Crystal structure of trans-di­aqua­(3,10-dimethyl-1,3,5,8,10,12-hexa­aza­cyclo­tetra­deca­ne)copper(II) pamoate

Tsymbal, L.V.; Andriichuk, I.L.; Arion, V.B.; Lampeka, Y.D.

doi:10.1107/S2056989019003852

Crystal structure of trans-diaqua(3,10-dimethyl-1,3,5,8,10,12-hexaazacyclotetradecane)copper(II) pamoate

L. V. Tsymbal, I. L. Andriichuk, V. B. Arion and Y. D. Lampeka

The complex cation of the title compound has a six-coordinate tetragonal–bipyramidal structure with four N atoms of the azamacrocyclic ligand in the equatorial plane and two O atom of the water molecules in the axial positions. In the crystal, the carboxylic groups of the non-coordinated dianion of pamoic acid accept N—H

O and O—H

O hydrogen bonds, forming sheets of ions lying parallel to the (1 $\overline{1}$ 1) plane.

Keywords: crystal structure; azamacrocyclic ligand; diazacyclam; copper; pamoic acid; hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019003852/hb7810sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019003852/hb7810Isup2.hkl Contains datablock I

CCDC reference: 1904400

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.040
wR factor = 0.090
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N6       --H6       .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2WA     ..O2       .       2.61 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.159 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         21 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............         10 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1      --O1W      .        7.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1      --N1       .        5.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1      --N3       .        5.5 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT793_ALERT_4_G Model has Chirality at N1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at N3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N4          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at N6          (Centro SPGR)          R Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.21 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu2       (II)      .       2.25 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          6 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         11 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  22 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   4 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

trans-Diaqua(3,10-dimethyl-1,3,5,8,10,12-hexaazacyclotetradecane-κ⁴N¹,N⁵,N⁸,N¹²)copper(II) 4,4'-methylenebis(3-hydroxynaphthalene-2-carboxylate) top

Crystal data top

[Cu(C₁₀H₂₆N₆)(H₂O)₂]C₂₃H₁₄O₆	Z = 2
M_r = 716.28	F(000) = 754
Triclinic, P1	D_x = 1.450 Mg m⁻³
a = 9.8877 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1406 (7) Å	Cell parameters from 8230 reflections
c = 14.5760 (9) Å	θ = 2.4–25.6°
α = 71.594 (3)°	µ = 0.73 mm⁻¹
β = 81.128 (3)°	T = 100 K
γ = 88.249 (3)°	Block, pink
V = 1640.06 (17) Å³	0.20 × 0.18 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	4540 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.080
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.868, T_max = 0.918	k = −14→14
52866 measured reflections	l = −17→17
6401 independent reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0378P)² + 0.6293P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6401 reflections	Δρ_max = 0.34 e Å⁻³
438 parameters	Δρ_min = −0.39 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	U_iso*/U_eq
Cu1	1.0000	0.5000	0.5000	0.01499 (12)
Cu2	0.5000	0.5000	0.0000	0.01582 (12)
N1	0.8280 (2)	0.58002 (17)	0.45737 (15)	0.0199 (5)
H1	0.8412	0.6050	0.3843	0.024*
N2	0.7064 (2)	0.40151 (18)	0.47031 (15)	0.0239 (5)
N3	0.9443 (2)	0.34915 (17)	0.48721 (14)	0.0194 (5)
H3	0.9644	0.3562	0.4162	0.023*
C4	0.8207 (3)	0.6863 (2)	0.48671 (19)	0.0223 (6)
H4A	0.7880	0.6669	0.5578	0.027*
H4B	0.7566	0.7417	0.4510	0.027*
C1	0.6994 (3)	0.5083 (2)	0.49364 (19)	0.0239 (6)
H1A	0.6785	0.4901	0.5656	0.029*
H1B	0.6232	0.5545	0.4650	0.029*
C2	0.7977 (3)	0.3164 (2)	0.52012 (19)	0.0235 (6)
H2A	0.7810	0.2416	0.5096	0.028*
H2B	0.7761	0.3046	0.5912	0.028*
C3	1.0361 (3)	0.2604 (2)	0.53813 (19)	0.0224 (6)
H3A	1.0350	0.1910	0.5164	0.027*
H3B	1.0057	0.2365	0.6097	0.027*
C5	0.7162 (3)	0.4154 (2)	0.3666 (2)	0.0332 (7)
H5A	0.7205	0.3388	0.3573	0.050*
H5B	0.6356	0.4560	0.3418	0.050*
H5C	0.7991	0.4607	0.3309	0.050*
N6	0.5743 (2)	0.35155 (17)	0.08194 (14)	0.0190 (5)
H6	0.6453	0.3239	0.0379	0.023*
N4	0.6263 (2)	0.58227 (17)	0.05243 (14)	0.0169 (5)
H4	0.5701	0.6038	0.1072	0.020*
N5	0.5995 (2)	0.77617 (18)	−0.06320 (15)	0.0234 (5)
C7	0.4716 (3)	0.2553 (2)	0.13005 (19)	0.0244 (6)
H7A	0.5187	0.1862	0.1671	0.029*
H7B	0.4038	0.2788	0.1776	0.029*
C8	0.6454 (3)	0.3839 (2)	0.15230 (18)	0.0229 (6)
H8A	0.7082	0.3217	0.1807	0.028*
H8B	0.5780	0.3952	0.2061	0.028*
C9	0.7253 (3)	0.4959 (2)	0.09671 (19)	0.0222 (6)
H9A	0.7709	0.5232	0.1418	0.027*
H9B	0.7963	0.4836	0.0452	0.027*
C6	0.6926 (3)	0.6918 (2)	−0.01746 (19)	0.0223 (6)
H6A	0.7471	0.7270	0.0181	0.027*
H6B	0.7568	0.6723	−0.0690	0.027*
C10	0.5140 (3)	0.8320 (2)	−0.0004 (2)	0.0290 (7)
H10A	0.4544	0.8878	−0.0391	0.043*
H10B	0.4577	0.7730	0.0525	0.043*
H10C	0.5724	0.8727	0.0276	0.043*
C11	0.4511 (3)	−0.3050 (2)	0.24922 (17)	0.0210 (6)
C12	0.4904 (3)	−0.1995 (2)	0.27246 (17)	0.0169 (6)
C13	0.6302 (3)	−0.1758 (2)	0.27572 (17)	0.0188 (6)
C14	0.6685 (3)	−0.0783 (2)	0.29585 (17)	0.0181 (6)
C15	0.5639 (3)	−0.0083 (2)	0.32585 (17)	0.0191 (6)
C16	0.5905 (3)	0.0822 (2)	0.36370 (18)	0.0250 (6)
H16	0.6820	0.0984	0.3687	0.030*
C17	0.4868 (3)	0.1461 (2)	0.3929 (2)	0.0327 (7)
H17	0.5068	0.2043	0.4199	0.039*
C18	0.3508 (3)	0.1271 (2)	0.3835 (2)	0.0346 (7)
H18	0.2799	0.1739	0.4022	0.041*
C19	0.3211 (3)	0.0418 (2)	0.34780 (19)	0.0275 (7)
H19	0.2292	0.0299	0.3409	0.033*
C20	0.4247 (3)	−0.0295 (2)	0.32067 (17)	0.0200 (6)
C21	0.3934 (3)	−0.1235 (2)	0.29063 (17)	0.0187 (6)
H21	0.3018	−0.1346	0.2827	0.022*
C22	1.0315 (3)	0.3478 (3)	0.2154 (2)	0.0297 (7)
C23	0.9735 (2)	0.2584 (2)	0.17946 (19)	0.0199 (6)
C24	0.9275 (3)	0.1467 (2)	0.24487 (18)	0.0216 (6)
C25	0.8696 (2)	0.0657 (2)	0.21366 (17)	0.0178 (6)
C26	0.8648 (2)	0.0906 (2)	0.11176 (18)	0.0168 (5)
C27	0.8225 (2)	0.0078 (2)	0.07126 (18)	0.0203 (6)
H27	0.7934	−0.0675	0.1132	0.024*
C28	0.8227 (3)	0.0346 (2)	−0.02714 (19)	0.0250 (6)
H28	0.7950	−0.0227	−0.0526	0.030*
C29	0.8634 (3)	0.1459 (2)	−0.09125 (19)	0.0285 (7)
H29	0.8607	0.1640	−0.1593	0.034*
C30	0.9069 (3)	0.2277 (2)	−0.05578 (19)	0.0253 (6)
H30	0.9349	0.3025	−0.0995	0.030*
C31	0.9107 (2)	0.2024 (2)	0.04560 (18)	0.0189 (6)
C32	0.9621 (2)	0.2839 (2)	0.08278 (19)	0.0203 (6)
H32	0.9897	0.3589	0.0393	0.024*
C33	0.8189 (3)	−0.0505 (2)	0.28762 (18)	0.0208 (6)
H33A	0.8729	−0.1128	0.2698	0.025*
H33B	0.8376	−0.0519	0.3528	0.025*
O1	0.32781 (19)	−0.32344 (15)	0.24857 (13)	0.0262 (4)
O2	0.54697 (19)	−0.37048 (15)	0.23045 (13)	0.0253 (4)
O3	0.72922 (18)	−0.25007 (14)	0.25674 (13)	0.0242 (4)
H3C	0.6944	−0.3007	0.2389	0.036*
O4	1.06005 (19)	0.44690 (16)	0.15717 (16)	0.0377 (5)
O5	1.0477 (2)	0.31618 (19)	0.30534 (15)	0.0416 (6)
O6	0.9387 (2)	0.11959 (17)	0.34181 (13)	0.0319 (5)
H6C	0.9751	0.1758	0.3514	0.048*
O1W	1.07942 (19)	0.56232 (16)	0.31930 (13)	0.0303 (5)
H1WA	1.1574	0.5988	0.2985	0.045*
H1WB	1.0603	0.5205	0.2849	0.045*
O2W	0.32694 (18)	0.51823 (16)	0.13556 (13)	0.0289 (5)
H2WA	0.3381	0.5611	0.1708	0.043*
H2WB	0.2426	0.4986	0.1394	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0177 (2)	0.0117 (2)	0.0152 (2)	−0.00018 (18)	−0.00184 (18)	−0.00397 (17)
Cu2	0.0159 (2)	0.0148 (2)	0.0163 (2)	−0.00108 (18)	−0.00325 (18)	−0.00389 (18)
N1	0.0235 (12)	0.0179 (11)	0.0181 (11)	−0.0009 (9)	−0.0016 (9)	−0.0062 (9)
N2	0.0277 (13)	0.0216 (12)	0.0224 (12)	−0.0033 (10)	−0.0082 (10)	−0.0044 (10)
N3	0.0248 (12)	0.0166 (11)	0.0157 (10)	0.0005 (9)	−0.0033 (9)	−0.0036 (9)
C4	0.0272 (15)	0.0188 (14)	0.0218 (14)	0.0048 (11)	−0.0041 (12)	−0.0075 (11)
C1	0.0198 (15)	0.0239 (15)	0.0252 (14)	0.0004 (11)	−0.0018 (11)	−0.0043 (12)
C2	0.0266 (16)	0.0189 (14)	0.0235 (14)	−0.0052 (12)	−0.0056 (12)	−0.0030 (12)
C3	0.0297 (16)	0.0142 (13)	0.0221 (14)	0.0029 (11)	−0.0045 (12)	−0.0040 (11)
C5	0.0401 (18)	0.0313 (16)	0.0332 (16)	−0.0010 (14)	−0.0185 (14)	−0.0109 (13)
N6	0.0192 (12)	0.0179 (11)	0.0183 (11)	0.0017 (9)	−0.0026 (9)	−0.0038 (9)
N4	0.0126 (11)	0.0189 (11)	0.0190 (11)	0.0020 (9)	−0.0014 (9)	−0.0065 (9)
N5	0.0256 (13)	0.0190 (12)	0.0239 (12)	−0.0029 (10)	0.0006 (10)	−0.0061 (10)
C7	0.0265 (16)	0.0194 (14)	0.0215 (14)	−0.0014 (12)	0.0010 (12)	−0.0003 (11)
C8	0.0223 (15)	0.0265 (15)	0.0206 (13)	0.0054 (12)	−0.0069 (11)	−0.0068 (12)
C9	0.0177 (14)	0.0282 (15)	0.0240 (14)	0.0044 (12)	−0.0077 (11)	−0.0111 (12)
C6	0.0169 (15)	0.0235 (15)	0.0260 (14)	−0.0055 (12)	0.0035 (12)	−0.0100 (12)
C10	0.0319 (17)	0.0210 (15)	0.0339 (16)	0.0007 (12)	−0.0008 (13)	−0.0106 (13)
C11	0.0306 (17)	0.0190 (14)	0.0108 (12)	−0.0038 (13)	−0.0002 (11)	−0.0021 (11)
C12	0.0226 (15)	0.0136 (13)	0.0131 (12)	−0.0037 (11)	0.0000 (10)	−0.0030 (10)
C13	0.0231 (15)	0.0154 (13)	0.0154 (13)	0.0013 (11)	0.0009 (11)	−0.0035 (11)
C14	0.0234 (15)	0.0148 (13)	0.0126 (12)	−0.0040 (11)	−0.0018 (11)	0.0004 (10)
C15	0.0287 (16)	0.0134 (13)	0.0112 (12)	−0.0029 (11)	0.0016 (11)	−0.0002 (10)
C16	0.0308 (16)	0.0223 (14)	0.0195 (14)	−0.0076 (12)	0.0022 (12)	−0.0050 (12)
C17	0.050 (2)	0.0204 (15)	0.0275 (15)	−0.0080 (14)	0.0092 (14)	−0.0135 (13)
C18	0.0360 (19)	0.0261 (16)	0.0377 (17)	0.0003 (14)	0.0134 (14)	−0.0137 (14)
C19	0.0242 (16)	0.0229 (15)	0.0311 (15)	−0.0015 (12)	0.0072 (12)	−0.0076 (13)
C20	0.0250 (15)	0.0139 (13)	0.0169 (13)	−0.0004 (11)	0.0029 (11)	−0.0016 (11)
C21	0.0182 (14)	0.0167 (13)	0.0175 (13)	−0.0047 (11)	−0.0009 (11)	−0.0007 (11)
C22	0.0136 (15)	0.0359 (18)	0.048 (2)	−0.0057 (13)	0.0084 (13)	−0.0299 (16)
C23	0.0114 (13)	0.0225 (14)	0.0286 (15)	−0.0029 (11)	0.0009 (11)	−0.0135 (12)
C24	0.0182 (14)	0.0287 (15)	0.0205 (13)	−0.0029 (12)	−0.0017 (11)	−0.0118 (12)
C25	0.0153 (14)	0.0188 (13)	0.0193 (13)	−0.0010 (11)	−0.0021 (11)	−0.0061 (11)
C26	0.0112 (13)	0.0169 (13)	0.0228 (13)	0.0003 (10)	−0.0025 (10)	−0.0072 (11)
C27	0.0176 (14)	0.0205 (14)	0.0233 (14)	−0.0017 (11)	−0.0018 (11)	−0.0080 (11)
C28	0.0206 (15)	0.0325 (16)	0.0267 (15)	−0.0009 (12)	−0.0049 (12)	−0.0151 (13)
C29	0.0248 (16)	0.0410 (18)	0.0190 (14)	0.0022 (13)	−0.0064 (12)	−0.0073 (13)
C30	0.0190 (15)	0.0272 (15)	0.0234 (14)	0.0004 (12)	−0.0025 (12)	0.0003 (12)
C31	0.0135 (13)	0.0205 (14)	0.0211 (13)	0.0040 (11)	−0.0024 (11)	−0.0047 (11)
C32	0.0110 (13)	0.0167 (13)	0.0317 (15)	0.0002 (10)	0.0000 (11)	−0.0070 (12)
C33	0.0237 (15)	0.0168 (13)	0.0206 (13)	−0.0015 (11)	−0.0072 (11)	−0.0020 (11)
O1	0.0259 (11)	0.0282 (10)	0.0274 (10)	−0.0085 (8)	−0.0012 (8)	−0.0133 (8)
O2	0.0339 (11)	0.0203 (10)	0.0270 (10)	0.0040 (9)	−0.0069 (9)	−0.0139 (8)
O3	0.0240 (10)	0.0182 (10)	0.0325 (11)	0.0020 (8)	−0.0035 (8)	−0.0116 (8)
O4	0.0215 (11)	0.0226 (11)	0.0751 (15)	−0.0041 (9)	−0.0059 (10)	−0.0245 (11)
O5	0.0363 (13)	0.0581 (15)	0.0435 (13)	−0.0177 (11)	0.0053 (10)	−0.0381 (12)
O6	0.0359 (12)	0.0423 (12)	0.0222 (10)	−0.0133 (10)	−0.0075 (9)	−0.0143 (9)
O1W	0.0328 (11)	0.0330 (11)	0.0267 (10)	−0.0130 (9)	0.0071 (9)	−0.0159 (9)
O2W	0.0228 (10)	0.0384 (11)	0.0321 (11)	−0.0106 (9)	0.0054 (8)	−0.0237 (9)

Geometric parameters (Å, º) top

Cu1—N3	2.000 (2)	C10—H10A	0.9800
Cu1—N3ⁱ	2.000 (2)	C10—H10B	0.9800
Cu1—N1	2.017 (2)	C10—H10C	0.9800
Cu1—N1ⁱ	2.017 (2)	C11—O1	1.248 (3)
Cu1—O1w	2.5033 (19)	C11—O2	1.271 (3)
Cu1—O1wⁱ	2.5033 (18)	C11—C12	1.501 (3)
Cu2—N4	1.9987 (19)	C12—C21	1.364 (3)
Cu2—N4ⁱⁱ	1.9987 (19)	C12—C13	1.431 (4)
Cu2—N6	2.0113 (19)	C13—O3	1.367 (3)
Cu2—N6ⁱⁱ	2.0114 (19)	C13—C14	1.383 (3)
Cu2—O2w	2.4681 (18)	C14—C15	1.424 (4)
Cu2—O2wⁱⁱ	2.4681 (18)	C14—C33	1.514 (3)
N1—C4	1.479 (3)	C15—C16	1.423 (3)
N1—C1	1.491 (3)	C15—C20	1.426 (4)
N1—H1	1.0000	C16—C17	1.363 (4)
N2—C1	1.438 (3)	C16—H16	0.9500
N2—C2	1.442 (3)	C17—C18	1.406 (4)
N2—C5	1.455 (3)	C17—H17	0.9500
N3—C3	1.476 (3)	C18—C19	1.355 (4)
N3—C2	1.480 (3)	C18—H18	0.9500
N3—H3	1.0000	C19—C20	1.411 (4)
C4—C3ⁱ	1.518 (4)	C19—H19	0.9500
C4—H4A	0.9900	C20—C21	1.403 (3)
C4—H4B	0.9900	C21—H21	0.9500
C1—H1A	0.9900	C22—O4	1.245 (3)
C1—H1B	0.9900	C22—O5	1.279 (4)
C2—H2A	0.9900	C22—C23	1.507 (4)
C2—H2B	0.9900	C23—C32	1.366 (4)
C3—C4ⁱ	1.518 (4)	C23—C24	1.429 (4)
C3—H3A	0.9900	C24—O6	1.367 (3)
C3—H3B	0.9900	C24—C25	1.378 (3)
C5—H5A	0.9800	C25—C26	1.427 (3)
C5—H5B	0.9800	C25—C33	1.523 (3)
C5—H5C	0.9800	C26—C27	1.417 (3)
N6—C8	1.481 (3)	C26—C31	1.434 (3)
N6—C7	1.492 (3)	C27—C28	1.366 (4)
N6—H6	1.0000	C27—H27	0.9500
N4—C9	1.476 (3)	C28—C29	1.407 (4)
N4—C6	1.493 (3)	C28—H28	0.9500
N4—H4	1.0000	C29—C30	1.362 (4)
N5—C6	1.429 (3)	C29—H29	0.9500
N5—C7ⁱⁱ	1.432 (3)	C30—C31	1.418 (3)
N5—C10	1.460 (3)	C30—H30	0.9500
C7—N5ⁱⁱ	1.432 (3)	C31—C32	1.409 (3)
C7—H7A	0.9900	C32—H32	0.9500
C7—H7B	0.9900	C33—H33A	0.9900
C8—C9	1.518 (4)	C33—H33B	0.9900
C8—H8A	0.9900	O3—H3C	0.8400
C8—H8B	0.9900	O6—H6C	0.8400
C9—H9A	0.9900	O1W—H1WA	0.8641
C9—H9B	0.9900	O1W—H1WB	0.8606
C6—H6A	0.9900	O2W—H2WA	0.8578
C6—H6B	0.9900	O2W—H2WB	0.8629

N3—Cu1—N3ⁱ	180.00	H9A—C9—H9B	108.6
N3—Cu1—N1	93.47 (8)	N5—C6—N4	114.6 (2)
N3ⁱ—Cu1—N1	86.53 (8)	N5—C6—H6A	108.6
N3—Cu1—N1ⁱ	86.53 (8)	N4—C6—H6A	108.6
N3ⁱ—Cu1—N1ⁱ	93.47 (8)	N5—C6—H6B	108.6
N1—Cu1—N1ⁱ	180.0	N4—C6—H6B	108.6
N4—Cu2—N4ⁱⁱ	180.00	H6A—C6—H6B	107.6
N4—Cu2—N6	86.53 (8)	N5—C10—H10A	109.5
N4ⁱⁱ—Cu2—N6	93.47 (8)	N5—C10—H10B	109.5
N4—Cu2—N6ⁱⁱ	93.47 (8)	H10A—C10—H10B	109.5
N4ⁱⁱ—Cu2—N6ⁱⁱ	86.53 (8)	N5—C10—H10C	109.5
N6—Cu2—N6ⁱⁱ	180.0	H10A—C10—H10C	109.5
C4—N1—C1	112.6 (2)	H10B—C10—H10C	109.5
C4—N1—Cu1	105.83 (15)	O1—C11—O2	123.7 (2)
C1—N1—Cu1	115.85 (15)	O1—C11—C12	118.9 (2)
C4—N1—H1	107.4	O2—C11—C12	117.4 (2)
C1—N1—H1	107.4	C21—C12—C13	118.5 (2)
Cu1—N1—H1	107.4	C21—C12—C11	120.6 (2)
C1—N2—C2	115.5 (2)	C13—C12—C11	120.9 (2)
C1—N2—C5	114.8 (2)	O3—C13—C14	118.8 (2)
C2—N2—C5	113.9 (2)	O3—C13—C12	119.5 (2)
C3—N3—C2	112.89 (18)	C14—C13—C12	121.7 (2)
C3—N3—Cu1	106.69 (15)	C13—C14—C15	118.4 (2)
C2—N3—Cu1	115.45 (16)	C13—C14—C33	119.6 (2)
C3—N3—H3	107.1	C15—C14—C33	122.0 (2)
C2—N3—H3	107.1	C16—C15—C14	123.1 (2)
Cu1—N3—H3	107.1	C16—C15—C20	117.2 (2)
N1—C4—C3ⁱ	107.4 (2)	C14—C15—C20	119.7 (2)
N1—C4—H4A	110.2	C17—C16—C15	121.1 (3)
C3ⁱ—C4—H4A	110.2	C17—C16—H16	119.5
N1—C4—H4B	110.2	C15—C16—H16	119.5
C3ⁱ—C4—H4B	110.2	C16—C17—C18	120.9 (3)
H4A—C4—H4B	108.5	C16—C17—H17	119.5
N2—C1—N1	113.6 (2)	C18—C17—H17	119.5
N2—C1—H1A	108.8	C19—C18—C17	119.8 (3)
N1—C1—H1A	108.8	C19—C18—H18	120.1
N2—C1—H1B	108.8	C17—C18—H18	120.1
N1—C1—H1B	108.8	C18—C19—C20	121.0 (3)
H1A—C1—H1B	107.7	C18—C19—H19	119.5
N2—C2—N3	113.67 (19)	C20—C19—H19	119.5
N2—C2—H2A	108.8	C21—C20—C19	121.3 (2)
N3—C2—H2A	108.8	C21—C20—C15	118.8 (2)
N2—C2—H2B	108.8	C19—C20—C15	119.9 (2)
N3—C2—H2B	108.8	C12—C21—C20	122.1 (2)
H2A—C2—H2B	107.7	C12—C21—H21	118.9
N3—C3—C4ⁱ	107.57 (19)	C20—C21—H21	118.9
N3—C3—H3A	110.2	O4—C22—O5	124.0 (3)
C4ⁱ—C3—H3A	110.2	O4—C22—C23	119.0 (3)
N3—C3—H3B	110.2	O5—C22—C23	117.0 (3)
C4ⁱ—C3—H3B	110.2	C32—C23—C24	118.5 (2)
H3A—C3—H3B	108.5	C32—C23—C22	120.0 (2)
N2—C5—H5A	109.5	C24—C23—C22	121.4 (2)
N2—C5—H5B	109.5	O6—C24—C25	118.7 (2)
H5A—C5—H5B	109.5	O6—C24—C23	119.3 (2)
N2—C5—H5C	109.5	C25—C24—C23	122.0 (2)
H5A—C5—H5C	109.5	C24—C25—C26	119.0 (2)
H5B—C5—H5C	109.5	C24—C25—C33	119.4 (2)
C8—N6—C7	113.11 (19)	C26—C25—C33	121.5 (2)
C8—N6—Cu2	105.86 (15)	C27—C26—C25	123.1 (2)
C7—N6—Cu2	115.23 (15)	C27—C26—C31	117.6 (2)
C8—N6—H6	107.4	C25—C26—C31	119.2 (2)
C7—N6—H6	107.4	C28—C27—C26	121.1 (2)
Cu2—N6—H6	107.4	C28—C27—H27	119.4
C9—N4—C6	113.30 (18)	C26—C27—H27	119.4
C9—N4—Cu2	106.73 (14)	C27—C28—C29	120.9 (2)
C6—N4—Cu2	116.27 (15)	C27—C28—H28	119.6
C9—N4—H4	106.6	C29—C28—H28	119.6
C6—N4—H4	106.6	C30—C29—C28	120.0 (2)
Cu2—N4—H4	106.6	C30—C29—H29	120.0
C6—N5—C7ⁱⁱ	115.2 (2)	C28—C29—H29	120.0
C6—N5—C10	116.4 (2)	C29—C30—C31	120.7 (2)
C7ⁱⁱ—N5—C10	114.1 (2)	C29—C30—H30	119.6
N5ⁱⁱ—C7—N6	113.9 (2)	C31—C30—H30	119.6
N5ⁱⁱ—C7—H7A	108.8	C32—C31—C30	121.4 (2)
N6—C7—H7A	108.8	C32—C31—C26	119.0 (2)
N5ⁱⁱ—C7—H7B	108.8	C30—C31—C26	119.5 (2)
N6—C7—H7B	108.8	C23—C32—C31	122.0 (2)
H7A—C7—H7B	107.7	C23—C32—H32	119.0
N6—C8—C9	107.5 (2)	C31—C32—H32	119.0
N6—C8—H8A	110.2	C14—C33—C25	115.6 (2)
C9—C8—H8A	110.2	C14—C33—H33A	108.4
N6—C8—H8B	110.2	C25—C33—H33A	108.4
C9—C8—H8B	110.2	C14—C33—H33B	108.4
H8A—C8—H8B	108.5	C25—C33—H33B	108.4
N4—C9—C8	107.08 (19)	H33A—C33—H33B	107.4
N4—C9—H9A	110.3	C13—O3—H3C	109.5
C8—C9—H9A	110.3	C24—O6—H6C	109.5
N4—C9—H9B	110.3	H1WA—O1W—H1WB	114.2
C8—C9—H9B	110.3	H2WA—O2W—H2WB	113.5

C1—N1—C4—C3ⁱ	169.94 (19)	C18—C19—C20—C15	−3.3 (4)
Cu1—N1—C4—C3ⁱ	42.4 (2)	C16—C15—C20—C21	−175.3 (2)
C2—N2—C1—N1	68.3 (3)	C14—C15—C20—C21	3.3 (3)
C5—N2—C1—N1	−67.3 (3)	C16—C15—C20—C19	3.2 (3)
C4—N1—C1—N2	−177.0 (2)	C14—C15—C20—C19	−178.3 (2)
Cu1—N1—C1—N2	−55.0 (2)	C13—C12—C21—C20	−5.8 (3)
C1—N2—C2—N3	−69.9 (3)	C11—C12—C21—C20	174.5 (2)
C5—N2—C2—N3	66.1 (3)	C19—C20—C21—C12	−174.1 (2)
C3—N3—C2—N2	−179.3 (2)	C15—C20—C21—C12	4.4 (3)
Cu1—N3—C2—N2	57.6 (2)	O4—C22—C23—C32	4.7 (4)
C2—N3—C3—C4ⁱ	−169.0 (2)	O5—C22—C23—C32	−175.6 (2)
Cu1—N3—C3—C4ⁱ	−41.1 (2)	O4—C22—C23—C24	−174.3 (2)
C8—N6—C7—N5ⁱⁱ	179.2 (2)	O5—C22—C23—C24	5.4 (4)
Cu2—N6—C7—N5ⁱⁱ	57.3 (3)	C32—C23—C24—O6	179.7 (2)
C7—N6—C8—C9	−169.3 (2)	C22—C23—C24—O6	−1.2 (4)
Cu2—N6—C8—C9	−42.3 (2)	C32—C23—C24—C25	−1.5 (4)
C6—N4—C9—C8	−171.1 (2)	C22—C23—C24—C25	177.6 (2)
Cu2—N4—C9—C8	−41.8 (2)	O6—C24—C25—C26	−176.4 (2)
N6—C8—C9—N4	57.0 (3)	C23—C24—C25—C26	4.8 (4)
C7ⁱⁱ—N5—C6—N4	−67.8 (3)	O6—C24—C25—C33	0.5 (4)
C10—N5—C6—N4	69.6 (3)	C23—C24—C25—C33	−178.3 (2)
C9—N4—C6—N5	178.7 (2)	C24—C25—C26—C27	172.3 (2)
Cu2—N4—C6—N5	54.5 (3)	C33—C25—C26—C27	−4.5 (4)
O1—C11—C12—C21	−1.3 (3)	C24—C25—C26—C31	−4.7 (4)
O2—C11—C12—C21	178.1 (2)	C33—C25—C26—C31	178.5 (2)
O1—C11—C12—C13	178.9 (2)	C25—C26—C27—C28	−178.4 (2)
O2—C11—C12—C13	−1.6 (3)	C31—C26—C27—C28	−1.3 (4)
C21—C12—C13—O3	−179.3 (2)	C26—C27—C28—C29	−0.8 (4)
C11—C12—C13—O3	0.5 (3)	C27—C28—C29—C30	1.8 (4)
C21—C12—C13—C14	−0.5 (3)	C28—C29—C30—C31	−0.5 (4)
C11—C12—C13—C14	179.2 (2)	C29—C30—C31—C32	176.6 (2)
O3—C13—C14—C15	−173.3 (2)	C29—C30—C31—C26	−1.7 (4)
C12—C13—C14—C15	7.9 (3)	C27—C26—C31—C32	−175.8 (2)
O3—C13—C14—C33	5.4 (3)	C25—C26—C31—C32	1.4 (3)
C12—C13—C14—C33	−173.4 (2)	C27—C26—C31—C30	2.6 (3)
C13—C14—C15—C16	169.3 (2)	C25—C26—C31—C30	179.7 (2)
C33—C14—C15—C16	−9.4 (3)	C24—C23—C32—C31	−2.1 (4)
C13—C14—C15—C20	−9.2 (3)	C22—C23—C32—C31	178.9 (2)
C33—C14—C15—C20	172.1 (2)	C30—C31—C32—C23	−176.3 (2)
C14—C15—C16—C17	−179.0 (2)	C26—C31—C32—C23	2.1 (4)
C20—C15—C16—C17	−0.5 (3)	C13—C14—C33—C25	119.6 (3)
C15—C16—C17—C18	−2.1 (4)	C15—C14—C33—C25	−61.7 (3)
C16—C17—C18—C19	2.0 (4)	C24—C25—C33—C14	120.9 (3)
C17—C18—C19—C20	0.7 (4)	C26—C25—C33—C14	−62.3 (3)
C18—C19—C20—C21	175.1 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱⁱⁱ	1.00	2.50	3.272 (3)	134
N3—H3···O5	1.00	1.89	2.836 (3)	156
N4—H4···O2ⁱⁱⁱ	1.00	1.90	2.822 (3)	152
O3—H3C···O2	0.84	1.75	2.502 (2)	148
O6—H6C···O5	0.84	1.75	2.514 (3)	150
O1W—H1WA···O1^iv	0.86	1.88	2.746 (2)	178
O1W—H1WB···O4	0.86	2.31	3.136 (3)	162
O1W—H1WB···O5	0.86	2.41	3.087 (3)	136
O2W—H2WA···O1ⁱⁱⁱ	0.86	2.05	2.901 (2)	169
O2W—H2WA···O2ⁱⁱⁱ	0.86	2.61	3.280 (2)	136
O2W—H2WB···O4^v	0.86	1.88	2.743 (3)	176
C2—H2B···O1^vi	0.99	2.48	3.435 (3)	162
C5—H5B···O2ⁱⁱⁱ	0.98	2.45	3.316 (3)	147

Symmetry codes: (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x−1, y, z; (vi) −x+1, −y, −z+1.

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Crystal structure of trans-di­aqua­(3,10-dimethyl-1,3,5,8,10,12-hexa­aza­cyclo­tetra­deca­ne)copper(II) pamoate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of trans-diaqua(3,10-dimethyl-1,3,5,8,10,12-hexaazacyclotetradecane)copper(II) pamoate