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In the title com­pound, [Cu2(C4H4O4)2(C11H10N4O)]n, mono-periodic coordination polymer ribbons are held into the crystal structure by means of N—H...O hydrogen bonding and crystal packing forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623007472/bh4078sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314623007472/bh4078Isup2.hkl
Contains datablock I

CCDC reference: 2290886

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.056
  • wR factor = 0.151
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00886 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C2 ..O3 . 99.60 Degree PLAT482_ALERT_4_C Small D-H..A Angle Rep for C19 ..O4 . 98.40 Degree PLAT601_ALERT_2_C Unit Cell Contains Solvent Accessible VOIDS of . 35 Ang   3 PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on Cu2 1.26 eA-3 PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on Cu1 1.11 eA-3
Alert level G PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension 1 Info PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT480_ALERT_4_G Long H...A H-Bond Reported H9 ..O5 . 2.74 Ang. PLAT480_ALERT_4_G Long H...A H-Bond Reported H19 ..O4 . 2.84 Ang. PLAT794_ALERT_5_G Tentative Bond Valency for Cu1 (II) . 2.09 Info PLAT794_ALERT_5_G Tentative Bond Valency for Cu2 (II) . 2.10 Info PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ........... 4.2 Low PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 5 ALERT type 4 Improvement, methodology, query or suggestion 4 ALERT type 5 Informative message, check

Computing details top

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: CrystalMakerX (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[µ-1,3-bis(pyridin-3-yl)urea]bis(µ4-succinato)dicopper(II)] top
Crystal data top
[Cu2(C4H4O4)2(C11H10N4O)]F(000) = 1160
Mr = 573.45Dx = 1.857 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.587 (2) ÅCell parameters from 2446 reflections
b = 6.7579 (10) Åθ = 2.8–25.1°
c = 20.942 (3) ŵ = 2.14 mm1
β = 111.614 (2)°T = 173 K
V = 2050.9 (5) Å3Plate, green
Z = 40.24 × 0.12 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
3758 independent reflections
Radiation source: sealed tube2378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.110
Detector resolution: 8.36 pixels mm-1θmax = 25.4°, θmin = 1.4°
ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 88
Tmin = 0.568, Tmax = 0.745l = 2525
15941 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0685P)2]
where P = (Fo2 + 2Fc2)/3
3758 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 1.12 e Å3
0 restraintsΔρmin = 0.60 e Å3
Special details top

Experimental. Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using omega scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structure was solved by the direct method using the SHELXT program and refined by least squares method on F2, SHELXL, incorporated in OLEX2.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.76095 (5)0.56430 (10)0.20555 (4)0.0199 (2)
Cu20.77124 (5)0.49295 (10)0.33295 (4)0.0198 (2)
O10.6695 (3)0.6855 (6)0.3154 (2)0.0241 (10)
O20.6730 (3)0.7626 (6)0.2124 (2)0.0257 (11)
O30.6784 (3)1.2834 (6)0.2892 (2)0.0250 (10)
O40.6616 (3)1.3542 (6)0.1809 (2)0.0228 (10)
O50.8617 (3)0.7122 (6)0.3540 (2)0.0272 (11)
O60.8587 (3)0.7601 (6)0.2474 (2)0.0269 (11)
O70.8683 (3)1.3085 (6)0.3309 (2)0.0284 (11)
O80.8527 (3)1.3529 (6)0.2213 (2)0.0232 (10)
O90.5334 (3)0.3287 (7)0.4400 (2)0.0355 (12)
N10.7897 (3)0.4419 (7)0.4394 (3)0.0190 (12)
N20.6521 (4)0.3177 (7)0.5442 (3)0.0226 (12)
H20.6650610.2981170.5883210.027*
N30.5065 (4)0.2208 (7)0.5341 (3)0.0225 (12)
H30.5333150.1956290.5782930.027*
N40.2765 (4)0.1280 (7)0.4043 (2)0.0207 (12)
C10.6429 (4)0.7848 (8)0.2603 (3)0.0196 (14)
C20.5697 (4)0.9394 (8)0.2500 (3)0.0194 (14)
H2A0.5792591.0029250.2947590.023*
H2B0.5085460.8740230.2340800.023*
C30.5692 (4)1.0992 (9)0.1984 (3)0.0190 (14)
H3A0.5766891.0346950.1583110.023*
H3B0.5081951.1651470.1819400.023*
C40.6433 (4)1.2555 (8)0.2259 (3)0.0181 (14)
C50.8876 (4)0.7960 (9)0.3111 (3)0.0197 (14)
C60.9644 (4)0.9500 (8)0.3372 (3)0.0225 (15)
H6A0.9618731.0104620.3795680.027*
H6B1.0245510.8816530.3497820.027*
C70.9604 (4)1.1147 (9)0.2866 (3)0.0240 (15)
H7A1.0214011.1805730.3016500.029*
H7B0.9489731.0548000.2410520.029*
C80.8870 (4)1.2704 (9)0.2789 (3)0.0213 (15)
C90.8712 (5)0.4774 (9)0.4890 (3)0.0280 (16)
H90.9220540.5137110.4768430.034*
C100.8834 (5)0.4625 (9)0.5578 (3)0.0279 (16)
H100.9420910.4879200.5922950.034*
C110.8108 (4)0.4111 (9)0.5757 (3)0.0250 (15)
H110.8184170.4012570.6226870.030*
C120.7253 (4)0.3733 (8)0.5245 (3)0.0213 (14)
C130.7181 (5)0.3899 (9)0.4566 (3)0.0234 (15)
H130.6602910.3633790.4210600.028*
C140.5621 (5)0.2911 (9)0.5012 (3)0.0235 (15)
C150.2276 (5)0.0979 (9)0.4441 (4)0.0260 (16)
H150.1639560.0661160.4232850.031*
C160.2677 (5)0.1121 (8)0.5150 (3)0.0253 (15)
H160.2314470.0933170.5424170.030*
C170.3608 (4)0.1539 (9)0.5456 (3)0.0249 (15)
H170.3896720.1608560.5941760.030*
C180.4114 (4)0.1852 (8)0.5044 (3)0.0188 (14)
C190.3656 (5)0.1700 (9)0.4340 (3)0.0251 (15)
H190.3999840.1908720.4053680.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0226 (5)0.0173 (4)0.0204 (4)0.0010 (3)0.0088 (4)0.0007 (3)
Cu20.0227 (5)0.0170 (4)0.0207 (4)0.0002 (3)0.0092 (4)0.0002 (3)
O10.030 (3)0.021 (2)0.025 (3)0.0066 (19)0.015 (2)0.0068 (19)
O20.034 (3)0.021 (2)0.025 (3)0.009 (2)0.015 (2)0.0029 (19)
O30.031 (3)0.023 (2)0.022 (3)0.007 (2)0.010 (2)0.0049 (19)
O40.026 (3)0.024 (2)0.018 (2)0.0066 (19)0.008 (2)0.0026 (19)
O50.032 (3)0.022 (2)0.025 (3)0.012 (2)0.007 (2)0.001 (2)
O60.032 (3)0.024 (3)0.028 (3)0.006 (2)0.015 (2)0.006 (2)
O70.029 (3)0.026 (3)0.032 (3)0.012 (2)0.012 (2)0.003 (2)
O80.025 (3)0.022 (2)0.021 (2)0.0053 (19)0.007 (2)0.0023 (19)
O90.028 (3)0.049 (3)0.027 (3)0.003 (2)0.006 (2)0.013 (2)
N10.019 (3)0.015 (3)0.019 (3)0.002 (2)0.004 (2)0.002 (2)
N20.029 (3)0.019 (3)0.024 (3)0.001 (2)0.015 (3)0.004 (2)
N30.029 (3)0.017 (3)0.021 (3)0.001 (2)0.009 (3)0.005 (2)
N40.028 (3)0.015 (3)0.019 (3)0.002 (2)0.008 (3)0.001 (2)
C10.024 (4)0.012 (3)0.025 (4)0.009 (3)0.012 (3)0.006 (3)
C20.018 (3)0.018 (3)0.024 (3)0.002 (3)0.010 (3)0.004 (3)
C30.018 (3)0.020 (3)0.021 (3)0.001 (3)0.009 (3)0.002 (3)
C40.016 (3)0.010 (3)0.026 (4)0.005 (2)0.005 (3)0.002 (3)
C50.013 (3)0.020 (3)0.024 (4)0.005 (3)0.003 (3)0.005 (3)
C60.017 (4)0.020 (4)0.028 (4)0.004 (3)0.005 (3)0.003 (3)
C70.021 (4)0.023 (4)0.028 (4)0.001 (3)0.009 (3)0.002 (3)
C80.021 (4)0.016 (3)0.032 (4)0.007 (3)0.014 (3)0.004 (3)
C90.023 (4)0.036 (4)0.028 (4)0.001 (3)0.013 (3)0.001 (3)
C100.024 (4)0.029 (4)0.021 (4)0.001 (3)0.002 (3)0.008 (3)
C110.032 (4)0.026 (4)0.017 (3)0.006 (3)0.009 (3)0.000 (3)
C120.028 (4)0.012 (3)0.027 (4)0.001 (3)0.014 (3)0.001 (3)
C130.031 (4)0.021 (4)0.019 (3)0.002 (3)0.011 (3)0.001 (3)
C140.027 (4)0.017 (3)0.029 (4)0.003 (3)0.012 (3)0.002 (3)
C150.019 (4)0.019 (4)0.040 (4)0.002 (3)0.011 (3)0.003 (3)
C160.038 (4)0.014 (3)0.033 (4)0.001 (3)0.024 (4)0.005 (3)
C170.026 (4)0.026 (4)0.024 (4)0.001 (3)0.011 (3)0.002 (3)
C180.024 (4)0.015 (3)0.018 (3)0.000 (3)0.008 (3)0.001 (3)
C190.029 (4)0.021 (4)0.027 (4)0.001 (3)0.013 (3)0.001 (3)
Geometric parameters (Å, º) top
Cu1—O21.960 (4)C2—H2A0.9900
Cu1—O4i2.023 (4)C2—H2B0.9900
Cu1—O61.963 (4)C2—C31.526 (8)
Cu1—O8i1.961 (4)C3—H3A0.9900
Cu1—N4ii2.197 (5)C3—H3B0.9900
Cu2—O11.979 (4)C3—C41.515 (8)
Cu2—O3i1.990 (4)C5—C61.528 (8)
Cu2—O51.980 (4)C6—H6A0.9900
Cu2—O7i1.973 (4)C6—H6B0.9900
Cu2—N12.167 (5)C6—C71.522 (8)
O1—C11.265 (7)C7—H7A0.9900
O2—C11.264 (7)C7—H7B0.9900
O3—C41.248 (7)C7—C81.519 (8)
O4—C41.271 (7)C9—H90.9500
O5—C51.249 (7)C9—C101.386 (9)
O6—C51.263 (7)C10—H100.9500
O7—C81.254 (7)C10—C111.361 (9)
O8—C81.256 (7)C11—H110.9500
O9—C141.218 (7)C11—C121.392 (8)
N1—C91.333 (8)C12—C131.389 (8)
N1—C131.340 (7)C13—H130.9500
N2—H20.8800C15—H150.9500
N2—C121.401 (8)C15—C161.387 (9)
N2—C141.371 (8)C16—H160.9500
N3—H30.8800C16—C171.383 (9)
N3—C141.376 (8)C17—H170.9500
N3—C181.400 (8)C17—C181.383 (8)
N4—C151.335 (8)C18—C191.385 (8)
N4—C191.327 (8)C19—H190.9500
C1—C21.504 (8)
O2—Cu1—O4i90.48 (18)O3—C4—O4125.4 (5)
O2—Cu1—O687.41 (18)O3—C4—C3119.0 (5)
O2—Cu1—O8i166.45 (17)O4—C4—C3115.5 (5)
O2—Cu1—N4ii91.11 (18)O5—C5—O6126.1 (6)
O4i—Cu1—N4ii89.25 (17)O5—C5—C6117.9 (6)
O6—Cu1—O4i169.11 (17)O6—C5—C6115.9 (5)
O6—Cu1—N4ii101.47 (18)C5—C6—H6A108.5
O8i—Cu1—O4i88.52 (17)C5—C6—H6B108.5
O8i—Cu1—O691.03 (18)H6A—C6—H6B107.5
O8i—Cu1—N4ii102.38 (18)C7—C6—C5115.0 (5)
O1—Cu2—O3i89.16 (18)C7—C6—H6A108.5
O1—Cu2—O590.34 (18)C7—C6—H6B108.5
O1—Cu2—N195.10 (17)C6—C7—H7A108.6
O3i—Cu2—N199.11 (18)C6—C7—H7B108.6
O5—Cu2—O3i166.52 (17)H7A—C7—H7B107.6
O5—Cu2—N194.36 (18)C8—C7—C6114.6 (5)
O7i—Cu2—O1168.62 (18)C8—C7—H7A108.6
O7i—Cu2—O3i88.50 (18)C8—C7—H7B108.6
O7i—Cu2—O589.35 (19)O7—C8—O8126.2 (6)
O7i—Cu2—N196.27 (18)O7—C8—C7117.2 (6)
C1—O1—Cu2119.2 (4)O8—C8—C7116.6 (5)
C1—O2—Cu1127.8 (4)N1—C9—H9119.2
C4—O3—Cu2iii123.8 (4)N1—C9—C10121.6 (6)
C4—O4—Cu1iii122.6 (4)C10—C9—H9119.2
C5—O5—Cu2124.8 (4)C9—C10—H10120.2
C5—O6—Cu1121.1 (4)C11—C10—C9119.7 (6)
C8—O7—Cu2iii125.0 (4)C11—C10—H10120.2
C8—O8—Cu1iii120.7 (4)C10—C11—H11120.3
C9—N1—Cu2120.0 (4)C10—C11—C12119.5 (6)
C9—N1—C13119.1 (5)C12—C11—H11120.3
C13—N1—Cu2120.7 (4)C11—C12—N2118.4 (6)
C12—N2—H2116.9C13—C12—N2123.7 (6)
C14—N2—H2116.9C13—C12—C11117.9 (6)
C14—N2—C12126.1 (5)N1—C13—C12122.3 (6)
C14—N3—H3116.7N1—C13—H13118.8
C14—N3—C18126.5 (5)C12—C13—H13118.8
C18—N3—H3116.7O9—C14—N2123.6 (6)
C15—N4—Cu1iv129.1 (4)O9—C14—N3122.9 (6)
C19—N4—Cu1iv111.2 (4)N2—C14—N3113.4 (6)
C19—N4—C15118.6 (6)N4—C15—H15119.2
O1—C1—C2118.4 (5)N4—C15—C16121.5 (6)
O2—C1—O1124.7 (6)C16—C15—H15119.2
O2—C1—C2116.9 (5)C15—C16—H16120.3
C1—C2—H2A108.9C17—C16—C15119.4 (6)
C1—C2—H2B108.9C17—C16—H16120.3
C1—C2—C3113.5 (5)C16—C17—H17120.5
H2A—C2—H2B107.7C18—C17—C16119.0 (6)
C3—C2—H2A108.9C18—C17—H17120.5
C3—C2—H2B108.9C17—C18—N3120.1 (6)
C2—C3—H3A108.6C17—C18—C19117.7 (6)
C2—C3—H3B108.6C19—C18—N3122.1 (6)
H3A—C3—H3B107.5N4—C19—C18123.7 (6)
C4—C3—C2114.8 (5)N4—C19—H19118.2
C4—C3—H3A108.6C18—C19—H19118.2
C4—C3—H3B108.6
Cu1—O2—C1—O14.2 (9)N4—C15—C16—C171.5 (9)
Cu1—O2—C1—C2175.2 (4)C1—C2—C3—C478.3 (7)
Cu1iii—O4—C4—O35.2 (8)C2—C3—C4—O322.2 (8)
Cu1iii—O4—C4—C3177.9 (4)C2—C3—C4—O4160.7 (5)
Cu1—O6—C5—O52.4 (9)C5—C6—C7—C875.8 (7)
Cu1—O6—C5—C6179.4 (4)C6—C7—C8—O732.4 (8)
Cu1iii—O8—C8—O70.4 (9)C6—C7—C8—O8149.6 (5)
Cu1iii—O8—C8—C7177.5 (4)C9—N1—C13—C120.7 (9)
Cu1iv—N4—C15—C16167.8 (4)C9—C10—C11—C120.3 (9)
Cu1iv—N4—C19—C18169.4 (5)C10—C11—C12—N2179.0 (6)
Cu2—O1—C1—O24.5 (8)C10—C11—C12—C130.0 (9)
Cu2—O1—C1—C2176.2 (4)C11—C12—C13—N10.5 (9)
Cu2iii—O3—C4—O40.4 (8)C12—N2—C14—O96.2 (9)
Cu2iii—O3—C4—C3176.4 (4)C12—N2—C14—N3175.0 (5)
Cu2—O5—C5—O62.4 (9)C13—N1—C9—C100.3 (9)
Cu2—O5—C5—C6174.6 (4)C14—N2—C12—C11174.2 (5)
Cu2iii—O7—C8—O85.8 (9)C14—N2—C12—C136.8 (9)
Cu2iii—O7—C8—C7176.4 (4)C14—N3—C18—C17166.6 (6)
Cu2—N1—C9—C10174.5 (5)C14—N3—C18—C1916.7 (9)
Cu2—N1—C13—C12174.1 (4)C15—N4—C19—C180.2 (9)
O1—C1—C2—C3157.7 (5)C15—C16—C17—C181.6 (9)
O2—C1—C2—C322.9 (8)C16—C17—C18—N3177.7 (5)
O5—C5—C6—C7150.1 (6)C16—C17—C18—C190.9 (9)
O6—C5—C6—C732.6 (8)C17—C18—C19—N40.3 (9)
N1—C9—C10—C110.2 (10)C18—N3—C14—O91.0 (10)
N2—C12—C13—N1179.5 (5)C18—N3—C14—N2177.8 (5)
N3—C18—C19—N4177.0 (5)C19—N4—C15—C160.8 (9)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4v0.882.213.042 (6)157
N3—H3···O4v0.882.363.174 (6)154
C2—H2A···O30.992.482.815 (7)100
C3—H3A···O20.992.382.744 (7)101
C6—H6A···O70.992.472.825 (7)100
C7—H7B···O60.992.472.824 (8)101
C9—H9···O50.952.743.196 (8)110
C13—H13···O90.952.172.800 (8)123
C19—H19···O2iv0.952.352.965 (8)122
C19—H19···O4vi0.952.843.126 (7)98
C19—H19···O90.952.152.786 (8)124
Symmetry codes: (iv) x+1, y1/2, z+1/2; (v) x, y+3/2, z+1/2; (vi) x+1, y3/2, z+1/2.
 

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