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The title coordination polymer, {[Cu2(C6H15N2O)2(C10H8N2)](ClO4)2}n, was synthesized from 4,4′-bipyridine, N-hydroxypropyl-1,3-propanediamine and copper(II) per­chlorate. Structural analysis shows that each copper ion is coordinated by the 4,4′-bipyridine mol­ecule through one N atom, and by two N-hydroxypropyl-1,3-propanediamine ligands through the O atom and two N atoms of one, and the O atom from the second, giving a distorted square-pyramidal geometry. There are centres of inversion at the mid-points of the Cu2O2 ring and the bridging ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053165/ez2054sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053165/ez2054Isup2.hkl
Contains datablock I

CCDC reference: 633689

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.015 Å
  • Disorder in main residue
  • R factor = 0.066
  • wR factor = 0.210
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. N3 .. 2.68 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.15 Ratio
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 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 3 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Poly[[dicopper(II)-µ-4,4'-bipyridyl-bis[µ-N-(hydroxylpropyl)propane-1,3- diamine]] bis(perchlorate)] top
Crystal data top
[Cu2(C6H15N2O)2(C10H8N2)](ClO4)2F(000) = 1536
Mr = 744.56Dx = 1.575 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.989 (2) ÅCell parameters from 1023 reflections
b = 19.699 (3) Åθ = 2.5–17.9°
c = 13.297 (3) ŵ = 1.58 mm1
β = 91.175 (3)°T = 293 K
V = 3139.7 (10) Å3Block, blue
Z = 40.40 × 0.32 × 0.28 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2748 independent reflections
Radiation source: fine-focus sealed tube1223 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1314
Tmin = 0.570, Tmax = 0.665k = 2321
8102 measured reflectionsl = 1514
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.096P)2 + ]
where P = (Fo2 + 2Fc2)/3
2748 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.56 e Å3
21 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/UeqOcc. (<1)
Cu10.72678 (9)0.32492 (5)0.01942 (7)0.0570 (4)
Cl10.50000.0801 (3)0.25000.1163 (16)
Cl20.50000.5154 (3)0.25000.1332 (18)
N10.7316 (9)0.3841 (4)0.1391 (6)0.113 (3)
H10.65800.39540.13930.135*
N20.7357 (7)0.4038 (3)0.0742 (5)0.079 (2)
H2A0.77040.38980.12990.095*
H2B0.66560.41530.09290.095*
N30.5274 (6)0.3118 (4)0.0296 (6)0.071 (2)
O10.3963 (9)0.1098 (6)0.2402 (8)0.196 (5)
O20.5053 (19)0.0770 (11)0.3658 (10)0.176 (8)0.50
O30.506 (3)0.0153 (7)0.2172 (13)0.160 (12)0.50
O40.5899 (12)0.5577 (6)0.2374 (9)0.228 (7)
O50.4805 (12)0.4786 (7)0.1659 (10)0.271 (8)
O60.7677 (5)0.2422 (2)0.0876 (4)0.0579 (15)
C10.8070 (9)0.2329 (5)0.1867 (7)0.084 (3)
H1A0.87440.20560.18590.101*
H1B0.75160.20810.22400.101*
C20.8319 (12)0.2990 (6)0.2397 (7)0.106 (4)
H2C0.85350.28960.30900.127*
H2D0.89450.32080.20780.127*
C30.7359 (15)0.3460 (6)0.2381 (8)0.130 (5)
H3A0.74320.37790.29340.156*
H3B0.66730.32060.24620.156*
C40.774 (2)0.4487 (7)0.1493 (13)0.120 (8)0.689 (16)
H4A0.85410.44520.16280.144*0.689 (16)
H4B0.74140.46980.20740.144*0.689 (16)
C50.756 (2)0.4940 (8)0.0611 (12)0.107 (7)0.689 (16)
H5A0.79580.53630.07390.128*0.689 (16)
H5B0.67760.50460.05550.128*0.689 (16)
C60.7932 (18)0.4665 (8)0.0373 (13)0.099 (6)0.689 (16)
H6A0.87250.45710.03200.119*0.689 (16)
H6B0.78280.50160.08780.119*0.689 (16)
C4'0.824 (3)0.4296 (18)0.121 (3)0.120 (8)0.311 (16)
H4'10.88990.40210.11320.144*0.311 (16)
H4'20.83530.45660.18170.144*0.311 (16)
C5'0.816 (4)0.478 (2)0.032 (3)0.107 (7)0.311 (16)
H5'10.88150.47240.00830.128*0.311 (16)
H5'20.81760.52460.05800.128*0.311 (16)
C6'0.711 (4)0.470 (2)0.036 (3)0.099 (6)0.311 (16)
H6'10.64290.47050.00220.119*0.311 (16)
H6'20.70710.50390.08860.119*0.311 (16)
C70.4961 (9)0.2528 (6)0.0654 (9)0.100 (4)
H70.54920.22690.10000.120*
C80.3899 (8)0.2267 (5)0.0551 (7)0.083 (3)
H80.37390.18410.08130.099*
C90.3074 (7)0.2633 (4)0.0060 (6)0.057 (2)
C100.3401 (8)0.3243 (5)0.0299 (8)0.080 (3)
H100.28850.35160.06390.096*
C110.4494 (9)0.3468 (5)0.0169 (8)0.089 (3)
H110.46810.38900.04280.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0587 (7)0.0559 (7)0.0566 (7)0.0017 (5)0.0010 (5)0.0001 (5)
Cl10.089 (3)0.097 (3)0.164 (5)0.0000.030 (3)0.000
Cl20.138 (5)0.127 (4)0.133 (4)0.0000.031 (4)0.000
N10.188 (11)0.064 (5)0.086 (6)0.026 (6)0.009 (6)0.007 (5)
N20.101 (6)0.065 (5)0.072 (5)0.004 (4)0.020 (4)0.004 (4)
N30.060 (5)0.077 (5)0.077 (5)0.007 (4)0.006 (4)0.014 (4)
O10.175 (8)0.206 (8)0.210 (8)0.064 (7)0.044 (7)0.064 (7)
O20.21 (2)0.20 (2)0.122 (16)0.021 (18)0.024 (15)0.021 (15)
O30.22 (2)0.098 (11)0.16 (3)0.001 (19)0.05 (3)0.031 (13)
O40.301 (18)0.211 (11)0.170 (10)0.100 (11)0.056 (13)0.022 (10)
O50.200 (13)0.310 (16)0.304 (15)0.057 (12)0.001 (11)0.212 (14)
O60.066 (4)0.062 (3)0.045 (3)0.009 (3)0.009 (3)0.001 (3)
C10.115 (9)0.072 (6)0.063 (6)0.008 (6)0.018 (6)0.007 (5)
C20.145 (12)0.118 (9)0.053 (6)0.031 (8)0.031 (7)0.003 (6)
C30.221 (18)0.102 (9)0.066 (8)0.001 (10)0.010 (9)0.012 (7)
C40.23 (2)0.056 (10)0.076 (13)0.014 (12)0.011 (12)0.024 (8)
C50.18 (2)0.051 (10)0.093 (13)0.002 (11)0.002 (13)0.024 (9)
C60.120 (17)0.068 (8)0.110 (11)0.027 (13)0.009 (15)0.025 (8)
C4'0.23 (2)0.056 (10)0.076 (13)0.014 (12)0.011 (12)0.024 (8)
C5'0.18 (2)0.051 (10)0.093 (13)0.002 (11)0.002 (13)0.024 (9)
C6'0.120 (17)0.068 (8)0.110 (11)0.027 (13)0.009 (15)0.025 (8)
C70.046 (7)0.118 (9)0.134 (10)0.001 (6)0.001 (6)0.048 (7)
C80.050 (6)0.084 (6)0.114 (8)0.003 (5)0.003 (5)0.042 (6)
C90.048 (5)0.065 (5)0.059 (5)0.006 (4)0.008 (4)0.010 (4)
C100.062 (7)0.068 (6)0.110 (8)0.009 (5)0.013 (5)0.022 (6)
C110.075 (8)0.059 (6)0.135 (9)0.004 (5)0.005 (7)0.012 (6)
Geometric parameters (Å, º) top
Cu1—O61.923 (5)C1—H1A0.9700
Cu1—O6i1.944 (5)C1—H1B0.9700
Cu1—N11.973 (8)C2—C31.476 (17)
Cu1—N21.996 (6)C2—H2C0.9700
Cu1—N32.411 (8)C2—H2D0.9700
Cu1—Cu1i3.0498 (19)C3—H3A0.9700
Cl1—O31.352 (12)C3—H3B0.9700
Cl1—O3ii1.352 (12)C4—C51.486 (15)
Cl1—O1ii1.378 (9)C4—H4A0.9700
Cl1—O11.378 (9)C4—H4B0.9700
Cl1—O21.541 (13)C5—C61.492 (16)
Cl1—O2ii1.541 (13)C5—H5A0.9700
Cl2—O51.349 (9)C5—H5B0.9700
Cl2—O5ii1.349 (9)C6—H6A0.9700
Cl2—O4ii1.375 (10)C6—H6B0.9700
Cl2—O41.375 (10)C4'—C5'1.53 (2)
N1—C41.378 (14)C4'—H4'10.9700
N1—C4'1.44 (2)C4'—H4'20.9700
N1—C31.515 (12)C5'—C6'1.54 (2)
N1—H10.9100C5'—H5'10.9700
N2—C6'1.43 (4)C5'—H5'20.9700
N2—C61.492 (19)C6'—H6'10.9700
N2—H2A0.9000C6'—H6'20.9700
N2—H2B0.9000C7—C81.377 (13)
N3—C111.307 (11)C7—H70.9300
N3—C71.313 (11)C8—C91.377 (11)
O2—O3ii1.65 (2)C8—H80.9300
O3—O3ii0.89 (4)C9—C101.355 (11)
O3—O2ii1.65 (2)C9—C9iii1.478 (16)
O6—C11.403 (9)C10—C111.391 (13)
O6—Cu1i1.944 (5)C10—H100.9300
C1—C21.507 (12)C11—H110.9300
O6—Cu1—O6i75.9 (2)O6—C1—H1B109.1
O6—Cu1—N196.7 (3)C2—C1—H1B109.1
O6i—Cu1—N1172.4 (3)H1A—C1—H1B107.8
O6—Cu1—N2159.6 (3)C3—C2—C1112.9 (10)
O6i—Cu1—N294.0 (3)C3—C2—H2C109.0
N1—Cu1—N292.4 (3)C1—C2—H2C109.0
O6—Cu1—N397.2 (3)C3—C2—H2D109.0
O6i—Cu1—N391.0 (2)C1—C2—H2D109.0
N1—Cu1—N391.8 (4)H2C—C2—H2D107.8
N2—Cu1—N3100.6 (3)C2—C3—N1109.6 (11)
O6—Cu1—Cu1i38.19 (14)C2—C3—H3A109.8
O6i—Cu1—Cu1i37.71 (14)N1—C3—H3A109.8
N1—Cu1—Cu1i134.9 (3)C2—C3—H3B109.8
N2—Cu1—Cu1i129.5 (2)N1—C3—H3B109.8
N3—Cu1—Cu1i95.17 (19)H3A—C3—H3B108.2
O3—Cl1—O1ii112.3 (17)N1—C4—C5115.5 (14)
O3ii—Cl1—O1ii115.0 (15)N1—C4—H4A108.4
O3—Cl1—O1115.0 (15)C5—C4—H4A108.4
O3ii—Cl1—O1112.3 (17)N1—C4—H4B108.4
O1ii—Cl1—O1129.7 (12)C5—C4—H4B108.4
O3—Cl1—O2106.4 (10)H4A—C4—H4B107.5
O3ii—Cl1—O269.0 (11)C4—C5—C6115.6 (14)
O1ii—Cl1—O284.5 (9)C4—C5—H5A108.4
O1—Cl1—O297.5 (8)C6—C5—H5A108.4
O3—Cl1—O2ii69.0 (11)C4—C5—H5B108.4
O3ii—Cl1—O2ii106.4 (10)C6—C5—H5B108.4
O1ii—Cl1—O2ii97.5 (8)H5A—C5—H5B107.4
O1—Cl1—O2ii84.5 (9)C5—C6—N2116.5 (15)
O2—Cl1—O2ii175.4 (16)C5—C6—H6A108.2
O5—Cl2—O5ii114.9 (15)N2—C6—H6A108.2
O5—Cl2—O4ii107.7 (8)C5—C6—H6B108.2
O5ii—Cl2—O4ii110.3 (8)N2—C6—H6B108.2
O5—Cl2—O4110.3 (8)H6A—C6—H6B107.3
O5ii—Cl2—O4107.7 (8)N1—C4'—C5'119 (4)
O4ii—Cl2—O4105.4 (13)N1—C4'—H4'1107.6
C4—N1—C3111.5 (10)C5'—C4'—H4'1107.6
C4'—N1—C3116 (2)N1—C4'—H4'2107.6
C4—N1—Cu1129.0 (10)C5'—C4'—H4'2107.6
C4'—N1—Cu1104.2 (18)H4'1—C4'—H4'2107.0
C3—N1—Cu1114.1 (6)C4'—C5'—C6'115 (4)
C4—N1—H197.7C4'—C5'—H5'1108.5
C4'—N1—H1126.3C6'—C5'—H5'1108.5
C3—N1—H197.7C4'—C5'—H5'2108.5
Cu1—N1—H197.7C6'—C5'—H5'2108.5
C6'—N2—Cu1118.2 (18)H5'1—C5'—H5'2107.5
C6—N2—Cu1118.0 (8)N2—C6'—C5'98 (3)
C6'—N2—H2A132.4N2—C6'—H6'1112.2
C6—N2—H2A107.8C5'—C6'—H6'1112.2
Cu1—N2—H2A107.8N2—C6'—H6'2112.2
C6'—N2—H2B70.9C5'—C6'—H6'2112.2
C6—N2—H2B107.8H6'1—C6'—H6'2109.8
Cu1—N2—H2B107.8N3—C7—C8124.4 (9)
H2A—N2—H2B107.1N3—C7—H7117.8
C11—N3—C7115.6 (9)C8—C7—H7117.8
C11—N3—Cu1128.1 (7)C9—C8—C7120.3 (9)
C7—N3—Cu1114.0 (6)C9—C8—H8119.8
Cl1—O2—O3ii50.1 (8)C7—C8—H8119.8
O3ii—O3—Cl170.9 (8)C10—C9—C8114.9 (8)
O3ii—O3—O2ii130.4 (16)C10—C9—C9iii123.4 (9)
Cl1—O3—O2ii60.9 (8)C8—C9—C9iii121.7 (9)
C1—O6—Cu1129.1 (5)C9—C10—C11121.2 (9)
C1—O6—Cu1i125.6 (5)C9—C10—H10119.4
Cu1—O6—Cu1i104.1 (2)C11—C10—H10119.4
O6—C1—C2112.7 (7)N3—C11—C10123.6 (9)
O6—C1—H1A109.1N3—C11—H11118.2
C2—C1—H1A109.1C10—C11—H11118.2
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+1, y, z+1/2; (iii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N30.912.683.163 (12)114
N2—H2A···O1iv0.902.323.173 (14)159
N2—H2B···O4v0.902.473.119 (13)129
Symmetry codes: (iv) x+1/2, y+1/2, z1/2; (v) x, y+1, z1/2.
 

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