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Tranexamic acid is an anti­fibrinolytic amino acid that exists as a zwitterion [trans-4-(ammonio­meth­yl)cyclo­hexane-1-carboxyl­ate] in the solid state. Its reaction with copper chloride lead to the formation of a copper(II) paddle-wheel structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017012543/wm5416sup1.cif
Contains datablocks I, Global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989017012543/wm5416Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989017012543/wm5416sup3.pdf
CSD search of axially Cl- ligated Cu-Cu paddle-wheel structures

CCDC reference: 1571897

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. H1WB .. 1.97 Ang.
Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of O1 Check PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00794 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.193 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 3 Report PLAT971_ALERT_2_C Check Calcd Residual Density 1.02A From O1 2.02 eA-3 PLAT971_ALERT_2_C Check Calcd Residual Density 0.90A From O2 1.74 eA-3 PLAT971_ALERT_2_C Check Calcd Residual Density 1.18A From Cu1 1.56 eA-3 PLAT975_ALERT_2_C Check Calcd Residual Density 0.93A From O2 0.46 eA-3 PLAT976_ALERT_2_C Check Calcd Residual Density 0.83A From O2W -0.40 eA-3 PLAT977_ALERT_2_C Check the Negative Difference Density on H1B -0.31 eA-3 PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 9 Note PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 6 Report PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.13 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 6 Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 9 Note 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 24 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 11 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2004); cell refinement: CELL in IPDS-I (Stoe & Cie, 2004); data reduction: INTEGRATE in IPDS-I (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS2016/6 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016/6 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Dichloro-tetrakis[µ-4-(ammoniomethyl)cyclohexane-1-carboxylato-O,O']dicopper(II) dichloride hexahydrate top
Crystal data top
[Cu2Cl2(C8H15NO2)4](Cl2)·6H2OF(000) = 1060
Mr = 1005.81Dx = 1.420 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 14.7100 (11) ÅCell parameters from 8000 reflections
b = 10.7163 (6) Åθ = 2.3–25.9°
c = 14.9312 (12) ŵ = 1.19 mm1
β = 91.828 (10)°T = 153 K
V = 2352.5 (3) Å3Plate, green
Z = 20.34 × 0.30 × 0.20 mm
Data collection top
STOE IPDS 1
diffractometer
4545 independent reflections
Radiation source: fine-focus sealed tube3172 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.091
φ rotation scansθmax = 25.9°, θmin = 2.3°
Absorption correction: multi-scan
(MULABS; Spek, 2009)
h = 1818
Tmin = 0.712, Tmax = 1.000k = 1313
18018 measured reflectionsl = 1818
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)] = 0.067Hydrogen site location: mixed
wR(F2) = 0.196H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.1331P)2]
where P = (Fo2 + 2Fc2)/3
4545 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 1.80 e Å3
9 restraintsΔρmin = 0.93 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.57200 (3)0.53341 (6)0.55087 (4)0.0195 (2)
Cl10.69386 (7)0.59126 (13)0.66374 (7)0.0253 (3)
O10.5727 (3)0.3572 (4)0.5833 (3)0.0384 (10)
O20.4505 (3)0.3014 (4)0.5009 (3)0.0369 (10)
O30.6477 (2)0.4905 (4)0.4471 (2)0.0297 (9)
O40.5250 (2)0.4381 (5)0.3640 (3)0.0445 (12)
N10.6876 (3)0.1791 (5)0.8123 (3)0.0339 (11)
H1A0.7156460.2074680.7627840.051*
H1B0.6887420.2395450.8550690.051*
H1C0.7171080.1101160.8336900.051*
N20.6727 (3)0.1961 (6)0.0237 (3)0.0451 (14)
H2A0.6746680.1300930.0146730.068*
H2B0.7021330.1759970.0743990.068*
H2C0.6136840.2150790.0380250.068*
C10.5154 (3)0.2771 (5)0.5551 (3)0.0244 (11)
C20.5225 (4)0.1471 (5)0.5916 (4)0.0299 (12)
H20.4901460.0892830.5487410.036*
C30.6224 (4)0.1033 (6)0.6034 (4)0.0377 (14)
H3A0.6501870.0988710.5439740.045*
H3B0.6570160.1652550.6400080.045*
C40.6295 (4)0.0230 (6)0.6482 (4)0.0388 (14)
H4A0.6944440.0456810.6571970.047*
H4B0.6003710.0867430.6088490.047*
C50.5841 (3)0.0227 (5)0.7379 (4)0.0288 (12)
H50.6149420.0422950.7761580.035*
C60.4837 (4)0.0149 (6)0.7258 (6)0.0472 (18)
H6A0.4510490.0482670.6886210.057*
H6B0.4553110.0177460.7849950.057*
C70.4754 (3)0.1418 (6)0.6811 (4)0.0372 (14)
H7A0.5024040.2057960.7216660.045*
H7B0.4102390.1621090.6712030.045*
C80.5915 (4)0.1465 (6)0.7881 (4)0.0397 (14)
H8A0.5563280.1412310.8434060.048*
H8B0.5645090.2135270.7501870.048*
C90.6099 (3)0.4514 (5)0.3760 (3)0.0244 (11)
C100.6679 (3)0.4182 (5)0.2966 (3)0.0244 (11)
H100.7335150.4276040.3150030.029*
C110.6461 (4)0.5081 (6)0.2187 (4)0.0288 (12)
H11A0.5798380.5072450.2048440.035*
H11B0.6635450.5939650.2365600.035*
C120.6970 (4)0.4710 (6)0.1351 (3)0.0299 (12)
H12A0.6816110.5300320.0859300.036*
H12B0.7633380.4759850.1479850.036*
C130.6722 (3)0.3405 (5)0.1063 (3)0.0262 (12)
H130.6048220.3374270.0952280.031*
C140.6965 (4)0.2495 (6)0.1830 (4)0.0332 (13)
H14A0.6778710.1641120.1649650.040*
H14B0.7632810.2492870.1937200.040*
C150.6507 (4)0.2838 (6)0.2693 (4)0.0319 (12)
H15A0.5844010.2701200.2615010.038*
H15B0.6735270.2279900.3178680.038*
C160.7174 (4)0.3051 (6)0.0196 (4)0.0347 (14)
H16A0.7146180.3769240.0220830.042*
H16B0.7822390.2854870.0326010.042*
Cl20.53120 (11)0.73439 (19)0.07190 (12)0.0537 (5)
O1W0.3515 (3)0.3850 (6)0.0849 (3)0.0600 (14)
H1WA0.385 (4)0.405 (9)0.038 (3)0.090*
H1WB0.393 (4)0.383 (9)0.130 (3)0.090*
O2W0.1694 (4)0.5612 (6)0.5040 (4)0.0651 (15)
H2WA0.134 (5)0.589 (9)0.548 (5)0.098*
H2WB0.222 (3)0.602 (8)0.514 (6)0.098*
O3W0.1194 (3)0.1039 (6)0.3118 (3)0.0619 (15)
H3WA0.104 (5)0.075 (8)0.259 (3)0.093*
H3WB0.073 (4)0.148 (8)0.329 (5)0.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0152 (3)0.0291 (4)0.0144 (3)0.0005 (2)0.0036 (2)0.0010 (2)
Cl10.0213 (6)0.0352 (8)0.0193 (6)0.0045 (5)0.0001 (4)0.0005 (5)
O10.035 (2)0.039 (3)0.041 (2)0.0092 (18)0.0129 (17)0.0117 (19)
O20.035 (2)0.033 (2)0.041 (2)0.0018 (17)0.0158 (17)0.0035 (19)
O30.0195 (16)0.050 (3)0.0195 (17)0.0029 (16)0.0022 (13)0.0049 (17)
O40.0187 (18)0.088 (4)0.027 (2)0.0061 (19)0.0057 (14)0.018 (2)
N10.031 (2)0.032 (3)0.038 (3)0.007 (2)0.0064 (19)0.001 (2)
N20.041 (3)0.056 (4)0.039 (3)0.001 (3)0.018 (2)0.019 (3)
C10.024 (2)0.031 (3)0.018 (2)0.004 (2)0.0067 (19)0.004 (2)
C20.032 (3)0.025 (3)0.032 (3)0.001 (2)0.008 (2)0.003 (2)
C30.032 (3)0.048 (4)0.034 (3)0.015 (3)0.016 (2)0.011 (3)
C40.039 (3)0.040 (4)0.038 (3)0.015 (3)0.001 (2)0.003 (3)
C50.020 (2)0.029 (3)0.037 (3)0.001 (2)0.002 (2)0.004 (2)
C60.022 (3)0.036 (4)0.084 (5)0.002 (2)0.010 (3)0.022 (4)
C70.019 (2)0.037 (4)0.056 (4)0.007 (2)0.010 (2)0.019 (3)
C80.028 (3)0.040 (4)0.051 (4)0.005 (3)0.004 (2)0.009 (3)
C90.022 (2)0.030 (3)0.022 (2)0.001 (2)0.0045 (19)0.004 (2)
C100.014 (2)0.039 (3)0.021 (2)0.001 (2)0.0046 (17)0.000 (2)
C110.034 (3)0.029 (3)0.024 (3)0.002 (2)0.008 (2)0.001 (2)
C120.032 (3)0.037 (4)0.021 (3)0.004 (2)0.010 (2)0.004 (2)
C130.020 (2)0.035 (3)0.024 (2)0.004 (2)0.0101 (18)0.006 (2)
C140.031 (3)0.030 (3)0.039 (3)0.002 (2)0.011 (2)0.000 (3)
C150.036 (3)0.031 (3)0.030 (3)0.003 (2)0.011 (2)0.002 (2)
C160.029 (3)0.047 (4)0.028 (3)0.003 (2)0.013 (2)0.012 (3)
Cl20.0453 (9)0.0647 (13)0.0518 (10)0.0012 (8)0.0122 (7)0.0128 (9)
O1W0.062 (3)0.068 (4)0.051 (3)0.008 (3)0.014 (2)0.021 (3)
O2W0.048 (3)0.075 (4)0.071 (4)0.012 (3)0.008 (3)0.019 (3)
O3W0.052 (3)0.081 (4)0.053 (3)0.018 (3)0.000 (2)0.034 (3)
Geometric parameters (Å, º) top
Cu1—Cu1i2.6649 (11)C6—H6A0.9900
Cu1—O11.950 (4)C6—H6B0.9900
Cu1—O2i1.955 (4)C7—H7A0.9900
Cu1—O4i1.965 (4)C7—H7B0.9900
Cu1—O31.991 (3)C8—H8A0.9900
Cu1—Cl12.4990 (12)C8—H8B0.9900
O1—C11.265 (7)C9—C101.526 (6)
O2—C11.258 (6)C10—C151.516 (8)
O3—C91.255 (6)C10—C111.536 (7)
O4—C91.264 (6)C10—H101.0000
N1—C81.489 (7)C11—C121.527 (7)
N1—H1A0.9100C11—H11A0.9900
N1—H1B0.9100C11—H11B0.9900
N1—H1C0.9100C12—C131.505 (8)
N2—C161.479 (8)C12—H12A0.9900
N2—H2A0.9100C12—H12B0.9900
N2—H2B0.9100C13—C161.522 (7)
N2—H2C0.9100C13—C141.538 (8)
C1—C21.499 (8)C13—H131.0000
C2—C71.526 (8)C14—C151.518 (7)
C2—C31.547 (7)C14—H14A0.9900
C2—H21.0000C14—H14B0.9900
C3—C41.512 (9)C15—H15A0.9900
C3—H3A0.9900C15—H15B0.9900
C3—H3B0.9900C16—H16A0.9900
C4—C51.515 (8)C16—H16B0.9900
C4—H4A0.9900O1W—H1WA0.89 (2)
C4—H4B0.9900O1W—H1WB0.90 (2)
C5—C81.526 (8)O2W—H2WA0.90 (2)
C5—C61.536 (7)O2W—H2WB0.90 (2)
C5—H51.0000O3W—H3WA0.88 (2)
C6—C71.518 (9)O3W—H3WB0.88 (2)
O1—Cu1—O2i167.02 (15)C5—C6—H6B109.6
O1—Cu1—O4i89.3 (2)H6A—C6—H6B108.1
O2i—Cu1—O4i89.9 (2)C6—C7—C2112.7 (5)
O1—Cu1—O388.33 (18)C6—C7—H7A109.0
O2i—Cu1—O389.60 (18)C2—C7—H7A109.0
O4i—Cu1—O3167.27 (15)C6—C7—H7B109.0
O1—Cu1—Cl194.31 (11)C2—C7—H7B109.0
O2i—Cu1—Cl198.68 (11)H7A—C7—H7B107.8
O4i—Cu1—Cl192.57 (11)N1—C8—C5112.0 (5)
O3—Cu1—Cl1100.08 (10)N1—C8—H8A109.2
O1—Cu1—Cu1i83.04 (11)C5—C8—H8A109.2
O2i—Cu1—Cu1i84.05 (11)N1—C8—H8B109.2
O4i—Cu1—Cu1i80.24 (11)C5—C8—H8B109.2
O3—Cu1—Cu1i87.06 (10)H8A—C8—H8B107.9
Cl1—Cu1—Cu1i172.34 (4)O3—C9—O4124.6 (5)
C1—O1—Cu1125.2 (3)O3—C9—C10119.4 (4)
C1—O2—Cu1i123.8 (4)O4—C9—C10116.0 (4)
C9—O3—Cu1119.4 (3)C15—C10—C9109.8 (4)
C9—O4—Cu1i128.7 (3)C15—C10—C11111.3 (4)
C8—N1—H1A109.5C9—C10—C11109.5 (4)
C8—N1—H1B109.5C15—C10—H10108.7
H1A—N1—H1B109.5C9—C10—H10108.7
C8—N1—H1C109.5C11—C10—H10108.7
H1A—N1—H1C109.5C12—C11—C10111.1 (4)
H1B—N1—H1C109.5C12—C11—H11A109.4
C16—N2—H2A109.5C10—C11—H11A109.4
C16—N2—H2B109.5C12—C11—H11B109.4
H2A—N2—H2B109.5C10—C11—H11B109.4
C16—N2—H2C109.5H11A—C11—H11B108.0
H2A—N2—H2C109.5C13—C12—C11110.8 (4)
H2B—N2—H2C109.5C13—C12—H12A109.5
O2—C1—O1123.9 (5)C11—C12—H12A109.5
O2—C1—C2118.0 (5)C13—C12—H12B109.5
O1—C1—C2118.1 (4)C11—C12—H12B109.5
C1—C2—C7108.9 (5)H12A—C12—H12B108.1
C1—C2—C3112.2 (5)C12—C13—C16111.5 (5)
C7—C2—C3110.2 (4)C12—C13—C14109.2 (4)
C1—C2—H2108.5C16—C13—C14112.2 (5)
C7—C2—H2108.5C12—C13—H13107.9
C3—C2—H2108.5C16—C13—H13107.9
C4—C3—C2112.0 (5)C14—C13—H13107.9
C4—C3—H3A109.2C15—C14—C13112.3 (5)
C2—C3—H3A109.2C15—C14—H14A109.1
C4—C3—H3B109.2C13—C14—H14A109.1
C2—C3—H3B109.2C15—C14—H14B109.1
H3A—C3—H3B107.9C13—C14—H14B109.1
C3—C4—C5111.3 (5)H14A—C14—H14B107.9
C3—C4—H4A109.4C10—C15—C14112.5 (5)
C5—C4—H4A109.4C10—C15—H15A109.1
C3—C4—H4B109.4C14—C15—H15A109.1
C5—C4—H4B109.4C10—C15—H15B109.1
H4A—C4—H4B108.0C14—C15—H15B109.1
C4—C5—C8113.9 (5)H15A—C15—H15B107.8
C4—C5—C6110.2 (5)N2—C16—C13111.6 (5)
C8—C5—C6109.8 (5)N2—C16—H16A109.3
C4—C5—H5107.5C13—C16—H16A109.3
C8—C5—H5107.5N2—C16—H16B109.3
C6—C5—H5107.5C13—C16—H16B109.3
C7—C6—C5110.5 (5)H16A—C16—H16B108.0
C7—C6—H6A109.6H1WA—O1W—H1WB102 (3)
C5—C6—H6A109.6H2WA—O2W—H2WB103 (3)
C7—C6—H6B109.6H3WA—O3W—H3WB106 (3)
Cu1i—O2—C1—O11.1 (7)Cu1—O3—C9—O41.0 (8)
Cu1i—O2—C1—C2178.1 (4)Cu1—O3—C9—C10179.8 (4)
Cu1—O1—C1—O20.9 (7)Cu1i—O4—C9—O32.3 (9)
Cu1—O1—C1—C2176.1 (4)Cu1i—O4—C9—C10178.5 (4)
O2—C1—C2—C794.2 (6)O3—C9—C10—C15122.8 (5)
O1—C1—C2—C782.9 (6)O4—C9—C10—C1557.9 (6)
O2—C1—C2—C3143.5 (5)O3—C9—C10—C11114.7 (5)
O1—C1—C2—C339.4 (7)O4—C9—C10—C1164.5 (6)
C1—C2—C3—C4174.7 (5)C15—C10—C11—C1253.7 (6)
C7—C2—C3—C453.1 (7)C9—C10—C11—C12175.2 (4)
C2—C3—C4—C556.3 (7)C10—C11—C12—C1358.9 (6)
C3—C4—C5—C8178.1 (5)C11—C12—C13—C16176.2 (4)
C3—C4—C5—C657.9 (7)C11—C12—C13—C1459.3 (5)
C4—C5—C6—C757.2 (8)C12—C13—C14—C1556.5 (6)
C8—C5—C6—C7176.5 (6)C16—C13—C14—C15179.4 (5)
C5—C6—C7—C255.9 (8)C9—C10—C15—C14172.3 (4)
C1—C2—C7—C6176.8 (5)C11—C10—C15—C1450.9 (6)
C3—C2—C7—C653.3 (7)C13—C14—C15—C1052.9 (6)
C4—C5—C8—N163.3 (7)C12—C13—C16—N2162.4 (5)
C6—C5—C8—N1172.5 (5)C14—C13—C16—N274.9 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1ii0.912.633.316 (5)133
N1—H1C···Cl1iii0.912.523.394 (5)160
N2—H2B···Cl1iv0.912.253.123 (5)160
N2—H2C···Cl2v0.912.243.151 (6)179
N1—H1B···O1Wvi0.911.902.760 (7)156
N2—H2A···O2Wvii0.912.062.789 (9)137
O1W—H1WA···Cl2v0.89 (2)2.57 (8)3.218 (6)130 (8)
O2W—H2WA···Cl2viii0.90 (2)2.46 (7)3.176 (6)137 (9)
O2W—H2WB···O3i0.90 (2)2.22 (8)2.820 (6)124 (8)
O3W—H3WA···Cl1ix0.88 (2)2.66 (6)3.258 (5)127 (6)
O3W—H3WB···Cl2x0.88 (2)2.35 (3)3.182 (5)158 (7)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x+3/2, y1/2, z+3/2; (iv) x+3/2, y1/2, z+1/2; (v) x+1, y+1, z; (vi) x+1, y, z+1; (vii) x+1/2, y+1/2, z1/2; (viii) x1/2, y+3/2, z+1/2; (ix) x1/2, y+1/2, z1/2; (x) x+1/2, y1/2, z+1/2.
 

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