(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra­azacyclo­tetra­deca­ne)zinc(II) diperchlorate

In the title mononuclear zinc(II) compound, [Zn(C₁₆H₃₆N₄)](ClO₄)₂, the Zn²⁺ atom lies on an inversion center and is coordinated by four N atoms from the macrocyclic ligand. The coordination geometry is slightly distorted square planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.109
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT702_ALERT_1_B Angle   Calc   106.3(19), Rep      102(2), Dev..       2.26 Sigma
              C4   -N1   -H1      1.555   1.555   1.555

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....         H1
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT701_ALERT_1_C Bond    Calc     0.91(3), Rep     0.85(3), Dev..       2.00 Sigma
              N1   -H1      1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane)zinc(II) diperchlorate

Crystal data

[Zn(C16H32N4)](ClO4)2	F(000) = 568
Mr = 544.74	Dx = 1.622 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.323 (2) Å	Cell parameters from 1989 reflections
b = 10.630 (2) Å	θ = 4.8–27.5°
c = 11.018 (2) Å	µ = 1.38 mm^−1
β = 111.71 (3)°	T = 293 K
V = 1123.3 (4) Å^3	Prism, colorless
Z = 2	0.45 × 0.35 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2645 independent reflections
Radiation source: fine-focus sealed tube	2448 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.580, Tmax = 0.625	k = −13→13
9499 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0422P)^2 + 1.108P] where P = (Fo^2 + 2Fc^2)/3
2645 reflections	(Δ/σ)max = 0.029
148 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.45 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	1.0000	1.0000	0.0000	0.02845 (14)
N1	0.8630 (2)	0.9560 (2)	0.0833 (2)	0.0253 (4)
H1	0.831 (3)	1.030 (3)	0.102 (3)	0.030*
N2	1.1395 (2)	0.9994 (2)	0.1803 (2)	0.0307 (5)
C5	0.7367 (3)	0.8844 (2)	−0.0014 (2)	0.0282 (5)
C4	0.9447 (3)	0.8970 (3)	0.2103 (2)	0.0360 (6)
H4A	0.9701	0.8118	0.1967	0.043*
H4B	0.8895	0.8936	0.2649	0.043*
C6	0.6603 (3)	0.9678 (3)	−0.1193 (3)	0.0341 (6)
H6A	0.5703	0.9295	−0.1665	0.041*
H6B	0.6425	1.0480	−0.0865	0.041*
C7	0.6386 (3)	0.8619 (3)	0.0722 (3)	0.0446 (7)
H7A	0.6803	0.8026	0.1415	0.067*
H7B	0.5515	0.8291	0.0130	0.067*
H7C	0.6225	0.9399	0.1083	0.067*
C2	1.2719 (3)	1.0060 (2)	0.2161 (3)	0.0312 (5)
C3	1.0735 (3)	0.9742 (3)	0.2756 (3)	0.0410 (7)
H3A	1.0492	1.0529	0.3065	0.049*
H3B	1.1377	0.9290	0.3500	0.049*
C8	0.7782 (3)	0.7596 (3)	−0.0438 (3)	0.0411 (7)
H8A	0.8496	0.7735	−0.0786	0.062*
H8B	0.6984	0.7221	−0.1097	0.062*
H8C	0.8128	0.7042	0.0301	0.062*
C1	1.3718 (3)	0.9849 (3)	0.3530 (3)	0.0471 (8)
H1A	1.3613	1.0506	0.4084	0.071*
H1B	1.4655	0.9853	0.3548	0.071*
H1C	1.3527	0.9051	0.3837	0.071*
Cl1	0.24339 (9)	0.83322 (7)	0.64896 (8)	0.0442 (2)
O1	0.2452 (4)	0.9624 (3)	0.6160 (3)	0.0821 (10)
O2	0.2126 (4)	0.8209 (3)	0.7643 (3)	0.0804 (10)
O3	0.1423 (3)	0.7649 (3)	0.5451 (3)	0.0793 (9)
O4	0.3757 (3)	0.7793 (3)	0.6711 (4)	0.0886 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0230 (2)	0.0394 (3)	0.0213 (2)	−0.00401 (16)	0.00622 (16)	0.00037 (16)
N1	0.0217 (10)	0.0288 (10)	0.0253 (10)	−0.0001 (8)	0.0087 (8)	−0.0013 (8)
N2	0.0251 (11)	0.0431 (12)	0.0214 (10)	−0.0043 (9)	0.0057 (8)	−0.0005 (8)
C5	0.0229 (11)	0.0319 (12)	0.0288 (12)	−0.0034 (9)	0.0083 (9)	−0.0004 (10)
C4	0.0328 (14)	0.0496 (16)	0.0262 (12)	−0.0033 (12)	0.0117 (11)	0.0063 (11)
C6	0.0204 (12)	0.0429 (14)	0.0368 (14)	0.0011 (10)	0.0079 (10)	0.0032 (11)
C7	0.0323 (15)	0.0607 (19)	0.0450 (17)	−0.0127 (14)	0.0192 (13)	0.0019 (14)
C2	0.0285 (13)	0.0320 (13)	0.0276 (13)	0.0001 (10)	0.0039 (10)	0.0012 (10)
C3	0.0350 (15)	0.0658 (19)	0.0205 (12)	−0.0076 (13)	0.0085 (11)	−0.0021 (12)
C8	0.0513 (18)	0.0288 (13)	0.0414 (16)	−0.0021 (12)	0.0151 (14)	−0.0040 (11)
C1	0.0319 (15)	0.067 (2)	0.0304 (14)	0.0007 (14)	−0.0028 (12)	0.0033 (13)
Cl1	0.0552 (5)	0.0368 (4)	0.0470 (4)	−0.0030 (3)	0.0264 (3)	0.0025 (3)
O1	0.140 (3)	0.0407 (14)	0.082 (2)	0.0018 (16)	0.061 (2)	0.0120 (14)
O2	0.139 (3)	0.0580 (16)	0.0692 (18)	0.0010 (17)	0.068 (2)	0.0059 (14)
O3	0.080 (2)	0.083 (2)	0.0591 (17)	−0.0234 (16)	0.0065 (15)	0.0064 (15)
O4	0.0564 (17)	0.072 (2)	0.142 (3)	0.0001 (15)	0.042 (2)	−0.009 (2)

Geometric parameters (Å, º)

Zn1—N2	1.976 (2)	C7—H7A	0.960
Zn1—N2^i	1.976 (2)	C7—H7B	0.960
Zn1—N1^i	2.005 (2)	C7—H7C	0.960
Zn1—N1	2.005 (2)	C2—C1	1.497 (4)
N1—C4	1.480 (3)	C2—C6^i	1.502 (4)
N1—C5	1.501 (3)	C3—H3A	0.970
N1—H1	0.85 (3)	C3—H3B	0.970
N2—C2	1.276 (4)	C8—H8A	0.960
N2—C3	1.472 (3)	C8—H8B	0.960
C5—C8	1.520 (4)	C8—H8C	0.960
C5—C6	1.529 (4)	C1—H1A	0.960
C5—C7	1.532 (4)	C1—H1B	0.960
C4—C3	1.501 (4)	C1—H1C	0.960
C4—H4A	0.970	Cl1—O4	1.417 (3)
C4—H4B	0.970	Cl1—O1	1.423 (3)
C6—C2^i	1.502 (4)	Cl1—O2	1.426 (3)
C6—H6A	0.970	Cl1—O3	1.429 (3)
C6—H6B	0.970
N2—Zn1—N2^i	180.0	C5—C7—H7A	109.5
N2—Zn1—N1^i	94.91 (9)	C5—C7—H7B	109.5
N2^i—Zn1—N1^i	85.09 (9)	H7A—C7—H7B	109.5
N2—Zn1—N1	85.09 (9)	C5—C7—H7C	109.5
N2^i—Zn1—N1	94.91 (9)	H7A—C7—H7C	109.5
N1^i—Zn1—N1	180.0	H7B—C7—H7C	109.5
C4—N1—C5	115.7 (2)	N2—C2—C1	124.2 (3)
C4—N1—Zn1	106.25 (15)	N2—C2—C6^i	121.2 (2)
C5—N1—Zn1	115.57 (15)	C1—C2—C6^i	114.5 (2)
C4—N1—H1	102 (2)	N2—C3—C4	108.6 (2)
C5—N1—H1	108 (2)	N2—C3—H3A	110.0
Zn1—N1—H1	108 (2)	C4—C3—H3A	110.0
C2—N2—C3	121.0 (2)	N2—C3—H3B	110.0
C2—N2—Zn1	127.51 (19)	C4—C3—H3B	110.0
C3—N2—Zn1	111.09 (17)	H3A—C3—H3B	108.3
N1—C5—C8	110.8 (2)	C5—C8—H8A	109.5
N1—C5—C6	106.9 (2)	C5—C8—H8B	109.5
C8—C5—C6	111.1 (2)	H8A—C8—H8B	109.5
N1—C5—C7	110.0 (2)	C5—C8—H8C	109.5
C8—C5—C7	110.1 (2)	H8A—C8—H8C	109.5
C6—C5—C7	107.8 (2)	H8B—C8—H8C	109.5
N1—C4—C3	108.4 (2)	C2—C1—H1A	109.5
N1—C4—H4A	110.0	C2—C1—H1B	109.5
C3—C4—H4A	110.0	H1A—C1—H1B	109.5
N1—C4—H4B	110.0	C2—C1—H1C	109.5
C3—C4—H4B	110.0	H1A—C1—H1C	109.5
H4A—C4—H4B	108.4	H1B—C1—H1C	109.5
C2^i—C6—C5	118.8 (2)	O4—Cl1—O1	109.4 (2)
C2^i—C6—H6A	107.6	O4—Cl1—O2	109.1 (2)
C5—C6—H6A	107.6	O1—Cl1—O2	110.12 (17)
C2^i—C6—H6B	107.6	O4—Cl1—O3	107.7 (2)
C5—C6—H6B	107.6	O1—Cl1—O3	111.2 (2)
H6A—C6—H6B	107.1	O2—Cl1—O3	109.2 (2)
N2—Zn1—N1—C4	−23.61 (17)	Zn1—N1—C5—C7	−177.70 (18)
N2^i—Zn1—N1—C4	156.39 (17)	C5—N1—C4—C3	174.5 (2)
N2—Zn1—N1—C5	−153.35 (18)	Zn1—N1—C4—C3	44.8 (3)
N2^i—Zn1—N1—C5	26.65 (18)	N1—C5—C6—C2^i	67.7 (3)
N1^i—Zn1—N2—C2	−9.4 (2)	C8—C5—C6—C2^i	−53.3 (3)
N1—Zn1—N2—C2	170.6 (2)	C7—C5—C6—C2^i	−174.1 (2)
N1^i—Zn1—N2—C3	177.67 (19)	C3—N2—C2—C1	2.3 (4)
N1—Zn1—N2—C3	−2.33 (19)	Zn1—N2—C2—C1	−170.0 (2)
C4—N1—C5—C8	−64.7 (3)	C3—N2—C2—C6^i	−179.7 (3)
Zn1—N1—C5—C8	60.3 (2)	Zn1—N2—C2—C6^i	8.0 (4)
C4—N1—C5—C6	174.1 (2)	C2—N2—C3—C4	−145.7 (3)
Zn1—N1—C5—C6	−60.9 (2)	Zn1—N2—C3—C4	27.7 (3)
C4—N1—C5—C7	57.3 (3)	N1—C4—C3—N2	−48.2 (3)

Symmetry code: (i) −x+2, −y+2, −z.