Aqua­dichloro­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)nickel(II)

Ding, C.-F.; Miao, Y.-F.; Tian, B.-Q.; Li, X.-M.; Zhang, S.-S.

doi:10.1107/S1600536806013250

Aquadichloro(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)nickel(II)

C.-F. Ding, Y.-F. Miao, B.-Q. Tian, X.-M. Li and S.-S. Zhang

In the title compound, [NiCl₂(C₁₄H₁₂N₂)(H₂O)], there are two molecules in the asymmetric unit. Each Ni atom is five-coordinate in a geometry between trigonal–bipyramidal and tetragonal–pyrimidal. Molecules are linked into a three-dimensional framework by O—H

Cl and C—H

Cl hydrogen bonds. The packing is further stabilized by π–π interactions between the phenanthroline ring systems.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013250/kp2015sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013250/kp2015Isup2.hkl Contains datablock I

CCDC reference: 608438

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.045
wR factor = 0.128
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     3.249
            Value of mu given      =     1.624
CHEMW03_ALERT_2_A ALERT: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           711.76
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   14.00  168.15
           H         1.01   14.00   14.11
           N        14.01    2.00   28.01
           O        16.00    1.00   16.00
           Cl       35.45    2.00   70.91
           Ni       58.69    1.00   58.69
           Calculated formula weight              355.88
DENSD01_ALERT_1_A  The ratio of the submitted crystal density and that
            calculated from the formula is outside the range 0.90 <> 1.10
            Crystal density given    =      1.556
            Calculated crystal density =      3.113
PLAT043_ALERT_1_A Check Reported Molecular Weight ................     711.76
PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent ....       3.11

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C28
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H14 Cl2 N2 Ni O

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C28 H28 Cl4 N4 Ni2 O2
            Atom count from the _atom_site data:  C14 H14 Cl2 N2 Ni1 O1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C28 H28 Cl4 N4 Ni2 O2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        112.00     56.00   56.00
           H        112.00     56.00   56.00
           Cl        16.00      8.00    8.00
           N         16.00      8.00    8.00
           Ni         8.00      4.00    4.00
           O          8.00      4.00    4.00

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

  10 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
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Aquadichloro(2,9-dimethyl-1,10-phenanthroline-κ²N,N')nickel(II) top

Crystal data top

[NiCl₂(C₁₄H₁₂N₂)(H₂O)]	Z = 4
M_r = 711.76	F(000) = 728
Triclinic, P1	D_x = 1.556 Mg m⁻³
a = 7.5631 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.501 (2) Å	Cell parameters from 3906 reflections
c = 18.924 (4) Å	θ = 2.5–26.0°
α = 106.692 (3)°	µ = 1.62 mm⁻¹
β = 93.545 (4)°	T = 293 K
γ = 103.467 (2)°	Plate, green
V = 1518.7 (5) Å³	0.30 × 0.16 × 0.06 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	5826 independent reflections
Radiation source: fine-focus sealed tube	4892 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.1°, θ_min = 1.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→14
T_min = 0.641, T_max = 0.909	l = −22→23
8714 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0726P)² + 0.9988P] where P = (F_o² + 2F_c²)/3
5826 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	1.58716 (6)	0.67800 (4)	0.34192 (2)	0.03713 (14)
Ni2	0.94287 (6)	0.33724 (4)	0.15800 (2)	0.03489 (14)
Cl1	1.37032 (13)	0.73474 (8)	0.27395 (5)	0.0477 (2)
Cl2	1.86982 (12)	0.64222 (8)	0.37593 (5)	0.0446 (2)
Cl3	0.70694 (14)	0.29197 (8)	0.22906 (5)	0.0496 (2)
Cl4	1.23711 (12)	0.38200 (8)	0.12324 (5)	0.0446 (2)
O1	1.5603 (4)	0.5290 (3)	0.25056 (16)	0.0637 (8)
O2	1.0076 (4)	0.5155 (2)	0.22627 (16)	0.0570 (7)
N1	1.6698 (4)	0.8525 (3)	0.42006 (16)	0.0376 (6)
N2	1.4477 (4)	0.6378 (3)	0.42570 (15)	0.0368 (6)
N3	0.8010 (4)	0.3136 (3)	0.05664 (16)	0.0411 (7)
N4	0.9095 (4)	0.1476 (3)	0.11276 (15)	0.0370 (6)
C1	1.8331 (6)	0.9566 (4)	0.3401 (2)	0.0606 (11)
H1B	1.7823	0.8743	0.3051	0.091*
H1C	1.9646	0.9770	0.3442	0.091*
H1D	1.7894	1.0173	0.3231	0.091*
C2	1.7756 (5)	0.9587 (3)	0.4143 (2)	0.0435 (8)
C3	1.8302 (5)	1.0684 (3)	0.4768 (2)	0.0491 (9)
H3A	1.9020	1.1423	0.4717	0.059*
C4	1.7786 (5)	1.0673 (3)	0.5446 (2)	0.0483 (9)
H4A	1.8154	1.1396	0.5855	0.058*
C5	1.6693 (5)	0.9553 (3)	0.5517 (2)	0.0420 (8)
C6	1.6092 (6)	0.9443 (4)	0.6204 (2)	0.0506 (9)
H6A	1.6465	1.0129	0.6635	0.061*
C7	1.4989 (6)	0.8353 (4)	0.6231 (2)	0.0535 (10)
H7A	1.4623	0.8298	0.6683	0.064*
C8	1.4376 (5)	0.7288 (4)	0.5583 (2)	0.0452 (8)
C9	1.3164 (6)	0.6160 (4)	0.5575 (2)	0.0534 (10)
H9A	1.2736	0.6067	0.6011	0.064*
C10	1.2616 (6)	0.5202 (4)	0.4924 (2)	0.0536 (10)
H10A	1.1786	0.4460	0.4917	0.064*
C11	1.3282 (5)	0.5311 (3)	0.4261 (2)	0.0448 (8)
C12	1.4990 (5)	0.7351 (3)	0.49064 (18)	0.0356 (7)
C13	1.6168 (5)	0.8503 (3)	0.48725 (19)	0.0362 (7)
C14	1.2658 (7)	0.4242 (4)	0.3551 (2)	0.0641 (12)
H14A	1.3234	0.4475	0.3155	0.096*
H14B	1.1349	0.4051	0.3432	0.096*
H14C	1.2991	0.3516	0.3609	0.096*
C15	0.8093 (8)	0.5331 (4)	0.0754 (3)	0.0771 (15)
H15A	0.8719	0.5414	0.1231	0.116*
H15B	0.7011	0.5628	0.0823	0.116*
H15C	0.8891	0.5819	0.0509	0.116*
C16	0.7561 (5)	0.3977 (4)	0.0288 (2)	0.0523 (10)
C17	0.6596 (6)	0.3603 (5)	−0.0446 (3)	0.0660 (12)
H17A	0.6292	0.4201	−0.0638	0.079*
C18	0.6123 (6)	0.2378 (5)	−0.0863 (2)	0.0668 (12)
H18A	0.5497	0.2139	−0.1342	0.080*
C19	0.6558 (5)	0.1468 (4)	−0.0584 (2)	0.0529 (10)
C20	0.6061 (6)	0.0135 (5)	−0.0978 (2)	0.0614 (12)
H20A	0.5401	−0.0154	−0.1454	0.074*
C21	0.6515 (6)	−0.0698 (4)	−0.0683 (2)	0.0566 (11)
H21A	0.6149	−0.1550	−0.0950	0.068*
C22	0.7564 (5)	−0.0286 (4)	0.0042 (2)	0.0458 (9)
C23	0.8121 (6)	−0.1090 (3)	0.0390 (2)	0.0529 (10)
H23A	0.7802	−0.1953	0.0150	0.063*
C24	0.9129 (6)	−0.0611 (3)	0.1077 (2)	0.0514 (10)
H24A	0.9487	−0.1148	0.1308	0.062*
C25	0.9631 (5)	0.0692 (3)	0.1440 (2)	0.0431 (8)
C26	0.8079 (5)	0.1011 (3)	0.04438 (19)	0.0390 (8)
C27	0.7537 (5)	0.1897 (3)	0.01369 (19)	0.0419 (8)
C28	1.0790 (6)	0.1253 (4)	0.2183 (2)	0.0564 (10)
H28A	1.0984	0.2150	0.2340	0.085*
H28B	1.1951	0.1053	0.2149	0.085*
H28C	1.0180	0.0917	0.2540	0.085*
H1W1	1.5539	0.4525	0.2266	0.068*
H2W1	1.5323	0.5635	0.2185	0.068*
H1W2	1.0953	0.5784	0.2272	0.068*
H2W2	0.9638	0.5366	0.2675	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0402 (3)	0.0310 (2)	0.0333 (2)	0.00561 (18)	0.00384 (18)	0.00275 (18)
Ni2	0.0405 (3)	0.0273 (2)	0.0317 (2)	0.00618 (18)	0.00371 (18)	0.00366 (17)
Cl1	0.0548 (6)	0.0366 (5)	0.0443 (5)	0.0086 (4)	−0.0039 (4)	0.0064 (4)
Cl2	0.0396 (5)	0.0396 (5)	0.0465 (5)	0.0075 (4)	0.0037 (4)	0.0035 (4)
Cl3	0.0563 (6)	0.0395 (5)	0.0479 (5)	0.0095 (4)	0.0198 (4)	0.0056 (4)
Cl4	0.0416 (5)	0.0362 (4)	0.0458 (5)	0.0047 (4)	0.0066 (4)	0.0013 (4)
O1	0.072 (2)	0.0508 (17)	0.0518 (17)	0.0284 (15)	−0.0143 (15)	−0.0140 (13)
O2	0.0560 (17)	0.0355 (14)	0.0594 (17)	−0.0008 (12)	0.0181 (14)	−0.0079 (12)
N1	0.0374 (16)	0.0313 (14)	0.0394 (16)	0.0058 (12)	0.0023 (12)	0.0074 (12)
N2	0.0399 (16)	0.0312 (14)	0.0363 (15)	0.0075 (12)	−0.0001 (12)	0.0084 (12)
N3	0.0379 (16)	0.0439 (17)	0.0391 (16)	0.0046 (13)	0.0069 (13)	0.0141 (13)
N4	0.0402 (16)	0.0315 (14)	0.0329 (15)	0.0037 (12)	0.0098 (12)	0.0041 (12)
C1	0.061 (3)	0.054 (2)	0.063 (3)	0.001 (2)	0.012 (2)	0.024 (2)
C2	0.0371 (19)	0.0373 (19)	0.054 (2)	0.0057 (15)	0.0024 (16)	0.0146 (17)
C3	0.042 (2)	0.0308 (18)	0.066 (3)	0.0009 (15)	−0.0040 (18)	0.0112 (17)
C4	0.044 (2)	0.0329 (19)	0.055 (2)	0.0079 (16)	−0.0061 (17)	−0.0011 (17)
C5	0.043 (2)	0.0315 (18)	0.047 (2)	0.0127 (15)	−0.0031 (16)	0.0035 (15)
C6	0.064 (3)	0.043 (2)	0.038 (2)	0.0202 (19)	−0.0025 (18)	−0.0003 (16)
C7	0.072 (3)	0.055 (2)	0.036 (2)	0.024 (2)	0.0118 (19)	0.0106 (18)
C8	0.050 (2)	0.043 (2)	0.044 (2)	0.0163 (17)	0.0054 (17)	0.0131 (16)
C9	0.058 (2)	0.056 (2)	0.051 (2)	0.012 (2)	0.0156 (19)	0.026 (2)
C10	0.053 (2)	0.046 (2)	0.060 (3)	−0.0003 (18)	0.0040 (19)	0.024 (2)
C11	0.045 (2)	0.0357 (19)	0.050 (2)	0.0033 (15)	−0.0029 (16)	0.0158 (16)
C12	0.0391 (18)	0.0298 (16)	0.0361 (17)	0.0110 (14)	0.0009 (14)	0.0070 (14)
C13	0.0355 (18)	0.0313 (17)	0.0377 (18)	0.0095 (14)	0.0000 (14)	0.0047 (14)
C14	0.076 (3)	0.040 (2)	0.057 (3)	−0.010 (2)	−0.011 (2)	0.0098 (19)
C15	0.084 (4)	0.058 (3)	0.099 (4)	0.021 (3)	0.002 (3)	0.040 (3)
C16	0.043 (2)	0.056 (2)	0.062 (3)	0.0071 (18)	0.0057 (18)	0.030 (2)
C17	0.058 (3)	0.081 (3)	0.073 (3)	0.014 (2)	0.005 (2)	0.050 (3)
C18	0.054 (3)	0.094 (4)	0.046 (2)	0.006 (2)	0.003 (2)	0.024 (2)
C19	0.039 (2)	0.072 (3)	0.043 (2)	0.0059 (19)	0.0099 (17)	0.019 (2)
C20	0.042 (2)	0.080 (3)	0.037 (2)	0.002 (2)	0.0003 (17)	−0.009 (2)
C21	0.041 (2)	0.054 (2)	0.051 (2)	−0.0009 (18)	0.0064 (18)	−0.009 (2)
C22	0.0330 (18)	0.043 (2)	0.044 (2)	−0.0023 (15)	0.0138 (15)	−0.0044 (16)
C23	0.051 (2)	0.0294 (18)	0.066 (3)	0.0019 (16)	0.023 (2)	0.0002 (18)
C24	0.055 (2)	0.037 (2)	0.063 (3)	0.0119 (17)	0.023 (2)	0.0146 (18)
C25	0.050 (2)	0.0349 (18)	0.046 (2)	0.0108 (16)	0.0188 (17)	0.0123 (16)
C26	0.0351 (18)	0.0404 (19)	0.0345 (18)	0.0052 (14)	0.0117 (14)	0.0033 (15)
C27	0.0346 (18)	0.049 (2)	0.0338 (18)	0.0020 (15)	0.0099 (14)	0.0069 (16)
C28	0.077 (3)	0.055 (2)	0.044 (2)	0.023 (2)	0.009 (2)	0.0197 (19)

Geometric parameters (Å, º) top

Ni1—O1	2.015 (3)	C8—C9	1.399 (5)
Ni1—N1	2.049 (3)	C8—C12	1.403 (5)
Ni1—N2	2.059 (3)	C9—C10	1.360 (6)
Ni1—Cl1	2.3431 (10)	C9—H9A	0.9300
Ni1—Cl2	2.3548 (10)	C10—C11	1.408 (6)
Ni2—O2	2.011 (3)	C10—H10A	0.9300
Ni2—N4	2.049 (3)	C11—C14	1.498 (5)
Ni2—N3	2.053 (3)	C12—C13	1.435 (5)
Ni2—Cl4	2.3435 (10)	C14—H14A	0.9600
Ni2—Cl3	2.3515 (10)	C14—H14B	0.9600
O1—H1W1	0.8541	C14—H14C	0.9600
O1—H2W1	0.8560	C15—C16	1.497 (6)
O2—H1W2	0.8552	C15—H15A	0.9600
O2—H2W2	0.8599	C15—H15B	0.9600
N1—C2	1.333 (4)	C15—H15C	0.9600
N1—C13	1.362 (4)	C16—C17	1.426 (6)
N2—C11	1.347 (4)	C17—C18	1.352 (7)
N2—C12	1.364 (4)	C17—H17A	0.9300
N3—C16	1.324 (5)	C18—C19	1.392 (6)
N3—C27	1.371 (5)	C18—H18A	0.9300
N4—C25	1.332 (5)	C19—C27	1.404 (5)
N4—C26	1.356 (4)	C19—C20	1.445 (6)
C1—C2	1.492 (6)	C20—C21	1.335 (7)
C1—H1B	0.9600	C20—H20A	0.9300
C1—H1C	0.9600	C21—C22	1.433 (6)
C1—H1D	0.9600	C21—H21A	0.9300
C2—C3	1.415 (5)	C22—C23	1.402 (6)
C3—C4	1.365 (6)	C22—C26	1.413 (5)
C3—H3A	0.9300	C23—C24	1.359 (6)
C4—C5	1.407 (5)	C23—H23A	0.9300
C4—H4A	0.9300	C24—C25	1.405 (5)
C5—C13	1.405 (5)	C24—H24A	0.9300
C5—C6	1.432 (5)	C25—C28	1.492 (5)
C6—C7	1.352 (6)	C26—C27	1.432 (5)
C6—H6A	0.9300	C28—H28A	0.9600
C7—C8	1.422 (5)	C28—H28B	0.9600
C7—H7A	0.9300	C28—H28C	0.9600

O1—Ni1—N1	163.92 (13)	C8—C9—H9A	120.3
O1—Ni1—N2	114.49 (13)	C9—C10—C11	121.2 (4)
N1—Ni1—N2	81.34 (11)	C9—C10—H10A	119.4
O1—Ni1—Cl1	86.19 (8)	C11—C10—H10A	119.4
N1—Ni1—Cl1	93.37 (8)	N2—C11—C10	120.5 (3)
N2—Ni1—Cl1	102.18 (8)	N2—C11—C14	119.2 (3)
O1—Ni1—Cl2	85.87 (8)	C10—C11—C14	120.3 (3)
N1—Ni1—Cl2	88.73 (8)	N2—C12—C8	123.5 (3)
N2—Ni1—Cl2	99.63 (8)	N2—C12—C13	116.8 (3)
Cl1—Ni1—Cl2	158.16 (4)	C8—C12—C13	119.6 (3)
O2—Ni2—N4	164.58 (12)	N1—C13—C5	123.1 (3)
O2—Ni2—N3	113.46 (13)	N1—C13—C12	117.4 (3)
N4—Ni2—N3	81.94 (12)	C5—C13—C12	119.5 (3)
O2—Ni2—Cl4	87.41 (8)	C11—C14—H14A	109.5
N4—Ni2—Cl4	91.66 (8)	C11—C14—H14B	109.5
N3—Ni2—Cl4	96.50 (8)	H14A—C14—H14B	109.5
O2—Ni2—Cl3	87.44 (8)	C11—C14—H14C	109.5
N4—Ni2—Cl3	88.35 (8)	H14A—C14—H14C	109.5
N3—Ni2—Cl3	102.81 (9)	H14B—C14—H14C	109.5
Cl4—Ni2—Cl3	160.50 (4)	C16—C15—H15A	109.5
Ni1—O1—H1W1	155.8	C16—C15—H15B	109.5
Ni1—O1—H2W1	97.2	H15A—C15—H15B	109.5
H1W1—O1—H2W1	106.8	C16—C15—H15C	109.5
Ni2—O2—H1W2	129.8	H15A—C15—H15C	109.5
Ni2—O2—H2W2	122.5	H15B—C15—H15C	109.5
H1W2—O2—H2W2	106.3	N3—C16—C17	120.7 (4)
C2—N1—C13	119.1 (3)	N3—C16—C15	118.9 (4)
C2—N1—Ni1	128.9 (3)	C17—C16—C15	120.4 (4)
C13—N1—Ni1	111.8 (2)	C18—C17—C16	119.9 (4)
C11—N2—C12	118.2 (3)	C18—C17—H17A	120.1
C11—N2—Ni1	130.0 (2)	C16—C17—H17A	120.1
C12—N2—Ni1	111.6 (2)	C17—C18—C19	120.9 (4)
C16—N3—C27	119.0 (3)	C17—C18—H18A	119.5
C16—N3—Ni2	130.1 (3)	C19—C18—H18A	119.5
C27—N3—Ni2	111.0 (2)	C18—C19—C27	116.5 (4)
C25—N4—C26	119.5 (3)	C18—C19—C20	124.9 (4)
C25—N4—Ni2	128.3 (2)	C27—C19—C20	118.6 (4)
C26—N4—Ni2	112.1 (2)	C21—C20—C19	122.3 (4)
C2—C1—H1B	109.5	C21—C20—H20A	118.8
C2—C1—H1C	109.5	C19—C20—H20A	118.8
H1B—C1—H1C	109.5	C20—C21—C22	120.4 (4)
C2—C1—H1D	109.5	C20—C21—H21A	119.8
H1B—C1—H1D	109.5	C22—C21—H21A	119.8
H1C—C1—H1D	109.5	C23—C22—C26	116.8 (4)
N1—C2—C3	120.6 (3)	C23—C22—C21	124.3 (4)
N1—C2—C1	117.5 (3)	C26—C22—C21	118.9 (4)
C3—C2—C1	121.9 (3)	C24—C23—C22	120.1 (3)
C4—C3—C2	120.8 (3)	C24—C23—H23A	120.0
C4—C3—H3A	119.6	C22—C23—H23A	120.0
C2—C3—H3A	119.6	C23—C24—C25	120.3 (4)
C3—C4—C5	119.2 (3)	C23—C24—H24A	119.9
C3—C4—H4A	120.4	C25—C24—H24A	119.9
C5—C4—H4A	120.4	N4—C25—C24	120.9 (4)
C13—C5—C4	117.2 (4)	N4—C25—C28	117.4 (3)
C13—C5—C6	119.4 (3)	C24—C25—C28	121.7 (4)
C4—C5—C6	123.4 (3)	N4—C26—C22	122.4 (3)
C7—C6—C5	120.6 (3)	N4—C26—C27	117.0 (3)
C7—C6—H6A	119.7	C22—C26—C27	120.5 (3)
C5—C6—H6A	119.7	N3—C27—C19	123.0 (4)
C6—C7—C8	121.3 (4)	N3—C27—C26	117.9 (3)
C6—C7—H7A	119.3	C19—C27—C26	119.1 (3)
C8—C7—H7A	119.3	C25—C28—H28A	109.5
C9—C8—C12	117.1 (3)	C25—C28—H28B	109.5
C9—C8—C7	123.5 (4)	H28A—C28—H28B	109.5
C12—C8—C7	119.4 (4)	C25—C28—H28C	109.5
C10—C9—C8	119.4 (4)	H28A—C28—H28C	109.5
C10—C9—H9A	120.3	H28B—C28—H28C	109.5

O1—Ni1—N1—C2	12.5 (6)	C9—C8—C12—N2	−0.4 (5)
N2—Ni1—N1—C2	−177.3 (3)	C7—C8—C12—N2	−180.0 (3)
Cl1—Ni1—N1—C2	−75.5 (3)	C9—C8—C12—C13	177.1 (3)
Cl2—Ni1—N1—C2	82.8 (3)	C7—C8—C12—C13	−2.4 (5)
O1—Ni1—N1—C13	−161.8 (3)	C2—N1—C13—C5	−0.3 (5)
N2—Ni1—N1—C13	8.4 (2)	Ni1—N1—C13—C5	174.6 (3)
Cl1—Ni1—N1—C13	110.3 (2)	C2—N1—C13—C12	178.4 (3)
Cl2—Ni1—N1—C13	−91.5 (2)	Ni1—N1—C13—C12	−6.7 (4)
O1—Ni1—N2—C11	−7.2 (3)	C4—C5—C13—N1	1.3 (5)
N1—Ni1—N2—C11	175.8 (3)	C6—C5—C13—N1	−179.2 (3)
Cl1—Ni1—N2—C11	84.2 (3)	C4—C5—C13—C12	−177.4 (3)
Cl2—Ni1—N2—C11	−97.0 (3)	C6—C5—C13—C12	2.1 (5)
O1—Ni1—N2—C12	168.1 (2)	N2—C12—C13—N1	−1.0 (4)
N1—Ni1—N2—C12	−9.0 (2)	C8—C12—C13—N1	−178.7 (3)
Cl1—Ni1—N2—C12	−100.6 (2)	N2—C12—C13—C5	177.8 (3)
Cl2—Ni1—N2—C12	78.2 (2)	C8—C12—C13—C5	0.1 (5)
O2—Ni2—N3—C16	4.2 (4)	C27—N3—C16—C17	0.2 (5)
N4—Ni2—N3—C16	−176.5 (3)	Ni2—N3—C16—C17	178.5 (3)
Cl4—Ni2—N3—C16	−85.7 (3)	C27—N3—C16—C15	−179.4 (4)
Cl3—Ni2—N3—C16	97.0 (3)	Ni2—N3—C16—C15	−1.2 (6)
O2—Ni2—N3—C27	−177.4 (2)	N3—C16—C17—C18	0.3 (6)
N4—Ni2—N3—C27	1.8 (2)	C15—C16—C17—C18	180.0 (4)
Cl4—Ni2—N3—C27	92.6 (2)	C16—C17—C18—C19	0.3 (7)
Cl3—Ni2—N3—C27	−84.6 (2)	C17—C18—C19—C27	−1.4 (6)
O2—Ni2—N4—C25	−1.0 (6)	C17—C18—C19—C20	178.0 (4)
N3—Ni2—N4—C25	−178.4 (3)	C18—C19—C20—C21	−180.0 (4)
Cl4—Ni2—N4—C25	85.3 (3)	C27—C19—C20—C21	−0.6 (6)
Cl3—Ni2—N4—C25	−75.2 (3)	C19—C20—C21—C22	−1.3 (6)
O2—Ni2—N4—C26	174.1 (4)	C20—C21—C22—C23	−179.2 (4)
N3—Ni2—N4—C26	−3.3 (2)	C20—C21—C22—C26	1.2 (6)
Cl4—Ni2—N4—C26	−99.6 (2)	C26—C22—C23—C24	−0.9 (5)
Cl3—Ni2—N4—C26	99.9 (2)	C21—C22—C23—C24	179.5 (4)
C13—N1—C2—C3	−0.9 (5)	C22—C23—C24—C25	−0.6 (6)
Ni1—N1—C2—C3	−174.9 (3)	C26—N4—C25—C24	−1.2 (5)
C13—N1—C2—C1	179.0 (3)	Ni2—N4—C25—C24	173.5 (3)
Ni1—N1—C2—C1	5.1 (5)	C26—N4—C25—C28	178.3 (3)
N1—C2—C3—C4	1.3 (6)	Ni2—N4—C25—C28	−7.0 (5)
C1—C2—C3—C4	−178.7 (4)	C23—C24—C25—N4	1.6 (6)
C2—C3—C4—C5	−0.3 (6)	C23—C24—C25—C28	−177.8 (4)
C3—C4—C5—C13	−0.9 (5)	C25—N4—C26—C22	−0.3 (5)
C3—C4—C5—C6	179.6 (4)	Ni2—N4—C26—C22	−175.8 (3)
C13—C5—C6—C7	−1.8 (6)	C25—N4—C26—C27	179.8 (3)
C4—C5—C6—C7	177.6 (4)	Ni2—N4—C26—C27	4.3 (4)
C5—C6—C7—C8	−0.6 (6)	C23—C22—C26—N4	1.3 (5)
C6—C7—C8—C9	−176.8 (4)	C21—C22—C26—N4	−179.0 (3)
C6—C7—C8—C12	2.7 (6)	C23—C22—C26—C27	−178.8 (3)
C12—C8—C9—C10	−1.2 (6)	C21—C22—C26—C27	0.9 (5)
C7—C8—C9—C10	178.3 (4)	C16—N3—C27—C19	−1.4 (5)
C8—C9—C10—C11	1.6 (6)	Ni2—N3—C27—C19	−180.0 (3)
C12—N2—C11—C10	−1.2 (5)	C16—N3—C27—C26	178.4 (3)
Ni1—N2—C11—C10	173.8 (3)	Ni2—N3—C27—C26	−0.1 (4)
C12—N2—C11—C14	178.4 (3)	C18—C19—C27—N3	2.0 (5)
Ni1—N2—C11—C14	−6.6 (5)	C20—C19—C27—N3	−177.4 (3)
C9—C10—C11—N2	−0.4 (6)	C18—C19—C27—C26	−177.9 (3)
C9—C10—C11—C14	−179.9 (4)	C20—C19—C27—C26	2.7 (5)
C11—N2—C12—C8	1.6 (5)	N4—C26—C27—N3	−2.9 (4)
Ni1—N2—C12—C8	−174.3 (3)	C22—C26—C27—N3	177.2 (3)
C11—N2—C12—C13	−176.0 (3)	N4—C26—C27—C19	177.0 (3)
Ni1—N2—C12—C13	8.1 (4)	C22—C26—C27—C19	−2.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W1···Cl3ⁱ	0.85	2.40	3.107 (4)	140
O1—H1W1···Cl4	0.85	2.80	3.106 (3)	103
O2—H1W2···Cl1	0.86	2.34	3.141 (3)	157
O1—H2W1···Cl4	0.86	2.79	3.106 (3)	104
O2—H2W2···Cl2ⁱⁱ	0.86	2.31	3.152 (3)	166
C14—H14A···O1	0.96	2.40	3.315 (6)	159
C15—H15A···O2	0.96	2.28	3.223 (6)	168
C17—H17A···Cl4ⁱⁱⁱ	0.93	2.83	3.634 (6)	145

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

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Aqua­dichloro­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)nickel(II)

Supporting information

Key indicators

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Aquadichloro(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)nickel(II)