(1,8-Dinitro-3,6,10,13,16,19-hexa­azabicyclo­[6.6.6]icosane)cobalt(III) tribromide

In the crystal structure of the title compound, [Co(C₁₄H₃₀N₈O₄)]Br₃, at 180 K, the cationic complexes lie on twofold rotation axes, and bromide anions lie either on twofold rotation axes or in general positions.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.073
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.71

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.224     0.304
            Tmin(prime) and Tmax expected:      0.288     0.304
            RR(prime) =      0.776
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT416_ALERT_2_C Short Intra D-H..H-D       H2     ..  H3      ..       1.95 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D       H4     ..  H4      ..       1.99 Ang.

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

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

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Computing details

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(1,8-Dinitro-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane)cobalt(III) tribromide

Crystal data

[Co(C14H30N8O4)]Br3	F(000) = 1336
Mr = 673.12	Dx = 1.932 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6123 reflections
a = 15.9928 (7) Å	θ = 2.6–28.2°
b = 13.4357 (6) Å	µ = 5.96 mm^−1
c = 10.7799 (4) Å	T = 180 K
β = 92.111 (2)°	Block, orange
V = 2314.75 (17) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker–Nonius X8APEX-II CCD diffractometer	2852 independent reflections
Radiation source: fine-focus sealed tube	2451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Thin–slice ω and φ scans	θmax = 28.3°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −20→21
Tmin = 0.224, Tmax = 0.304	k = −15→17
13612 measured reflections	l = −14→9

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 4.1623P] where P = (Fo^2 + 2Fc^2)/3
2852 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.64 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
Br1	0.297633 (16)	0.435631 (19)	0.08264 (3)	0.03095 (9)
Br2	0.5000	0.06221 (3)	0.7500	0.03222 (11)
Co1	0.5000	0.25871 (3)	0.2500	0.01618 (11)
O1	0.31094 (14)	0.2213 (2)	0.6336 (2)	0.0538 (7)
O2	0.40819 (13)	0.31934 (16)	0.70047 (17)	0.0388 (5)
N1	0.37558 (14)	0.26563 (17)	0.62128 (19)	0.0288 (5)
N2	0.56089 (12)	0.25333 (15)	0.41178 (17)	0.0199 (4)
H2	0.5990	0.3057	0.4115	0.024*
N3	0.42727 (12)	0.36563 (14)	0.30822 (18)	0.0202 (4)
H3	0.3853	0.3727	0.2468	0.024*
N4	0.42042 (12)	0.15676 (15)	0.30474 (17)	0.0194 (4)
H4	0.4481	0.0962	0.2982	0.023*
C1	0.41822 (15)	0.25953 (18)	0.4961 (2)	0.0224 (5)
C2	0.51175 (15)	0.26740 (19)	0.5249 (2)	0.0236 (5)
H2A	0.5245	0.3336	0.5611	0.028*
H2B	0.5285	0.2164	0.5872	0.028*
C3	0.61227 (16)	0.16043 (19)	0.4146 (2)	0.0251 (5)
H3A	0.5767	0.1017	0.4296	0.030*
H3B	0.6564	0.1641	0.4812	0.030*
C4	0.38323 (16)	0.34964 (19)	0.4255 (2)	0.0250 (5)
H4A	0.3228	0.3395	0.4064	0.030*
H4B	0.3894	0.4096	0.4784	0.030*
C5	0.47545 (16)	0.46083 (18)	0.3076 (2)	0.0246 (5)
H5A	0.4368	0.5184	0.3076	0.029*
H5B	0.5135	0.4651	0.3820	0.029*
C6	0.39209 (16)	0.16133 (19)	0.4348 (2)	0.0241 (5)
H6A	0.4168	0.1052	0.4831	0.029*
H6B	0.3304	0.1548	0.4348	0.029*
C7	0.34939 (16)	0.1530 (2)	0.2103 (2)	0.0253 (5)
H7A	0.3104	0.2091	0.2226	0.030*
H7B	0.3181	0.0898	0.2173	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02818 (15)	0.02857 (15)	0.03497 (16)	−0.00588 (10)	−0.01428 (11)	0.00917 (10)
Br2	0.0487 (2)	0.01810 (18)	0.0301 (2)	0.000	0.00455 (16)	0.000
Co1	0.0195 (2)	0.0159 (2)	0.0129 (2)	0.000	−0.00330 (15)	0.000
O1	0.0383 (12)	0.0900 (19)	0.0341 (12)	−0.0228 (13)	0.0161 (9)	−0.0210 (12)
O2	0.0489 (12)	0.0467 (12)	0.0207 (9)	−0.0020 (10)	0.0017 (8)	−0.0118 (8)
N1	0.0335 (12)	0.0358 (12)	0.0172 (10)	0.0069 (10)	0.0020 (8)	−0.0007 (8)
N2	0.0230 (10)	0.0213 (10)	0.0153 (9)	0.0014 (8)	−0.0030 (7)	0.0014 (7)
N3	0.0239 (10)	0.0190 (9)	0.0174 (9)	0.0011 (8)	−0.0046 (7)	−0.0009 (7)
N4	0.0225 (10)	0.0201 (10)	0.0154 (9)	−0.0007 (8)	−0.0004 (7)	−0.0020 (7)
C1	0.0250 (12)	0.0281 (12)	0.0142 (11)	0.0024 (10)	0.0011 (9)	−0.0032 (9)
C2	0.0268 (12)	0.0285 (13)	0.0153 (11)	0.0007 (10)	−0.0017 (9)	−0.0006 (9)
C3	0.0271 (13)	0.0272 (13)	0.0206 (12)	0.0068 (10)	−0.0038 (9)	0.0045 (9)
C4	0.0275 (13)	0.0264 (13)	0.0210 (12)	0.0042 (10)	0.0009 (9)	−0.0031 (9)
C5	0.0280 (13)	0.0171 (11)	0.0281 (13)	0.0015 (10)	−0.0055 (10)	−0.0042 (9)
C6	0.0281 (13)	0.0272 (13)	0.0172 (11)	−0.0033 (10)	0.0032 (9)	0.0003 (9)
C7	0.0240 (12)	0.0311 (13)	0.0205 (12)	−0.0069 (10)	−0.0029 (9)	−0.0021 (9)

Geometric parameters (Å, º)

Co1—N3^i	1.966 (2)	C1—C2	1.520 (3)
Co1—N3	1.966 (2)	C1—C4	1.525 (3)
Co1—N2	1.9672 (19)	C1—C6	1.527 (3)
Co1—N2^i	1.9672 (19)	C2—H2A	0.990
Co1—N4^i	1.975 (2)	C2—H2B	0.990
Co1—N4	1.975 (2)	C3—C7^i	1.503 (3)
O1—N1	1.205 (3)	C3—H3A	0.990
O2—N1	1.220 (3)	C3—H3B	0.990
N1—C1	1.536 (3)	C4—H4A	0.990
N2—C2	1.487 (3)	C4—H4B	0.990
N2—C3	1.494 (3)	C5—C5^i	1.493 (5)
N2—H2	0.930	C5—H5A	0.990
N3—C4	1.486 (3)	C5—H5B	0.990
N3—C5	1.493 (3)	C6—H6A	0.990
N3—H3	0.930	C6—H6B	0.990
N4—C6	1.491 (3)	C7—C3^i	1.503 (3)
N4—C7	1.498 (3)	C7—H7A	0.990
N4—H4	0.930	C7—H7B	0.990
N3—Co1—N3^i	86.10 (12)	C2—C1—N1	106.42 (18)
N3^i—Co1—N2	91.74 (8)	C4—C1—N1	103.25 (19)
N3—Co1—N2	91.33 (8)	C6—C1—N1	107.6 (2)
N3^i—Co1—N2^i	91.33 (8)	N2—C2—C1	111.71 (18)
N3—Co1—N2^i	91.74 (8)	N2—C2—H2A	109.3
N2—Co1—N2^i	175.79 (12)	C1—C2—H2A	109.3
N3^i—Co1—N4^i	90.91 (8)	N2—C2—H2B	109.3
N3—Co1—N4^i	176.15 (8)	C1—C2—H2B	109.3
N2—Co1—N4^i	86.33 (8)	H2A—C2—H2B	107.9
N2^i—Co1—N4^i	90.75 (8)	N2—C3—C7^i	106.24 (19)
N3^i—Co1—N4	176.16 (8)	N2—C3—H3A	110.5
N3—Co1—N4	90.92 (8)	C7^i—C3—H3A	110.5
N2—Co1—N4	90.75 (8)	N2—C3—H3B	110.5
N2^i—Co1—N4	86.33 (8)	C7^i—C3—H3B	110.5
N4—Co1—N4^i	92.17 (12)	H3A—C3—H3B	108.7
O1—N1—O2	124.2 (2)	N3—C4—C1	111.27 (19)
O1—N1—C1	118.8 (2)	N3—C4—H4A	109.4
O2—N1—C1	117.0 (2)	C1—C4—H4A	109.4
C2—N2—C3	113.37 (18)	N3—C4—H4B	109.4
C2—N2—Co1	117.57 (14)	C1—C4—H4B	109.4
C3—N2—Co1	107.61 (14)	H4A—C4—H4B	108.0
C2—N2—H2	105.8	C5^i—C5—N3	106.92 (15)
C3—N2—H2	105.8	C5^i—C5—H5A	110.3
Co1—N2—H2	105.8	N3—C5—H5A	110.3
C4—N3—C5	112.87 (18)	C5^i—C5—H5B	110.3
C4—N3—Co1	118.08 (15)	N3—C5—H5B	110.3
C5—N3—Co1	108.23 (15)	H5A—C5—H5B	108.6
C4—N3—H3	105.5	N4—C6—C1	110.78 (19)
C5—N3—H3	105.5	N4—C6—H6A	109.5
Co1—N3—H3	105.5	C1—C6—H6A	109.5
C6—N4—C7	113.06 (19)	N4—C6—H6B	109.5
C6—N4—Co1	118.30 (14)	C1—C6—H6B	109.5
C7—N4—Co1	107.52 (14)	H6A—C6—H6B	108.1
C6—N4—H4	105.7	N4—C7—C3^i	106.40 (19)
C7—N4—H4	105.7	N4—C7—H7A	110.4
Co1—N4—H4	105.7	C3^i—C7—H7A	110.4
C2—C1—C4	112.8 (2)	N4—C7—H7B	110.4
C2—C1—C6	113.6 (2)	C3^i—C7—H7B	110.4
C4—C1—C6	112.36 (19)	H7A—C7—H7B	108.6
N3^i—Co1—N2—C2	123.71 (17)	O1—N1—C1—C4	92.5 (3)
N3—Co1—N2—C2	37.57 (17)	O2—N1—C1—C4	−84.4 (3)
N4^i—Co1—N2—C2	−145.48 (17)	O1—N1—C1—C6	−26.5 (3)
N4—Co1—N2—C2	−53.36 (17)	O2—N1—C1—C6	156.6 (2)
N3^i—Co1—N2—C3	−106.86 (16)	C3—N2—C2—C1	−113.2 (2)
N3—Co1—N2—C3	167.00 (16)	Co1—N2—C2—C1	13.5 (3)
N4^i—Co1—N2—C3	−16.05 (16)	C4—C1—C2—N2	−72.6 (2)
N4—Co1—N2—C3	76.07 (16)	C6—C1—C2—N2	56.7 (3)
N3^i—Co1—N3—C4	−144.2 (2)	N1—C1—C2—N2	174.88 (18)
N2—Co1—N3—C4	−52.56 (17)	C2—N2—C3—C7^i	174.60 (19)
N2^i—Co1—N3—C4	124.56 (17)	Co1—N2—C3—C7^i	42.8 (2)
N4—Co1—N3—C4	38.21 (17)	C5—N3—C4—C1	−114.9 (2)
N3^i—Co1—N3—C5	−14.46 (11)	Co1—N3—C4—C1	12.7 (3)
N2—Co1—N3—C5	77.20 (15)	C2—C1—C4—N3	56.8 (3)
N2^i—Co1—N3—C5	−105.68 (15)	C6—C1—C4—N3	−73.1 (3)
N4—Co1—N3—C5	167.97 (15)	N1—C1—C4—N3	171.23 (19)
N3—Co1—N4—C6	−52.01 (17)	C4—N3—C5—C5^i	173.0 (2)
N2—Co1—N4—C6	39.34 (17)	Co1—N3—C5—C5^i	40.4 (2)
N2^i—Co1—N4—C6	−143.70 (18)	C7—N4—C6—C1	−115.7 (2)
N4^i—Co1—N4—C6	125.69 (19)	Co1—N4—C6—C1	11.2 (3)
N3—Co1—N4—C7	77.53 (16)	C2—C1—C6—N4	−71.1 (3)
N2—Co1—N4—C7	168.87 (15)	C4—C1—C6—N4	58.4 (3)
N2^i—Co1—N4—C7	−14.16 (15)	N1—C1—C6—N4	171.41 (19)
N4^i—Co1—N4—C7	−104.77 (16)	C6—N4—C7—C3^i	173.72 (19)
O1—N1—C1—C2	−148.6 (3)	Co1—N4—C7—C3^i	41.3 (2)
O2—N1—C1—C2	34.5 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1^i	0.93	2.40	3.333 (2)	177
N3—H3···Br1	0.93	2.37	3.275 (2)	163
N4—H4···Br2^ii	0.93	2.35	3.268 (2)	169

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