Crystal structure of (1R,5S)-endo-(8-methyl-8-azoniabi­cyclo­[3.2.1]oct-3-yl)ammonium aqua­tri­chlorido­nitratocopper(II)

The title compound is a salt containing a protonated endo-3-amino­tropane cage and a novel anionic copper(II) complex, [CuCl₃(NO₃)(H₂O)]²⁻.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.018
• wR factor = 0.049
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O2 Check

Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1    --  O1      ..       11.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1    --  Ow1     ..        5.4 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C5      (Centro SPGR)          S Verify
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

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

---

Computing details

Data collection: Apex2 (Bruker, 2015); cell refinement: Saint (Bruker, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) Olex2-1.2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(1R,5S)-endo-(8-Methyl-8-azoniabicyclo[3.2.1]oct-3-yl)ammonium aquatrichloridonitratocopper(II)

Crystal data

(C8H18N2)[CuCl3(NO3)(H2O)]	F(000) = 804
Mr = 392.16	Dx = 1.788 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2464 (3) Å	Cell parameters from 9865 reflections
b = 13.5674 (6) Å	θ = 2.8–35.0°
c = 17.4584 (8) Å	µ = 2.06 mm^−1
β = 100.128 (1)°	T = 150 K
V = 1456.50 (12) Å^3	Block, green
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	3523 independent reflections
Radiation source: fine-focus sealed tube	3382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 28.0°, θmin = 1.9°
Absorption correction: multi-scan SADABS (Sheldrick, 2015)	h = −8→8
	k = −17→17
16933 measured reflections	l = −23→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.018	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.049	w = 1/[σ^2(Fo^2) + (0.0249P)^2 + 0.617P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3523 reflections	Δρmax = 0.43 e Å^−3
197 parameters	Δρmin = −0.31 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
C1	0.3006 (2)	0.09472 (10)	0.65317 (7)	0.0272 (3)
H1	0.1897	0.0452	0.6581	0.033*
C2	0.2156 (2)	0.19808 (10)	0.66403 (8)	0.0296 (3)
H2A	0.1662	0.2008	0.7136	0.036*
H2B	0.0906	0.2101	0.6236	0.036*
C3	0.3811 (2)	0.28074 (9)	0.66170 (7)	0.0255 (2)
H3	0.3426	0.3338	0.6949	0.031*
C4	0.6143 (2)	0.24969 (10)	0.69599 (7)	0.0273 (2)
H4A	0.7142	0.2906	0.6733	0.033*
H4B	0.6397	0.2624	0.7515	0.033*
C5	0.66665 (19)	0.14187 (10)	0.68295 (7)	0.0253 (2)
H5	0.8146	0.1257	0.7089	0.030*
C6	0.6311 (2)	0.11169 (11)	0.59713 (8)	0.0323 (3)
H6A	0.7268	0.0578	0.5892	0.039*
H6B	0.6579	0.1668	0.5647	0.039*
C7	0.3908 (3)	0.07923 (11)	0.57794 (8)	0.0347 (3)
H7A	0.3115	0.1189	0.5361	0.042*
H7B	0.3798	0.0105	0.5624	0.042*
N8	0.50100 (18)	0.07935 (8)	0.71434 (6)	0.0239 (2)
C8	0.5664 (3)	−0.02653 (10)	0.72557 (9)	0.0375 (3)
H8A	0.4508	−0.0632	0.7418	0.056*
H8B	0.6950	−0.0313	0.7646	0.056*
H8C	0.5955	−0.0530	0.6774	0.056*
N3	0.3612 (2)	0.32304 (9)	0.58084 (7)	0.0285 (2)
Cu1	0.77174 (2)	0.33409 (2)	0.41227 (2)	0.02287 (5)
Cl1	0.45571 (5)	0.24722 (2)	0.41328 (2)	0.03028 (7)
Cl2	0.84844 (5)	0.40007 (2)	0.55338 (2)	0.03060 (7)
Cl3	0.60443 (6)	0.45734 (2)	0.33880 (2)	0.03453 (8)
N1	0.94979 (18)	0.15675 (8)	0.40161 (7)	0.0286 (2)
O1	0.94479 (15)	0.21792 (7)	0.45717 (5)	0.02895 (19)
O2	0.8758 (2)	0.18232 (10)	0.33464 (7)	0.0465 (3)
O3	1.0312 (2)	0.07521 (9)	0.41756 (10)	0.0614 (4)
OW1	1.05693 (16)	0.38867 (8)	0.38441 (6)	0.02756 (19)
H8	0.484 (3)	0.1001 (12)	0.7547 (10)	0.024 (4)*
H3A	0.374 (3)	0.2818 (15)	0.5454 (11)	0.040 (5)*
HW1A	1.164 (3)	0.3573 (15)	0.3938 (11)	0.042 (5)*
H3B	0.234 (4)	0.3451 (15)	0.5664 (12)	0.050 (6)*
HW1B	1.080 (3)	0.4426 (17)	0.4001 (12)	0.046 (5)*
H3C	0.451 (4)	0.3683 (17)	0.5810 (12)	0.052 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0225 (6)	0.0289 (6)	0.0282 (6)	−0.0064 (5)	−0.0009 (5)	0.0005 (5)
C2	0.0210 (6)	0.0344 (7)	0.0346 (7)	0.0010 (5)	0.0081 (5)	0.0051 (5)
C3	0.0302 (6)	0.0244 (6)	0.0232 (5)	0.0014 (5)	0.0080 (5)	0.0003 (4)
C4	0.0276 (6)	0.0269 (6)	0.0261 (6)	−0.0073 (5)	0.0010 (5)	0.0004 (5)
C5	0.0187 (5)	0.0295 (6)	0.0271 (6)	−0.0010 (5)	0.0021 (4)	0.0046 (5)
C6	0.0343 (7)	0.0362 (7)	0.0287 (6)	0.0089 (6)	0.0116 (5)	0.0015 (5)
C7	0.0431 (8)	0.0345 (7)	0.0241 (6)	−0.0017 (6)	−0.0006 (5)	−0.0059 (5)
N8	0.0271 (5)	0.0236 (5)	0.0206 (5)	−0.0025 (4)	0.0031 (4)	0.0005 (4)
C8	0.0471 (8)	0.0242 (6)	0.0394 (7)	0.0014 (6)	0.0029 (6)	0.0052 (5)
N3	0.0303 (6)	0.0289 (6)	0.0267 (6)	0.0020 (5)	0.0059 (5)	0.0035 (4)
Cu1	0.01998 (8)	0.02360 (8)	0.02488 (8)	0.00238 (5)	0.00351 (6)	0.00206 (5)
Cl1	0.02233 (14)	0.03309 (16)	0.03568 (16)	−0.00169 (11)	0.00582 (11)	0.00026 (12)
Cl2	0.03173 (16)	0.03230 (16)	0.02900 (15)	−0.00508 (12)	0.00873 (12)	−0.00633 (12)
Cl3	0.03283 (16)	0.02662 (15)	0.04061 (18)	0.00540 (12)	−0.00329 (13)	0.00498 (13)
N1	0.0203 (5)	0.0242 (5)	0.0404 (6)	−0.0028 (4)	0.0033 (4)	−0.0055 (4)
O1	0.0292 (5)	0.0287 (5)	0.0280 (4)	0.0026 (4)	0.0024 (4)	0.0006 (4)
O2	0.0488 (7)	0.0601 (8)	0.0312 (5)	−0.0034 (6)	0.0087 (5)	−0.0084 (5)
O3	0.0518 (7)	0.0272 (6)	0.0952 (11)	0.0092 (5)	−0.0145 (7)	−0.0147 (6)
OW1	0.0238 (5)	0.0249 (5)	0.0342 (5)	0.0009 (4)	0.0057 (4)	0.0006 (4)

Geometric parameters (Å, º)

C1—H1	0.9800	C7—H7B	0.9700
C1—C2	1.5231 (19)	N8—C8	1.4970 (17)
C1—C7	1.5318 (19)	N8—H8	0.783 (17)
C1—N8	1.5103 (16)	C8—H8A	0.9600
C2—H2A	0.9700	C8—H8B	0.9600
C2—H2B	0.9700	C8—H8C	0.9600
C2—C3	1.5305 (18)	N3—H3A	0.85 (2)
C3—H3	0.9800	N3—H3B	0.85 (2)
C3—C4	1.5333 (18)	N3—H3C	0.83 (2)
C3—N3	1.5086 (16)	Cu1—Cl1	2.3019 (3)
C4—H4A	0.9700	Cu1—Cl2	2.5856 (4)
C4—H4B	0.9700	Cu1—Cl3	2.2499 (3)
C4—C5	1.5247 (18)	Cu1—O1	1.9923 (9)
C5—H5	0.9800	Cu1—OW1	2.0646 (10)
C5—C6	1.5313 (18)	N1—O1	1.2811 (15)
C5—N8	1.5132 (16)	N1—O2	1.2292 (17)
C6—H6A	0.9700	N1—O3	1.2289 (16)
C6—H6B	0.9700	OW1—HW1A	0.79 (2)
C6—C7	1.543 (2)	OW1—HW1B	0.79 (2)
C7—H7A	0.9700
C2—C1—H1	110.7	C6—C7—H7A	110.7
C2—C1—C7	114.95 (11)	C6—C7—H7B	110.7
C7—C1—H1	110.7	H7A—C7—H7B	108.8
N8—C1—H1	110.7	C1—N8—C5	101.59 (9)
N8—C1—C2	107.63 (10)	C1—N8—H8	110.9 (12)
N8—C1—C7	101.74 (10)	C5—N8—H8	109.7 (12)
C1—C2—H2A	108.6	C8—N8—C1	113.48 (10)
C1—C2—H2B	108.6	C8—N8—C5	113.39 (11)
C1—C2—C3	114.80 (10)	C8—N8—H8	107.7 (12)
H2A—C2—H2B	107.5	N8—C8—H8A	109.5
C3—C2—H2A	108.6	N8—C8—H8B	109.5
C3—C2—H2B	108.6	N8—C8—H8C	109.5
C2—C3—H3	106.6	H8A—C8—H8B	109.5
C2—C3—C4	112.83 (10)	H8A—C8—H8C	109.5
C4—C3—H3	106.6	H8B—C8—H8C	109.5
N3—C3—C2	111.03 (11)	C3—N3—H3A	115.4 (13)
N3—C3—H3	106.6	C3—N3—H3B	109.3 (15)
N3—C3—C4	112.70 (10)	C3—N3—H3C	109.5 (15)
C3—C4—H4A	108.6	H3A—N3—H3B	102.9 (18)
C3—C4—H4B	108.6	H3A—N3—H3C	109.8 (19)
H4A—C4—H4B	107.5	H3B—N3—H3C	110 (2)
C5—C4—C3	114.79 (10)	Cl1—Cu1—Cl2	100.684 (12)
C5—C4—H4A	108.6	Cl3—Cu1—Cl1	94.122 (14)
C5—C4—H4B	108.6	Cl3—Cu1—Cl2	105.990 (13)
C4—C5—H5	110.8	O1—Cu1—Cl1	89.92 (3)
C4—C5—C6	113.86 (11)	O1—Cu1—Cl2	84.38 (3)
C6—C5—H5	110.8	O1—Cu1—Cl3	167.91 (3)
N8—C5—C4	107.79 (10)	O1—Cu1—OW1	86.88 (4)
N8—C5—H5	110.8	OW1—Cu1—Cl1	164.17 (3)
N8—C5—C6	102.33 (10)	OW1—Cu1—Cl2	94.43 (3)
C5—C6—H6A	110.8	OW1—Cu1—Cl3	86.14 (3)
C5—C6—H6B	110.8	O2—N1—O1	118.83 (11)
C5—C6—C7	104.90 (11)	O3—N1—O1	118.42 (13)
H6A—C6—H6B	108.8	O3—N1—O2	122.75 (13)
C7—C6—H6A	110.8	N1—O1—Cu1	107.35 (8)
C7—C6—H6B	110.8	Cu1—OW1—HW1A	119.7 (15)
C1—C7—C6	105.36 (10)	Cu1—OW1—HW1B	111.5 (15)
C1—C7—H7A	110.7	HW1A—OW1—HW1B	109 (2)
C1—C7—H7B	110.7
C1—C2—C3—C4	−33.81 (15)	C6—C5—N8—C1	−46.59 (12)
C1—C2—C3—N3	93.81 (13)	C6—C5—N8—C8	75.54 (13)
C2—C1—C7—C6	86.42 (13)	C7—C1—C2—C3	−56.77 (15)
C2—C1—N8—C5	−74.06 (12)	C7—C1—N8—C5	47.14 (12)
C2—C1—N8—C8	163.87 (11)	C7—C1—N8—C8	−74.93 (13)
C2—C3—C4—C5	33.45 (15)	N8—C1—C2—C3	55.76 (14)
C3—C4—C5—C6	57.78 (14)	N8—C1—C7—C6	−29.54 (13)
C3—C4—C5—N8	−55.00 (13)	N8—C5—C6—C7	27.56 (13)
C4—C5—C6—C7	−88.46 (13)	N3—C3—C4—C5	−93.28 (13)
C4—C5—N8—C1	73.74 (12)	O2—N1—O1—Cu1	7.68 (14)
C4—C5—N8—C8	−164.13 (11)	O3—N1—O1—Cu1	−173.23 (11)
C5—C6—C7—C1	1.22 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···OW1^i	0.783 (17)	2.236 (17)	2.9600 (15)	154.0 (15)
OW1—HW1A···Cl1^ii	0.79 (2)	2.33 (2)	3.1145 (11)	172.4 (19)
OW1—HW1B···Cl2^iii	0.79 (2)	2.30 (2)	3.0851 (11)	179 (2)

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