4 (4)
C3—C5—C9—C10	59.4 (3)	C22—C21—C24—N3	154.9 (2)
C4—C3—C5—C9	−58.8 (3)	C23—N2—C19—C20	−1.6 (4)
C4—C6—C7—C11	−60.8 (3)	C24—N3—C17—C15	−34.5 (4)
C4—C6—C10—C9	59.5 (3)	C24—N3—C17—C18	148.9 (3)
C5—C3—C4—C6	58.9 (3)	C24—C21—C22—C23	168.9 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3^vi	0.87 (1)	2.04 (2)	2.886 (3)	163 (3)
O6—H6B···O2^i	0.85 (2)	1.86 (2)	2.684 (3)	163 (3)
N3—H3···O1W	0.88	1.94	2.769 (3)	157
O1W—H1WA···O4^vii	0.84 (2)	2.00 (2)	2.831 (3)	169 (4)
O1W—H1WB···O2^iii	0.84 (2)	2.10 (2)	2.921 (3)	165 (4)

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