Crystal structure of [3,10-bis­(4-fluoro­pheneth­yl)-1,3,5,8,10,12-hexa­aza­cyclo­tetra­deca­ne]nickel(II) diperchlorate

A new nickel(II) complex of a hexa­aza­macrocycle containing 4-flurophenethyl pendant arms was synthesized by metal template condensation in a one-pot reaction of formaldehyde and amines in the presence of nickel(II) ions and its X-ray crystal structure was determined.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma]() = 0.000 Å
• Disorder in main residue
• R factor = 0.068
• wR factor = 0.159
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.19 Do !

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         43 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      12.01 Why ?
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records         17 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of Ni1        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F1         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F1'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N1         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N1'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N2'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N3         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N3'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C1         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C1'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C2'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C3         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C3'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C4         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C4'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C5         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C5'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C6         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C6'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C7         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C7'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C8         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C8'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C9         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C9'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C10        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C10'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C11        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C11'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C12        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C12'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1'B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H2'B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3'B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6A        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6B        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H8'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H4'B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H9         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H9'        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H5'B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H11'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6'A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H12        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H12'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H6'B       Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  1  )      39.50 Check
PLAT607_ALERT_4_G VOID Test Skipped Due to Severe Disorder .......          ! Info
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #         69 Check
PLAT793_ALERT_4_G Model has Chirality at N2          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N2'         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N3          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at N3'         (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        492 Note

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

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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).

[3,10-Bis(4-fluorophenethyl)-1,3,5,8,10,12-hexaazacyclotetradecane]nickel(II) bis(perchlorate)

Crystal data

[Ni(C24H36F2N6)](ClO4)2	F(000) = 1464
Mr = 704.20	Dx = 1.583 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.9910 (12) Å	Cell parameters from 3600 reflections
b = 15.5187 (11) Å	θ = 1.8–28.3°
c = 13.8864 (9) Å	µ = 0.91 mm^−1
β = 126.189 (1)°	T = 173 K
V = 2955.1 (4) Å^3	Block, yellow
Z = 4	0.40 × 0.35 × 0.20 mm

Data collection

Bruker SMART CCD area detector diffractometer	Rint = 0.083
phi and ω scans	θmax = 28.3°, θmin = 2.0°
9357 measured reflections	h = −21→19
3400 independent reflections	k = −19→18
2737 reflections with I > 2σ(I)	l = −18→15

Refinement

Refinement on F^2	492 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 12.0119P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
3400 reflections	Δρmax = 0.88 e Å^−3
282 parameters	Δρmin = −0.63 e Å^−3

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	0.50831 (10)	0.37625 (4)	0.25924 (13)	0.0174 (2)*	0.5
F1	0.0633 (8)	0.3851 (12)	0.5651 (8)	0.071 (3)	0.5
N1	0.2930 (6)	0.3576 (6)	0.2078 (8)	0.0457 (18)	0.5
N2	0.4195 (8)	0.4599 (6)	0.2494 (14)	0.0285 (16)	0.5
H2	0.440274	0.471036	0.330822	0.034*	0.5
N3	0.4422 (6)	0.2796 (5)	0.2689 (8)	0.0315 (17)	0.5
H3	0.464913	0.275912	0.352038	0.038*	0.5
C1	0.3129 (7)	0.4353 (7)	0.1751 (11)	0.0438 (19)	0.5
H1A	0.276898	0.481023	0.180846	0.053*	0.5
H1B	0.289042	0.431370	0.092254	0.053*	0.5
C2	0.3322 (7)	0.2838 (6)	0.1930 (9)	0.0407 (18)	0.5
H2A	0.307538	0.280024	0.109821	0.049*	0.5
H2B	0.308648	0.233687	0.210625	0.049*	0.5
C3	0.4317 (10)	0.5416 (7)	0.2027 (12)	0.043 (2)	0.5
H3A	0.398839	0.537629	0.117278	0.052*	0.5
H3B	0.404620	0.589837	0.218621	0.052*	0.5
C4	0.4734 (8)	0.1987 (5)	0.2428 (11)	0.042 (2)	0.5
H4A	0.462776	0.149576	0.277068	0.050*	0.5
H4B	0.436522	0.190069	0.157356	0.050*	0.5
C5	0.2772 (7)	0.3584 (7)	0.3011 (9)	0.043 (2)	0.5
H5A	0.324764	0.396071	0.365491	0.051*	0.5
H5B	0.286668	0.300782	0.333287	0.051*	0.5
C6	0.1754 (10)	0.3892 (15)	0.2521 (13)	0.0436 (17)	0.5
H6A	0.169116	0.448576	0.226476	0.052*	0.5
H6B	0.129079	0.355294	0.181870	0.052*	0.5
C7	0.1472 (8)	0.3846 (10)	0.3366 (10)	0.0368 (12)	0.5
C8	0.1429 (10)	0.3083 (10)	0.3863 (11)	0.048 (3)	0.5
H8	0.157393	0.256297	0.366611	0.057*	0.5
C9	0.1173 (10)	0.3085 (10)	0.4650 (11)	0.054 (3)	0.5
H9	0.119223	0.257617	0.501639	0.065*	0.5
C10	0.0891 (15)	0.3847 (12)	0.4885 (15)	0.0519 (18)	0.5
C11	0.0973 (19)	0.4610 (12)	0.447 (2)	0.046 (2)	0.5
H11	0.084266	0.512687	0.469261	0.055*	0.5
C12	0.126 (2)	0.4599 (11)	0.371 (2)	0.039 (2)	0.5
H12	0.130349	0.512186	0.342290	0.047*	0.5
F1'	0.9281 (8)	0.3557 (11)	−0.0646 (8)	0.071 (3)	0.5
N1'	0.7183 (6)	0.3953 (6)	0.3006 (8)	0.0457 (18)	0.5
N2'	0.5718 (8)	0.4730 (6)	0.2422 (15)	0.0315 (17)	0.5
H2'	0.548837	0.474605	0.158805	0.038*	0.5
N3'	0.5922 (6)	0.2927 (5)	0.2582 (8)	0.0285 (16)	0.5
H3'	0.570787	0.286557	0.175710	0.034*	0.5
C1'	0.6818 (7)	0.4693 (6)	0.3192 (10)	0.0407 (18)	0.5
H1'A	0.706114	0.519692	0.303050	0.049*	0.5
H1'B	0.706349	0.471549	0.402388	0.049*	0.5
C2'	0.6995 (7)	0.3171 (7)	0.3348 (10)	0.0438 (19)	0.5
H2'A	0.722435	0.321528	0.417275	0.053*	0.5
H2'B	0.736204	0.271471	0.330180	0.053*	0.5
C3'	0.5385 (10)	0.5534 (7)	0.2658 (12)	0.042 (2)	0.5
H3'A	0.551526	0.603098	0.234804	0.050*	0.5
H3'B	0.571198	0.561228	0.350715	0.050*	0.5
C4'	0.5786 (8)	0.2082 (5)	0.2969 (10)	0.043 (2)	0.5
H4'A	0.600078	0.161811	0.270542	0.052*	0.5
H4'B	0.616559	0.206027	0.383173	0.052*	0.5
C5'	0.7323 (7)	0.3938 (7)	0.2050 (9)	0.043 (2)	0.5
H5'A	0.695637	0.440331	0.149100	0.051*	0.5
H5'B	0.708406	0.339732	0.161773	0.051*	0.5
C6'	0.8384 (11)	0.4037 (15)	0.2587 (14)	0.0436 (17)	0.5
H6'A	0.874819	0.360440	0.320403	0.052*	0.5
H6'B	0.860033	0.459795	0.296500	0.052*	0.5
C7'	0.8622 (8)	0.3952 (10)	0.1701 (10)	0.0368 (12)	0.5
C8'	0.8807 (9)	0.3129 (9)	0.1490 (10)	0.039 (2)	0.5
H8'	0.875962	0.266112	0.187145	0.047*	0.5
C9'	0.9059 (10)	0.2994 (10)	0.0724 (11)	0.046 (2)	0.5
H9'	0.923553	0.245074	0.062804	0.055*	0.5
C10'	0.9039 (15)	0.3693 (11)	0.0113 (15)	0.0519 (18)	0.5
C11'	0.893 (2)	0.4515 (12)	0.034 (2)	0.054 (3)	0.5
H11'	0.902900	0.497780	−0.000650	0.065*	0.5
C12'	0.868 (2)	0.4641 (12)	0.112 (2)	0.048 (3)	0.5
H12'	0.854488	0.519427	0.124343	0.057*	0.5
Cl1	0.6115 (4)	0.3604 (3)	0.5699 (5)	0.0469 (4)	0.795 (7)
O1	0.6801 (6)	0.3549 (5)	0.6978 (5)	0.082 (3)	0.795 (7)
O2	0.5813 (5)	0.2776 (4)	0.5188 (5)	0.102 (2)	0.795 (7)
O3	0.6555 (5)	0.3981 (6)	0.5233 (6)	0.113 (3)	0.795 (7)
O4	0.5284 (5)	0.4091 (5)	0.5368 (6)	0.089 (2)	0.795 (7)
Cl1'	0.6086 (16)	0.3675 (13)	0.5680 (19)	0.0469 (4)	0.205 (7)
O1'	0.6497 (18)	0.3241 (14)	0.6781 (19)	0.049 (4)	0.205 (7)
O2'	0.6325 (17)	0.3288 (16)	0.4980 (16)	0.074 (4)	0.205 (7)
O3'	0.6267 (19)	0.4551 (13)	0.574 (2)	0.097 (6)	0.205 (7)
O4'	0.5058 (15)	0.3669 (16)	0.5057 (19)	0.067 (4)	0.205 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.074 (3)	0.112 (11)	0.060 (2)	0.010 (4)	0.0571 (19)	0.004 (3)
N1	0.035 (2)	0.063 (6)	0.054 (3)	−0.001 (2)	0.034 (2)	0.005 (3)
N2	0.034 (3)	0.030 (3)	0.034 (3)	0.007 (2)	0.028 (3)	0.006 (3)
N3	0.037 (3)	0.031 (3)	0.039 (4)	−0.003 (3)	0.029 (3)	−0.002 (3)
C1	0.031 (3)	0.057 (5)	0.049 (4)	0.012 (3)	0.026 (3)	0.011 (4)
C2	0.038 (3)	0.050 (4)	0.043 (4)	−0.014 (3)	0.029 (3)	−0.007 (3)
C3	0.067 (6)	0.031 (3)	0.060 (6)	0.013 (3)	0.054 (5)	0.010 (3)
C4	0.073 (7)	0.022 (3)	0.062 (6)	−0.003 (3)	0.057 (6)	−0.001 (3)
C5	0.033 (3)	0.061 (8)	0.045 (3)	−0.001 (3)	0.028 (2)	0.002 (3)
C6	0.032 (4)	0.066 (6)	0.040 (3)	−0.003 (4)	0.025 (3)	−0.003 (5)
C7	0.029 (2)	0.052 (3)	0.033 (2)	0.003 (5)	0.020 (2)	−0.002 (4)
C8	0.045 (6)	0.053 (4)	0.046 (7)	0.009 (4)	0.027 (6)	0.010 (4)
C9	0.051 (7)	0.073 (5)	0.041 (7)	0.000 (5)	0.029 (6)	0.011 (5)
C10	0.041 (3)	0.086 (6)	0.041 (2)	0.010 (6)	0.031 (2)	0.008 (5)
C11	0.036 (5)	0.068 (4)	0.032 (5)	0.007 (4)	0.020 (5)	−0.003 (4)
C12	0.036 (5)	0.052 (4)	0.028 (5)	0.003 (4)	0.019 (4)	0.003 (4)
F1'	0.074 (3)	0.112 (11)	0.060 (2)	0.010 (4)	0.0571 (19)	0.004 (3)
N1'	0.035 (2)	0.063 (6)	0.054 (3)	−0.001 (2)	0.034 (2)	0.005 (3)
N2'	0.037 (3)	0.031 (3)	0.039 (4)	−0.003 (3)	0.029 (3)	−0.002 (3)
N3'	0.034 (3)	0.030 (3)	0.034 (3)	0.007 (2)	0.028 (3)	0.006 (3)
C1'	0.038 (3)	0.050 (4)	0.043 (4)	−0.014 (3)	0.029 (3)	−0.007 (3)
C2'	0.031 (3)	0.057 (5)	0.049 (4)	0.012 (3)	0.026 (3)	0.011 (4)
C3'	0.073 (7)	0.022 (3)	0.062 (6)	−0.003 (3)	0.057 (6)	−0.001 (3)
C4'	0.067 (6)	0.031 (3)	0.060 (6)	0.013 (3)	0.054 (5)	0.010 (3)
C5'	0.033 (3)	0.061 (8)	0.045 (3)	−0.001 (3)	0.028 (2)	0.002 (3)
C6'	0.032 (4)	0.066 (6)	0.040 (3)	−0.003 (4)	0.025 (3)	−0.003 (5)
C7'	0.029 (2)	0.052 (3)	0.033 (2)	0.003 (5)	0.020 (2)	−0.002 (4)
C8'	0.036 (5)	0.052 (4)	0.028 (5)	0.003 (4)	0.019 (4)	0.003 (4)
C9'	0.036 (5)	0.068 (4)	0.032 (5)	0.007 (4)	0.020 (5)	−0.003 (4)
C10'	0.041 (3)	0.086 (6)	0.041 (2)	0.010 (6)	0.031 (2)	0.008 (5)
C11'	0.051 (7)	0.073 (5)	0.041 (7)	0.000 (5)	0.029 (6)	0.011 (5)
C12'	0.045 (6)	0.053 (4)	0.046 (7)	0.009 (4)	0.027 (6)	0.010 (4)
Cl1	0.0583 (8)	0.0582 (11)	0.0380 (6)	0.0229 (7)	0.0361 (6)	0.0149 (7)
O1	0.089 (5)	0.116 (6)	0.038 (3)	0.058 (4)	0.035 (3)	0.014 (3)
O2	0.119 (5)	0.063 (3)	0.077 (4)	0.015 (3)	0.032 (3)	0.012 (3)
O3	0.113 (5)	0.162 (6)	0.094 (4)	−0.035 (4)	0.077 (4)	0.015 (4)
O4	0.081 (4)	0.108 (5)	0.062 (4)	0.056 (4)	0.033 (3)	0.010 (3)
Cl1'	0.0583 (8)	0.0582 (11)	0.0380 (6)	0.0229 (7)	0.0361 (6)	0.0149 (7)
O1'	0.068 (8)	0.052 (8)	0.050 (7)	0.028 (6)	0.047 (6)	0.017 (6)
O2'	0.093 (8)	0.095 (9)	0.039 (6)	0.040 (8)	0.042 (6)	0.016 (7)
O3'	0.108 (9)	0.081 (8)	0.084 (8)	0.002 (7)	0.046 (7)	0.013 (6)
O4'	0.073 (7)	0.093 (9)	0.050 (7)	0.007 (7)	0.044 (5)	0.008 (7)

Geometric parameters (Å, º)

Ni1—N3	1.925 (7)	N1'—C1'	1.400 (11)
Ni1—N2	1.933 (9)	N1'—C2'	1.408 (12)
Ni1—N3'	1.934 (7)	N1'—C5'	1.481 (10)
Ni1—N2'	1.943 (9)	N2'—C3'	1.484 (10)
F1—C10	1.370 (10)	N2'—C1'	1.510 (11)
N1—C1	1.398 (11)	N2'—H2'	0.9800
N1—C2	1.401 (11)	N3'—C4'	1.486 (10)
N1—C5	1.469 (10)	N3'—C2'	1.519 (12)
N2—C3	1.495 (11)	N3'—H3'	0.9800
N2—C1	1.511 (11)	C1'—H1'A	0.9700
N2—H2	0.9800	C1'—H1'B	0.9700
N3—C4	1.488 (9)	C2'—H2'A	0.9700
N3—C2	1.511 (12)	C2'—H2'B	0.9700
N3—H3	0.9800	C3'—H3'A	0.9700
C1—H1A	0.9700	C3'—H3'B	0.9700
C1—H1B	0.9700	C4'—H4'A	0.9700
C2—H2A	0.9700	C4'—H4'B	0.9700
C2—H2B	0.9700	C5'—C6'	1.498 (12)
C3—C3'	1.489 (13)	C5'—H5'A	0.9700
C3—H3A	0.9700	C5'—H5'B	0.9700
C3—H3B	0.9700	C6'—C7'	1.510 (10)
C4—C4'	1.482 (17)	C6'—H6'A	0.9700
C4—H4A	0.9700	C6'—H6'B	0.9700
C4—H4B	0.9700	C7'—C12'	1.380 (11)
C5—C6	1.515 (11)	C7'—C8'	1.387 (11)
C5—H5A	0.9700	C8'—C9'	1.377 (11)
C5—H5B	0.9700	C8'—H8'	0.9300
C6—C7	1.509 (10)	C9'—C10'	1.366 (12)
C6—H6A	0.9700	C9'—H9'	0.9300
C6—H6B	0.9700	C10'—C11'	1.351 (12)
C7—C8	1.393 (11)	C11'—C12'	1.395 (12)
C7—C12	1.394 (11)	C11'—H11'	0.9300
C8—C9	1.394 (12)	C12'—H12'	0.9300
C8—H8	0.9300	Cl1—O3	1.376 (7)
C9—C10	1.385 (12)	Cl1—O2	1.410 (7)
C9—H9	0.9300	Cl1—O4	1.418 (6)
C10—C11	1.357 (12)	Cl1—O1	1.440 (6)
C11—C12	1.396 (11)	Cl1'—O3'	1.386 (17)
C11—H11	0.9300	Cl1'—O2'	1.392 (17)
C12—H12	0.9300	Cl1'—O4'	1.420 (17)
F1'—C10'	1.356 (10)	Cl1'—O1'	1.421 (16)
N2—Ni1—N3	93.7 (4)	C3'—N2'—C1'	110.4 (9)
N3—Ni1—N3'	86.6 (3)	C3'—N2'—Ni1	108.1 (8)
N2—Ni1—N3'	176.4 (4)	C1'—N2'—Ni1	115.4 (8)
N3—Ni1—N2'	177.5 (5)	C3'—N2'—H2'	107.5
N2—Ni1—N2'	86.5 (2)	C1'—N2'—H2'	107.5
N3'—Ni1—N2'	93.0 (4)	Ni1—N2'—H2'	107.5
C1—N1—C2	115.5 (7)	C4'—N3'—C2'	110.2 (8)
C1—N1—C5	118.9 (9)	C4'—N3'—Ni1	108.5 (6)
C2—N1—C5	119.1 (8)	C2'—N3'—Ni1	114.4 (6)
C3—N2—C1	109.6 (9)	C4'—N3'—H3'	107.9
C3—N2—Ni1	107.3 (7)	C2'—N3'—H3'	107.9
C1—N2—Ni1	116.7 (7)	Ni1—N3'—H3'	107.9
C3—N2—H2	107.6	N1'—C1'—N2'	113.4 (8)
C1—N2—H2	107.6	N1'—C1'—H1'A	108.9
Ni1—N2—H2	107.6	N2'—C1'—H1'A	108.9
C4—N3—C2	109.7 (7)	N1'—C1'—H1'B	108.9
C4—N3—Ni1	109.6 (5)	N2'—C1'—H1'B	108.9
C2—N3—Ni1	116.8 (6)	H1'A—C1'—H1'B	107.7
C4—N3—H3	106.7	N1'—C2'—N3'	113.3 (7)
C2—N3—H3	106.7	N1'—C2'—H2'A	108.9
Ni1—N3—H3	106.7	N3'—C2'—H2'A	108.9
N1—C1—N2	114.7 (8)	N1'—C2'—H2'B	108.9
N1—C1—H1A	108.6	N3'—C2'—H2'B	108.9
N2—C1—H1A	108.6	H2'A—C2'—H2'B	107.7
N1—C1—H1B	108.6	N2'—C3'—C3	105.0 (11)
N2—C1—H1B	108.6	N2'—C3'—H3'A	110.8
H1A—C1—H1B	107.6	C3—C3'—H3'A	110.8
N1—C2—N3	115.7 (7)	N2'—C3'—H3'B	110.8
N1—C2—H2A	108.4	C3—C3'—H3'B	110.8
N3—C2—H2A	108.4	H3'A—C3'—H3'B	108.8
N1—C2—H2B	108.4	C4—C4'—N3'	107.6 (8)
N3—C2—H2B	108.4	C4—C4'—H4'A	110.2
H2A—C2—H2B	107.4	N3'—C4'—H4'A	110.2
C3'—C3—N2	106.4 (10)	C4—C4'—H4'B	110.2
C3'—C3—H3A	110.4	N3'—C4'—H4'B	110.2
N2—C3—H3A	110.4	H4'A—C4'—H4'B	108.5
C3'—C3—H3B	110.4	N1'—C5'—C6'	109.6 (8)
N2—C3—H3B	110.4	N1'—C5'—H5'A	109.8
H3A—C3—H3B	108.6	C6'—C5'—H5'A	109.8
C4'—C4—N3	106.8 (8)	N1'—C5'—H5'B	109.8
C4'—C4—H4A	110.4	C6'—C5'—H5'B	109.8
N3—C4—H4A	110.4	H5'A—C5'—H5'B	108.2
C4'—C4—H4B	110.4	C5'—C6'—C7'	114.0 (8)
N3—C4—H4B	110.4	C5'—C6'—H6'A	108.7
H4A—C4—H4B	108.6	C7'—C6'—H6'A	108.7
N1—C5—C6	111.1 (8)	C5'—C6'—H6'B	108.7
N1—C5—H5A	109.4	C7'—C6'—H6'B	108.7
C6—C5—H5A	109.4	H6'A—C6'—H6'B	107.6
N1—C5—H5B	109.4	C12'—C7'—C8'	119.1 (9)
C6—C5—H5B	109.4	C12'—C7'—C6'	123.8 (11)
H5A—C5—H5B	108.0	C8'—C7'—C6'	117.1 (11)
C7—C6—C5	116.0 (8)	C9'—C8'—C7'	121.1 (10)
C7—C6—H6A	108.3	C9'—C8'—H8'	119.4
C5—C6—H6A	108.3	C7'—C8'—H8'	119.4
C7—C6—H6B	108.3	C10'—C9'—C8'	117.0 (10)
C5—C6—H6B	108.3	C10'—C9'—H9'	121.5
H6A—C6—H6B	107.4	C8'—C9'—H9'	121.5
C8—C7—C12	116.1 (9)	C11'—C10'—F1'	118.1 (11)
C8—C7—C6	124.0 (11)	C11'—C10'—C9'	124.3 (10)
C12—C7—C6	119.9 (11)	F1'—C10'—C9'	116.8 (12)
C7—C8—C9	121.1 (11)	C10'—C11'—C12'	117.2 (13)
C7—C8—H8	119.4	C10'—C11'—H11'	121.4
C9—C8—H8	119.4	C12'—C11'—H11'	121.4
C10—C9—C8	119.9 (11)	C7'—C12'—C11'	120.5 (13)
C10—C9—H9	120.0	C7'—C12'—H12'	119.8
C8—C9—H9	120.0	C11'—C12'—H12'	119.8
C11—C10—F1	118.8 (12)	O3—Cl1—O2	106.7 (6)
C11—C10—C9	120.7 (10)	O3—Cl1—O4	109.5 (6)
F1—C10—C9	120.1 (11)	O2—Cl1—O4	109.0 (6)
C10—C11—C12	118.4 (12)	O3—Cl1—O1	109.6 (6)
C10—C11—H11	120.8	O2—Cl1—O1	110.9 (5)
C12—C11—H11	120.8	O4—Cl1—O1	110.9 (5)
C7—C12—C11	123.4 (12)	O3'—Cl1'—O2'	108.4 (19)
C7—C12—H12	118.3	O3'—Cl1'—O4'	101.1 (17)
C11—C12—H12	118.3	O2'—Cl1'—O4'	109.5 (18)
C1'—N1'—C2'	115.6 (7)	O3'—Cl1'—O1'	116.9 (18)
C1'—N1'—C5'	120.1 (8)	O2'—Cl1'—O1'	112.8 (18)
C2'—N1'—C5'	118.5 (9)	O4'—Cl1'—O1'	107.4 (18)
C2—N1—C1—N2	−64.3 (13)	C5'—N1'—C1'—N2'	86.6 (11)
C5—N1—C1—N2	87.3 (12)	C3'—N2'—C1'—N1'	−179.4 (10)
C3—N2—C1—N1	177.6 (10)	Ni1—N2'—C1'—N1'	57.6 (13)
Ni1—N2—C1—N1	55.4 (13)	C1'—N1'—C2'—N3'	67.6 (12)
C1—N1—C2—N3	63.7 (12)	C5'—N1'—C2'—N3'	−85.8 (10)
C5—N1—C2—N3	−87.7 (11)	C4'—N3'—C2'—N1'	178.0 (8)
C4—N3—C2—N1	−179.3 (8)	Ni1—N3'—C2'—N1'	−59.5 (10)
Ni1—N3—C2—N1	−53.9 (10)	C1'—N2'—C3'—C3	−169.8 (8)
C1—N2—C3—C3'	−170.4 (8)	Ni1—N2'—C3'—C3	−42.7 (11)
Ni1—N2—C3—C3'	−42.7 (11)	N2—C3—C3'—N2'	55.7 (7)
C2—N3—C4—C4'	166.7 (7)	N3—C4—C4'—N3'	−49.6 (8)
Ni1—N3—C4—C4'	37.3 (9)	C2'—N3'—C4'—C4	165.1 (7)
C1—N1—C5—C6	78.6 (14)	Ni1—N3'—C4'—C4	39.3 (9)
C2—N1—C5—C6	−130.9 (14)	C1'—N1'—C5'—C6'	103.5 (13)
N1—C5—C6—C7	174.2 (12)	C2'—N1'—C5'—C6'	−104.4 (13)
C5—C6—C7—C8	−61.5 (16)	N1'—C5'—C6'—C7'	174.9 (12)
C5—C6—C7—C12	117 (2)	C5'—C6'—C7'—C12'	93 (2)
C12—C7—C8—C9	0.7 (16)	C5'—C6'—C7'—C8'	−88.0 (15)
C6—C7—C8—C9	179.3 (10)	C12'—C7'—C8'—C9'	1.0 (16)
C7—C8—C9—C10	4 (2)	C6'—C7'—C8'—C9'	−178.0 (10)
C8—C9—C10—C11	−8 (2)	C7'—C8'—C9'—C10'	−5.3 (19)
C8—C9—C10—F1	179.6 (14)	C8'—C9'—C10'—C11'	10 (3)
F1—C10—C11—C12	179 (2)	C8'—C9'—C10'—F1'	−179.6 (13)
C9—C10—C11—C12	6 (3)	F1'—C10'—C11'—C12'	180 (2)
C8—C7—C12—C11	−3 (3)	C9'—C10'—C11'—C12'	−11 (3)
C6—C7—C12—C11	178.8 (18)	C8'—C7'—C12'—C11'	−1 (3)
C10—C11—C12—C7	−1 (4)	C6'—C7'—C12'—C11'	177.8 (18)
C2'—N1'—C1'—N2'	−66.3 (12)	C10'—C11'—C12'—C7'	6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4	0.98	2.51	3.355 (17)	144
N2—H2···O4^i	0.98	2.44	3.260 (16)	141
N2′—H2′···O4^ii	0.98	2.43	3.332 (18)	152
N2′—H2′···O4^iii	0.98	2.36	3.089 (17)	131
N3—H3···O2	0.98	1.97	2.819 (11)	144
N3′—H3′···O2^ii	0.98	2.40	3.186 (11)	137
C1′—H1′A···O1^iii	0.97	2.31	3.198 (13)	151
C1—H1B···O3^ii	0.97	2.35	3.156 (16)	140
C1′—H1′B···O3	0.97	2.56	3.309 (15)	134
C2—H2B···O1^iv	0.97	2.50	3.394 (16)	154
C3—H3B···O1^i	0.97	2.48	3.35 (2)	149
C2′—H2′B···O1^v	0.97	2.58	3.551 (16)	175
C4—H4A···F1^vi	0.97	2.54	3.341 (19)	140
C3′—H3′A···O4^iii	0.97	2.54	3.136 (17)	119
C4′—H4′B···O2	0.97	2.54	3.239 (14)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y, −z+1/2; (iii) x, −y+1, z−1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) −x+3/2, −y+1/2, −z+1; (vi) −x+1/2, −y+1/2, −z+1.