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The experimental electron-density distributions in crystals of five chain polymers [
M(μ-
X)
2(py)
2] (
M = Zn, Cd;
X = Cl, Br; py = 3,5-substituted pyridine) have been obtained from high-resolution X-ray diffraction data sets (sin θ/λ > 1.1 Å
−1) at 100 K. Topological analyses following Bader's `Atoms in Molecules' approach not only confirmed the existence of (3, −1) critical points for the chemically reasonable and presumably strong covalent and coordinative bonds, but also for four different secondary interactions which are expected to play a role in stabilizing the polymeric structures which are unusual for Zn as the metal center. These weaker contacts comprise intra- and inter-strand C—H
X—
M hydrogen bonds on the one hand and C—
XX—C interhalogen contacts on the other hand. According to the experimental electron-density studies, the non-classical hydrogen bonds are associated with higher electron density in the (3, −1) critical points than the halogen bonds and hence are the dominant interactions both with respect to intra- and inter-chain contacts.
Supporting information
CCDC references: 760187; 760188; 760189; 760190; 760191; 760192; 760193; 760194; 760195; 760196
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b) for comp1iam, comp2iam, comp3iam, comp4iam, comp5iam; XD2006 (Volkov et al., (2006)) for comp1multi; Volkov et al., (2006) for comp2multi, comp3multi, comp4multi, comp5multi. Molecular graphics: PLATON (Spek, 2003) for comp1iam, comp1multi, comp2iam, comp3iam, comp4iam, comp5iam, comp5multi; Volkov et al., (2006) for comp2multi, comp3multi, comp4multi. Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) for comp1iam, comp1multi, comp2iam, comp3iam, comp4iam, comp5iam; Volkov et al., (2006) for comp2multi, comp3multi, comp4multi, comp5multi.
Crystal data top
C10H6Cl6N2Zn | Dx = 2.074 Mg m−3 |
Mr = 432.24 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7837 reflections |
Hall symbol: P -4 -2ab | θ = 3.0–52.6° |
a = 13.7958 (4) Å | µ = 2.91 mm−1 |
c = 3.6371 (2) Å | T = 100 K |
V = 692.23 (5) Å3 | Rod, colorless |
Z = 2 | 0.60 × 0.15 × 0.15 mm |
F(000) = 424 | |
Data collection top
CCD area detector diffractometer | 4347 independent reflections |
Radiation source: fine-focus sealed tube | 3850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ω scans | θmax = 54.4°, θmin = 3.0° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −31→31 |
Tmin = 0.241, Tmax = 0.678 | k = −31→31 |
54172 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + (0.021P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.003 |
4347 reflections | Δρmax = 0.45 e Å−3 |
46 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.014 (6) |
Crystal data top
C10H6Cl6N2Zn | Z = 2 |
Mr = 432.24 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 2.91 mm−1 |
a = 13.7958 (4) Å | T = 100 K |
c = 3.6371 (2) Å | 0.60 × 0.15 × 0.15 mm |
V = 692.23 (5) Å3 | |
Data collection top
CCD area detector diffractometer | 4347 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3850 reflections with I > 2σ(I) |
Tmin = 0.241, Tmax = 0.678 | Rint = 0.053 |
54172 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.049 | Δρmax = 0.45 e Å−3 |
S = 1.09 | Δρmin = −0.39 e Å−3 |
4347 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
46 parameters | Absolute structure parameter: 0.014 (6) |
0 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 1.0000 | 0.5000 | 0.5000 | 0.00882 (2) | |
Cl1 | 0.913154 (9) | 0.413154 (9) | 1.0000 | 0.00976 (3) | |
Cl2 | 0.608693 (11) | 0.629607 (13) | 0.75111 (6) | 0.01630 (3) | |
N1 | 0.88761 (3) | 0.61239 (3) | 0.5000 | 0.01034 (8) | |
C1 | 0.79635 (4) | 0.59074 (5) | 0.60068 (18) | 0.01091 (8) | |
H1 | 0.7804 | 0.5240 | 0.6711 | 0.014* | |
C2 | 0.72398 (5) | 0.66115 (5) | 0.60688 (18) | 0.01124 (8) | |
C3 | 0.74396 (4) | 0.75604 (4) | 0.5000 | 0.01247 (10) | |
H3 | 0.6937 | 0.8063 | 0.5000 | 0.016* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.00845 (3) | 0.00845 (3) | 0.00956 (4) | 0.00140 (3) | 0.000 | 0.000 |
Cl1 | 0.00974 (4) | 0.00974 (4) | 0.00980 (5) | −0.00107 (4) | −0.00090 (5) | 0.00090 (5) |
Cl2 | 0.00990 (5) | 0.02002 (6) | 0.01897 (6) | 0.00157 (4) | 0.00225 (6) | 0.00139 (6) |
N1 | 0.00961 (12) | 0.00961 (12) | 0.0118 (2) | 0.00165 (15) | −0.0001 (2) | −0.0001 (2) |
C1 | 0.00928 (19) | 0.0107 (2) | 0.01271 (19) | 0.00155 (15) | −0.00045 (16) | 0.00026 (17) |
C2 | 0.00935 (19) | 0.0136 (2) | 0.01079 (18) | 0.00216 (15) | −0.00019 (16) | 0.00015 (17) |
C3 | 0.01213 (15) | 0.01213 (15) | 0.0131 (2) | 0.0037 (2) | 0.0002 (2) | 0.0002 (2) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.1927 (6) | N1—C1 | 1.3449 (7) |
Zn1—N1i | 2.1927 (6) | N1—C1iv | 1.3449 (7) |
Zn1—Cl1i | 2.4856 (1) | C1—C2 | 1.3931 (9) |
Zn1—Cl1ii | 2.4856 (1) | C1—H1 | 0.9800 |
Zn1—Cl1 | 2.4856 (1) | C2—C3 | 1.3932 (8) |
Zn1—Cl1iii | 2.4856 (1) | C3—C2iv | 1.3931 (8) |
Cl2—C2 | 1.7304 (7) | C3—H3 | 0.9800 |
| | | |
N1—Zn1—N1i | 180.0 | C1—N1—Zn1 | 120.33 (4) |
N1—Zn1—Cl1i | 90.0 | C1iv—N1—Zn1 | 120.33 (4) |
N1—Zn1—Cl1ii | 90.0 | N1—C1—C2 | 121.36 (6) |
N1i—Zn1—Cl1ii | 90.0 | N1—C1—H1 | 119.3 |
Cl1i—Zn1—Cl1ii | 94.050 (7) | C2—C1—H1 | 119.3 |
Cl1i—Zn1—Cl1 | 85.951 (7) | C1—C2—C3 | 120.59 (6) |
Cl1ii—Zn1—Cl1 | 180.0 | C1—C2—Cl2 | 119.23 (5) |
N1—Zn1—Cl1iii | 90.0 | C3—C2—Cl2 | 120.18 (5) |
N1i—Zn1—Cl1iii | 90.0 | C2iv—C3—C2 | 116.72 (7) |
Zn1v—Cl1—Zn1 | 94.049 (7) | C2iv—C3—H3 | 121.6 |
C1—N1—C1iv | 119.34 (7) | C2—C3—H3 | 121.6 |
Symmetry codes: (i) −x+2, −y+1, z; (ii) −x+2, −y+1, z−1; (iii) x, y, z−1; (iv) −y+3/2, −x+3/2, −z+1; (v) x, y, z+1. |
Crystal data top
C10H6Cl6N2Zn | Dx = 2.074 Mg m−3 |
Mr = 432.24 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7837 reflections |
Hall symbol: P -4 -2ab | θ = 3.0–52.6° |
a = 13.7958 (4) Å | µ = 2.91 mm−1 |
c = 3.6371 (2) Å | T = 100 K |
V = 692.23 (5) Å3 | Rod, colorless |
Z = 2 | 0.60 × 0.15 × 0.15 mm |
F(000) = 424 | |
Data collection top
CCD area detector diffractometer | 4347 independent reflections |
Radiation source: fine-focus sealed tube | 3850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ω scans | θmax = 54.4°, θmin = 3.0° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −31→31 |
Tmin = 0.38, Tmax = 0.50 | k = −31→31 |
54172 measured reflections | l = −8→8 |
Refinement top
Refinement on F | 180 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.02 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.018 | (Δ/σ)max = 0.003 |
S = 1.75 | Δρmax = 0.11 e Å−3 |
3963 reflections | Δρmin = −0.19 e Å−3 |
Crystal data top
C10H6Cl6N2Zn | Z = 2 |
Mr = 432.24 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 2.91 mm−1 |
a = 13.7958 (4) Å | T = 100 K |
c = 3.6371 (2) Å | 0.60 × 0.15 × 0.15 mm |
V = 692.23 (5) Å3 | |
Data collection top
CCD area detector diffractometer | 4347 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3850 reflections with I > 2σ(I) |
Tmin = 0.38, Tmax = 0.50 | Rint = 0.053 |
54172 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.02 | 180 parameters |
wR(F2) = 0.018 | 0 restraints |
S = 1.75 | Δρmax = 0.11 e Å−3 |
3963 reflections | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.5 | 0 | 0.5 | 0.009 | |
Cl1 | 0.586859 (8) | 0.086859 (8) | 0 | 0.01 | |
Cl2 | 0.370387 (13) | 0.391274 (11) | 0.24873 (6) | 0.017 | |
N1 | 0.38763 (4) | 0.11237 (4) | 0.5 | 0.011 | |
C3 | 0.24388 (3) | 0.25612 (3) | 0.5 | 0.013 | |
C1 | 0.40932 (4) | 0.20365 (4) | 0.39982 (18) | 0.011 | |
C2 | 0.33884 (5) | 0.27615 (4) | 0.39285 (17) | 0.012 | |
H3 | 0.18837 | 0.311631 | 0.5 | 0.025 | |
H1 | 0.483114 | 0.216077 | 0.309848 | 0.025 | |
DUM0 | 0.5 | 0 | 0 | 0 | 0 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.00881 (3) | 0.00881 (3) | 0.00967 (4) | 0.00138 (3) | 0 | 0 |
Cl1 | 0.01022 (4) | 0.01022 (4) | 0.01010 (6) | −0.00105 (4) | 0.00098 (6) | −0.00098 (6) |
Cl2 | 0.02056 (7) | 0.01051 (5) | 0.01908 (6) | 0.00163 (5) | 0.00143 (7) | 0.00220 (6) |
N1 | 0.00983 (12) | 0.00983 (12) | 0.0128 (2) | 0.00182 (18) | 0.0008 (3) | 0.0008 (3) |
C3 | 0.01247 (14) | 0.01247 (14) | 0.0143 (2) | 0.0038 (2) | 0.0007 (3) | 0.0007 (3) |
C1 | 0.01083 (19) | 0.00947 (18) | 0.01374 (18) | 0.00152 (14) | 0.00076 (16) | −0.00003 (16) |
C2 | 0.0137 (2) | 0.00994 (18) | 0.01147 (18) | 0.00223 (15) | 0.00048 (17) | −0.00021 (16) |
Geometric parameters (Å, º) top
Zn1—Cl1 | 2.4857 (1) | C3—C2i | 1.3945 (7) |
Cl2—C2 | 1.7282 (6) | C3—H3 | 1.083 |
N1—C1 | 1.3447 (7) | C1—C2 | 1.3951 (8) |
N1—C1i | 1.3447 (7) | C1—H1 | 1.083 |
C3—C2 | 1.3945 (7) | | |
| | | |
Cl1—Zn1—Cl1ii | 94.040 (5) | N1i—C1—H1 | 116.06 |
Zn1iii—Cl1—Zn1i | 94.040 (5) | C2—C1—H1 | 122.42 |
C1—N1—C1i | 119.35 (7) | Cl2—C2—C3 | 120.23 (4) |
C2—C3—C2i | 116.77 (7) | Cl2—C2—C3i | 120.23 (4) |
C2—C3—H3 | 121.62 | Cl2—C2—C1 | 119.27 (5) |
N1—C1—C2 | 121.42 (6) | C3—C2—C1 | 120.51 (6) |
N1—C1—H1 | 116.06 | C3i—C2—C1 | 120.51 (6) |
N1i—C1—C2 | 121.42 (6) | | |
Symmetry codes: (i) −y+1/2, −x+1/2, −z+1; (ii) x, y, z+1; (iii) −y+1/2, −x+1/2, −z. |
Crystal data top
C10H6Br4Cl2N2Zn | Dx = 2.861 Mg m−3 |
Mr = 610.08 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 6095 reflections |
Hall symbol: P -4 -2ab | θ = 3.0–44.9° |
a = 13.8260 (2) Å | µ = 13.38 mm−1 |
c = 3.7044 (1) Å | T = 100 K |
V = 708.13 (2) Å3 | Rod, colourless |
Z = 2 | 0.24 × 0.09 × 0.09 mm |
F(000) = 568 | |
Data collection top
CCD area detector diffractometer | 4284 independent reflections |
Radiation source: fine-focus sealed tube | 3189 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scans | θmax = 54.5°, θmin = 3.0° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −30→31 |
Tmin = 0.151, Tmax = 0.397 | k = −28→30 |
35317 measured reflections | l = −7→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.050 | w = 1/[σ2(Fo2) + (0.015P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4284 reflections | Δρmax = 1.99 e Å−3 |
46 parameters | Δρmin = −1.23 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.002 (6) |
Crystal data top
C10H6Br4Cl2N2Zn | Z = 2 |
Mr = 610.08 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 13.38 mm−1 |
a = 13.8260 (2) Å | T = 100 K |
c = 3.7044 (1) Å | 0.24 × 0.09 × 0.09 mm |
V = 708.13 (2) Å3 | |
Data collection top
CCD area detector diffractometer | 4284 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3189 reflections with I > 2σ(I) |
Tmin = 0.151, Tmax = 0.397 | Rint = 0.074 |
35317 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.050 | Δρmax = 1.99 e Å−3 |
S = 1.02 | Δρmin = −1.23 e Å−3 |
4284 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
46 parameters | Absolute structure parameter: −0.002 (6) |
0 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.601880 (9) | 0.630241 (10) | 0.79139 (4) | 0.00951 (3) | |
Zn1 | 1.0000 | 0.5000 | 0.5000 | 0.00737 (5) | |
Cl1 | 0.91425 (2) | 0.41425 (2) | 1.0000 | 0.00815 (6) | |
N1 | 0.88778 (8) | 0.61222 (8) | 0.5000 | 0.0088 (2) | |
C1 | 0.79759 (9) | 0.59182 (9) | 0.6136 (4) | 0.00827 (19) | |
H1 | 0.7826 | 0.5281 | 0.6914 | 0.010* | |
C2 | 0.72656 (9) | 0.66163 (9) | 0.6191 (3) | 0.00796 (18) | |
C3 | 0.74504 (8) | 0.75496 (8) | 0.5000 | 0.0086 (2) | |
H3 | 0.6965 | 0.8035 | 0.5000 | 0.010* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.00631 (4) | 0.01021 (5) | 0.01202 (5) | 0.00025 (4) | 0.00118 (4) | 0.00108 (4) |
Zn1 | 0.00620 (7) | 0.00620 (7) | 0.00970 (11) | 0.00119 (8) | 0.000 | 0.000 |
Cl1 | 0.00693 (9) | 0.00693 (9) | 0.01058 (15) | −0.00050 (11) | −0.00056 (9) | 0.00056 (9) |
N1 | 0.0080 (3) | 0.0080 (3) | 0.0105 (6) | 0.0008 (4) | −0.0002 (3) | −0.0002 (3) |
C1 | 0.0060 (4) | 0.0074 (4) | 0.0114 (5) | 0.0001 (4) | −0.0004 (3) | 0.0007 (3) |
C2 | 0.0056 (4) | 0.0088 (5) | 0.0095 (5) | 0.0001 (3) | 0.0004 (3) | −0.0004 (4) |
C3 | 0.0077 (4) | 0.0077 (4) | 0.0104 (6) | 0.0019 (5) | −0.0001 (4) | −0.0001 (4) |
Geometric parameters (Å, º) top
Br1—C2 | 1.8887 (13) | N1—C1 | 1.3460 (15) |
Zn1—N1i | 2.1942 (15) | N1—C1iv | 1.3460 (15) |
Zn1—N1 | 2.1942 (15) | C1—C2 | 1.3771 (17) |
Zn1—Cl1 | 2.4984 (3) | C1—H1 | 0.9500 |
Zn1—Cl1ii | 2.4984 (3) | C2—C3 | 1.3874 (15) |
Zn1—Cl1i | 2.4984 (3) | C3—C2iv | 1.3874 (15) |
Zn1—Cl1iii | 2.4984 (3) | C3—H3 | 0.9500 |
| | | |
N1i—Zn1—N1 | 180.0 | Zn1—Cl1—Zn1v | 95.695 (14) |
N1i—Zn1—Cl1 | 90.0 | C1—N1—C1iv | 119.08 (15) |
N1—Zn1—Cl1 | 90.00 (2) | C1—N1—Zn1 | 120.46 (8) |
N1i—Zn1—Cl1ii | 90.0 | C1iv—N1—Zn1 | 120.46 (8) |
N1—Zn1—Cl1ii | 90.0 | N1—C1—C2 | 121.23 (12) |
Cl1—Zn1—Cl1ii | 95.694 (14) | N1—C1—H1 | 119.4 |
Cl1—Zn1—Cl1i | 84.306 (14) | C2—C1—H1 | 119.4 |
Cl1ii—Zn1—Cl1i | 180.0 | C1—C2—C3 | 121.05 (13) |
N1i—Zn1—Cl1iii | 90.0 | C1—C2—Br1 | 119.66 (10) |
N1—Zn1—Cl1iii | 90.0 | C3—C2—Br1 | 119.29 (10) |
Cl1—Zn1—Cl1iii | 180.0 | C2iv—C3—C2 | 116.34 (16) |
Cl1ii—Zn1—Cl1iii | 84.307 (14) | C2iv—C3—H3 | 121.8 |
Cl1i—Zn1—Cl1iii | 95.693 (14) | C2—C3—H3 | 121.8 |
Symmetry codes: (i) −x+2, −y+1, z; (ii) x, y, z−1; (iii) −x+2, −y+1, z−1; (iv) −y+3/2, −x+3/2, −z+1; (v) x, y, z+1. |
Crystal data top
C10H6Br4Cl2N2Zn | Dx = 2.861 Mg m−3 |
Mr = 610.08 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 6095 reflections |
Hall symbol: P -4 -2ab | θ = 3.0–44.9° |
a = 13.8260 (2) Å | µ = 13.38 mm−1 |
c = 3.7044 (1) Å | T = 100 K |
V = 708.13 (2) Å3 | Rod, colourless |
Z = 2 | 0.24 × 0.09 × 0.09 mm |
F(000) = 568 | |
Data collection top
CCD area detector diffractometer | 4284 independent reflections |
Radiation source: fine-focus sealed tube | 3189 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω scans | θmax = 54.5°, θmin = 3.0° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −30→31 |
Tmin = 0.151, Tmax = 0.397 | k = −28→30 |
35317 measured reflections | l = −7→8 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.017 | (Δ/σ)max < 0.001 |
S = 1.21 | Δρmax = 0.41 e Å−3 |
2834 reflections | Δρmin = −0.29 e Å−3 |
173 parameters | |
Crystal data top
C10H6Br4Cl2N2Zn | Z = 2 |
Mr = 610.08 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 13.38 mm−1 |
a = 13.8260 (2) Å | T = 100 K |
c = 3.7044 (1) Å | 0.24 × 0.09 × 0.09 mm |
V = 708.13 (2) Å3 | |
Data collection top
CCD area detector diffractometer | 4284 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3189 reflections with I > 2σ(I) |
Tmin = 0.151, Tmax = 0.397 | Rint = 0.074 |
35317 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.017 | H-atom parameters constrained |
S = 1.21 | Δρmax = 0.41 e Å−3 |
2834 reflections | Δρmin = −0.29 e Å−3 |
173 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
BR(1) | 0.601883 (10) | 0.630238 (11) | 0.79146 (4) | 0.009 | |
Zn(1) | 1 | 0.5 | 0.5 | 0.007 | |
Cl(1) | 0.91425 (2) | 0.41425 (2) | 1 | 0.008 | |
N(1) | 0.88785 (13) | 0.61215 (13) | 0.5 | 0.008 | |
C(1) | 0.79794 (14) | 0.59142 (13) | 0.6135 (5) | 0.008 | |
C(2) | 0.72650 (14) | 0.66173 (15) | 0.6205 (5) | 0.008 | |
C(3) | 0.74484 (13) | 0.75516 (13) | 0.5 | 0.009 | |
H(1) | 0.78042 | 0.518941 | 0.703111 | 0.011 | |
H(3) | 0.689453 | 0.810549 | 0.500001 | 0.011 | |
DUM0 | 1 | 0.5 | 1 | 0 | 0 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
BR(1) | 0.00606 (5) | 0.00995 (6) | 0.01161 (6) | 0.00027 (4) | 0.00116 (5) | 0.00108 (5) |
Zn(1) | 0.00604 (18) | 0.00604 (18) | 0.0085 (4) | 0.0012 (3) | 0 | 0 |
Cl(1) | 0.00677 (11) | 0.00677 (11) | 0.01004 (19) | −0.00051 (14) | −0.00048 (11) | 0.00048 (11) |
N(1) | 0.0061 (5) | 0.0061 (5) | 0.0118 (10) | 0.0009 (7) | 0.0006 (6) | 0.0006 (6) |
C(1) | 0.0059 (6) | 0.0069 (7) | 0.0116 (7) | 0.0008 (5) | 0.0002 (5) | 0.0017 (5) |
C(2) | 0.0067 (6) | 0.0073 (7) | 0.0100 (7) | 0.0000 (6) | −0.0001 (5) | −0.0001 (6) |
C(3) | 0.0069 (5) | 0.0069 (5) | 0.0122 (9) | 0.0013 (7) | 0.0008 (6) | 0.0008 (6) |
Geometric parameters (Å, º) top
Br(1)—C(2) | 1.8866 (19) | C(1)—H(1) | 1.083 |
Zn(1)—Cl(1)i | 2.4984 (3) | C(2)—C(3) | 1.390 (2) |
Cl(1)—Cl(1)ii | 3.3535 (9) | C(2)—C(3)iii | 1.390 (2) |
N(1)—C(1) | 1.343 (2) | C(3)—H(3) | 1.083 |
C(1)—C(2) | 1.386 (2) | | |
| | | |
Cl(1)i—Zn(1)—Cl(1) | 95.692 (15) | C(2)—C(1)—H(1) | 118.94 |
Cl(1)iv—Zn(1)—Cl(1)v | 180.00 (2) | Br(1)—C(2)—C(1) | 119.68 (16) |
Zn(1)—Cl(1)—Zn(1)vi | 95.692 (15) | Br(1)—C(2)—C(3) | 119.27 (15) |
C(1)—N(1)—C(1)iii | 119.5 (2) | Br(1)—C(2)—C(3)iii | 119.27 (15) |
N(1)—C(1)—C(2) | 121.0 (2) | C(1)—C(2)—C(3) | 121.0 (2) |
N(1)—C(1)—H(1) | 120.02 | C(1)—C(2)—C(3)iii | 121.0 (2) |
N(1)iii—C(1)—C(2) | 121.0 (2) | C(2)—C(3)—C(2)iii | 116.2 (2) |
N(1)iii—C(1)—H(1) | 120.02 | C(2)—C(3)—H(3) | 121.88 |
Symmetry codes: (i) x, y, z−1; (ii) −y+3/2, −x+3/2, −z+2; (iii) −y+3/2, −x+3/2, −z+1; (iv) −x+2, −y+1, z; (v) y+1/2, x−1/2, −z+1; (vi) y+1/2, x−1/2, −z+2. |
Crystal data top
C14H18Br2CdN2 | Dx = 1.968 Mg m−3 |
Mr = 486.52 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7959 reflections |
Hall symbol: P -4 -2ab | θ = 2.8–39.9° |
a = 14.4457 (3) Å | µ = 6.19 mm−1 |
c = 3.9345 (1) Å | T = 100 K |
V = 821.04 (3) Å3 | Rod, colorless |
Z = 2 | 0.28 × 0.07 × 0.07 mm |
F(000) = 468 | |
Data collection top
CCD area detector diffractometer | 5146 independent reflections |
Radiation source: fine-focus sealed tube | 3889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω scans | θmax = 54.5°, θmin = 2.8° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −32→31 |
Tmin = 0.276, Tmax = 0.671 | k = −32→30 |
45933 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.045 | w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5146 reflections | Δρmax = 1.24 e Å−3 |
47 parameters | Δρmin = −2.62 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.010 (9) |
Crystal data top
C14H18Br2CdN2 | Z = 2 |
Mr = 486.52 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 6.19 mm−1 |
a = 14.4457 (3) Å | T = 100 K |
c = 3.9345 (1) Å | 0.28 × 0.07 × 0.07 mm |
V = 821.04 (3) Å3 | |
Data collection top
CCD area detector diffractometer | 5146 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3889 reflections with I > 2σ(I) |
Tmin = 0.276, Tmax = 0.671 | Rint = 0.067 |
45933 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.045 | Δρmax = 1.24 e Å−3 |
S = 1.06 | Δρmin = −2.62 e Å−3 |
5146 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
47 parameters | Absolute structure parameter: 0.010 (9) |
0 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cd | 0.5000 | 0.0000 | 0.5000 | 0.00945 (2) | |
Br1 | 0.404724 (5) | 0.095276 (5) | 1.0000 | 0.01117 (2) | |
N | 0.61526 (5) | 0.11526 (5) | 0.5000 | 0.01338 (16) | |
C1 | 0.59616 (8) | 0.20127 (8) | 0.6038 (3) | 0.01419 (17) | |
H1 | 0.5349 | 0.2148 | 0.6768 | 0.017* | |
C2 | 0.66155 (8) | 0.27183 (8) | 0.6101 (3) | 0.01422 (18) | |
C3 | 0.75039 (6) | 0.25039 (6) | 0.5000 | 0.01605 (19) | |
H3 | 0.7969 | 0.2969 | 0.5000 | 0.019* | |
C4 | 0.63666 (11) | 0.36715 (9) | 0.7325 (4) | 0.0221 (2) | |
H4A | 0.6883 | 0.3928 | 0.8635 | 0.033* | |
H4B | 0.5815 | 0.3637 | 0.8770 | 0.033* | |
H4C | 0.6239 | 0.4071 | 0.5368 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd | 0.00905 (3) | 0.00905 (3) | 0.01024 (4) | −0.00118 (3) | 0.000 | 0.000 |
Br1 | 0.01150 (3) | 0.01150 (3) | 0.01051 (4) | 0.00262 (3) | 0.00110 (9) | 0.00110 (9) |
N | 0.0124 (2) | 0.0124 (2) | 0.0154 (4) | −0.0023 (3) | −0.0012 (8) | 0.0012 (8) |
C1 | 0.0135 (4) | 0.0123 (4) | 0.0168 (4) | −0.0025 (3) | 0.0006 (3) | 0.0002 (3) |
C2 | 0.0174 (5) | 0.0118 (4) | 0.0135 (4) | −0.0036 (3) | −0.0001 (3) | 0.0002 (3) |
C3 | 0.0166 (3) | 0.0166 (3) | 0.0149 (4) | −0.0072 (4) | 0.0001 (9) | −0.0001 (9) |
C4 | 0.0265 (7) | 0.0144 (5) | 0.0253 (6) | −0.0037 (4) | 0.0024 (5) | −0.0032 (4) |
Geometric parameters (Å, º) top
Cd—N | 2.3546 (10) | C1—H1 | 0.9500 |
Cd—Ni | 2.3547 (10) | C2—C3 | 1.3894 (14) |
Cd—Br1 | 2.7674 (1) | C2—C4 | 1.5024 (17) |
Cd—Br1ii | 2.7674 (1) | C3—C2iv | 1.3894 (14) |
Cd—Br1iii | 2.7674 (1) | C3—H3 | 0.9500 |
Cd—Br1i | 2.7674 (1) | C4—H4A | 0.9800 |
N—C1 | 1.3368 (12) | C4—H4B | 0.9800 |
N—C1iv | 1.3368 (12) | C4—H4C | 0.9800 |
C1—C2 | 1.3899 (16) | | |
| | | |
N—Cd—Ni | 180.00 (5) | C1iv—N—Cd | 120.75 (6) |
N—Cd—Br1 | 90.00 (1) | N—C1—C2 | 123.15 (11) |
Ni—Cd—Br1 | 90.00 (1) | N—C1—H1 | 118.4 |
N—Cd—Br1ii | 90.00 (1) | C2—C1—H1 | 118.4 |
Ni—Cd—Br1ii | 90.00 (1) | C1—C2—C3 | 117.30 (11) |
Br1—Cd—Br1ii | 90.610 (4) | C1—C2—C4 | 121.00 (12) |
N—Cd—Br1iii | 90.00 (1) | C3—C2—C4 | 121.69 (11) |
Ni—Cd—Br1iii | 90.00 (1) | C2—C3—C2iv | 120.60 (13) |
Br1ii—Cd—Br1iii | 89.390 (4) | C2—C3—H3 | 119.7 |
Ni—Cd—Br1i | 90.0 | C2iv—C3—H3 | 119.7 |
Br1—Cd—Br1i | 89.390 (4) | C2—C4—H4A | 109.5 |
Br1ii—Cd—Br1i | 180.000 (3) | C2—C4—H4B | 109.5 |
Br1iii—Cd—Br1i | 90.610 (4) | H4A—C4—H4B | 109.5 |
Cdv—Br1—Cd | 90.610 (4) | C2—C4—H4C | 109.5 |
C1—N—C1iv | 118.50 (12) | H4A—C4—H4C | 109.5 |
C1—N—Cd | 120.75 (6) | H4B—C4—H4C | 109.5 |
Symmetry codes: (i) −x+1, −y, z; (ii) x, y, z−1; (iii) −x+1, −y, z−1; (iv) y+1/2, x−1/2, −z+1; (v) x, y, z+1. |
Crystal data top
C14H18Br2CdN2 | Dx = 1.968 Mg m−3 |
Mr = 486.52 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7959 reflections |
Hall symbol: P -4 -2ab | θ = 2.8–39.9° |
a = 14.4457 (3) Å | µ = 6.19 mm−1 |
c = 3.9345 (1) Å | T = 100 K |
V = 821.04 (3) Å3 | Rod, colorless |
Z = 2 | 0.28 × 0.07 × 0.07 mm |
F(000) = 468 | |
Data collection top
CCD area detector diffractometer | 5146 independent reflections |
Radiation source: fine-focus sealed tube | 3889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω scans | θmax = 54.5°, θmin = 2.8° |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | h = −32→31 |
Tmin = 0.276, Tmax = 0.671 | k = −32→30 |
45933 measured reflections | l = −8→8 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.019 | (Δ/σ)max < 0.001 |
S = 1.28 | Δρmax = 0.37 e Å−3 |
3549 reflections | Δρmin = −0.14 e Å−3 |
172 parameters | |
Crystal data top
C14H18Br2CdN2 | Z = 2 |
Mr = 486.52 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 6.19 mm−1 |
a = 14.4457 (3) Å | T = 100 K |
c = 3.9345 (1) Å | 0.28 × 0.07 × 0.07 mm |
V = 821.04 (3) Å3 | |
Data collection top
CCD area detector diffractometer | 5146 independent reflections |
Absorption correction: numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | 3889 reflections with I > 2σ(I) |
Tmin = 0.276, Tmax = 0.671 | Rint = 0.067 |
45933 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.019 | H-atom parameters constrained |
S = 1.28 | Δρmax = 0.37 e Å−3 |
3549 reflections | Δρmin = −0.14 e Å−3 |
172 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cd(1) | 0.5 | 0 | 0.5 | 0.009 | |
Br(1) | 0.404714 (6) | 0.095286 (6) | 1 | 0.011 | |
N(1) | 0.61535 (10) | 0.11535 (10) | 0.5 | 0.013 | |
C(1) | 0.59600 (14) | 0.20153 (12) | 0.6029 (5) | 0.014 | |
C(2) | 0.66179 (14) | 0.27184 (13) | 0.6092 (6) | 0.014 | |
C(3) | 0.75067 (11) | 0.25067 (11) | 0.5 | 0.016 | |
C(4) | 0.63650 (17) | 0.36713 (15) | 0.7318 (6) | 0.023 | |
H(1) | 0.526272 | 0.216752 | 0.687133 | 0.017 | |
H(3) | 0.803687 | 0.303686 | 0.500001 | 0.019 | |
H(4A) | 0.693568 | 0.395448 | 0.876863 | 0.033 | |
H(4B) | 0.5757 | 0.363297 | 0.892237 | 0.033 | |
H(4C) | 0.622537 | 0.411436 | 0.515751 | 0.033 | |
DUM0 | 0.5 | 0 | 1 | 0 | 0 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd(1) | 0.00893 (4) | 0.00893 (4) | 0.01026 (6) | −0.00113 (6) | 0 | 0 |
Br(1) | 0.01150 (4) | 0.01150 (4) | 0.01057 (5) | 0.00259 (4) | 0.00127 (12) | 0.00127 (12) |
N(1) | 0.0119 (4) | 0.0119 (4) | 0.0167 (8) | −0.0028 (6) | −0.0009 (17) | 0.0009 (17) |
C(1) | 0.0135 (7) | 0.0114 (7) | 0.0179 (6) | −0.0035 (5) | 0.0016 (6) | −0.0007 (5) |
C(2) | 0.0157 (7) | 0.0112 (7) | 0.0160 (7) | −0.0032 (6) | 0.0005 (6) | −0.0002 (5) |
C(3) | 0.0162 (4) | 0.0162 (4) | 0.0156 (7) | −0.0071 (6) | 0.0013 (16) | −0.0013 (16) |
C(4) | 0.0258 (10) | 0.0155 (8) | 0.0273 (9) | −0.0049 (6) | 0.0018 (8) | −0.0052 (7) |
Geometric parameters (Å, º) top
N(1)—C(1) | 1.339 (2) | C(2)—C(4) | 1.504 (3) |
N(1)—C(1)i | 1.339 (2) | C(3)—H(3) | 1.083 |
C(1)—C(2) | 1.391 (2) | C(4)—H(4A) | 1.083 |
C(1)—H(1) | 1.083 | C(4)—H(4B) | 1.083 |
C(2)—C(3) | 1.388 (2) | C(4)—H(4C) | 1.083 |
C(2)—C(3)i | 1.388 (2) | | |
| | | |
C(1)—N(1)—C(1)i | 118.7 (2) | C(3)i—C(2)—C(4) | 121.72 (18) |
N(1)—C(1)—C(2) | 122.8 (2) | C(2)—C(3)—C(2)i | 120.2 (2) |
N(1)—C(1)—H(1) | 118.40 | C(2)—C(3)—H(3) | 119.89 |
N(1)i—C(1)—C(2) | 122.8 (2) | C(2)—C(4)—H(4A) | 109.26 |
N(1)i—C(1)—H(1) | 118.40 | C(2)—C(4)—H(4B) | 109.71 |
C(2)—C(1)—H(1) | 118.79 | C(2)—C(4)—H(4C) | 109.55 |
C(1)—C(2)—C(3) | 117.7 (2) | H(4A)—C(4)—H(4B) | 109.23 |
C(1)—C(2)—C(3)i | 117.7 (2) | H(4A)—C(4)—H(4C) | 109.4 |
C(1)—C(2)—C(4) | 120.5 (2) | H(4B)—C(4)—H(4C) | 109.7 |
C(3)—C(2)—C(4) | 121.72 (18) | | |
Symmetry code: (i) y+1/2, x−1/2, −z+1. |
Crystal data top
C10H6Br2CdCl4N2 | F(000) = 1064 |
Mr = 568.19 | Dx = 2.421 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 9254 reflections |
a = 20.0345 (5) Å | θ = 2.9–41.8° |
b = 20.4024 (6) Å | µ = 7.20 mm−1 |
c = 3.8561 (2) Å | T = 100 K |
β = 98.518 (2)° | Rod, colourless |
V = 1558.80 (10) Å3 | 0.23 × 0.07 × 0.05 mm |
Z = 4 | |
Data collection top
CCD area detector diffractometer | 8536 independent reflections |
Radiation source: fine-focus sealed tube | 6007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 52.2°, θmin = 2.9° |
Absorption correction: multi-scan SADABS (1996) | h = −44→41 |
Tmin = 0.278, Tmax = 0.702 | k = −45→43 |
39526 measured reflections | l = −7→8 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3 |
8536 reflections | (Δ/σ)max < 0.001 |
96 parameters | Δρmax = 1.35 e Å−3 |
0 restraints | Δρmin = −1.61 e Å−3 |
Crystal data top
C10H6Br2CdCl4N2 | V = 1558.80 (10) Å3 |
Mr = 568.19 | Z = 4 |
Monoclinic, C2/m | Mo Kα radiation |
a = 20.0345 (5) Å | µ = 7.20 mm−1 |
b = 20.4024 (6) Å | T = 100 K |
c = 3.8561 (2) Å | 0.23 × 0.07 × 0.05 mm |
β = 98.518 (2)° | |
Data collection top
CCD area detector diffractometer | 8536 independent reflections |
Absorption correction: multi-scan SADABS (1996) | 6007 reflections with I > 2σ(I) |
Tmin = 0.278, Tmax = 0.702 | Rint = 0.058 |
39526 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 0.96 | Δρmax = 1.35 e Å−3 |
8536 reflections | Δρmin = −1.61 e Å−3 |
96 parameters | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cd2 | 0.0000 | 0.5000 | 0.0000 | 0.00815 (3) | |
Br2 | −0.097939 (7) | 0.5000 | 0.42274 (4) | 0.01006 (3) | |
Cl2 | 0.128212 (16) | 0.241967 (14) | 0.33822 (8) | 0.01940 (6) | |
N2 | 0.0000 | 0.38317 (6) | 0.0000 | 0.0122 (2) | |
C4 | 0.05528 (6) | 0.35004 (5) | 0.1406 (3) | 0.01215 (18) | |
H4 | 0.0945 | 0.3735 | 0.2388 | 0.015* | |
C5 | 0.05604 (6) | 0.28210 (5) | 0.1450 (3) | 0.01260 (18) | |
C6 | 0.0000 | 0.24661 (7) | 0.0000 | 0.0141 (3) | |
H6 | 0.0000 | 0.2000 | 0.0000 | 0.017* | |
Cd1 | 0.0000 | 0.0000 | 0.0000 | 0.00833 (3) | |
Br1 | 0.0000 | 0.094906 (7) | 0.5000 | 0.01087 (3) | |
Cl1 | 0.254588 (16) | 0.132311 (16) | −0.12422 (9) | 0.02354 (6) | |
N1 | 0.12005 (6) | 0.0000 | 0.0589 (3) | 0.0125 (2) | |
C1 | 0.15195 (5) | 0.05676 (6) | 0.0216 (3) | 0.01333 (18) | |
H1 | 0.1300 | 0.0970 | 0.0566 | 0.016* | |
C2 | 0.21661 (6) | 0.05775 (6) | −0.0675 (3) | 0.01438 (19) | |
C3 | 0.24969 (8) | 0.0000 | −0.1191 (4) | 0.0147 (3) | |
H3 | 0.2934 | 0.0000 | −0.1872 | 0.018* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd2 | 0.00872 (6) | 0.00762 (5) | 0.00819 (6) | 0.000 | 0.00154 (4) | 0.000 |
Br2 | 0.00772 (6) | 0.01415 (6) | 0.00836 (6) | 0.000 | 0.00142 (4) | 0.000 |
Cl2 | 0.01807 (13) | 0.01373 (12) | 0.02496 (14) | 0.00476 (10) | −0.00157 (10) | 0.00268 (10) |
N2 | 0.0118 (5) | 0.0099 (5) | 0.0151 (6) | 0.000 | 0.0031 (4) | 0.000 |
C4 | 0.0125 (4) | 0.0101 (4) | 0.0140 (5) | 0.0001 (3) | 0.0024 (3) | 0.0001 (3) |
C5 | 0.0142 (5) | 0.0114 (4) | 0.0124 (4) | 0.0029 (4) | 0.0024 (3) | 0.0010 (3) |
C6 | 0.0204 (7) | 0.0086 (6) | 0.0135 (6) | 0.000 | 0.0031 (5) | 0.000 |
Cd1 | 0.00726 (6) | 0.00943 (6) | 0.00860 (6) | 0.000 | 0.00220 (4) | 0.000 |
Br1 | 0.01541 (7) | 0.00824 (6) | 0.00916 (6) | 0.000 | 0.00250 (5) | 0.000 |
Cl1 | 0.01582 (13) | 0.02229 (14) | 0.03306 (17) | −0.00652 (11) | 0.00539 (11) | 0.00490 (12) |
N1 | 0.0092 (5) | 0.0146 (6) | 0.0137 (6) | 0.000 | 0.0024 (4) | 0.000 |
C1 | 0.0098 (4) | 0.0144 (5) | 0.0158 (5) | 0.0000 (4) | 0.0021 (3) | 0.0001 (4) |
C2 | 0.0099 (4) | 0.0192 (5) | 0.0138 (5) | −0.0038 (4) | 0.0012 (3) | 0.0019 (4) |
C3 | 0.0089 (6) | 0.0245 (8) | 0.0107 (6) | 0.000 | 0.0015 (5) | 0.000 |
Geometric parameters (Å, º) top
Cd2—N2 | 2.3837 (13) | Cd1—N1v | 2.3821 (13) |
Cd2—N2i | 2.3838 (13) | Cd1—N1 | 2.3822 (13) |
Cd2—Br2 | 2.7304 (2) | Cd1—Br1vi | 2.7325 (1) |
Cd2—Br2i | 2.7304 (2) | Cd1—Br1v | 2.7325 (1) |
Cd2—Br2ii | 2.7406 (2) | Cd1—Br1ii | 2.7325 (1) |
Cd2—Br2iii | 2.7407 (2) | Cd1—Br1 | 2.7325 (1) |
Cl2—C5 | 1.7312 (11) | Cl1—C2 | 1.7292 (12) |
N2—C4iv | 1.3415 (13) | N1—C1vii | 1.3407 (13) |
N2—C4 | 1.3415 (13) | N1—C1 | 1.3407 (13) |
C4—C5 | 1.3863 (15) | C1—C2 | 1.3886 (15) |
C4—H4 | 0.9500 | C1—H1 | 0.9500 |
C5—C6 | 1.3826 (14) | C2—C3 | 1.3806 (14) |
C6—C5iv | 1.3826 (14) | C3—C2vii | 1.3806 (14) |
C6—H6 | 0.9500 | C3—H3 | 0.9500 |
| | | |
N2—Cd2—N2i | 180.0 | N1v—Cd1—N1 | 180.0 |
N2—Cd2—Br2 | 90.00 (1) | N1—Cd1—Br1vi | 92.19 (2) |
N2—Cd2—Br2i | 90.00 (1) | N1—Cd1—Br1v | 87.81 (2) |
Br2—Cd2—Br2i | 180.0 | Br1vi—Cd1—Br1v | 89.755 (5) |
N2—Cd2—Br2ii | 90.00 (1) | N1—Cd1—Br1ii | 87.81 (2) |
Br2—Cd2—Br2ii | 89.630 (5) | Br1vi—Cd1—Br1ii | 180.000 (4) |
Br2i—Cd2—Br2ii | 90.370 (5) | Br1v—Cd1—Br1ii | 90.245 (6) |
N2—Cd2—Br2iii | 90.00 (1) | N1—Cd1—Br1 | 92.19 (2) |
Br2—Cd2—Br2iii | 90.370 (5) | Br1vi—Cd1—Br1 | 90.245 (6) |
Br2i—Cd2—Br2iii | 89.630 (5) | Br1v—Cd1—Br1 | 180.0 |
Br2ii—Cd2—Br2iii | 180.0 | Br1ii—Cd1—Br1 | 89.755 (5) |
Cd2—Br2—Cd2viii | 89.630 (5) | Cd1viii—Br1—Cd1 | 89.755 (6) |
C4iv—N2—C4 | 119.49 (13) | C1vii—N1—C1 | 119.48 (13) |
C4iv—N2—Cd2 | 120.25 (7) | C1vii—N1—Cd1 | 118.71 (7) |
C4—N2—Cd2 | 120.25 (7) | C1—N1—Cd1 | 118.71 (7) |
N2—C4—C5 | 121.04 (11) | N1—C1—C2 | 121.07 (11) |
N2—C4—H4 | 119.5 | N1—C1—H1 | 119.5 |
C5—C4—H4 | 119.5 | C2—C1—H1 | 119.5 |
C6—C5—C4 | 120.79 (11) | C3—C2—C1 | 120.57 (11) |
C6—C5—Cl2 | 120.19 (9) | C3—C2—Cl1 | 120.20 (9) |
C4—C5—Cl2 | 119.02 (9) | C1—C2—Cl1 | 119.21 (9) |
C5—C6—C5iv | 116.84 (14) | C2—C3—C2vii | 117.17 (14) |
C5—C6—H6 | 121.6 | C2—C3—H3 | 121.4 |
C5iv—C6—H6 | 121.6 | C2vii—C3—H3 | 121.4 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y, z−1; (iii) −x, −y+1, −z+1; (iv) −x, y, −z; (v) −x, −y, −z; (vi) −x, −y, −z+1; (vii) x, −y, z; (viii) x, y, z+1. |
Crystal data top
C10H6Br2CdCl4N2 | F(000) = 1064 |
Mr = 568.19 | Dx = 2.421 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 9254 reflections |
a = 20.0345 (5) Å | θ = 2.9–41.8° |
b = 20.4024 (6) Å | µ = 7.20 mm−1 |
c = 3.8561 (2) Å | T = 100 K |
β = 98.518 (2)° | Rod, colourless |
V = 1558.80 (10) Å3 | 0.23 × 0.07 × 0.05 mm |
Z = 4 | |
Data collection top
CCD area detector diffractometer | 8536 independent reflections |
Radiation source: fine-focus sealed tube | 6007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 52.2°, θmin = 2.9° |
Absorption correction: multi-scan SADABS (1996) | h = −44→41 |
Tmin = 0.278, Tmax = 0.702 | k = −45→43 |
39526 measured reflections | l = −7→8 |
Refinement top
Refinement on F | 304 parameters |
Least-squares matrix: full | 0 restraints |
R[F2 > 2σ(F2)] = 0.024 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.016 | (Δ/σ)max = 0.00034 |
S = 0.96 | Δρmax = 0.51 e Å−3 |
5082 reflections | Δρmin = −0.51 e Å−3 |
Crystal data top
C10H6Br2CdCl4N2 | V = 1558.80 (10) Å3 |
Mr = 568.19 | Z = 4 |
Monoclinic, C2/m | Mo Kα radiation |
a = 20.0345 (5) Å | µ = 7.20 mm−1 |
b = 20.4024 (6) Å | T = 100 K |
c = 3.8561 (2) Å | 0.23 × 0.07 × 0.05 mm |
β = 98.518 (2)° | |
Data collection top
CCD area detector diffractometer | 8536 independent reflections |
Absorption correction: multi-scan SADABS (1996) | 6007 reflections with I > 2σ(I) |
Tmin = 0.278, Tmax = 0.702 | Rint = 0.058 |
39526 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.024 | 304 parameters |
wR(F2) = 0.016 | 0 restraints |
S = 0.96 | Δρmax = 0.51 e Å−3 |
5082 reflections | Δρmin = −0.51 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cd(2) | 0 | 0.5 | 0 | 0.008 | |
Cd(1) | 0 | 0 | 0 | 0.008 | |
Br(1) | 0 | 0.094906 (8) | 0.5 | 0.011 | |
Br(2) | −0.097946 (8) | 0.5 | 0.42275 (4) | 0.01 | |
CL(2) | 0.128242 (19) | 0.242009 (17) | 0.33837 (10) | 0.019 | |
CL(1) | 0.25458 (2) | 0.13231 (2) | −0.12441 (12) | 0.023 | |
N(2) | 0 | 0.38314 (12) | 0 | 0.012 | |
N(1) | 0.12047 (13) | 0 | 0.0605 (7) | 0.012 | |
C(4) | 0.05517 (9) | 0.35016 (9) | 0.1410 (4) | 0.013 | |
C(5) | 0.05615 (9) | 0.28189 (8) | 0.1454 (4) | 0.013 | |
C(6) | 0 | 0.24644 (12) | 0 | 0.015 | |
C(1) | 0.15185 (9) | 0.05659 (9) | 0.0229 (4) | 0.014 | |
C(2) | 0.21649 (9) | 0.05819 (9) | −0.0676 (4) | 0.014 | |
C(3) | 0.24981 (12) | 0 | −0.1198 (6) | 0.015 | |
H(4) | 0.100027 | 0.376769 | 0.252595 | 0.015 | |
H(6) | 0.00000 | 0.193358 | 0.00000 | 0.017 | |
H(1) | 0.12692 | 0.102552 | 0.061503 | 0.016 | |
H(3) | 0.299678 | 0 | −0.196408 | 0.018 | |
DUM0 | 0.055118 | 0.383132 | 0.140988 | 0 | 0 |
DUM1 | −0.097946 | 0 | 0.422758 | 0 | 0 |
DUM2 | 0 | 0.5 | 0.5 | 0 | 0 |
DUM3 | 0 | 0.094909 | 0 | 0 | 0 |
DUM4 | 0.11996 | 0.5 | 0.05929 | 0 | 0 |
DUM5 | 0.249855 | 0.5 | −0.119417 | 0 | 0 |
DUM6 | 0.299693 | 0.5 | −0.196437 | 0 | 0 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd(2) | 0.00828 (9) | 0.00724 (9) | 0.00823 (10) | 0 | 0.00145 (7) | 0 |
Cd(1) | 0.00699 (9) | 0.00900 (9) | 0.00847 (10) | 0 | 0.00204 (7) | 0 |
Br(1) | 0.01504 (8) | 0.00799 (7) | 0.00887 (8) | 0 | 0.00249 (6) | 0 |
Br(2) | 0.00751 (7) | 0.01380 (8) | 0.00805 (7) | 0 | 0.00141 (5) | 0 |
CL(2) | 0.01814 (17) | 0.01308 (16) | 0.02498 (18) | 0.00453 (13) | −0.00157 (13) | 0.00275 (12) |
CL(1) | 0.01536 (17) | 0.02229 (19) | 0.0328 (2) | −0.00622 (14) | 0.00537 (15) | 0.00483 (16) |
N(2) | 0.0117 (10) | 0.0077 (8) | 0.0169 (10) | 0 | 0.0010 (8) | 0 |
N(1) | 0.0084 (9) | 0.0122 (10) | 0.0173 (10) | 0 | 0.0044 (7) | 0 |
C(4) | 0.0122 (6) | 0.0086 (6) | 0.0163 (7) | −0.0002 (6) | 0.0009 (5) | 0.0000 (5) |
C(5) | 0.0137 (7) | 0.0096 (6) | 0.0153 (7) | 0.0021 (6) | 0.0019 (5) | 0.0006 (5) |
C(6) | 0.0193 (10) | 0.0077 (8) | 0.0161 (10) | 0 | 0.0002 (8) | 0 |
C(1) | 0.0079 (6) | 0.0132 (7) | 0.0208 (7) | −0.0007 (6) | 0.0037 (5) | 0.0002 (5) |
C(2) | 0.0099 (6) | 0.0171 (7) | 0.0169 (7) | −0.0019 (6) | 0.0034 (5) | 0.0022 (6) |
C(3) | 0.0071 (9) | 0.0222 (11) | 0.0156 (10) | 0 | 0.0034 (7) | 0 |
Geometric parameters (Å, º) top
Cl(2)—C(5) | 1.7272 (17) | C(5)—C(6) | 1.384 (2) |
Cl(1)—C(2) | 1.7225 (18) | C(5)—C(6)i | 1.384 (2) |
N(2)—C(4) | 1.339 (2) | C(6)—H(6) | 1.083 |
N(2)—C(4)i | 1.339 (2) | C(1)—C(2) | 1.391 (2) |
N(1)—C(1) | 1.333 (2) | C(1)—H(1) | 1.083 |
N(1)—C(1)ii | 1.333 (2) | C(2)—C(3) | 1.391 (2) |
C(4)—C(5) | 1.393 (2) | C(2)—C(3)ii | 1.391 (2) |
C(4)—H(4) | 1.083 | C(3)—H(3) | 1.083 |
| | | |
C(4)—N(2)—C(4)i | 119.6 (2) | C(5)—C(6)—H(6) | 121.50 |
C(1)—N(1)—C(1)ii | 120.1 (2) | N(1)—C(1)—C(2) | 121.29 (19) |
N(2)—C(4)—C(5) | 121.12 (19) | N(1)—C(1)—H(1) | 120.04 (16) |
N(2)—C(4)—H(4) | 119.73 | N(1)ii—C(1)—C(2) | 121.29 (19) |
N(2)i—C(4)—C(5) | 121.12 (19) | N(1)ii—C(1)—H(1) | 120.04 |
N(2)i—C(4)—H(4) | 119.73 | C(2)—C(1)—H(1) | 118.67 |
C(5)—C(4)—H(4) | 119.15 | CL(1)—C(2)—C(1) | 119.93 (15) |
CL(2)—C(5)—C(4) | 119.05 (15) | CL(1)—C(2)—C(3) | 119.99 (14) |
CL(2)—C(5)—C(6) | 120.40 (14) | CL(1)—C(2)—C(3)ii | 119.99 (14) |
CL(2)—C(5)—C(6)i | 120.40 (14) | C(1)—C(2)—C(3) | 120.06 (18) |
C(4)—C(5)—C(6) | 120.55 (18) | C(1)—C(2)—C(3)ii | 120.06 (18) |
C(4)—C(5)—C(6)i | 120.55 (18) | C(2)—C(3)—C(2)ii | 117.2 (2) |
C(5)—C(6)—C(5)i | 117.0 (2) | C(2)—C(3)—H(3) | 121.42 |
Symmetry codes: (i) −x, y, −z; (ii) x, −y, z. |
Crystal data top
C10H6Br6CdN2 | Dx = 3.078 Mg m−3 |
Mr = 746.03 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7789 reflections |
Hall symbol: P -4 -2ab | θ = 2.8–39.7° |
a = 14.3513 (2) Å | µ = 16.23 mm−1 |
c = 3.9082 (1) Å | T = 100 K |
V = 804.93 (3) Å3 | Rod, colourless |
Z = 2 | 0.18 × 0.06 × 0.06 mm |
F(000) = 676 | |
Data collection top
CCD area detector diffractometer | 5090 independent reflections |
Radiation source: Incoatec Microfocus Source | 4364 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.049 |
ω scans | θmax = 54.8°, θmin = 2.8° |
Absorption correction: multi-scan SADABS (1996) | h = −32→32 |
Tmin = 0.158, Tmax = 0.443 | k = −32→32 |
42311 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.051 | w = 1/[σ2(Fo2) + (0.017P)2 + 0.050P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
5090 reflections | Δρmax = 3.10 e Å−3 |
46 parameters | Δρmin = −0.86 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.030 (5) |
Crystal data top
C10H6Br6CdN2 | Z = 2 |
Mr = 746.03 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 16.23 mm−1 |
a = 14.3513 (2) Å | T = 100 K |
c = 3.9082 (1) Å | 0.18 × 0.06 × 0.06 mm |
V = 804.93 (3) Å3 | |
Data collection top
CCD area detector diffractometer | 5090 independent reflections |
Absorption correction: multi-scan SADABS (1996) | 4364 reflections with I > 2σ(I) |
Tmin = 0.158, Tmax = 0.443 | Rint = 0.049 |
42311 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.051 | Δρmax = 3.10 e Å−3 |
S = 1.03 | Δρmin = −0.86 e Å−3 |
5090 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
46 parameters | Absolute structure parameter: 0.030 (5) |
0 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cd | 0.5000 | −0.0000 | 0.5000 | 0.00838 (2) | |
Br1 | 0.405530 (7) | 0.094470 (7) | 1.0000 | 0.00990 (2) | |
Br2 | 0.632768 (9) | 0.393627 (8) | 0.76783 (4) | 0.01475 (2) | |
N | 0.61772 (6) | 0.11772 (6) | 0.5000 | 0.01188 (18) | |
C1 | 0.59743 (8) | 0.20423 (8) | 0.6049 (3) | 0.01169 (16) | |
H1 | 0.5359 | 0.2184 | 0.6775 | 0.014* | |
C2 | 0.66496 (8) | 0.27374 (8) | 0.6092 (3) | 0.01126 (15) | |
C3 | 0.75516 (7) | 0.25516 (7) | 0.5000 | 0.01203 (19) | |
H3 | 0.8020 | 0.3020 | 0.5000 | 0.014* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd | 0.00750 (3) | 0.00750 (3) | 0.01014 (4) | −0.00098 (3) | −0.000 | −0.000 |
Br1 | 0.00947 (3) | 0.00947 (3) | 0.01076 (5) | 0.00225 (4) | 0.00099 (4) | 0.00099 (4) |
Br2 | 0.01565 (5) | 0.00959 (4) | 0.01902 (5) | −0.00134 (3) | 0.00133 (4) | −0.00232 (4) |
N | 0.0101 (2) | 0.0101 (2) | 0.0155 (5) | −0.0021 (3) | −0.0004 (4) | 0.0004 (4) |
C1 | 0.0098 (4) | 0.0096 (4) | 0.0157 (4) | −0.0014 (3) | 0.0006 (3) | 0.0012 (3) |
C2 | 0.0123 (4) | 0.0087 (3) | 0.0128 (4) | −0.0015 (3) | 0.0009 (3) | −0.0002 (3) |
C3 | 0.0111 (3) | 0.0111 (3) | 0.0139 (5) | −0.0030 (4) | −0.0006 (4) | 0.0006 (4) |
Geometric parameters (Å, º) top
Cd—N | 2.3892 (12) | N—C1v | 1.3395 (14) |
Cd—Ni | 2.3892 (12) | N—C1 | 1.3395 (13) |
Cd—Br1ii | 2.7376 (1) | C1—C2 | 1.3909 (16) |
Cd—Br1i | 2.7377 (1) | C1—H1 | 0.9500 |
Cd—Br1iii | 2.7377 (1) | C2—C3 | 1.3889 (14) |
Cd—Br1 | 2.7377 (1) | C3—C2v | 1.3889 (14) |
Br1—Cdiv | 2.7376 (1) | C3—H3 | 0.9500 |
Br2—C2 | 1.8862 (12) | | |
| | | |
N—Cd—Ni | 180.0 | Br1iii—Cd—Br1 | 180.0 |
N—Cd—Br1ii | 90.0 | Cdiv—Br1—Cd | 91.088 (4) |
Ni—Cd—Br1ii | 90.0 | C1v—N—C1 | 119.78 (13) |
N—Cd—Br1i | 90.0 | C1v—N—Cd | 120.11 (7) |
Ni—Cd—Br1i | 90.0 | C1—N—Cd | 120.11 (7) |
Br1ii—Cd—Br1i | 180.0 | N—C1—C2 | 121.14 (11) |
N—Cd—Br1iii | 89.999 (1) | N—C1—H1 | 119.4 |
Ni—Cd—Br1iii | 90.00 (2) | C2—C1—H1 | 119.4 |
Br1ii—Cd—Br1iii | 88.912 (4) | C3—C2—C1 | 120.52 (11) |
Br1i—Cd—Br1iii | 91.088 (4) | C3—C2—Br2 | 120.29 (8) |
N—Cd—Br1 | 90.00 (2) | C1—C2—Br2 | 119.18 (9) |
Ni—Cd—Br1 | 90.0 | C2—C3—C2v | 116.90 (13) |
Br1ii—Cd—Br1 | 91.088 (4) | C2—C3—H3 | 121.6 |
Br1i—Cd—Br1 | 88.912 (4) | C2v—C3—H3 | 121.6 |
Symmetry codes: (i) −x+1, −y, z; (ii) x, y, z−1; (iii) −x+1, −y, z−1; (iv) x, y, z+1; (v) y+1/2, x−1/2, −z+1. |
Crystal data top
C10H6Br6CdN2 | Dx = 3.078 Mg m−3 |
Mr = 746.03 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P4b2 | Cell parameters from 7789 reflections |
a = 14.3513 (2) Å | θ = 2.8–39.7° |
c = 3.9082 (1) Å | µ = 16.23 mm−1 |
V = 804.93 (3) Å3 | T = 100 K |
Z = 2 | Rod, colourless |
F(000) = 676 | 0.18 × 0.06 × 0.06 mm |
Data collection top
CCD area detector diffractometer | 5090 independent reflections |
Radiation source: Incoatec Microfocus Source | 4364 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.049 |
ω scans | θmax = 54.8°, θmin = 2.8° |
Absorption correction: multi-scan SADABS (1996) | h = −32→32 |
Tmin = 0.158, Tmax = 0.443 | k = −32→32 |
42311 measured reflections | l = −8→8 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.021 | w1 = 1/[s2(Fo)] |
wR(F2) = 0.019 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.46 e Å−3 |
4088 reflections | Δρmin = −0.28 e Å−3 |
174 parameters | |
Crystal data top
C10H6Br6CdN2 | Z = 2 |
Mr = 746.03 | Mo Kα radiation |
Tetragonal, P4b2 | µ = 16.23 mm−1 |
a = 14.3513 (2) Å | T = 100 K |
c = 3.9082 (1) Å | 0.18 × 0.06 × 0.06 mm |
V = 804.93 (3) Å3 | |
Data collection top
CCD area detector diffractometer | 5090 independent reflections |
Absorption correction: multi-scan SADABS (1996) | 4364 reflections with I > 2σ(I) |
Tmin = 0.158, Tmax = 0.443 | Rint = 0.049 |
42311 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.021 | 0 restraints |
wR(F2) = 0.019 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.46 e Å−3 |
4088 reflections | Δρmin = −0.28 e Å−3 |
174 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
CD(1) | 0.5 | 0 | 0.5 | 0.008 | |
BR(1) | 0.405529 (6) | 0.094471 (6) | 1 | 0.010 | |
BR(2) | 0.632768 (9) | 0.393619 (8) | 0.76790 (4) | 0.015 | |
N(1) | 0.61772 (8) | 0.11772 (8) | 0.5 | 0.012 | |
C(1) | 0.59762 (9) | 0.20429 (10) | 0.6042 (4) | 0.012 | |
C(2) | 0.66479 (10) | 0.27392 (9) | 0.6091 (4) | 0.011 | |
C(3) | 0.75528 (8) | 0.25528 (8) | 0.5 | 0.012 | |
H(1) | 0.527063 | 0.220746 | 0.681774 | 0.014 | |
H(3) | 0.808639 | 0.308638 | 0.5 | 0.013 | |
DUM0 | 0.5 | 0 | 1 | 0 | 0 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
CD(1) | 0.00758 (3) | 0.00758 (3) | 0.00993 (5) | −0.00098 (4) | 0 | 0 |
BR(1) | 0.00938 (3) | 0.00938 (3) | 0.01075 (5) | 0.00226 (4) | 0.00097 (4) | 0.00097 (4) |
BR(2) | 0.01556 (5) | 0.00958 (4) | 0.01891 (5) | −0.00134 (3) | 0.00135 (4) | −0.00238 (4) |
N(1) | 0.0093 (3) | 0.0093 (3) | 0.0171 (7) | −0.0018 (4) | −0.0001 (6) | 0.0001 (6) |
C(1) | 0.0100 (4) | 0.0094 (4) | 0.0156 (5) | −0.0022 (4) | 0.0008 (4) | 0.0002 (4) |
C(2) | 0.0115 (5) | 0.0086 (4) | 0.0139 (5) | −0.0019 (4) | 0.0012 (4) | −0.0005 (4) |
C(3) | 0.0107 (3) | 0.0107 (3) | 0.0145 (6) | −0.0029 (4) | −0.0000 (6) | 0.0000 (6) |
Geometric parameters (Å, º) top
BR(2)—C(2) | 1.8834 (13) | C(1)—H(1) | 1.083 |
N(1)—C(1) | 1.3389 (16) | C(2)—C(3) | 1.3928 (16) |
N(1)—C(1)i | 1.3389 (16) | C(2)—C(3)i | 1.3928 (16) |
C(1)—C(2) | 1.3887 (18) | C(3)—H(3) | 1.083 |
| | | |
C(1)—N(1)—C(1)i | 119.49 (17) | BR(2)—C(2)—C(3) | 120.24 (10) |
N(1)—C(1)—C(2) | 121.49 (14) | BR(2)—C(2)—C(3)i | 120.24 (10) |
N(1)—C(1)—H(1) | 119.27 | C(1)—C(2)—C(3) | 120.32 (13) |
N(1)i—C(1)—C(2) | 121.49 (14) | C(1)—C(2)—C(3)i | 120.32 (13) |
N(1)i—C(1)—H(1) | 119.27 | C(2)—C(3)—C(2)i | 116.87 (15) |
C(2)—C(1)—H(1) | 119.23 | C(2)—C(3)—H(3) | 121.56 |
BR(2)—C(2)—C(1) | 119.44 (11) | | |
Symmetry code: (i) y+1/2, x−1/2, −z+1. |
Experimental details
| (comp1iam) | (comp1multi) | (comp2iam) | (comp2multi) |
Crystal data |
Chemical formula | C10H6Cl6N2Zn | C10H6Cl6N2Zn | C10H6Br4Cl2N2Zn | C10H6Br4Cl2N2Zn |
Mr | 432.24 | 432.24 | 610.08 | 610.08 |
Crystal system, space group | Tetragonal, P4b2 | Tetragonal, P4b2 | Tetragonal, P4b2 | Tetragonal, P4b2 |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 13.7958 (4), 13.7958 (4), 3.6371 (2) | 13.7958 (4), 13.7958 (4), 3.6371 (2) | 13.8260 (2), 13.8260 (2), 3.7044 (1) | 13.8260 (2), 13.8260 (2), 3.7044 (1) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 692.23 (5) | 692.23 (5) | 708.13 (2) | 708.13 (2) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 2.91 | 2.91 | 13.38 | 13.38 |
Crystal size (mm) | 0.60 × 0.15 × 0.15 | 0.60 × 0.15 × 0.15 | 0.24 × 0.09 × 0.09 | 0.24 × 0.09 × 0.09 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. |
Tmin, Tmax | 0.241, 0.678 | 0.38, 0.50 | 0.151, 0.397 | 0.151, 0.397 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 54172, 4347, 3850 | 54172, 4347, 3850 | 35317, 4284, 3189 | 35317, 4284, 3189 |
Rint | 0.053 | 0.053 | 0.074 | 0.074 |
(sin θ/λ)max (Å−1) | 1.144 | 1.144 | 1.145 | 1.145 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.049, 1.09 | 0.02, 0.018, 1.75 | 0.028, 0.050, 1.02 | 0.024, 0.017, 1.21 |
No. of reflections | 4347 | 3963 | 4284 | 2834 |
No. of parameters | 46 | 180 | 46 | 173 |
H-atom treatment | H-atom parameters constrained | ? | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.39 | 0.11, −0.19 | 1.99, −1.23 | 0.41, −0.29 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | 0.014 (6) | ? | −0.002 (6) | ? |
| (comp3iam) | (comp3multi) | (comp4iam) | (comp4multi) |
Crystal data |
Chemical formula | C14H18Br2CdN2 | C14H18Br2CdN2 | C10H6Br2CdCl4N2 | C10H6Br2CdCl4N2 |
Mr | 486.52 | 486.52 | 568.19 | 568.19 |
Crystal system, space group | Tetragonal, P4b2 | Tetragonal, P4b2 | Monoclinic, C2/m | Monoclinic, C2/m |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 14.4457 (3), 14.4457 (3), 3.9345 (1) | 14.4457 (3), 14.4457 (3), 3.9345 (1) | 20.0345 (5), 20.4024 (6), 3.8561 (2) | 20.0345 (5), 20.4024 (6), 3.8561 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 98.518 (2), 90 | 90, 98.518 (2), 90 |
V (Å3) | 821.04 (3) | 821.04 (3) | 1558.80 (10) | 1558.80 (10) |
Z | 2 | 2 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 6.19 | 6.19 | 7.20 | 7.20 |
Crystal size (mm) | 0.28 × 0.07 × 0.07 | 0.28 × 0.07 × 0.07 | 0.23 × 0.07 × 0.05 | 0.23 × 0.07 × 0.05 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | Numerical J. De Meulenaer, H. Tompa, Acta Crystallogr. 19 (1965) 1014. | Multi-scan SADABS (1996) | Multi-scan SADABS (1996) |
Tmin, Tmax | 0.276, 0.671 | 0.276, 0.671 | 0.278, 0.702 | 0.278, 0.702 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 45933, 5146, 3889 | 45933, 5146, 3889 | 39526, 8536, 6007 | 39526, 8536, 6007 |
Rint | 0.067 | 0.067 | 0.058 | 0.058 |
(sin θ/λ)max (Å−1) | 1.145 | 1.145 | 1.112 | 1.112 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.045, 1.06 | 0.024, 0.019, 1.28 | 0.031, 0.048, 0.96 | 0.024, 0.016, 0.96 |
No. of reflections | 5146 | 3549 | 8536 | 5082 |
No. of parameters | 47 | 172 | 96 | 304 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | ? |
Δρmax, Δρmin (e Å−3) | 1.24, −2.62 | 0.37, −0.14 | 1.35, −1.61 | 0.51, −0.51 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | ? | ? |
Absolute structure parameter | 0.010 (9) | ? | ? | ? |
| (comp5iam) | (comp5multi) |
Crystal data |
Chemical formula | C10H6Br6CdN2 | C10H6Br6CdN2 |
Mr | 746.03 | 746.03 |
Crystal system, space group | Tetragonal, P4b2 | Tetragonal, P4b2 |
Temperature (K) | 100 | 100 |
a, b, c (Å) | 14.3513 (2), 14.3513 (2), 3.9082 (1) | 14.3513 (2), 14.3513 (2), 3.9082 (1) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 804.93 (3) | 804.93 (3) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 16.23 | 16.23 |
Crystal size (mm) | 0.18 × 0.06 × 0.06 | 0.18 × 0.06 × 0.06 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan SADABS (1996) | Multi-scan SADABS (1996) |
Tmin, Tmax | 0.158, 0.443 | 0.158, 0.443 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42311, 5090, 4364 | 42311, 5090, 4364 |
Rint | 0.049 | 0.049 |
(sin θ/λ)max (Å−1) | 1.149 | 1.149 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.051, 1.03 | 0.021, 0.019, 1.12 |
No. of reflections | 5090 | 4088 |
No. of parameters | 46 | 174 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 3.10, −0.86 | 0.46, −0.28 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | 0.030 (5) | ? |
Selected geometric parameters (Å, º) for (comp1multi) topZn1—Cl1 | 2.4857 (1) | C3—C2i | 1.3945 (7) |
Cl2—C2 | 1.7282 (6) | C3—H3 | 1.083 |
N1—C1 | 1.3447 (7) | C1—C2 | 1.3951 (8) |
N1—C1i | 1.3447 (7) | C1—H1 | 1.083 |
C3—C2 | 1.3945 (7) | | |
| | | |
Cl1—Zn1—Cl1ii | 94.040 (5) | N1i—C1—H1 | 116.06 |
Zn1iii—Cl1—Zn1i | 94.040 (5) | C2—C1—H1 | 122.42 |
C1—N1—C1i | 119.35 (7) | Cl2—C2—C3 | 120.23 (4) |
C2—C3—C2i | 116.77 (7) | Cl2—C2—C3i | 120.23 (4) |
C2—C3—H3 | 121.62 | Cl2—C2—C1 | 119.27 (5) |
N1—C1—C2 | 121.42 (6) | C3—C2—C1 | 120.51 (6) |
N1—C1—H1 | 116.06 | C3i—C2—C1 | 120.51 (6) |
N1i—C1—C2 | 121.42 (6) | | |
Symmetry codes: (i) −y+1/2, −x+1/2, −z+1; (ii) x, y, z+1; (iii) −y+1/2, −x+1/2, −z. |
Selected geometric parameters (Å, º) for (comp2multi) topBr(1)—C(2) | 1.8866 (19) | C(1)—H(1) | 1.083 |
Zn(1)—Cl(1)i | 2.4984 (3) | C(2)—C(3) | 1.390 (2) |
Cl(1)—Cl(1)ii | 3.3535 (9) | C(2)—C(3)iii | 1.390 (2) |
N(1)—C(1) | 1.343 (2) | C(3)—H(3) | 1.083 |
C(1)—C(2) | 1.386 (2) | | |
| | | |
Cl(1)i—Zn(1)—Cl(1) | 95.692 (15) | C(2)—C(1)—H(1) | 118.94 |
Cl(1)iv—Zn(1)—Cl(1)v | 180.00 (2) | Br(1)—C(2)—C(1) | 119.68 (16) |
Zn(1)—Cl(1)—Zn(1)vi | 95.692 (15) | Br(1)—C(2)—C(3) | 119.27 (15) |
C(1)—N(1)—C(1)iii | 119.5 (2) | Br(1)—C(2)—C(3)iii | 119.27 (15) |
N(1)—C(1)—C(2) | 121.0 (2) | C(1)—C(2)—C(3) | 121.0 (2) |
N(1)—C(1)—H(1) | 120.02 | C(1)—C(2)—C(3)iii | 121.0 (2) |
N(1)iii—C(1)—C(2) | 121.0 (2) | C(2)—C(3)—C(2)iii | 116.2 (2) |
N(1)iii—C(1)—H(1) | 120.02 | C(2)—C(3)—H(3) | 121.88 |
Symmetry codes: (i) x, y, z−1; (ii) −y+3/2, −x+3/2, −z+2; (iii) −y+3/2, −x+3/2, −z+1; (iv) −x+2, −y+1, z; (v) y+1/2, x−1/2, −z+1; (vi) y+1/2, x−1/2, −z+2. |
Selected geometric parameters (Å, º) for (comp3multi) topN(1)—C(1) | 1.339 (2) | C(2)—C(4) | 1.504 (3) |
N(1)—C(1)i | 1.339 (2) | C(3)—H(3) | 1.083 |
C(1)—C(2) | 1.391 (2) | C(4)—H(4A) | 1.083 |
C(1)—H(1) | 1.083 | C(4)—H(4B) | 1.083 |
C(2)—C(3) | 1.388 (2) | C(4)—H(4C) | 1.083 |
C(2)—C(3)i | 1.388 (2) | | |
| | | |
C(1)—N(1)—C(1)i | 118.7 (2) | C(3)i—C(2)—C(4) | 121.72 (18) |
N(1)—C(1)—C(2) | 122.8 (2) | C(2)—C(3)—C(2)i | 120.2 (2) |
N(1)—C(1)—H(1) | 118.40 | C(2)—C(3)—H(3) | 119.89 |
N(1)i—C(1)—C(2) | 122.8 (2) | C(2)—C(4)—H(4A) | 109.26 |
N(1)i—C(1)—H(1) | 118.40 | C(2)—C(4)—H(4B) | 109.71 |
C(2)—C(1)—H(1) | 118.79 | C(2)—C(4)—H(4C) | 109.55 |
C(1)—C(2)—C(3) | 117.7 (2) | H(4A)—C(4)—H(4B) | 109.23 |
C(1)—C(2)—C(3)i | 117.7 (2) | H(4A)—C(4)—H(4C) | 109.4 |
C(1)—C(2)—C(4) | 120.5 (2) | H(4B)—C(4)—H(4C) | 109.7 |
C(3)—C(2)—C(4) | 121.72 (18) | | |
Symmetry code: (i) y+1/2, x−1/2, −z+1. |
Selected geometric parameters (Å, º) for (comp4multi) topCl(2)—C(5) | 1.7272 (17) | C(5)—C(6) | 1.384 (2) |
Cl(1)—C(2) | 1.7225 (18) | C(5)—C(6)i | 1.384 (2) |
N(2)—C(4) | 1.339 (2) | C(6)—H(6) | 1.083 |
N(2)—C(4)i | 1.339 (2) | C(1)—C(2) | 1.391 (2) |
N(1)—C(1) | 1.333 (2) | C(1)—H(1) | 1.083 |
N(1)—C(1)ii | 1.333 (2) | C(2)—C(3) | 1.391 (2) |
C(4)—C(5) | 1.393 (2) | C(2)—C(3)ii | 1.391 (2) |
C(4)—H(4) | 1.083 | C(3)—H(3) | 1.083 |
| | | |
C(4)—N(2)—C(4)i | 119.6 (2) | C(5)—C(6)—H(6) | 121.50 |
C(1)—N(1)—C(1)ii | 120.1 (2) | N(1)—C(1)—C(2) | 121.29 (19) |
N(2)—C(4)—C(5) | 121.12 (19) | N(1)—C(1)—H(1) | 120.04 (16) |
N(2)—C(4)—H(4) | 119.73 | N(1)ii—C(1)—C(2) | 121.29 (19) |
N(2)i—C(4)—C(5) | 121.12 (19) | N(1)ii—C(1)—H(1) | 120.04 |
N(2)i—C(4)—H(4) | 119.73 | C(2)—C(1)—H(1) | 118.67 |
C(5)—C(4)—H(4) | 119.15 | CL(1)—C(2)—C(1) | 119.93 (15) |
CL(2)—C(5)—C(4) | 119.05 (15) | CL(1)—C(2)—C(3) | 119.99 (14) |
CL(2)—C(5)—C(6) | 120.40 (14) | CL(1)—C(2)—C(3)ii | 119.99 (14) |
CL(2)—C(5)—C(6)i | 120.40 (14) | C(1)—C(2)—C(3) | 120.06 (18) |
C(4)—C(5)—C(6) | 120.55 (18) | C(1)—C(2)—C(3)ii | 120.06 (18) |
C(4)—C(5)—C(6)i | 120.55 (18) | C(2)—C(3)—C(2)ii | 117.2 (2) |
C(5)—C(6)—C(5)i | 117.0 (2) | C(2)—C(3)—H(3) | 121.42 |
Symmetry codes: (i) −x, y, −z; (ii) x, −y, z. |
Selected geometric parameters (Å, º) for (comp5multi) topBR(2)—C(2) | 1.8834 (13) | C(1)—H(1) | 1.083 |
N(1)—C(1) | 1.3389 (16) | C(2)—C(3) | 1.3928 (16) |
N(1)—C(1)i | 1.3389 (16) | C(2)—C(3)i | 1.3928 (16) |
C(1)—C(2) | 1.3887 (18) | C(3)—H(3) | 1.083 |
| | | |
C(1)—N(1)—C(1)i | 119.49 (17) | BR(2)—C(2)—C(3) | 120.24 (10) |
N(1)—C(1)—C(2) | 121.49 (14) | BR(2)—C(2)—C(3)i | 120.24 (10) |
N(1)—C(1)—H(1) | 119.27 | C(1)—C(2)—C(3) | 120.32 (13) |
N(1)i—C(1)—C(2) | 121.49 (14) | C(1)—C(2)—C(3)i | 120.32 (13) |
N(1)i—C(1)—H(1) | 119.27 | C(2)—C(3)—C(2)i | 116.87 (15) |
C(2)—C(1)—H(1) | 119.23 | C(2)—C(3)—H(3) | 121.56 |
BR(2)—C(2)—C(1) | 119.44 (11) | | |
Symmetry code: (i) y+1/2, x−1/2, −z+1. |
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