[1-(Anthracen-9-ylmeth­yl)-1,4,7,10-tetra­aza­cyclododeca­ne]chlorido­zinc(II) nitrate

In the title salt, [ZnCl(C₂₃H₃₀N₄)]NO₃, the central Zn^II atom of the complex cation is coordinated in a square-pyramidal arrangement by four nitro­gen atoms from cyclen (1,4,7,10-tetra­aza­cyclo­dodeca­ne) in the basal plane and one chlorido ligand in the apical position. The anthracene group attached to cyclen contributes to the crystal packing through inter­molecular T-shaped π inter­actions. Additionally, the nitrate anion participates in inter­molecular N—H...O hydrogen bonds with cyclen.

Computing details

[1-(Anthracen-9-ylmethyl)-1,4,7,10-tetraazacyclododecane]chloridozinc(II) nitrate

Crystal data

C23H30ClN4Zn^+·NO3^−	F(000) = 1096
Mr = 525.34	Dx = 1.497 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 15.9086 (1) Å	Cell parameters from 16543 reflections
b = 7.8088 (1) Å	θ = 2.4–68.3°
c = 19.5342 (2) Å	µ = 2.81 mm^−1
β = 106.157 (1)°	T = 93 K
V = 2330.83 (4) Å^3	Plate, yellow
Z = 4	0.35 × 0.25 × 0.12 mm

Data collection

Rigaku XtaLAB Synergy-i diffractometer	4097 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm^-1	Rint = 0.027
ω scans	θmax = 68.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −19→19
Tmin = 0.619, Tmax = 1.000	k = −9→9
21217 measured reflections	l = −23→22
4271 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 5.0389P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4271 reflections	Δρmax = 1.65 e Å^−3
298 parameters	Δρmin = −0.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.38731 (2)	0.45659 (4)	0.35923 (2)	0.01650 (12)
Cl1	0.48909 (4)	0.66348 (8)	0.38926 (4)	0.02646 (17)
O1	0.38618 (12)	0.6627 (3)	0.16411 (10)	0.0250 (4)
O2	0.35799 (13)	0.6797 (3)	0.04891 (10)	0.0283 (4)
N1	0.24737 (14)	0.5751 (3)	0.32627 (12)	0.0179 (4)
N2	0.34428 (15)	0.3815 (3)	0.25262 (12)	0.0210 (5)
H2	0.354759	0.475940	0.221385	0.025*
N3	0.44297 (14)	0.2069 (3)	0.37340 (13)	0.0234 (5)
H3	0.507715	0.216524	0.381655	0.028*
O3	0.27592 (15)	0.5258 (4)	0.09680 (12)	0.0425 (6)
N4	0.34614 (15)	0.3897 (3)	0.44943 (12)	0.0233 (5)
H4	0.393328	0.423402	0.492937	0.028*
N5	0.33966 (14)	0.6225 (3)	0.10271 (12)	0.0223 (5)
C1	0.18291 (16)	0.8823 (3)	0.30190 (14)	0.0178 (5)
C2	0.13492 (16)	0.9487 (3)	0.34735 (14)	0.0183 (5)
C7	0.06198 (17)	1.0620 (3)	0.31847 (15)	0.0194 (5)
C17	0.24931 (17)	0.3503 (3)	0.23785 (15)	0.0213 (5)
H17A	0.238613	0.257067	0.268744	0.026*
H17B	0.224518	0.315513	0.187516	0.026*
C15	0.26134 (16)	0.7645 (3)	0.33143 (14)	0.0173 (5)
H15A	0.306094	0.792998	0.306741	0.021*
H15B	0.286579	0.793243	0.382389	0.021*
C8	0.03866 (17)	1.1046 (3)	0.24673 (15)	0.0209 (5)
H8	−0.010901	1.175629	0.227958	0.025*
C9	0.08644 (17)	1.0455 (3)	0.20166 (15)	0.0205 (5)
C14	0.16158 (17)	0.9372 (3)	0.22978 (14)	0.0192 (5)
C6	0.01563 (17)	1.1335 (3)	0.36509 (15)	0.0234 (6)
H6	−0.033418	1.205501	0.345867	0.028*
C16	0.20644 (18)	0.5133 (4)	0.25238 (15)	0.0236 (6)
H16A	0.212198	0.602408	0.217920	0.028*
H16B	0.143295	0.492520	0.245818	0.028*
C10	0.06288 (19)	1.0952 (4)	0.12807 (15)	0.0270 (6)
H10	0.012570	1.164427	0.109607	0.032*
C13	0.21288 (19)	0.8961 (3)	0.18199 (15)	0.0241 (6)
H13	0.265276	0.832090	0.199311	0.029*
C3	0.15766 (17)	0.9180 (4)	0.42258 (14)	0.0218 (5)
H3A	0.205360	0.844130	0.443490	0.026*
C5	0.04022 (18)	1.1008 (4)	0.43543 (16)	0.0267 (6)
H5	0.009087	1.150559	0.465472	0.032*
C19	0.40575 (18)	0.1105 (4)	0.30722 (16)	0.0257 (6)
H19A	0.348153	0.062604	0.307287	0.031*
H19B	0.444945	0.014239	0.303947	0.031*
C4	0.11287 (18)	0.9915 (4)	0.46489 (15)	0.0262 (6)
H4A	0.130287	0.969705	0.514699	0.031*
C20	0.4252 (2)	0.1301 (4)	0.43712 (16)	0.0287 (6)
H20A	0.474231	0.155658	0.479727	0.034*
H20B	0.420519	0.004167	0.431476	0.034*
C21	0.34052 (19)	0.2010 (4)	0.44747 (16)	0.0276 (6)
H21A	0.290232	0.163987	0.407747	0.033*
H21B	0.331815	0.157511	0.492607	0.033*
C18	0.39519 (19)	0.2283 (4)	0.24406 (16)	0.0270 (6)
H18A	0.453501	0.263582	0.240278	0.032*
H18B	0.364569	0.167201	0.199724	0.032*
C22	0.26506 (19)	0.4805 (4)	0.45083 (15)	0.0253 (6)
H22A	0.280205	0.594958	0.472524	0.030*
H22B	0.235127	0.415636	0.480764	0.030*
C23	0.20380 (17)	0.5006 (4)	0.37670 (16)	0.0233 (6)
H23A	0.179688	0.387098	0.358880	0.028*
H23B	0.154274	0.575060	0.378989	0.028*
C12	0.1885 (2)	0.9464 (4)	0.11281 (17)	0.0316 (7)
H12	0.223574	0.915233	0.082604	0.038*
C11	0.1111 (2)	1.0449 (4)	0.08451 (17)	0.0326 (7)
H11	0.093660	1.075128	0.035468	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.01667 (19)	0.01153 (19)	0.0223 (2)	−0.00095 (12)	0.00709 (14)	0.00115 (12)
Cl1	0.0282 (3)	0.0217 (3)	0.0285 (3)	−0.0034 (3)	0.0061 (3)	0.0003 (3)
O1	0.0227 (9)	0.0308 (11)	0.0192 (9)	−0.0042 (8)	0.0023 (8)	−0.0008 (8)
O2	0.0308 (11)	0.0339 (11)	0.0207 (10)	−0.0004 (9)	0.0078 (8)	0.0065 (8)
N1	0.0166 (10)	0.0125 (10)	0.0242 (11)	0.0007 (8)	0.0053 (9)	0.0022 (9)
N2	0.0226 (11)	0.0188 (11)	0.0233 (11)	−0.0027 (9)	0.0092 (9)	0.0002 (9)
N3	0.0175 (11)	0.0171 (11)	0.0329 (13)	0.0024 (9)	0.0026 (9)	−0.0025 (10)
O3	0.0292 (12)	0.0666 (17)	0.0279 (11)	−0.0246 (11)	0.0017 (9)	0.0031 (11)
N4	0.0245 (12)	0.0216 (12)	0.0244 (12)	0.0023 (10)	0.0079 (9)	0.0047 (9)
N5	0.0195 (11)	0.0242 (12)	0.0229 (12)	0.0011 (9)	0.0052 (9)	0.0005 (9)
C1	0.0161 (12)	0.0106 (11)	0.0259 (13)	−0.0026 (9)	0.0043 (10)	−0.0008 (10)
C2	0.0144 (12)	0.0138 (12)	0.0253 (13)	−0.0024 (9)	0.0033 (10)	−0.0015 (10)
C7	0.0154 (12)	0.0138 (12)	0.0272 (14)	−0.0021 (10)	0.0027 (10)	−0.0019 (10)
C17	0.0224 (13)	0.0163 (13)	0.0246 (13)	−0.0023 (10)	0.0055 (11)	0.0013 (10)
C15	0.0152 (11)	0.0123 (12)	0.0246 (13)	0.0003 (9)	0.0056 (10)	0.0015 (10)
C8	0.0165 (12)	0.0133 (12)	0.0309 (14)	0.0004 (10)	0.0029 (10)	0.0015 (11)
C9	0.0190 (13)	0.0137 (12)	0.0267 (14)	−0.0025 (10)	0.0030 (11)	0.0026 (10)
C14	0.0195 (12)	0.0109 (11)	0.0268 (14)	−0.0032 (10)	0.0060 (11)	−0.0005 (10)
C6	0.0176 (12)	0.0173 (13)	0.0343 (15)	0.0012 (10)	0.0056 (11)	−0.0037 (11)
C16	0.0223 (13)	0.0164 (13)	0.0277 (14)	0.0004 (11)	−0.0002 (11)	0.0010 (11)
C10	0.0258 (14)	0.0223 (14)	0.0309 (15)	0.0005 (11)	0.0047 (12)	0.0077 (12)
C13	0.0289 (14)	0.0153 (13)	0.0300 (15)	0.0029 (11)	0.0111 (12)	0.0036 (11)
C3	0.0157 (12)	0.0226 (13)	0.0249 (14)	0.0010 (10)	0.0022 (10)	−0.0006 (11)
C5	0.0208 (13)	0.0277 (15)	0.0324 (15)	0.0011 (12)	0.0084 (11)	−0.0086 (12)
C19	0.0216 (13)	0.0184 (13)	0.0363 (16)	0.0023 (11)	0.0066 (12)	−0.0066 (12)
C4	0.0215 (14)	0.0308 (15)	0.0244 (14)	0.0004 (12)	0.0032 (11)	−0.0030 (12)
C20	0.0331 (15)	0.0173 (13)	0.0297 (15)	0.0034 (12)	−0.0012 (12)	0.0033 (11)
C21	0.0303 (15)	0.0228 (14)	0.0285 (15)	−0.0033 (12)	0.0062 (12)	0.0079 (12)
C18	0.0262 (14)	0.0263 (15)	0.0327 (15)	−0.0018 (12)	0.0151 (12)	−0.0081 (12)
C22	0.0295 (15)	0.0220 (14)	0.0284 (15)	−0.0003 (11)	0.0146 (12)	0.0009 (11)
C23	0.0193 (13)	0.0188 (13)	0.0356 (15)	−0.0001 (11)	0.0138 (12)	0.0035 (12)
C12	0.0414 (18)	0.0260 (15)	0.0320 (16)	0.0036 (13)	0.0177 (14)	0.0051 (12)
C11	0.0415 (18)	0.0297 (16)	0.0260 (15)	0.0025 (13)	0.0084 (13)	0.0092 (12)

Geometric parameters (Å, º)

Zn1—Cl1	2.2466 (7)	C9—C14	1.442 (4)
Zn1—N1	2.330 (2)	C9—C10	1.435 (4)
Zn1—N2	2.087 (2)	C14—C13	1.437 (4)
Zn1—N3	2.127 (2)	C6—H6	0.9500
Zn1—N4	2.109 (2)	C6—C5	1.344 (4)
O1—N5	1.261 (3)	C16—H16A	0.9900
O2—N5	1.249 (3)	C16—H16B	0.9900
N1—C15	1.495 (3)	C10—H10	0.9500
N1—C16	1.489 (3)	C10—C11	1.353 (4)
N1—C23	1.473 (3)	C13—H13	0.9500
N2—H2	1.0000	C13—C12	1.356 (4)
N2—C17	1.477 (3)	C3—H3A	0.9500
N2—C18	1.480 (4)	C3—C4	1.359 (4)
N3—H3	1.0000	C5—H5	0.9500
N3—C19	1.471 (4)	C5—C4	1.423 (4)
N3—C20	1.478 (4)	C19—H19A	0.9900
O3—N5	1.244 (3)	C19—H19B	0.9900
N4—H4	1.0000	C19—C18	1.510 (4)
N4—C21	1.476 (4)	C4—H4A	0.9500
N4—C22	1.479 (4)	C20—H20A	0.9900
C1—C2	1.420 (4)	C20—H20B	0.9900
C1—C15	1.528 (3)	C20—C21	1.521 (4)
C1—C14	1.420 (4)	C21—H21A	0.9900
C2—C7	1.443 (4)	C21—H21B	0.9900
C2—C3	1.433 (4)	C18—H18A	0.9900
C7—C8	1.387 (4)	C18—H18B	0.9900
C7—C6	1.435 (4)	C22—H22A	0.9900
C17—H17A	0.9900	C22—H22B	0.9900
C17—H17B	0.9900	C22—C23	1.512 (4)
C17—C16	1.508 (4)	C23—H23A	0.9900
C15—H15A	0.9900	C23—H23B	0.9900
C15—H15B	0.9900	C12—H12	0.9500
C8—H8	0.9500	C12—C11	1.426 (4)
C8—C9	1.392 (4)	C11—H11	0.9500
Cl1—Zn1—N1	110.50 (6)	C7—C6—H6	119.3
N2—Zn1—Cl1	118.36 (6)	C5—C6—C7	121.3 (3)
N2—Zn1—N1	79.22 (8)	C5—C6—H6	119.3
N2—Zn1—N3	83.20 (9)	N1—C16—C17	110.9 (2)
N2—Zn1—N4	132.23 (9)	N1—C16—H16A	109.4
N3—Zn1—Cl1	112.42 (6)	N1—C16—H16B	109.5
N3—Zn1—N1	136.98 (8)	C17—C16—H16A	109.4
N4—Zn1—Cl1	109.19 (7)	C17—C16—H16B	109.4
N4—Zn1—N1	80.46 (8)	H16A—C16—H16B	108.0
N4—Zn1—N3	83.05 (9)	C9—C10—H10	119.5
C15—N1—Zn1	105.17 (14)	C11—C10—C9	121.1 (3)
C16—N1—Zn1	105.40 (15)	C11—C10—H10	119.5
C16—N1—C15	113.8 (2)	C14—C13—H13	119.1
C23—N1—Zn1	104.45 (15)	C12—C13—C14	121.7 (3)
C23—N1—C15	115.8 (2)	C12—C13—H13	119.1
C23—N1—C16	111.1 (2)	C2—C3—H3A	119.1
Zn1—N2—H2	109.7	C4—C3—C2	121.8 (3)
C17—N2—Zn1	105.96 (16)	C4—C3—H3A	119.1
C17—N2—H2	109.7	C6—C5—H5	120.0
C17—N2—C18	114.0 (2)	C6—C5—C4	120.0 (3)
C18—N2—Zn1	107.57 (17)	C4—C5—H5	120.0
C18—N2—H2	109.7	N3—C19—H19A	109.8
Zn1—N3—H3	109.0	N3—C19—H19B	109.8
C19—N3—Zn1	107.67 (16)	N3—C19—C18	109.4 (2)
C19—N3—H3	109.0	H19A—C19—H19B	108.2
C19—N3—C20	114.1 (2)	C18—C19—H19A	109.8
C20—N3—Zn1	108.13 (17)	C18—C19—H19B	109.8
C20—N3—H3	109.0	C3—C4—C5	120.8 (3)
Zn1—N4—H4	108.1	C3—C4—H4A	119.6
C21—N4—Zn1	104.84 (17)	C5—C4—H4A	119.6
C21—N4—H4	108.1	N3—C20—H20A	109.6
C21—N4—C22	115.6 (2)	N3—C20—H20B	109.6
C22—N4—Zn1	111.83 (17)	N3—C20—C21	110.4 (2)
C22—N4—H4	108.1	H20A—C20—H20B	108.1
O2—N5—O1	119.9 (2)	C21—C20—H20A	109.6
O3—N5—O1	119.1 (2)	C21—C20—H20B	109.6
O3—N5—O2	121.0 (2)	N4—C21—C20	108.5 (2)
C2—C1—C15	120.5 (2)	N4—C21—H21A	110.0
C2—C1—C14	119.2 (2)	N4—C21—H21B	110.0
C14—C1—C15	120.0 (2)	C20—C21—H21A	110.0
C1—C2—C7	119.5 (2)	C20—C21—H21B	110.0
C1—C2—C3	123.6 (2)	H21A—C21—H21B	108.4
C3—C2—C7	116.7 (2)	N2—C18—C19	109.9 (2)
C8—C7—C2	120.1 (2)	N2—C18—H18A	109.7
C8—C7—C6	120.5 (2)	N2—C18—H18B	109.7
C6—C7—C2	119.3 (2)	C19—C18—H18A	109.7
N2—C17—H17A	110.0	C19—C18—H18B	109.7
N2—C17—H17B	110.0	H18A—C18—H18B	108.2
N2—C17—C16	108.4 (2)	N4—C22—H22A	109.3
H17A—C17—H17B	108.4	N4—C22—H22B	109.3
C16—C17—H17A	110.0	N4—C22—C23	111.4 (2)
C16—C17—H17B	110.0	H22A—C22—H22B	108.0
N1—C15—C1	118.7 (2)	C23—C22—H22A	109.3
N1—C15—H15A	107.6	C23—C22—H22B	109.3
N1—C15—H15B	107.6	N1—C23—C22	112.6 (2)
C1—C15—H15A	107.6	N1—C23—H23A	109.1
C1—C15—H15B	107.6	N1—C23—H23B	109.1
H15A—C15—H15B	107.1	C22—C23—H23A	109.1
C7—C8—H8	119.3	C22—C23—H23B	109.1
C7—C8—C9	121.3 (2)	H23A—C23—H23B	107.8
C9—C8—H8	119.3	C13—C12—H12	119.4
C8—C9—C14	119.6 (2)	C13—C12—C11	121.3 (3)
C8—C9—C10	120.5 (2)	C11—C12—H12	119.4
C10—C9—C14	119.9 (3)	C10—C11—C12	119.5 (3)
C1—C14—C9	119.9 (2)	C10—C11—H11	120.3
C1—C14—C13	123.7 (2)	C12—C11—H11	120.3
C13—C14—C9	116.4 (2)
Zn1—N1—C15—C1	170.33 (18)	C15—C1—C2—C3	2.8 (4)
Zn1—N1—C16—C17	23.5 (2)	C15—C1—C14—C9	178.7 (2)
Zn1—N1—C23—C22	37.1 (2)	C15—C1—C14—C13	−3.6 (4)
Zn1—N2—C17—C16	58.9 (2)	C8—C7—C6—C5	−176.5 (3)
Zn1—N2—C18—C19	40.9 (2)	C8—C9—C14—C1	4.2 (4)
Zn1—N3—C19—C18	37.5 (2)	C8—C9—C14—C13	−173.7 (2)
Zn1—N3—C20—C21	29.3 (3)	C8—C9—C10—C11	176.9 (3)
Zn1—N4—C21—C20	49.6 (2)	C9—C14—C13—C12	−4.5 (4)
Zn1—N4—C22—C23	36.5 (3)	C9—C10—C11—C12	−2.3 (5)
N2—C17—C16—N1	−55.4 (3)	C14—C1—C2—C7	3.9 (4)
N3—C19—C18—N2	−53.5 (3)	C14—C1—C2—C3	−172.3 (2)
N3—C20—C21—N4	−54.3 (3)	C14—C1—C15—N1	−90.1 (3)
N4—C22—C23—N1	−51.2 (3)	C14—C9—C10—C11	−1.4 (4)
C1—C2—C7—C8	0.4 (4)	C14—C13—C12—C11	1.0 (5)
C1—C2—C7—C6	−177.8 (2)	C6—C7—C8—C9	175.7 (2)
C1—C2—C3—C4	176.3 (3)	C6—C5—C4—C3	−0.6 (5)
C1—C14—C13—C12	177.7 (3)	C16—N1—C15—C1	55.5 (3)
C2—C1—C15—N1	94.8 (3)	C16—N1—C23—C22	150.2 (2)
C2—C1—C14—C9	−6.2 (4)	C10—C9—C14—C1	−177.5 (2)
C2—C1—C14—C13	171.5 (2)	C10—C9—C14—C13	4.7 (4)
C2—C7—C8—C9	−2.5 (4)	C13—C12—C11—C10	2.6 (5)
C2—C7—C6—C5	1.8 (4)	C3—C2—C7—C8	176.9 (2)
C2—C3—C4—C5	1.0 (4)	C3—C2—C7—C6	−1.4 (4)
C7—C2—C3—C4	0.1 (4)	C19—N3—C20—C21	−90.4 (3)
C7—C8—C9—C14	0.2 (4)	C20—N3—C19—C18	157.5 (2)
C7—C8—C9—C10	−178.1 (2)	C21—N4—C22—C23	−83.4 (3)
C7—C6—C5—C4	−0.8 (4)	C18—N2—C17—C16	177.0 (2)
C17—N2—C18—C19	−76.3 (3)	C22—N4—C21—C20	173.2 (2)
C15—N1—C16—C17	138.2 (2)	C23—N1—C15—C1	−75.0 (3)
C15—N1—C23—C22	−78.0 (3)	C23—N1—C16—C17	−89.0 (3)
C15—C1—C2—C7	179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	1.00	1.98	2.983 (3)	175
N3—H3···O1^i	1.00	2.16	3.025 (3)	144

Symmetry code: (i) −x+1, y−1/2, −z+1/2.