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
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
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)·6H2O | F(000) = 1060 |
Mr = 1005.81 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.7100 (11) Å | Cell parameters from 8000 reflections |
b = 10.7163 (6) Å | θ = 2.3–25.9° |
c = 14.9312 (12) Å | µ = 1.19 mm−1 |
β = 91.828 (10)° | T = 153 K |
V = 2352.5 (3) Å3 | Plate, green |
Z = 2 | 0.34 × 0.30 × 0.20 mm |
Data collection top
STOE IPDS 1 diffractometer | 4545 independent reflections |
Radiation source: fine-focus sealed tube | 3172 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.091 |
φ rotation scans | θmax = 25.9°, θmin = 2.3° |
Absorption correction: multi-scan (MULABS; Spek, 2009) | h = −18→18 |
Tmin = 0.712, Tmax = 1.000 | k = −13→13 |
18018 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: mixed |
wR(F2) = 0.196 | H 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 parameters | Δρmax = 1.80 e Å−3 |
9 restraints | Δρmin = −0.93 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.57200 (3) | 0.53341 (6) | 0.55087 (4) | 0.0195 (2) | |
Cl1 | 0.69386 (7) | 0.59126 (13) | 0.66374 (7) | 0.0253 (3) | |
O1 | 0.5727 (3) | 0.3572 (4) | 0.5833 (3) | 0.0384 (10) | |
O2 | 0.4505 (3) | 0.3014 (4) | 0.5009 (3) | 0.0369 (10) | |
O3 | 0.6477 (2) | 0.4905 (4) | 0.4471 (2) | 0.0297 (9) | |
O4 | 0.5250 (2) | 0.4381 (5) | 0.3640 (3) | 0.0445 (12) | |
N1 | 0.6876 (3) | −0.1791 (5) | 0.8123 (3) | 0.0339 (11) | |
H1A | 0.715646 | −0.207468 | 0.762784 | 0.051* | |
H1B | 0.688742 | −0.239545 | 0.855069 | 0.051* | |
H1C | 0.717108 | −0.110116 | 0.833690 | 0.051* | |
N2 | 0.6727 (3) | 0.1961 (6) | −0.0237 (3) | 0.0451 (14) | |
H2A | 0.674668 | 0.130093 | 0.014673 | 0.068* | |
H2B | 0.702133 | 0.175997 | −0.074399 | 0.068* | |
H2C | 0.613684 | 0.215079 | −0.038025 | 0.068* | |
C1 | 0.5154 (3) | 0.2771 (5) | 0.5551 (3) | 0.0244 (11) | |
C2 | 0.5225 (4) | 0.1471 (5) | 0.5916 (4) | 0.0299 (12) | |
H2 | 0.490146 | 0.089283 | 0.548741 | 0.036* | |
C3 | 0.6224 (4) | 0.1033 (6) | 0.6034 (4) | 0.0377 (14) | |
H3A | 0.650187 | 0.098871 | 0.543974 | 0.045* | |
H3B | 0.657016 | 0.165255 | 0.640008 | 0.045* | |
C4 | 0.6295 (4) | −0.0230 (6) | 0.6482 (4) | 0.0388 (14) | |
H4A | 0.694444 | −0.045681 | 0.657197 | 0.047* | |
H4B | 0.600371 | −0.086743 | 0.608849 | 0.047* | |
C5 | 0.5841 (3) | −0.0227 (5) | 0.7379 (4) | 0.0288 (12) | |
H5 | 0.614942 | 0.042295 | 0.776158 | 0.035* | |
C6 | 0.4837 (4) | 0.0149 (6) | 0.7258 (6) | 0.0472 (18) | |
H6A | 0.451049 | −0.048267 | 0.688621 | 0.057* | |
H6B | 0.455311 | 0.017746 | 0.784995 | 0.057* | |
C7 | 0.4754 (3) | 0.1418 (6) | 0.6811 (4) | 0.0372 (14) | |
H7A | 0.502404 | 0.205796 | 0.721666 | 0.045* | |
H7B | 0.410239 | 0.162109 | 0.671203 | 0.045* | |
C8 | 0.5915 (4) | −0.1465 (6) | 0.7881 (4) | 0.0397 (14) | |
H8A | 0.556328 | −0.141231 | 0.843406 | 0.048* | |
H8B | 0.564509 | −0.213527 | 0.750187 | 0.048* | |
C9 | 0.6099 (3) | 0.4514 (5) | 0.3760 (3) | 0.0244 (11) | |
C10 | 0.6679 (3) | 0.4182 (5) | 0.2966 (3) | 0.0244 (11) | |
H10 | 0.733515 | 0.427604 | 0.315003 | 0.029* | |
C11 | 0.6461 (4) | 0.5081 (6) | 0.2187 (4) | 0.0288 (12) | |
H11A | 0.579838 | 0.507245 | 0.204844 | 0.035* | |
H11B | 0.663545 | 0.593965 | 0.236560 | 0.035* | |
C12 | 0.6970 (4) | 0.4710 (6) | 0.1351 (3) | 0.0299 (12) | |
H12A | 0.681611 | 0.530032 | 0.085930 | 0.036* | |
H12B | 0.763338 | 0.475985 | 0.147985 | 0.036* | |
C13 | 0.6722 (3) | 0.3405 (5) | 0.1063 (3) | 0.0262 (12) | |
H13 | 0.604822 | 0.337427 | 0.095228 | 0.031* | |
C14 | 0.6965 (4) | 0.2495 (6) | 0.1830 (4) | 0.0332 (13) | |
H14A | 0.677871 | 0.164112 | 0.164965 | 0.040* | |
H14B | 0.763281 | 0.249287 | 0.193720 | 0.040* | |
C15 | 0.6507 (4) | 0.2838 (6) | 0.2693 (4) | 0.0319 (12) | |
H15A | 0.584401 | 0.270120 | 0.261501 | 0.038* | |
H15B | 0.673527 | 0.227990 | 0.317868 | 0.038* | |
C16 | 0.7174 (4) | 0.3051 (6) | 0.0196 (4) | 0.0347 (14) | |
H16A | 0.714618 | 0.376924 | −0.022083 | 0.042* | |
H16B | 0.782239 | 0.285487 | 0.032601 | 0.042* | |
Cl2 | 0.53120 (11) | 0.73439 (19) | 0.07190 (12) | 0.0537 (5) | |
O1W | 0.3515 (3) | 0.3850 (6) | 0.0849 (3) | 0.0600 (14) | |
H1WA | 0.385 (4) | 0.405 (9) | 0.038 (3) | 0.090* | |
H1WB | 0.393 (4) | 0.383 (9) | 0.130 (3) | 0.090* | |
O2W | 0.1694 (4) | 0.5612 (6) | 0.5040 (4) | 0.0651 (15) | |
H2WA | 0.134 (5) | 0.589 (9) | 0.548 (5) | 0.098* | |
H2WB | 0.222 (3) | 0.602 (8) | 0.514 (6) | 0.098* | |
O3W | 0.1194 (3) | 0.1039 (6) | 0.3118 (3) | 0.0619 (15) | |
H3WA | 0.104 (5) | 0.075 (8) | 0.259 (3) | 0.093* | |
H3WB | 0.073 (4) | 0.148 (8) | 0.329 (5) | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0152 (3) | 0.0291 (4) | 0.0144 (3) | 0.0005 (2) | 0.0036 (2) | 0.0010 (2) |
Cl1 | 0.0213 (6) | 0.0352 (8) | 0.0193 (6) | −0.0045 (5) | 0.0001 (4) | 0.0005 (5) |
O1 | 0.035 (2) | 0.039 (3) | 0.041 (2) | −0.0092 (18) | −0.0129 (17) | 0.0117 (19) |
O2 | 0.035 (2) | 0.033 (2) | 0.041 (2) | 0.0018 (17) | −0.0158 (17) | −0.0035 (19) |
O3 | 0.0195 (16) | 0.050 (3) | 0.0195 (17) | −0.0029 (16) | 0.0022 (13) | −0.0049 (17) |
O4 | 0.0187 (18) | 0.088 (4) | 0.027 (2) | −0.0061 (19) | 0.0057 (14) | −0.018 (2) |
N1 | 0.031 (2) | 0.032 (3) | 0.038 (3) | 0.007 (2) | −0.0064 (19) | 0.001 (2) |
N2 | 0.041 (3) | 0.056 (4) | 0.039 (3) | 0.001 (3) | 0.018 (2) | −0.019 (3) |
C1 | 0.024 (2) | 0.031 (3) | 0.018 (2) | 0.004 (2) | 0.0067 (19) | 0.004 (2) |
C2 | 0.032 (3) | 0.025 (3) | 0.032 (3) | 0.001 (2) | −0.008 (2) | −0.003 (2) |
C3 | 0.032 (3) | 0.048 (4) | 0.034 (3) | 0.015 (3) | 0.016 (2) | 0.011 (3) |
C4 | 0.039 (3) | 0.040 (4) | 0.038 (3) | 0.015 (3) | −0.001 (2) | 0.003 (3) |
C5 | 0.020 (2) | 0.029 (3) | 0.037 (3) | 0.001 (2) | −0.002 (2) | 0.004 (2) |
C6 | 0.022 (3) | 0.036 (4) | 0.084 (5) | 0.002 (2) | 0.010 (3) | 0.022 (4) |
C7 | 0.019 (2) | 0.037 (4) | 0.056 (4) | 0.007 (2) | 0.010 (2) | 0.019 (3) |
C8 | 0.028 (3) | 0.040 (4) | 0.051 (4) | 0.005 (3) | 0.004 (2) | 0.009 (3) |
C9 | 0.022 (2) | 0.030 (3) | 0.022 (2) | 0.001 (2) | 0.0045 (19) | 0.004 (2) |
C10 | 0.014 (2) | 0.039 (3) | 0.021 (2) | 0.001 (2) | 0.0046 (17) | 0.000 (2) |
C11 | 0.034 (3) | 0.029 (3) | 0.024 (3) | 0.002 (2) | 0.008 (2) | −0.001 (2) |
C12 | 0.032 (3) | 0.037 (4) | 0.021 (3) | 0.004 (2) | 0.010 (2) | 0.004 (2) |
C13 | 0.020 (2) | 0.035 (3) | 0.024 (2) | 0.004 (2) | 0.0101 (18) | −0.006 (2) |
C14 | 0.031 (3) | 0.030 (3) | 0.039 (3) | 0.002 (2) | 0.011 (2) | 0.000 (3) |
C15 | 0.036 (3) | 0.031 (3) | 0.030 (3) | 0.003 (2) | 0.011 (2) | 0.002 (2) |
C16 | 0.029 (3) | 0.047 (4) | 0.028 (3) | 0.003 (2) | 0.013 (2) | −0.012 (3) |
Cl2 | 0.0453 (9) | 0.0647 (13) | 0.0518 (10) | −0.0012 (8) | 0.0122 (7) | 0.0128 (9) |
O1W | 0.062 (3) | 0.068 (4) | 0.051 (3) | 0.008 (3) | 0.014 (2) | 0.021 (3) |
O2W | 0.048 (3) | 0.075 (4) | 0.071 (4) | 0.012 (3) | −0.008 (3) | −0.019 (3) |
O3W | 0.052 (3) | 0.081 (4) | 0.053 (3) | 0.018 (3) | 0.000 (2) | −0.034 (3) |
Geometric parameters (Å, º) top
Cu1—Cu1i | 2.6649 (11) | C6—H6A | 0.9900 |
Cu1—O1 | 1.950 (4) | C6—H6B | 0.9900 |
Cu1—O2i | 1.955 (4) | C7—H7A | 0.9900 |
Cu1—O4i | 1.965 (4) | C7—H7B | 0.9900 |
Cu1—O3 | 1.991 (3) | C8—H8A | 0.9900 |
Cu1—Cl1 | 2.4990 (12) | C8—H8B | 0.9900 |
O1—C1 | 1.265 (7) | C9—C10 | 1.526 (6) |
O2—C1 | 1.258 (6) | C10—C15 | 1.516 (8) |
O3—C9 | 1.255 (6) | C10—C11 | 1.536 (7) |
O4—C9 | 1.264 (6) | C10—H10 | 1.0000 |
N1—C8 | 1.489 (7) | C11—C12 | 1.527 (7) |
N1—H1A | 0.9100 | C11—H11A | 0.9900 |
N1—H1B | 0.9100 | C11—H11B | 0.9900 |
N1—H1C | 0.9100 | C12—C13 | 1.505 (8) |
N2—C16 | 1.479 (8) | C12—H12A | 0.9900 |
N2—H2A | 0.9100 | C12—H12B | 0.9900 |
N2—H2B | 0.9100 | C13—C16 | 1.522 (7) |
N2—H2C | 0.9100 | C13—C14 | 1.538 (8) |
C1—C2 | 1.499 (8) | C13—H13 | 1.0000 |
C2—C7 | 1.526 (8) | C14—C15 | 1.518 (7) |
C2—C3 | 1.547 (7) | C14—H14A | 0.9900 |
C2—H2 | 1.0000 | C14—H14B | 0.9900 |
C3—C4 | 1.512 (9) | C15—H15A | 0.9900 |
C3—H3A | 0.9900 | C15—H15B | 0.9900 |
C3—H3B | 0.9900 | C16—H16A | 0.9900 |
C4—C5 | 1.515 (8) | C16—H16B | 0.9900 |
C4—H4A | 0.9900 | O1W—H1WA | 0.89 (2) |
C4—H4B | 0.9900 | O1W—H1WB | 0.90 (2) |
C5—C8 | 1.526 (8) | O2W—H2WA | 0.90 (2) |
C5—C6 | 1.536 (7) | O2W—H2WB | 0.90 (2) |
C5—H5 | 1.0000 | O3W—H3WA | 0.88 (2) |
C6—C7 | 1.518 (9) | O3W—H3WB | 0.88 (2) |
| | | |
O1—Cu1—O2i | 167.02 (15) | C5—C6—H6B | 109.6 |
O1—Cu1—O4i | 89.3 (2) | H6A—C6—H6B | 108.1 |
O2i—Cu1—O4i | 89.9 (2) | C6—C7—C2 | 112.7 (5) |
O1—Cu1—O3 | 88.33 (18) | C6—C7—H7A | 109.0 |
O2i—Cu1—O3 | 89.60 (18) | C2—C7—H7A | 109.0 |
O4i—Cu1—O3 | 167.27 (15) | C6—C7—H7B | 109.0 |
O1—Cu1—Cl1 | 94.31 (11) | C2—C7—H7B | 109.0 |
O2i—Cu1—Cl1 | 98.68 (11) | H7A—C7—H7B | 107.8 |
O4i—Cu1—Cl1 | 92.57 (11) | N1—C8—C5 | 112.0 (5) |
O3—Cu1—Cl1 | 100.08 (10) | N1—C8—H8A | 109.2 |
O1—Cu1—Cu1i | 83.04 (11) | C5—C8—H8A | 109.2 |
O2i—Cu1—Cu1i | 84.05 (11) | N1—C8—H8B | 109.2 |
O4i—Cu1—Cu1i | 80.24 (11) | C5—C8—H8B | 109.2 |
O3—Cu1—Cu1i | 87.06 (10) | H8A—C8—H8B | 107.9 |
Cl1—Cu1—Cu1i | 172.34 (4) | O3—C9—O4 | 124.6 (5) |
C1—O1—Cu1 | 125.2 (3) | O3—C9—C10 | 119.4 (4) |
C1—O2—Cu1i | 123.8 (4) | O4—C9—C10 | 116.0 (4) |
C9—O3—Cu1 | 119.4 (3) | C15—C10—C9 | 109.8 (4) |
C9—O4—Cu1i | 128.7 (3) | C15—C10—C11 | 111.3 (4) |
C8—N1—H1A | 109.5 | C9—C10—C11 | 109.5 (4) |
C8—N1—H1B | 109.5 | C15—C10—H10 | 108.7 |
H1A—N1—H1B | 109.5 | C9—C10—H10 | 108.7 |
C8—N1—H1C | 109.5 | C11—C10—H10 | 108.7 |
H1A—N1—H1C | 109.5 | C12—C11—C10 | 111.1 (4) |
H1B—N1—H1C | 109.5 | C12—C11—H11A | 109.4 |
C16—N2—H2A | 109.5 | C10—C11—H11A | 109.4 |
C16—N2—H2B | 109.5 | C12—C11—H11B | 109.4 |
H2A—N2—H2B | 109.5 | C10—C11—H11B | 109.4 |
C16—N2—H2C | 109.5 | H11A—C11—H11B | 108.0 |
H2A—N2—H2C | 109.5 | C13—C12—C11 | 110.8 (4) |
H2B—N2—H2C | 109.5 | C13—C12—H12A | 109.5 |
O2—C1—O1 | 123.9 (5) | C11—C12—H12A | 109.5 |
O2—C1—C2 | 118.0 (5) | C13—C12—H12B | 109.5 |
O1—C1—C2 | 118.1 (4) | C11—C12—H12B | 109.5 |
C1—C2—C7 | 108.9 (5) | H12A—C12—H12B | 108.1 |
C1—C2—C3 | 112.2 (5) | C12—C13—C16 | 111.5 (5) |
C7—C2—C3 | 110.2 (4) | C12—C13—C14 | 109.2 (4) |
C1—C2—H2 | 108.5 | C16—C13—C14 | 112.2 (5) |
C7—C2—H2 | 108.5 | C12—C13—H13 | 107.9 |
C3—C2—H2 | 108.5 | C16—C13—H13 | 107.9 |
C4—C3—C2 | 112.0 (5) | C14—C13—H13 | 107.9 |
C4—C3—H3A | 109.2 | C15—C14—C13 | 112.3 (5) |
C2—C3—H3A | 109.2 | C15—C14—H14A | 109.1 |
C4—C3—H3B | 109.2 | C13—C14—H14A | 109.1 |
C2—C3—H3B | 109.2 | C15—C14—H14B | 109.1 |
H3A—C3—H3B | 107.9 | C13—C14—H14B | 109.1 |
C3—C4—C5 | 111.3 (5) | H14A—C14—H14B | 107.9 |
C3—C4—H4A | 109.4 | C10—C15—C14 | 112.5 (5) |
C5—C4—H4A | 109.4 | C10—C15—H15A | 109.1 |
C3—C4—H4B | 109.4 | C14—C15—H15A | 109.1 |
C5—C4—H4B | 109.4 | C10—C15—H15B | 109.1 |
H4A—C4—H4B | 108.0 | C14—C15—H15B | 109.1 |
C4—C5—C8 | 113.9 (5) | H15A—C15—H15B | 107.8 |
C4—C5—C6 | 110.2 (5) | N2—C16—C13 | 111.6 (5) |
C8—C5—C6 | 109.8 (5) | N2—C16—H16A | 109.3 |
C4—C5—H5 | 107.5 | C13—C16—H16A | 109.3 |
C8—C5—H5 | 107.5 | N2—C16—H16B | 109.3 |
C6—C5—H5 | 107.5 | C13—C16—H16B | 109.3 |
C7—C6—C5 | 110.5 (5) | H16A—C16—H16B | 108.0 |
C7—C6—H6A | 109.6 | H1WA—O1W—H1WB | 102 (3) |
C5—C6—H6A | 109.6 | H2WA—O2W—H2WB | 103 (3) |
C7—C6—H6B | 109.6 | H3WA—O3W—H3WB | 106 (3) |
| | | |
Cu1i—O2—C1—O1 | 1.1 (7) | Cu1—O3—C9—O4 | 1.0 (8) |
Cu1i—O2—C1—C2 | 178.1 (4) | Cu1—O3—C9—C10 | −179.8 (4) |
Cu1—O1—C1—O2 | 0.9 (7) | Cu1i—O4—C9—O3 | −2.3 (9) |
Cu1—O1—C1—C2 | −176.1 (4) | Cu1i—O4—C9—C10 | 178.5 (4) |
O2—C1—C2—C7 | −94.2 (6) | O3—C9—C10—C15 | 122.8 (5) |
O1—C1—C2—C7 | 82.9 (6) | O4—C9—C10—C15 | −57.9 (6) |
O2—C1—C2—C3 | 143.5 (5) | O3—C9—C10—C11 | −114.7 (5) |
O1—C1—C2—C3 | −39.4 (7) | O4—C9—C10—C11 | 64.5 (6) |
C1—C2—C3—C4 | 174.7 (5) | C15—C10—C11—C12 | −53.7 (6) |
C7—C2—C3—C4 | 53.1 (7) | C9—C10—C11—C12 | −175.2 (4) |
C2—C3—C4—C5 | −56.3 (7) | C10—C11—C12—C13 | 58.9 (6) |
C3—C4—C5—C8 | −178.1 (5) | C11—C12—C13—C16 | 176.2 (4) |
C3—C4—C5—C6 | 57.9 (7) | C11—C12—C13—C14 | −59.3 (5) |
C4—C5—C6—C7 | −57.2 (8) | C12—C13—C14—C15 | 56.5 (6) |
C8—C5—C6—C7 | 176.5 (6) | C16—C13—C14—C15 | −179.4 (5) |
C5—C6—C7—C2 | 55.9 (8) | C9—C10—C15—C14 | 172.3 (4) |
C1—C2—C7—C6 | −176.8 (5) | C11—C10—C15—C14 | 50.9 (6) |
C3—C2—C7—C6 | −53.3 (7) | C13—C14—C15—C10 | −52.9 (6) |
C4—C5—C8—N1 | 63.3 (7) | C12—C13—C16—N2 | −162.4 (5) |
C6—C5—C8—N1 | −172.5 (5) | C14—C13—C16—N2 | 74.9 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1ii | 0.91 | 2.63 | 3.316 (5) | 133 |
N1—H1C···Cl1iii | 0.91 | 2.52 | 3.394 (5) | 160 |
N2—H2B···Cl1iv | 0.91 | 2.25 | 3.123 (5) | 160 |
N2—H2C···Cl2v | 0.91 | 2.24 | 3.151 (6) | 179 |
N1—H1B···O1Wvi | 0.91 | 1.90 | 2.760 (7) | 156 |
N2—H2A···O2Wvii | 0.91 | 2.06 | 2.789 (9) | 137 |
O1W—H1WA···Cl2v | 0.89 (2) | 2.57 (8) | 3.218 (6) | 130 (8) |
O2W—H2WA···Cl2viii | 0.90 (2) | 2.46 (7) | 3.176 (6) | 137 (9) |
O2W—H2WB···O3i | 0.90 (2) | 2.22 (8) | 2.820 (6) | 124 (8) |
O3W—H3WA···Cl1ix | 0.88 (2) | 2.66 (6) | 3.258 (5) | 127 (6) |
O3W—H3WB···Cl2x | 0.88 (2) | 2.35 (3) | 3.182 (5) | 158 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1, −y+1, −z; (vi) −x+1, −y, −z+1; (vii) x+1/2, −y+1/2, z−1/2; (viii) x−1/2, −y+3/2, z+1/2; (ix) x−1/2, −y+1/2, z−1/2; (x) −x+1/2, y−1/2, −z+1/2. |