Crystal structure of hexa­aqua­nickel(II) bis­{5-bromo-7-[(2-hy­droxy­eth­yl)amino]-1-methyl-6-oxido­quinolin-1-ium-3-sulfonate} monohydrate

The packing of the title compound is built up by columns of π–π stacking quinoline derivatives running along the c axis, which are inter­connected by [Ni(H₂O)₆]²⁺ complex cations through hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.056
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H21    ..  H23B    ..       2.05 Ang.

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  BR16    ..       3.02 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C12 H12 Br N2 O5 S
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5 Report
PLAT976_ALERT_2_C Check Calcd Residual Density  0.97A From     O25      -0.45 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on    H25A      -0.39 eA-3

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          7 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.20 Why ?
PLAT233_ALERT_4_G Hirshfeld (M-X Solvent)    Ni22   --  O23     ..        5.3 s.u.
PLAT233_ALERT_4_G Hirshfeld (M-X Solvent)    Ni22   --  O25     ..        5.0 s.u.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C5     -C7            1.43 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           8 Note

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

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

---

Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Hexaaquanickel(II) bis{5-bromo-7-[(2-hydroxyethyl)amino]-1-methyl-6-oxidoquinoline-1-ium-3-sulfonate} monohydrate

Crystal data

[Ni(H2O)6](C12H12BrN2O5S)2·H2O	F(000) = 1904
Mr = 937.23	Dx = 1.887 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7315 (4) Å	Cell parameters from 5359 reflections
b = 27.4581 (13) Å	θ = 2.8–29.0°
c = 13.7943 (6) Å	µ = 3.22 mm^−1
β = 94.061 (4)°	T = 100 K
V = 3298.9 (3) Å^3	Plate, orange
Z = 4	0.4 × 0.2 × 0.1 mm

Data collection

Agilent SuperNova (single source at offset, Eos detector) diffractometer	3372 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3041 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	k = −34→32
Tmin = 0.546, Tmax = 0.725	l = −12→17
9171 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0207P)^2 + 5.2045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
3372 reflections	Δρmax = 0.41 e Å^−3
235 parameters	Δρmin = −0.49 e Å^−3
0 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
N1	0.90237 (18)	0.43668 (6)	0.37155 (11)	0.0110 (3)
C2	0.9801 (2)	0.39411 (8)	0.37514 (14)	0.0132 (4)
H2	0.9254	0.3642	0.3739	0.016*
C3	1.1379 (2)	0.39384 (8)	0.38056 (14)	0.0131 (4)
C4	1.2182 (2)	0.43770 (8)	0.38321 (13)	0.0134 (4)
H4	1.3273	0.4374	0.3877	0.016*
C5	1.1403 (2)	0.48189 (8)	0.37930 (13)	0.0108 (4)
C6	0.9750 (2)	0.48132 (8)	0.37471 (13)	0.0104 (4)
C7	1.2125 (2)	0.52820 (8)	0.38177 (14)	0.0119 (4)
C8	1.1373 (2)	0.57248 (8)	0.38109 (13)	0.0122 (4)
C9	0.9683 (2)	0.56934 (8)	0.37556 (13)	0.0110 (4)
C10	0.8918 (2)	0.52466 (8)	0.37301 (13)	0.0113 (4)
H10	0.7828	0.5238	0.3701	0.014*
C11	0.7332 (2)	0.43449 (8)	0.36504 (14)	0.0128 (4)
H11A	0.6923	0.4543	0.3101	0.019*
H11B	0.6950	0.4470	0.4253	0.019*
H11C	0.6999	0.4006	0.3553	0.019*
S12	1.23734 (6)	0.33760 (2)	0.37750 (4)	0.01589 (12)
O13	1.3871 (2)	0.34725 (7)	0.42443 (13)	0.0360 (5)
O14	1.24175 (17)	0.32666 (6)	0.27422 (10)	0.0200 (3)
O15	1.1481 (2)	0.30278 (6)	0.42858 (12)	0.0323 (4)
Br16	1.42949 (2)	0.53172 (2)	0.38060 (2)	0.01722 (7)
O17	1.19947 (16)	0.61482 (5)	0.38363 (10)	0.0154 (3)
N18	0.89569 (19)	0.61215 (7)	0.37205 (12)	0.0136 (4)
H18	0.9506	0.6391	0.3730	0.016*
C19	0.7298 (2)	0.61683 (8)	0.35993 (15)	0.0139 (4)
H19A	0.6846	0.6070	0.4208	0.017*
H19B	0.6892	0.5947	0.3075	0.017*
C20	0.6831 (2)	0.66848 (8)	0.33499 (15)	0.0162 (4)
H20A	0.5699	0.6704	0.3248	0.019*
H20B	0.7159	0.6902	0.3899	0.019*
O21	0.75070 (19)	0.68455 (6)	0.24924 (11)	0.0229 (4)
H21	0.760 (3)	0.6610 (11)	0.213 (2)	0.034*
Ni22	0.2500	0.7500	0.5000	0.01747 (10)
O23	0.35588 (18)	0.75193 (6)	0.37316 (12)	0.0273 (4)
H23A	0.3304	0.7799	0.3392	0.041*
H23B	0.3270	0.7270	0.3322	0.041*
O24	0.31091 (17)	0.67782 (6)	0.52289 (12)	0.0237 (4)
H24A	0.4136	0.6748	0.5315	0.036*
H24B	0.2816	0.6604	0.4695	0.036*
O25	0.44976 (16)	0.77588 (5)	0.57273 (12)	0.0196 (3)
H25A	0.5337	0.7662	0.5414	0.029*
H25B	0.4680	0.7661	0.6357	0.029*
O26	0.5000	0.73024 (9)	0.7500	0.0218 (5)
H26	0.570 (3)	0.7142 (10)	0.746 (2)	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0109 (8)	0.0116 (9)	0.0102 (8)	0.0017 (7)	0.0001 (6)	−0.0009 (7)
C2	0.0169 (10)	0.0120 (10)	0.0106 (9)	0.0023 (8)	−0.0005 (8)	0.0001 (8)
C3	0.0151 (10)	0.0137 (11)	0.0102 (9)	0.0061 (8)	0.0001 (7)	−0.0021 (8)
C4	0.0125 (10)	0.0178 (11)	0.0098 (9)	0.0049 (8)	0.0007 (7)	−0.0004 (8)
C5	0.0103 (9)	0.0153 (11)	0.0070 (8)	0.0009 (8)	0.0010 (7)	−0.0001 (8)
C6	0.0118 (9)	0.0132 (11)	0.0064 (8)	−0.0002 (8)	0.0014 (7)	−0.0001 (8)
C7	0.0075 (9)	0.0184 (11)	0.0099 (9)	0.0003 (8)	0.0009 (7)	0.0005 (8)
C8	0.0109 (10)	0.0178 (11)	0.0078 (9)	−0.0010 (8)	0.0003 (7)	0.0001 (8)
C9	0.0111 (10)	0.0142 (11)	0.0077 (9)	0.0018 (8)	0.0003 (7)	−0.0011 (8)
C10	0.0079 (9)	0.0150 (11)	0.0111 (9)	0.0017 (8)	0.0007 (7)	0.0001 (8)
C11	0.0079 (9)	0.0140 (11)	0.0166 (10)	0.0003 (8)	0.0005 (7)	0.0003 (8)
S12	0.0176 (3)	0.0156 (3)	0.0141 (2)	0.0096 (2)	−0.00095 (19)	−0.0023 (2)
O13	0.0268 (9)	0.0349 (11)	0.0431 (11)	0.0212 (8)	−0.0198 (8)	−0.0210 (9)
O14	0.0243 (8)	0.0199 (9)	0.0156 (7)	0.0105 (7)	0.0008 (6)	−0.0038 (6)
O15	0.0481 (11)	0.0194 (9)	0.0315 (9)	0.0170 (8)	0.0186 (8)	0.0112 (8)
Br16	0.00740 (10)	0.02418 (13)	0.02029 (11)	0.00080 (8)	0.00253 (7)	0.00294 (9)
O17	0.0144 (7)	0.0140 (8)	0.0177 (7)	−0.0023 (6)	−0.0002 (6)	0.0003 (6)
N18	0.0113 (8)	0.0107 (9)	0.0189 (9)	−0.0004 (7)	0.0006 (7)	0.0002 (7)
C19	0.0094 (10)	0.0138 (11)	0.0184 (10)	0.0013 (8)	0.0001 (8)	0.0003 (9)
C20	0.0162 (10)	0.0160 (11)	0.0163 (10)	0.0034 (9)	−0.0004 (8)	−0.0003 (9)
O21	0.0355 (9)	0.0159 (9)	0.0179 (8)	0.0045 (7)	0.0053 (7)	0.0017 (7)
Ni22	0.00750 (18)	0.0097 (2)	0.0349 (2)	−0.00015 (14)	−0.00080 (16)	−0.00713 (17)
O23	0.0182 (8)	0.0217 (9)	0.0422 (10)	−0.0036 (7)	0.0036 (7)	−0.0123 (8)
O24	0.0136 (7)	0.0140 (8)	0.0422 (10)	0.0032 (6)	−0.0073 (7)	−0.0106 (7)
O25	0.0107 (7)	0.0148 (8)	0.0331 (9)	−0.0003 (6)	0.0004 (6)	−0.0042 (7)
O26	0.0133 (11)	0.0133 (12)	0.0403 (14)	0.000	0.0117 (10)	0.000

Geometric parameters (Å, º)

N1—C2	1.351 (3)	S12—O15	1.4474 (18)
N1—C6	1.380 (3)	N18—H18	0.8806
N1—C11	1.475 (2)	N18—C19	1.452 (2)
C2—H2	0.9500	C19—H19A	0.9900
C2—C3	1.374 (3)	C19—H19B	0.9900
C3—C4	1.393 (3)	C19—C20	1.509 (3)
C3—S12	1.774 (2)	C20—H20A	0.9900
C4—H4	0.9500	C20—H20B	0.9900
C4—C5	1.390 (3)	C20—O21	1.429 (3)
C5—C6	1.440 (3)	O21—H21	0.83 (3)
C5—C7	1.418 (3)	Ni22—O23^i	2.0366 (17)
C6—C10	1.394 (3)	Ni22—O23	2.0366 (17)
C7—C8	1.381 (3)	Ni22—O24	2.0704 (15)
C7—Br16	1.8983 (19)	Ni22—O24^i	2.0704 (15)
C8—C9	1.474 (3)	Ni22—O25	2.0750 (14)
C8—O17	1.283 (3)	Ni22—O25^i	2.0750 (14)
C9—C10	1.397 (3)	O23—H23A	0.9191
C9—N18	1.335 (3)	O23—H23B	0.9115
C10—H10	0.9500	O24—H24A	0.9003
C11—H11A	0.9800	O24—H24B	0.9001
C11—H11B	0.9800	O25—H25A	0.9163
C11—H11C	0.9800	O25—H25B	0.9128
S12—O13	1.4420 (17)	O26—H26	0.76 (3)
S12—O14	1.4592 (15)
C2—N1—C6	122.61 (17)	O15—S12—O14	113.06 (10)
C2—N1—C11	117.74 (18)	C9—N18—H18	118.8
C6—N1—C11	119.64 (17)	C9—N18—C19	123.35 (18)
N1—C2—H2	119.8	C19—N18—H18	117.7
N1—C2—C3	120.4 (2)	N18—C19—H19A	109.4
C3—C2—H2	119.8	N18—C19—H19B	109.4
C2—C3—C4	119.84 (19)	N18—C19—C20	111.15 (17)
C2—C3—S12	119.61 (17)	H19A—C19—H19B	108.0
C4—C3—S12	120.46 (15)	C20—C19—H19A	109.4
C3—C4—H4	119.7	C20—C19—H19B	109.4
C5—C4—C3	120.66 (19)	C19—C20—H20A	109.4
C5—C4—H4	119.7	C19—C20—H20B	109.4
C4—C5—C6	118.55 (19)	H20A—C20—H20B	108.0
C4—C5—C7	124.51 (18)	O21—C20—C19	111.00 (17)
C7—C5—C6	116.92 (18)	O21—C20—H20A	109.4
N1—C6—C5	117.92 (18)	O21—C20—H20B	109.4
N1—C6—C10	121.32 (18)	C20—O21—H21	109 (2)
C10—C6—C5	120.76 (19)	O23^i—Ni22—O23	180.00 (4)
C5—C7—Br16	119.16 (15)	O23^i—Ni22—O24	88.36 (7)
C8—C7—C5	125.37 (18)	O23—Ni22—O24^i	88.36 (7)
C8—C7—Br16	115.42 (15)	O23—Ni22—O24	91.64 (7)
C7—C8—C9	114.98 (19)	O23^i—Ni22—O24^i	91.64 (7)
O17—C8—C7	126.71 (18)	O23^i—Ni22—O25^i	89.39 (6)
O17—C8—C9	118.31 (18)	O23—Ni22—O25	89.39 (6)
C10—C9—C8	121.87 (19)	O23^i—Ni22—O25	90.61 (6)
N18—C9—C8	114.94 (18)	O23—Ni22—O25^i	90.61 (6)
N18—C9—C10	123.18 (18)	O24—Ni22—O24^i	180.0
C6—C10—C9	120.10 (18)	O24^i—Ni22—O25	86.79 (6)
C6—C10—H10	120.0	O24—Ni22—O25	93.21 (6)
C9—C10—H10	120.0	O24—Ni22—O25^i	86.79 (6)
N1—C11—H11A	109.5	O24^i—Ni22—O25^i	93.21 (6)
N1—C11—H11B	109.5	O25^i—Ni22—O25	180.0
N1—C11—H11C	109.5	Ni22—O23—H23A	110.6
H11A—C11—H11B	109.5	Ni22—O23—H23B	113.0
H11A—C11—H11C	109.5	H23A—O23—H23B	105.3
H11B—C11—H11C	109.5	Ni22—O24—H24A	110.6
O13—S12—C3	105.03 (10)	Ni22—O24—H24B	109.2
O13—S12—O14	112.98 (10)	H24A—O24—H24B	106.3
O13—S12—O15	113.89 (12)	Ni22—O25—H25A	110.3
O14—S12—C3	104.43 (9)	Ni22—O25—H25B	116.3
O15—S12—C3	106.39 (10)	H25A—O25—H25B	105.9
N1—C2—C3—C4	0.5 (3)	C6—N1—C2—C3	−1.1 (3)
N1—C2—C3—S12	−176.06 (14)	C6—C5—C7—C8	0.7 (3)
N1—C6—C10—C9	−179.52 (17)	C6—C5—C7—Br16	−176.56 (13)
C2—N1—C6—C5	1.8 (3)	C7—C5—C6—N1	179.55 (16)
C2—N1—C6—C10	−178.59 (17)	C7—C5—C6—C10	−0.1 (3)
C2—C3—C4—C5	−0.7 (3)	C7—C8—C9—C10	1.1 (3)
C2—C3—S12—O13	−156.31 (17)	C7—C8—C9—N18	−178.14 (17)
C2—C3—S12—O14	84.58 (17)	C8—C9—C10—C6	−0.6 (3)
C2—C3—S12—O15	−35.24 (19)	C8—C9—N18—C19	175.77 (17)
C3—C4—C5—C6	1.4 (3)	C9—N18—C19—C20	−166.55 (18)
C3—C4—C5—C7	179.87 (18)	C10—C9—N18—C19	−3.5 (3)
C4—C3—S12—O13	27.10 (19)	C11—N1—C2—C3	179.54 (17)
C4—C3—S12—O14	−92.01 (17)	C11—N1—C6—C5	−178.90 (16)
C4—C3—S12—O15	148.17 (17)	C11—N1—C6—C10	0.8 (3)
C4—C5—C6—N1	−1.9 (3)	S12—C3—C4—C5	175.84 (14)
C4—C5—C6—C10	178.47 (17)	Br16—C7—C8—C9	176.19 (13)
C4—C5—C7—C8	−177.81 (18)	Br16—C7—C8—O17	−3.0 (3)
C4—C5—C7—Br16	5.0 (3)	O17—C8—C9—C10	−179.67 (17)
C5—C6—C10—C9	0.1 (3)	O17—C8—C9—N18	1.1 (3)
C5—C7—C8—C9	−1.1 (3)	N18—C9—C10—C6	178.53 (17)
C5—C7—C8—O17	179.72 (18)	N18—C19—C20—O21	57.0 (2)

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···O17^ii	0.83 (3)	1.89 (3)	2.707 (2)	170 (3)
C11—H11B···Br16^iii	0.98	3.02	3.987 (2)	171
C19—H19A···O13^iii	0.99	2.59	3.360 (3)	134
N18—H18···O25^iv	0.88	2.58	3.422 (2)	159
O23—H23A···O14^v	0.92	2.09	2.971 (2)	161
O23—H23B···O21^vi	0.91	1.72	2.630 (2)	172
O24—H24A···O13^iii	0.90	1.90	2.772 (2)	162
O24—H24B···O17^vii	0.90	1.83	2.714 (2)	165
O25—H25A···O15^viii	0.92	2.16	2.826 (2)	129
O25—H25B···O26	0.91	1.86	2.755 (2)	165
O26—H26···O14^iii	0.76 (3)	2.03 (3)	2.783 (2)	175 (3)

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