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In the copper–mefenamate complex, the asymmetric unit comprises a CuII cation coordinated to two mefenamate ligands solvated with a water mol­ecule and diglyme mol­ecule. The complex adopts a paddlewheel motif and is compared to structural analogues crystallized with di­methyl­formamide and dimethyl sulfoxide.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022010647/ex2060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022010647/ex2060Isup2.hkl
Contains datablock I

link

Link https://doi.org/10.15129/39f97ad1-8173-4999-b0b6-41c6ae923fe6
repository link to the raw and processed diffraction data used in publication

CCDC reference: 2217265

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 105 K
  • R factor = 0.033
  • wR factor = 0.089
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ Please Check
Author Response: The reported formula is correct and difference is attributed to the modelled disorder of the diglyme component
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of       N10A Check
Author Response: The molecular structure and geometry around the N10A position is as one would expect. Structure refinement was performed without the bonded hydrogen incase the site was deprotonated however this did not resolve the issue
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         34 Report
Author Response: reflection with esd > |5|, ommitted during refinement

Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 21 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 56 Report PLAT012_ALERT_1_G No _shelx_res_checksum Found in CIF ...... Please Check PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 9 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 11 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 14 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Cu1 --O1A . 5.3 s.u. PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2 ) 100% Note PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 3 ) 100% Note PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 2 ) 15.41 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 3 ) 7.59 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 46 Note PLAT794_ALERT_5_G Tentative Bond Valency for Cu1 (II) . 2.17 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 410 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 4 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 3 Note PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 8 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 20 ALERT level G = General information/check it is not something unexpected 2 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 4 ALERT type 3 Indicator that the structure quality may be low 10 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL004_ALERT_1_A The contact author's name and address are missing, _publ_contact_author_name and _publ_contact_author_address.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing # start Validation Reply Form _vrf_PUBL004_GLOBAL ; PROBLEM: The contact author's name and address are missing, RESPONSE: ... ; # end Validation Reply Form

Reference check results

The following references were not checked in detail as they were not recognized as references to journal articles

Abbas, N., Oswald, I. D. H. & Pulham, C. R. (2017). Pharmaceutics 9, 16.

British Pharmacopoeia (2017). Part III. London: Medicines and Healthcare products Regulatory Agency; mefenamic acid (Ph. Eur. Monograph 1240).

Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. [software reference?]

Mague, J. & Ouzidan, Y. (2017). CSD Communication (refcode XYANAC06). CCDC, Cambridge, England

Reichardt, C. & Welton, T. (2011). Editors. Solvents and Solvent Effects in Organic Chemistry, 4th ed., p. 550. Weinheim: Wiley-VCH. [book reference?]

The following references may be incorrectly formatted

Chong, M. W. S., Argent, S. P., Moreau, F., Trenholme, W. J. F., Morris, C. G., Lewis, W., Easun, T. L. & Schr\"oder, M. (2022). Chem. Eur. J., https://doi. org/10.1002/chem. 202201188.
[Unrecognized journal title. Missing final page numbers?]

Facchin, G., Torre, M. H., Kremer, E., Piro, O. E. & Baran, E. J. (2014). Z. Naturforsch., B: J. Chem. Sci. 53, 871--874.
[Unrecognized journal title.]

McConnell, J. F. & Company, F. Z. (1976). Cryst. Struct. Commun. 5, 861.
[Missing final page numbers?]

Mys'kiv, M. G., Olijnik, V. V., Kriss, E. E., Konakhovich, N. F. & Grigor'eva, A. S. (1982). Koord. Khim. (Russ.), 8, 1415.
[Unrecognized journal title. Missing final page numbers?]

Yatsimirskii, K. B., Mys'kiv, m. G., Grigor'eva, A. S., Kris, E. E. & Gladyshevskii, E. I. (1979). Dokl. Akad. Nauk, 247, 1204.
[Author surname with no initials? Missing final page numbers?]

The following references do not appear to be cited

Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171--179.

Mys'kiv, M. G., Olijnik, V. V., Kriss, E. E., Konakhovich, N. F. & Grigor'eva, A. S. (1982). Koord. Khim. (Russ.), 8, 1415.

Citation comments

2 dates found in data_global _publ_body_contents that could be part of a citation but not found in reference list: 2021, 1982


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Tetrakis[µ-2-(2,3-dimethylanilino)benzoato-κ2O:O']bis[aquacopper(II)]–1-methoxy-2-(2-methoxyethoxy)ethane (1/2) top
Crystal data top
[Cu2(C15H14NO2)4(H2O)2]·2C6H14O3F(000) = 1468
Mr = 1392.54Dx = 1.307 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 15.5420 (3) ÅCell parameters from 9398 reflections
b = 14.0010 (3) Åθ = 4.9–68.2°
c = 16.3217 (3) ŵ = 1.30 mm1
β = 94.791 (1)°T = 105 K
V = 3539.25 (12) Å3Block, clear green
Z = 20.2 × 0.15 × 0.1 mm
Data collection top
Bruker Photon100 CMOS
diffractometer
5989 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus Cu sourceRint = 0.039
φ and ω scansθmax = 68.3°, θmin = 4.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1818
Tmin = 0.781, Tmax = 0.881k = 1616
209288 measured reflectionsl = 1919
6424 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0435P)2 + 2.0003P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
6424 reflectionsΔρmax = 0.28 e Å3
477 parametersΔρmin = 0.40 e Å3
410 restraints
Special details top

Experimental. The X-ray intensities were collected on a Bruker D8 Venture diffractometer using a Photon 100 Detector. The data were reduced using APEX3 and absorption correction applied using SADABS (Bruker, 2016). The crystal structure was solved and refined using SHELXT and SHELXL via the Olex2 refinement package (Dolomanov et al., 2009). Non-hydrogen atom positions were refined anisotropically.

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.

Refinement. RIGU restarint applied. Diglyme disorder modelled using DFIX and SADI restraints. The ADPs for both diglyme parts were constrained using EADP constraint.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu10.54253 (2)0.42405 (2)0.48032 (2)0.02442 (8)
O1B0.51049 (8)0.45091 (8)0.36430 (7)0.0329 (3)
O2B0.43845 (8)0.58088 (8)0.39902 (7)0.0326 (3)
O1A0.43605 (8)0.35049 (8)0.48736 (7)0.0351 (3)
O2A0.36511 (7)0.48032 (8)0.52427 (7)0.0331 (3)
O10S0.62229 (8)0.30515 (9)0.46326 (8)0.0376 (3)
N10B0.37240 (10)0.69540 (10)0.28457 (9)0.0362 (3)
O2S10.7835 (9)0.2813 (9)0.5321 (12)0.0540 (12)0.666 (3)
C3B0.46922 (10)0.52671 (11)0.34617 (9)0.0265 (3)
C9B0.41162 (10)0.63824 (11)0.22997 (9)0.0285 (3)
C3A0.37072 (10)0.39031 (11)0.51303 (9)0.0284 (3)
C4A0.29745 (11)0.32888 (12)0.53288 (10)0.0308 (3)
C4B0.45728 (10)0.55460 (11)0.25802 (9)0.0269 (3)
O5S10.73581 (16)0.15001 (18)0.40989 (17)0.0438 (6)0.666 (3)
C11B0.33426 (11)0.78619 (12)0.27016 (10)0.0312 (3)
C8B0.40932 (11)0.65984 (13)0.14555 (10)0.0345 (4)
H8B0.37940.71520.12500.041*
C5B0.49629 (11)0.49735 (13)0.20199 (10)0.0348 (4)
H5B0.52620.44140.22120.042*
C5A0.30263 (12)0.23152 (12)0.51507 (10)0.0349 (4)
H5A0.35010.20880.48750.042*
N10A0.21962 (12)0.45875 (13)0.59054 (14)0.0588 (5)
C16A0.17474 (12)0.58519 (13)0.67658 (11)0.0367 (4)
O8S10.5611 (3)0.1715 (4)0.3438 (5)0.0604 (14)0.666 (3)
C16B0.36286 (11)0.86224 (12)0.32109 (10)0.0322 (3)
C15A0.10932 (12)0.64349 (13)0.70386 (11)0.0388 (4)
C6B0.49276 (13)0.51950 (15)0.11960 (11)0.0447 (4)
H6B0.51920.47920.08210.054*
C7B0.44963 (13)0.60229 (15)0.09242 (11)0.0429 (4)
H7B0.44810.61930.03600.052*
C17A0.26827 (12)0.60465 (15)0.70369 (12)0.0441 (4)
H17A0.29480.64000.66050.066*
H17B0.29870.54400.71390.066*
H17C0.27200.64260.75430.066*
C6A0.24089 (12)0.16743 (13)0.53636 (11)0.0400 (4)
H6A0.24460.10180.52220.048*
C9A0.22586 (11)0.36315 (13)0.57261 (12)0.0395 (4)
C17B0.43678 (13)0.85116 (14)0.38602 (11)0.0418 (4)
H17D0.41450.84980.44040.063*
H17E0.47660.90510.38300.063*
H17F0.46740.79140.37700.063*
C11A0.15206 (12)0.50948 (14)0.62317 (13)0.0453 (4)
C12B0.26720 (12)0.79882 (15)0.20959 (12)0.0439 (4)
H12B0.24760.74650.17600.053*
C14A0.02351 (12)0.62150 (15)0.68039 (12)0.0447 (4)
H14A0.02100.65950.70020.054*
C18A0.13044 (14)0.72995 (17)0.75676 (13)0.0536 (5)
H18A0.15760.70960.81030.080*
H18B0.07730.76510.76470.080*
H18C0.17030.77140.72970.080*
C15B0.32210 (14)0.95162 (14)0.30921 (12)0.0453 (4)
C14B0.25653 (16)0.96269 (16)0.24775 (13)0.0561 (6)
H14B0.22991.02340.23950.067*
C7A0.17319 (12)0.20059 (14)0.57892 (11)0.0422 (4)
H7A0.13190.15670.59640.051*
C8A0.16519 (13)0.29586 (15)0.59604 (13)0.0473 (5)
H8A0.11770.31700.62430.057*
C13B0.22881 (14)0.88734 (18)0.19800 (13)0.0561 (6)
H13B0.18350.89620.15590.067*
C6S10.6846 (5)0.0737 (6)0.3762 (5)0.0517 (16)0.666 (3)
H6SA0.65300.04350.41960.062*0.666 (3)
H6SB0.72200.02470.35350.062*0.666 (3)
C13A0.00184 (13)0.54565 (16)0.62903 (15)0.0534 (5)
H13A0.05720.53130.61430.064*
C12A0.06577 (13)0.49027 (16)0.59881 (16)0.0569 (6)
H12A0.05090.43950.56170.068*
C3S10.8407 (4)0.2105 (3)0.5096 (3)0.0564 (12)0.666 (3)
H3SA0.88080.19360.55770.068*0.666 (3)
H3SB0.87530.23560.46610.068*0.666 (3)
C7S10.6224 (2)0.1110 (2)0.3099 (2)0.0487 (8)0.666 (3)
H7SA0.65380.14720.26970.058*0.666 (3)
H7SB0.59220.05700.28080.058*0.666 (3)
C18B0.3508 (2)1.03494 (17)0.36428 (18)0.0787 (8)
H18D0.34001.02000.42120.118*
H18E0.31821.09220.34630.118*
H18F0.41261.04640.36090.118*
C1S10.8212 (6)0.3611 (4)0.5730 (4)0.0698 (15)0.666 (3)
H1SA0.85720.39520.53610.105*0.666 (3)
H1SB0.85710.34000.62190.105*0.666 (3)
H1SC0.77580.40370.58960.105*0.666 (3)
C4S10.7934 (3)0.1233 (3)0.4788 (3)0.0558 (10)0.666 (3)
H4SA0.83470.07460.46230.067*0.666 (3)
H4SB0.76050.09590.52260.067*0.666 (3)
H10C0.3857 (14)0.6801 (16)0.3367 (15)0.049 (6)*
H10D0.2643 (16)0.4898 (18)0.5786 (15)0.057 (7)*
H10A0.6808 (5)0.2953 (16)0.4844 (13)0.064 (7)*
H10B0.6103 (14)0.2545 (13)0.4247 (13)0.085 (9)*
C9S20.4948 (9)0.2144 (16)0.3063 (12)0.0550 (15)0.31 (3)
H9SD0.47590.17470.25860.082*0.31 (3)
H9SE0.49220.28190.29030.082*0.31 (3)
H9SF0.45680.20330.35030.082*0.31 (3)
O2S20.795 (2)0.274 (2)0.536 (2)0.0540 (12)0.334 (3)
C3S20.8316 (8)0.1859 (8)0.5313 (7)0.0564 (12)0.334 (3)
H3SC0.81150.14450.57500.068*0.334 (3)
H3SD0.89510.19220.54100.068*0.334 (3)
C1S20.8244 (13)0.3376 (10)0.5961 (9)0.0698 (15)0.334 (3)
H1SD0.79600.39950.58620.105*0.334 (3)
H1SE0.88700.34540.59490.105*0.334 (3)
H1SF0.81160.31320.65000.105*0.334 (3)
C4S20.8103 (7)0.1404 (7)0.4509 (6)0.0558 (10)0.334 (3)
H4SC0.82810.18270.40680.067*0.334 (3)
H4SD0.84260.07960.44830.067*0.334 (3)
O5S20.7218 (4)0.1224 (4)0.4386 (3)0.0438 (6)0.334 (3)
C6S20.6944 (11)0.0843 (14)0.3610 (11)0.0517 (16)0.334 (3)
H6SC0.71200.01650.35890.062*0.334 (3)
H6SD0.72300.11930.31800.062*0.334 (3)
C7S20.6002 (5)0.0912 (5)0.3437 (5)0.0487 (8)0.334 (3)
H7SC0.58130.05600.29270.058*0.334 (3)
H7SD0.57050.06370.38960.058*0.334 (3)
O8S20.5806 (7)0.1903 (9)0.3344 (11)0.0604 (14)0.334 (3)
C9S10.5085 (5)0.2183 (6)0.2840 (7)0.0550 (15)0.69 (3)
H9SA0.54420.25500.24860.082*0.69 (3)
H9SB0.46970.26170.31030.082*0.69 (3)
H9SC0.47430.17130.25080.082*0.69 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.03002 (14)0.02114 (13)0.02236 (13)0.00405 (8)0.00367 (9)0.00087 (8)
O1B0.0443 (6)0.0296 (6)0.0245 (5)0.0110 (5)0.0006 (5)0.0010 (4)
O2B0.0447 (7)0.0288 (6)0.0245 (5)0.0108 (5)0.0040 (5)0.0000 (4)
O1A0.0371 (6)0.0271 (6)0.0420 (6)0.0001 (5)0.0089 (5)0.0062 (5)
O2A0.0346 (6)0.0259 (6)0.0394 (6)0.0001 (5)0.0078 (5)0.0027 (5)
O10S0.0403 (7)0.0311 (6)0.0403 (7)0.0141 (5)0.0020 (5)0.0086 (5)
N10B0.0532 (9)0.0289 (7)0.0262 (7)0.0110 (6)0.0012 (6)0.0013 (6)
O2S10.045 (4)0.046 (2)0.066 (2)0.0094 (16)0.020 (2)0.0047 (19)
C3B0.0281 (7)0.0246 (7)0.0268 (7)0.0014 (6)0.0016 (6)0.0018 (6)
C9B0.0307 (8)0.0270 (8)0.0273 (7)0.0023 (6)0.0005 (6)0.0005 (6)
C3A0.0351 (8)0.0281 (8)0.0213 (7)0.0004 (6)0.0015 (6)0.0016 (6)
C4A0.0350 (8)0.0298 (8)0.0272 (8)0.0032 (6)0.0004 (6)0.0011 (6)
C4B0.0295 (7)0.0265 (7)0.0243 (7)0.0008 (6)0.0000 (6)0.0008 (6)
O5S10.0477 (11)0.0355 (14)0.0483 (16)0.0125 (10)0.0050 (10)0.0008 (10)
C11B0.0338 (8)0.0309 (8)0.0296 (8)0.0056 (6)0.0063 (6)0.0038 (6)
C8B0.0415 (9)0.0342 (9)0.0269 (8)0.0021 (7)0.0024 (7)0.0022 (7)
C5B0.0409 (9)0.0349 (9)0.0281 (8)0.0064 (7)0.0003 (7)0.0022 (7)
C5A0.0436 (9)0.0321 (8)0.0284 (8)0.0026 (7)0.0001 (7)0.0021 (7)
N10A0.0418 (9)0.0365 (9)0.1029 (16)0.0080 (7)0.0353 (10)0.0175 (9)
C16A0.0372 (9)0.0356 (9)0.0390 (9)0.0052 (7)0.0128 (7)0.0097 (7)
O8S10.057 (2)0.045 (2)0.075 (2)0.0121 (18)0.018 (2)0.0332 (19)
C16B0.0368 (8)0.0312 (8)0.0297 (8)0.0053 (7)0.0099 (7)0.0026 (6)
C15A0.0424 (9)0.0416 (10)0.0337 (9)0.0107 (8)0.0103 (7)0.0103 (7)
C6B0.0567 (11)0.0521 (11)0.0254 (8)0.0160 (9)0.0036 (8)0.0046 (8)
C7B0.0528 (11)0.0512 (11)0.0243 (8)0.0080 (9)0.0001 (7)0.0024 (7)
C17A0.0387 (9)0.0484 (11)0.0462 (11)0.0061 (8)0.0093 (8)0.0007 (9)
C6A0.0521 (10)0.0306 (9)0.0364 (9)0.0079 (8)0.0010 (8)0.0018 (7)
C9A0.0370 (9)0.0341 (9)0.0478 (10)0.0039 (7)0.0062 (8)0.0050 (8)
C17B0.0481 (10)0.0396 (10)0.0371 (9)0.0009 (8)0.0005 (8)0.0044 (8)
C11A0.0384 (9)0.0359 (9)0.0645 (12)0.0005 (8)0.0205 (9)0.0007 (9)
C12B0.0419 (10)0.0491 (11)0.0396 (10)0.0082 (8)0.0038 (8)0.0009 (8)
C14A0.0396 (10)0.0490 (11)0.0474 (10)0.0120 (8)0.0141 (8)0.0103 (9)
C18A0.0523 (12)0.0632 (13)0.0456 (11)0.0199 (10)0.0059 (9)0.0103 (10)
C15B0.0596 (12)0.0338 (9)0.0444 (10)0.0148 (8)0.0160 (9)0.0014 (8)
C14B0.0713 (14)0.0515 (12)0.0467 (11)0.0362 (11)0.0115 (10)0.0074 (9)
C7A0.0441 (10)0.0414 (10)0.0403 (10)0.0143 (8)0.0004 (8)0.0007 (8)
C8A0.0400 (10)0.0432 (10)0.0604 (12)0.0096 (8)0.0142 (9)0.0069 (9)
C13B0.0518 (12)0.0723 (14)0.0433 (11)0.0313 (11)0.0020 (9)0.0054 (10)
C6S10.071 (2)0.033 (2)0.051 (3)0.0145 (16)0.006 (2)0.009 (2)
C13A0.0347 (10)0.0564 (13)0.0707 (14)0.0004 (9)0.0128 (9)0.0044 (11)
C12A0.0415 (10)0.0480 (12)0.0837 (16)0.0075 (9)0.0195 (10)0.0120 (11)
C3S10.0391 (17)0.053 (3)0.075 (3)0.0136 (18)0.0069 (19)0.0068 (19)
C7S10.067 (2)0.0370 (16)0.042 (2)0.0056 (13)0.0058 (14)0.0119 (14)
C18B0.123 (2)0.0385 (12)0.0743 (17)0.0224 (14)0.0046 (16)0.0143 (11)
C1S10.0702 (18)0.057 (3)0.076 (4)0.001 (3)0.032 (3)0.005 (2)
C4S10.058 (2)0.041 (2)0.067 (3)0.0176 (15)0.0042 (19)0.0105 (18)
C9S20.057 (2)0.0484 (16)0.059 (4)0.0007 (19)0.001 (2)0.009 (3)
O2S20.045 (4)0.046 (2)0.066 (2)0.0094 (16)0.020 (2)0.0047 (19)
C3S20.0391 (17)0.053 (3)0.075 (3)0.0136 (18)0.0069 (19)0.0068 (19)
C1S20.0702 (18)0.057 (3)0.076 (4)0.001 (3)0.032 (3)0.005 (2)
C4S20.058 (2)0.041 (2)0.067 (3)0.0176 (15)0.0042 (19)0.0105 (18)
O5S20.0477 (11)0.0355 (14)0.0483 (16)0.0125 (10)0.0050 (10)0.0008 (10)
C6S20.071 (2)0.033 (2)0.051 (3)0.0145 (16)0.006 (2)0.009 (2)
C7S20.067 (2)0.0370 (16)0.042 (2)0.0056 (13)0.0058 (14)0.0119 (14)
O8S20.057 (2)0.045 (2)0.075 (2)0.0121 (18)0.018 (2)0.0332 (19)
C9S10.057 (2)0.0484 (16)0.059 (4)0.0007 (19)0.001 (2)0.009 (3)
Geometric parameters (Å, º) top
Cu1—Cu1i2.6126 (4)C11A—C12A1.393 (3)
Cu1—O1B1.9539 (11)C12B—H12B0.9500
Cu1—O2Bi1.9682 (11)C12B—C13B1.382 (3)
Cu1—O1A1.9608 (12)C14A—H14A0.9500
Cu1—O2Ai1.9689 (11)C14A—C13A1.377 (3)
Cu1—O10S2.1078 (11)C18A—H18A0.9800
O1B—C3B1.2624 (19)C18A—H18B0.9800
O2B—Cu1i1.9682 (11)C18A—H18C0.9800
O2B—C3B1.2715 (19)C15B—C14B1.378 (3)
O1A—C3A1.260 (2)C15B—C18B1.517 (3)
O2A—Cu1i1.9690 (11)C14B—H14B0.9500
O2A—C3A1.278 (2)C14B—C13B1.378 (3)
O10S—H10A0.956 (3)C7A—H7A0.9500
O10S—H10B0.956 (3)C7A—C8A1.371 (3)
N10B—C9B1.377 (2)C8A—H8A0.9500
N10B—C11B1.414 (2)C13B—H13B0.9500
N10B—H10C0.88 (2)C6S1—H6SA0.9900
O2S1—C3S11.401 (10)C6S1—H6SB0.9900
O2S1—C1S11.404 (10)C6S1—C7S11.484 (8)
C3B—C4B1.487 (2)C13A—H13A0.9500
C9B—C4B1.425 (2)C13A—C12A1.383 (3)
C9B—C8B1.408 (2)C12A—H12A0.9500
C3A—C4A1.484 (2)C3S1—H3SA0.9900
C4A—C5A1.397 (2)C3S1—H3SB0.9900
C4A—C9A1.418 (2)C3S1—C4S11.490 (7)
C4B—C5B1.392 (2)C7S1—H7SA0.9900
O5S1—C6S11.416 (8)C7S1—H7SB0.9900
O5S1—C4S11.428 (5)C18B—H18D0.9800
C11B—C16B1.400 (2)C18B—H18E0.9800
C11B—C12B1.387 (2)C18B—H18F0.9800
C8B—H8B0.9500C1S1—H1SA0.9800
C8B—C7B1.373 (3)C1S1—H1SB0.9800
C5B—H5B0.9500C1S1—H1SC0.9800
C5B—C6B1.377 (2)C4S1—H4SA0.9900
C5A—H5A0.9500C4S1—H4SB0.9900
C5A—C6A1.379 (3)C9S2—H9SD0.9800
N10A—C9A1.375 (2)C9S2—H9SE0.9800
N10A—C11A1.409 (2)C9S2—H9SF0.9800
N10A—H10D0.86 (2)C9S2—O8S21.414 (14)
C16A—C15A1.405 (2)O2S2—C3S21.369 (19)
C16A—C17A1.509 (3)O2S2—C1S21.37 (2)
C16A—C11A1.399 (3)C3S2—H3SC0.9900
O8S1—C7S11.421 (7)C3S2—H3SD0.9900
O8S1—C9S11.383 (8)C3S2—C4S21.471 (15)
C16B—C17B1.505 (2)C1S2—H1SD0.9800
C16B—C15B1.409 (2)C1S2—H1SE0.9800
C15A—C14A1.391 (3)C1S2—H1SF0.9800
C15A—C18A1.507 (3)C4S2—H4SC0.9900
C6B—H6B0.9500C4S2—H4SD0.9900
C6B—C7B1.393 (3)C4S2—O5S21.397 (12)
C7B—H7B0.9500O5S2—C6S21.407 (17)
C17A—H17A0.9800C6S2—H6SC0.9900
C17A—H17B0.9800C6S2—H6SD0.9900
C17A—H17C0.9800C6S2—C7S21.471 (17)
C6A—H6A0.9500C7S2—H7SC0.9900
C6A—C7A1.388 (3)C7S2—H7SD0.9900
C9A—C8A1.408 (3)C7S2—O8S21.426 (14)
C17B—H17D0.9800C9S1—H9SA0.9800
C17B—H17E0.9800C9S1—H9SB0.9800
C17B—H17F0.9800C9S1—H9SC0.9800
O1B—Cu1—Cu1i89.34 (3)H18A—C18A—H18C109.5
O1B—Cu1—O2Bi168.92 (5)H18B—C18A—H18C109.5
O1B—Cu1—O1A90.57 (5)C16B—C15B—C18B119.69 (19)
O1B—Cu1—O2Ai87.70 (5)C14B—C15B—C16B119.80 (19)
O1B—Cu1—O10S97.42 (5)C14B—C15B—C18B120.51 (19)
O2Bi—Cu1—Cu1i79.58 (3)C15B—C14B—H14B119.4
O2Bi—Cu1—O2Ai90.74 (5)C15B—C14B—C13B121.24 (18)
O2Bi—Cu1—O10S93.65 (5)C13B—C14B—H14B119.4
O1A—Cu1—Cu1i88.07 (3)C6A—C7A—H7A119.6
O1A—Cu1—O2Bi88.85 (5)C8A—C7A—C6A120.85 (17)
O1A—Cu1—O2Ai168.82 (5)C8A—C7A—H7A119.6
O1A—Cu1—O10S95.82 (5)C9A—C8A—H8A119.3
O2Ai—Cu1—Cu1i80.87 (3)C7A—C8A—C9A121.44 (18)
O2Ai—Cu1—O10S95.36 (5)C7A—C8A—H8A119.3
O10S—Cu1—Cu1i172.15 (4)C12B—C13B—H13B120.1
C3B—O1B—Cu1118.18 (10)C14B—C13B—C12B119.72 (19)
C3B—O2B—Cu1i128.64 (10)C14B—C13B—H13B120.1
C3A—O1A—Cu1119.63 (10)O5S1—C6S1—H6SA109.8
C3A—O2A—Cu1i127.34 (10)O5S1—C6S1—H6SB109.8
Cu1—O10S—H10A128.2 (12)O5S1—C6S1—C7S1109.2 (6)
Cu1—O10S—H10B126.1 (13)H6SA—C6S1—H6SB108.3
H10A—O10S—H10B104.9 (7)C7S1—C6S1—H6SA109.8
C9B—N10B—C11B128.08 (14)C7S1—C6S1—H6SB109.8
C9B—N10B—H10C113.6 (14)C14A—C13A—H13A119.9
C11B—N10B—H10C116.1 (15)C14A—C13A—C12A120.19 (19)
C3S1—O2S1—C1S1116.0 (10)C12A—C13A—H13A119.9
O1B—C3B—O2B123.71 (14)C11A—C12A—H12A120.2
O1B—C3B—C4B117.85 (13)C13A—C12A—C11A119.6 (2)
O2B—C3B—C4B118.43 (13)C13A—C12A—H12A120.2
N10B—C9B—C4B120.34 (14)O2S1—C3S1—H3SA109.4
N10B—C9B—C8B122.13 (15)O2S1—C3S1—H3SB109.4
C8B—C9B—C4B117.53 (15)O2S1—C3S1—C4S1111.3 (7)
O1A—C3A—O2A123.41 (15)H3SA—C3S1—H3SB108.0
O1A—C3A—C4A118.05 (14)C4S1—C3S1—H3SA109.4
O2A—C3A—C4A118.53 (14)C4S1—C3S1—H3SB109.4
C5A—C4A—C3A117.47 (15)O8S1—C7S1—C6S1110.1 (5)
C5A—C4A—C9A119.10 (16)O8S1—C7S1—H7SA109.6
C9A—C4A—C3A123.33 (15)O8S1—C7S1—H7SB109.6
C9B—C4B—C3B123.03 (14)C6S1—C7S1—H7SA109.6
C5B—C4B—C3B117.28 (14)C6S1—C7S1—H7SB109.6
C5B—C4B—C9B119.64 (14)H7SA—C7S1—H7SB108.1
C6S1—O5S1—C4S1113.8 (4)C15B—C18B—H18D109.5
C16B—C11B—N10B118.49 (15)C15B—C18B—H18E109.5
C12B—C11B—N10B120.86 (16)C15B—C18B—H18F109.5
C12B—C11B—C16B120.58 (16)H18D—C18B—H18E109.5
C9B—C8B—H8B119.5H18D—C18B—H18F109.5
C7B—C8B—C9B121.08 (16)H18E—C18B—H18F109.5
C7B—C8B—H8B119.5O2S1—C1S1—H1SA109.5
C4B—C5B—H5B119.1O2S1—C1S1—H1SB109.5
C6B—C5B—C4B121.86 (16)O2S1—C1S1—H1SC109.5
C6B—C5B—H5B119.1H1SA—C1S1—H1SB109.5
C4A—C5A—H5A119.0H1SA—C1S1—H1SC109.5
C6A—C5A—C4A121.92 (17)H1SB—C1S1—H1SC109.5
C6A—C5A—H5A119.0O5S1—C4S1—C3S1108.0 (4)
C9A—N10A—C11A129.73 (17)O5S1—C4S1—H4SA110.1
C9A—N10A—H10D111.9 (16)O5S1—C4S1—H4SB110.1
C11A—N10A—H10D118.3 (16)C3S1—C4S1—H4SA110.1
C15A—C16A—C17A120.49 (17)C3S1—C4S1—H4SB110.1
C11A—C16A—C15A119.10 (17)H4SA—C4S1—H4SB108.4
C11A—C16A—C17A120.41 (16)H9SD—C9S2—H9SE109.5
C9S1—O8S1—C7S1112.6 (8)H9SD—C9S2—H9SF109.5
C11B—C16B—C17B121.71 (15)H9SE—C9S2—H9SF109.5
C11B—C16B—C15B118.49 (16)O8S2—C9S2—H9SD109.5
C15B—C16B—C17B119.78 (17)O8S2—C9S2—H9SE109.5
C16A—C15A—C18A121.28 (17)O8S2—C9S2—H9SF109.5
C14A—C15A—C16A119.14 (18)C3S2—O2S2—C1S2121 (2)
C14A—C15A—C18A119.57 (17)O2S2—C3S2—H3SC109.1
C5B—C6B—H6B120.7O2S2—C3S2—H3SD109.1
C5B—C6B—C7B118.52 (17)O2S2—C3S2—C4S2112.4 (15)
C7B—C6B—H6B120.7H3SC—C3S2—H3SD107.9
C8B—C7B—C6B121.35 (16)C4S2—C3S2—H3SC109.1
C8B—C7B—H7B119.3C4S2—C3S2—H3SD109.1
C6B—C7B—H7B119.3O2S2—C1S2—H1SD109.5
C16A—C17A—H17A109.5O2S2—C1S2—H1SE109.5
C16A—C17A—H17B109.5O2S2—C1S2—H1SF109.5
C16A—C17A—H17C109.5H1SD—C1S2—H1SE109.5
H17A—C17A—H17B109.5H1SD—C1S2—H1SF109.5
H17A—C17A—H17C109.5H1SE—C1S2—H1SF109.5
H17B—C17A—H17C109.5C3S2—C4S2—H4SC109.5
C5A—C6A—H6A120.6C3S2—C4S2—H4SD109.5
C5A—C6A—C7A118.74 (17)H4SC—C4S2—H4SD108.1
C7A—C6A—H6A120.6O5S2—C4S2—C3S2110.6 (9)
N10A—C9A—C4A119.92 (16)O5S2—C4S2—H4SC109.5
N10A—C9A—C8A122.18 (17)O5S2—C4S2—H4SD109.5
C8A—C9A—C4A117.82 (17)C4S2—O5S2—C6S2114.8 (10)
C16B—C17B—H17D109.5O5S2—C6S2—H6SC109.3
C16B—C17B—H17E109.5O5S2—C6S2—H6SD109.3
C16B—C17B—H17F109.5O5S2—C6S2—C7S2111.7 (14)
H17D—C17B—H17E109.5H6SC—C6S2—H6SD107.9
H17D—C17B—H17F109.5C7S2—C6S2—H6SC109.3
H17E—C17B—H17F109.5C7S2—C6S2—H6SD109.3
C16A—C11A—N10A117.43 (17)C6S2—C7S2—H7SC110.4
C12A—C11A—N10A121.68 (19)C6S2—C7S2—H7SD110.4
C12A—C11A—C16A120.71 (18)H7SC—C7S2—H7SD108.6
C11B—C12B—H12B119.9O8S2—C7S2—C6S2106.5 (10)
C13B—C12B—C11B120.15 (19)O8S2—C7S2—H7SC110.4
C13B—C12B—H12B119.9O8S2—C7S2—H7SD110.4
C15A—C14A—H14A119.4C9S2—O8S2—C7S2117.0 (13)
C13A—C14A—C15A121.22 (18)O8S1—C9S1—H9SA109.5
C13A—C14A—H14A119.4O8S1—C9S1—H9SB109.5
C15A—C18A—H18A109.5O8S1—C9S1—H9SC109.5
C15A—C18A—H18B109.5H9SA—C9S1—H9SB109.5
C15A—C18A—H18C109.5H9SA—C9S1—H9SC109.5
H18A—C18A—H18B109.5H9SB—C9S1—H9SC109.5
Cu1—O1B—C3B—O2B8.6 (2)C5B—C6B—C7B—C8B1.7 (3)
Cu1—O1B—C3B—C4B170.41 (10)C5A—C4A—C9A—N10A179.92 (18)
Cu1i—O2B—C3B—O1B9.2 (2)C5A—C4A—C9A—C8A3.2 (3)
Cu1i—O2B—C3B—C4B169.80 (10)C5A—C6A—C7A—C8A3.2 (3)
Cu1—O1A—C3A—O2A10.2 (2)N10A—C9A—C8A—C7A178.9 (2)
Cu1—O1A—C3A—C4A168.37 (10)N10A—C11A—C12A—C13A176.3 (2)
Cu1i—O2A—C3A—O1A8.7 (2)C16A—C15A—C14A—C13A2.0 (3)
Cu1i—O2A—C3A—C4A169.93 (10)C16A—C11A—C12A—C13A1.2 (3)
O1B—C3B—C4B—C9B179.72 (14)C16B—C11B—C12B—C13B1.1 (3)
O1B—C3B—C4B—C5B3.1 (2)C16B—C15B—C14B—C13B1.0 (3)
O2B—C3B—C4B—C9B1.2 (2)C15A—C16A—C11A—N10A173.66 (18)
O2B—C3B—C4B—C5B176.01 (15)C15A—C16A—C11A—C12A1.6 (3)
O1A—C3A—C4A—C5A5.4 (2)C15A—C14A—C13A—C12A0.8 (3)
O1A—C3A—C4A—C9A171.06 (16)C17A—C16A—C15A—C14A177.50 (17)
O2A—C3A—C4A—C5A175.93 (14)C17A—C16A—C15A—C18A3.5 (3)
O2A—C3A—C4A—C9A7.6 (2)C17A—C16A—C11A—N10A5.6 (3)
N10B—C9B—C4B—C3B3.1 (2)C17A—C16A—C11A—C12A179.1 (2)
N10B—C9B—C4B—C5B179.74 (15)C6A—C7A—C8A—C9A1.2 (3)
N10B—C9B—C8B—C7B179.34 (17)C9A—C4A—C5A—C6A1.2 (3)
N10B—C11B—C16B—C17B4.4 (2)C9A—N10A—C11A—C16A144.7 (2)
N10B—C11B—C16B—C15B177.08 (16)C9A—N10A—C11A—C12A40.0 (4)
N10B—C11B—C12B—C13B177.97 (18)C17B—C16B—C15B—C14B177.61 (19)
O2S1—C3S1—C4S1—O5S158.7 (11)C17B—C16B—C15B—C18B2.4 (3)
C3B—C4B—C5B—C6B176.76 (17)C11A—N10A—C9A—C4A174.3 (2)
C9B—N10B—C11B—C16B124.92 (18)C11A—N10A—C9A—C8A8.9 (4)
C9B—N10B—C11B—C12B58.1 (3)C11A—C16A—C15A—C14A3.2 (3)
C9B—C4B—C5B—C6B0.5 (3)C11A—C16A—C15A—C18A175.80 (18)
C9B—C8B—C7B—C6B1.3 (3)C12B—C11B—C16B—C17B178.61 (17)
C3A—C4A—C5A—C6A175.39 (15)C12B—C11B—C16B—C15B0.1 (3)
C3A—C4A—C9A—N10A3.7 (3)C14A—C13A—C12A—C11A2.4 (4)
C3A—C4A—C9A—C8A173.24 (17)C18A—C15A—C14A—C13A177.00 (19)
C4A—C5A—C6A—C7A2.0 (3)C15B—C14B—C13B—C12B0.0 (4)
C4A—C9A—C8A—C7A2.0 (3)C6S1—O5S1—C4S1—C3S1178.1 (5)
C4B—C9B—C8B—C7B0.0 (3)C18B—C15B—C14B—C13B179.0 (2)
C4B—C5B—C6B—C7B0.8 (3)C1S1—O2S1—C3S1—C4S1171.1 (12)
O5S1—C6S1—C7S1—O8S167.3 (7)C4S1—O5S1—C6S1—C7S1175.2 (4)
C11B—N10B—C9B—C4B171.23 (16)O2S2—C3S2—C4S2—O5S264 (2)
C11B—N10B—C9B—C8B8.1 (3)C3S2—C4S2—O5S2—C6S2176.1 (11)
C11B—C16B—C15B—C14B0.9 (3)C1S2—O2S2—C3S2—C4S2163 (3)
C11B—C16B—C15B—C18B179.1 (2)C4S2—O5S2—C6S2—C7S2164.7 (10)
C11B—C12B—C13B—C14B1.0 (3)O5S2—C6S2—C7S2—O8S268.1 (17)
C8B—C9B—C4B—C3B176.22 (15)C6S2—C7S2—O8S2—C9S2171.6 (16)
C8B—C9B—C4B—C5B0.9 (2)C9S1—O8S1—C7S1—C6S1172.0 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10A—H10D···O2A0.86 (3)1.86 (3)2.604 (2)143 (2)
N10B—H10C···O2B0.89 (2)1.87 (2)2.6065 (18)139 (2)
Comparison of selected geometries (Å, °) top
Coordinates are unavailable for entry MPANCU10. There are two values per structure, corresponding to the two mefenamate units in the asymmetric unit as denoted A and B in our atom-numbering scheme.
This workMPANCU20SUTPIG
Space groupP21/nP21/cP1
O1—C3—C4—C9171.1 (2)179.7 (1)170.98179.70153 (1)180 (1)
C4—C9—N10—C11174.3 (2)171.2 (2)-166.40171.56171 (1)172 (1)
C9—N10—C11—C16144.7 (2)-124.9 (2)-155.25-109.34-107 (2)135 (2)
Cu—Omefenamate1.961 (1)1.954 (1)1.97371.96051.972 (7)1.949 (7)
Cu—Osolvent2.108 (1)2.15612.17 (1)
Cu···Cu2.6126 (4)2.61202.627 (3)
 

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