Crystal structure of the one-dimensional coordination polymer formed by the macrocyclic [Ni(cyclam)]²⁺ cation and the dianion of di­phenyl­silanediylbis(4-benzoic acid)

The title coordination polymer consists of parallel zigzag-like chains of [Ni(cyclam)]²⁺ cations bridged by the dianions of the acid in the axial positions of the trans-NiN₄O₂ coordination polyhedron. Polymeric chains propagating along the [101] direction are assembled into a three-dimensional network by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.066
• wR factor = 0.147
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      8.122 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT300_ALERT_4_G Atom Site Occupancy of O1W        Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1WA       Constrained at       0.75 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1WB       Constrained at       0.75 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT793_ALERT_4_G Model has Chirality at N1          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N2          (Centro SPGR)          S Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.04 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        694 Note
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           4 Units
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           2 Units
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           4 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           2 Units

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

   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   6 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[[(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)nickel(II)]-µ-4,4'-(diphenylsilanediyl)dibenzoato-κ²O:O'] sesquihydrate]

Crystal data

[Ni(C26H18O4Si)(C10H24N4)]·1.5H2O	F(000) = 1500
Mr = 1417.11	Dx = 1.390 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.390 (4) Å	Cell parameters from 1577 reflections
b = 7.3865 (10) Å	θ = 2.6–29.5°
c = 18.2424 (16) Å	µ = 0.66 mm^−1
β = 98.161 (10)°	T = 200 K
V = 3386.6 (8) Å^3	Prism, clear light yellow
Z = 2	0.35 × 0.10 × 0.10 mm

Data collection

Agilent Xcalibur, Eos diffractometer	3926 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2512 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 16.1593 pixels mm^-1	θmax = 29.5°, θmin = 2.6°
ω scans	h = −31→21
Absorption correction: multi-scan (CrysAlisPro; Agilent, 2014),	k = −10→9
Tmin = 0.964, Tmax = 1.000	l = −21→23
7999 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)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 4.2041P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3926 reflections	Δρmax = 0.51 e Å^−3
219 parameters	Δρmin = −0.51 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	Occ. (<1)
Ni1	0.250000	0.250000	0.000000	0.0273 (2)
Si1	0.500000	0.95105 (19)	0.250000	0.0256 (3)
O1	0.30989 (10)	0.3756 (4)	0.07669 (14)	0.0372 (7)
O2	0.27252 (11)	0.4301 (4)	0.17836 (15)	0.0514 (8)
N1	0.19897 (12)	0.2120 (5)	0.07732 (17)	0.0377 (8)
H1	0.214580	0.275668	0.122344	0.045*
N2	0.27921 (12)	−0.0047 (4)	0.03013 (18)	0.0381 (8)
H2	0.262042	−0.087426	−0.007954	0.046*
C1	0.20090 (17)	0.0146 (6)	0.0952 (2)	0.0464 (11)
H1A	0.177654	−0.051687	0.057721	0.056*
H1B	0.188941	−0.005714	0.142697	0.056*
C2	0.25790 (17)	−0.0508 (6)	0.0976 (2)	0.0480 (11)
H2A	0.279912	0.003615	0.139702	0.058*
H2B	0.259044	−0.181115	0.104319	0.058*
C3	0.33655 (17)	−0.0306 (6)	0.0316 (2)	0.0490 (12)
H3A	0.345186	−0.156556	0.042523	0.059*
H3B	0.355364	0.042076	0.071235	0.059*
C4	0.14439 (17)	0.4804 (6)	0.0397 (2)	0.0477 (11)
H4A	0.108246	0.524309	0.038067	0.057*
H4B	0.166204	0.543620	0.079585	0.057*
C5	0.14505 (15)	0.2795 (6)	0.0585 (2)	0.0435 (11)
H5A	0.125675	0.260021	0.100024	0.052*
H5B	0.127171	0.212343	0.016526	0.052*
C6	0.30912 (15)	0.4468 (5)	0.1389 (2)	0.0319 (9)
C7	0.35609 (14)	0.5657 (5)	0.16868 (18)	0.0247 (8)
C8	0.40442 (14)	0.5475 (5)	0.14241 (19)	0.0312 (9)
H8	0.408530	0.458487	0.107630	0.037*
C9	0.44678 (14)	0.6610 (5)	0.1675 (2)	0.0329 (9)
H9	0.479200	0.644164	0.150332	0.039*
C10	0.44174 (14)	0.8002 (5)	0.21810 (18)	0.0264 (8)
C11	0.39244 (14)	0.8183 (5)	0.24315 (18)	0.0296 (8)
H11	0.387380	0.911020	0.275947	0.035*
C12	0.35091 (14)	0.7001 (5)	0.21976 (19)	0.0309 (9)
H12	0.319013	0.711608	0.238874	0.037*
C13	0.51508 (14)	1.1037 (5)	0.1735 (2)	0.0285 (8)
C14	0.55319 (15)	1.2399 (5)	0.1896 (2)	0.0371 (9)
H14	0.571043	1.249604	0.237641	0.044*
C15	0.56512 (17)	1.3597 (6)	0.1370 (2)	0.0466 (11)
H15	0.590586	1.449113	0.149517	0.056*
C16	0.53943 (17)	1.3472 (6)	0.0658 (2)	0.0458 (11)
H16	0.547953	1.426763	0.029713	0.055*
C17	0.50098 (17)	1.2169 (6)	0.0477 (2)	0.0464 (11)
H17	0.483033	1.210014	−0.000366	0.056*
C18	0.48907 (15)	1.0964 (5)	0.1009 (2)	0.0361 (9)
H18	0.463175	1.008505	0.088027	0.043*
O1W	0.19429 (16)	0.6528 (6)	0.2165 (2)	0.0640 (12)	0.75
H1WA	0.205149	0.708674	0.256534	0.096*	0.75
H1WB	0.218579	0.582004	0.206074	0.096*	0.75

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0236 (4)	0.0255 (4)	0.0312 (4)	−0.0020 (3)	−0.0015 (3)	−0.0022 (3)
Si1	0.0214 (7)	0.0242 (7)	0.0295 (7)	0.000	−0.0019 (6)	0.000
O1	0.0313 (15)	0.0442 (17)	0.0345 (14)	−0.0102 (13)	−0.0009 (11)	−0.0133 (14)
O2	0.0425 (19)	0.065 (2)	0.0492 (17)	−0.0234 (16)	0.0151 (14)	−0.0184 (16)
N1	0.0339 (19)	0.043 (2)	0.0352 (18)	−0.0042 (16)	0.0013 (14)	−0.0049 (16)
N2	0.035 (2)	0.0298 (18)	0.047 (2)	0.0013 (15)	−0.0039 (15)	0.0018 (17)
C1	0.046 (3)	0.039 (2)	0.054 (3)	−0.011 (2)	0.005 (2)	0.004 (2)
C2	0.052 (3)	0.041 (3)	0.051 (3)	0.008 (2)	0.006 (2)	0.016 (2)
C3	0.040 (3)	0.046 (3)	0.060 (3)	0.016 (2)	0.003 (2)	0.002 (2)
C4	0.037 (3)	0.050 (3)	0.053 (3)	0.004 (2)	−0.001 (2)	−0.004 (2)
C5	0.028 (2)	0.059 (3)	0.044 (2)	−0.002 (2)	0.0067 (18)	−0.009 (2)
C6	0.032 (2)	0.025 (2)	0.036 (2)	−0.0021 (17)	−0.0012 (17)	0.0018 (18)
C7	0.0252 (19)	0.0228 (18)	0.0245 (18)	−0.0011 (15)	−0.0023 (14)	0.0033 (16)
C8	0.033 (2)	0.028 (2)	0.031 (2)	0.0018 (17)	−0.0005 (16)	−0.0102 (17)
C9	0.021 (2)	0.033 (2)	0.043 (2)	−0.0005 (17)	0.0023 (16)	−0.0034 (19)
C10	0.0216 (19)	0.0271 (19)	0.0277 (18)	0.0005 (15)	−0.0060 (14)	0.0048 (16)
C11	0.030 (2)	0.034 (2)	0.0238 (18)	−0.0023 (17)	−0.0003 (15)	−0.0045 (17)
C12	0.0223 (19)	0.039 (2)	0.0311 (19)	−0.0028 (17)	0.0026 (15)	−0.0015 (18)
C13	0.024 (2)	0.0255 (19)	0.036 (2)	0.0017 (16)	0.0037 (15)	0.0035 (18)
C14	0.038 (2)	0.032 (2)	0.040 (2)	−0.0025 (19)	0.0004 (17)	0.002 (2)
C15	0.041 (3)	0.032 (2)	0.067 (3)	−0.005 (2)	0.008 (2)	0.004 (2)
C16	0.046 (3)	0.039 (3)	0.054 (3)	0.011 (2)	0.015 (2)	0.017 (2)
C17	0.049 (3)	0.053 (3)	0.036 (2)	0.010 (2)	0.0020 (19)	0.008 (2)
C18	0.028 (2)	0.038 (2)	0.040 (2)	−0.0006 (18)	−0.0031 (17)	0.003 (2)
O1W	0.050 (3)	0.070 (3)	0.072 (3)	0.000 (2)	0.009 (2)	−0.012 (3)

Geometric parameters (Å, º)

Ni1—O1^i	2.128 (2)	C4—C5	1.523 (6)
Ni1—O1	2.128 (2)	C5—H5A	0.9700
Ni1—N1	2.066 (3)	C5—H5B	0.9700
Ni1—N1^i	2.065 (3)	C6—C7	1.518 (5)
Ni1—N2^i	2.068 (3)	C7—C8	1.386 (5)
Ni1—N2	2.068 (3)	C7—C12	1.381 (5)
Si1—C10^ii	1.878 (4)	C8—H8	0.9300
Si1—C10	1.878 (4)	C8—C9	1.389 (5)
Si1—C13^ii	1.875 (4)	C9—H9	0.9300
Si1—C13	1.875 (4)	C9—C10	1.399 (5)
O1—C6	1.254 (4)	C10—C11	1.399 (5)
O2—C6	1.260 (4)	C11—H11	0.9300
N1—H1	0.9800	C11—C12	1.389 (5)
N1—C1	1.493 (5)	C12—H12	0.9300
N1—C5	1.452 (5)	C13—C14	1.398 (5)
N2—H2	0.9800	C13—C18	1.395 (5)
N2—C2	1.455 (5)	C14—H14	0.9300
N2—C3	1.465 (5)	C14—C15	1.371 (5)
C1—H1A	0.9700	C15—H15	0.9300
C1—H1B	0.9700	C15—C16	1.372 (6)
C1—C2	1.520 (5)	C16—H16	0.9300
C2—H2A	0.9700	C16—C17	1.377 (6)
C2—H2B	0.9700	C17—H17	0.9300
C3—H3A	0.9700	C17—C18	1.382 (5)
C3—H3B	0.9700	C18—H18	0.9300
C3—C4^i	1.497 (6)	O1W—H1WA	0.8499
C4—H4A	0.9700	O1W—H1WB	0.8504
C4—H4B	0.9700
O1—Ni1—O1^i	180.0	C3^i—C4—H4A	108.2
N1^i—Ni1—O1^i	93.98 (11)	C3^i—C4—H4B	108.2
N1^i—Ni1—O1	86.02 (11)	C3^i—C4—C5	116.3 (4)
N1—Ni1—O1	93.98 (11)	H4A—C4—H4B	107.4
N1—Ni1—O1^i	86.02 (11)	C5—C4—H4A	108.2
N1^i—Ni1—N1	180.0	C5—C4—H4B	108.2
N1—Ni1—N2^i	93.95 (13)	N1—C5—C4	111.6 (3)
N1—Ni1—N2	86.05 (13)	N1—C5—H5A	109.3
N1^i—Ni1—N2	93.95 (13)	N1—C5—H5B	109.3
N1^i—Ni1—N2^i	86.05 (13)	C4—C5—H5A	109.3
N2—Ni1—O1^i	88.51 (11)	C4—C5—H5B	109.3
N2—Ni1—O1	91.49 (11)	H5A—C5—H5B	108.0
N2^i—Ni1—O1	88.51 (11)	O1—C6—O2	125.7 (3)
N2^i—Ni1—O1^i	91.49 (11)	O1—C6—C7	117.0 (3)
N2—Ni1—N2^i	180.0	O2—C6—C7	117.3 (3)
C10—Si1—C10^ii	107.2 (2)	C8—C7—C6	120.6 (3)
C13^ii—Si1—C10^ii	111.20 (15)	C12—C7—C6	120.8 (3)
C13—Si1—C10	111.20 (15)	C12—C7—C8	118.5 (3)
C13^ii—Si1—C10	110.63 (16)	C7—C8—H8	119.7
C13—Si1—C10^ii	110.63 (16)	C7—C8—C9	120.7 (3)
C13—Si1—C13^ii	106.1 (2)	C9—C8—H8	119.7
C6—O1—Ni1	132.6 (2)	C8—C9—H9	119.3
Ni1—N1—H1	106.8	C8—C9—C10	121.4 (3)
C1—N1—Ni1	106.1 (2)	C10—C9—H9	119.3
C1—N1—H1	106.8	C9—C10—Si1	119.9 (3)
C5—N1—Ni1	117.0 (3)	C11—C10—Si1	123.0 (3)
C5—N1—H1	106.8	C11—C10—C9	117.1 (3)
C5—N1—C1	112.8 (3)	C10—C11—H11	119.5
Ni1—N2—H2	105.8	C12—C11—C10	121.0 (3)
C2—N2—Ni1	106.0 (2)	C12—C11—H11	119.5
C2—N2—H2	105.8	C7—C12—C11	121.2 (3)
C2—N2—C3	116.2 (3)	C7—C12—H12	119.4
C3—N2—Ni1	116.2 (3)	C11—C12—H12	119.4
C3—N2—H2	105.8	C14—C13—Si1	119.0 (3)
N1—C1—H1A	110.0	C18—C13—Si1	124.3 (3)
N1—C1—H1B	110.0	C18—C13—C14	116.6 (3)
N1—C1—C2	108.6 (3)	C13—C14—H14	118.9
H1A—C1—H1B	108.4	C15—C14—C13	122.2 (4)
C2—C1—H1A	110.0	C15—C14—H14	118.9
C2—C1—H1B	110.0	C14—C15—H15	120.1
N2—C2—C1	111.6 (3)	C14—C15—C16	119.8 (4)
N2—C2—H2A	109.3	C16—C15—H15	120.1
N2—C2—H2B	109.3	C15—C16—H16	120.0
C1—C2—H2A	109.3	C15—C16—C17	120.0 (4)
C1—C2—H2B	109.3	C17—C16—H16	120.0
H2A—C2—H2B	108.0	C16—C17—H17	120.0
N2—C3—H3A	108.9	C16—C17—C18	120.0 (4)
N2—C3—H3B	108.9	C18—C17—H17	120.0
N2—C3—C4^i	113.2 (3)	C13—C18—H18	119.3
H3A—C3—H3B	107.7	C17—C18—C13	121.4 (4)
C4^i—C3—H3A	108.9	C17—C18—H18	119.3
C4^i—C3—H3B	108.9	H1WA—O1W—H1WB	109.5
Ni1—O1—C6—O2	14.6 (6)	C8—C9—C10—Si1	−179.6 (3)
Ni1—O1—C6—C7	−164.5 (2)	C8—C9—C10—C11	0.9 (5)
Ni1—N1—C1—C2	38.6 (4)	C9—C10—C11—C12	1.4 (5)
Ni1—N1—C5—C4	−55.8 (4)	C10^ii—Si1—C10—C9	−51.0 (3)
Ni1—N2—C2—C1	38.2 (4)	C10^ii—Si1—C10—C11	128.4 (3)
Ni1—N2—C3—C4^i	−54.2 (4)	C10^ii—Si1—C13—C14	−68.5 (3)
Si1—C10—C11—C12	−178.0 (3)	C10—Si1—C13—C14	172.6 (3)
Si1—C13—C14—C15	−178.1 (3)	C10^ii—Si1—C13—C18	114.3 (3)
Si1—C13—C18—C17	177.9 (3)	C10—Si1—C13—C18	−4.6 (4)
O1—C6—C7—C8	−21.4 (5)	C10—C11—C12—C7	−2.8 (5)
O1—C6—C7—C12	155.4 (3)	C12—C7—C8—C9	0.6 (5)
O2—C6—C7—C8	159.4 (4)	C13^ii—Si1—C10—C9	−172.4 (3)
O2—C6—C7—C12	−23.9 (5)	C13—Si1—C10—C9	70.0 (3)
N1—C1—C2—N2	−53.4 (4)	C13^ii—Si1—C10—C11	7.0 (3)
C1—N1—C5—C4	−179.3 (3)	C13—Si1—C10—C11	−110.6 (3)
C2—N2—C3—C4^i	180.0 (4)	C13^ii—Si1—C13—C14	52.2 (3)
C3—N2—C2—C1	169.0 (3)	C13^ii—Si1—C13—C18	−125.0 (4)
C3^i—C4—C5—N1	70.1 (5)	C13—C14—C15—C16	−0.3 (6)
C5—N1—C1—C2	168.0 (3)	C14—C13—C18—C17	0.6 (6)
C6—C7—C8—C9	177.4 (3)	C14—C15—C16—C17	1.3 (6)
C6—C7—C12—C11	−175.1 (3)	C15—C16—C17—C18	−1.3 (6)
C7—C8—C9—C10	−2.0 (5)	C16—C17—C18—C13	0.3 (6)
C8—C7—C12—C11	1.8 (5)	C18—C13—C14—C15	−0.7 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.98	2.02	2.916 (4)	151
O1W—H1WA···O2^iii	0.85	2.05	2.850 (5)	156
O1W—H1WB···O2	0.85	1.89	2.744 (5)	177

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