Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011045/qa0332sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011045/qa0332Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011045/qa0332IIsup3.hkl |
CCDC references: 150728; 150729
For both compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CRYSDA (Beurskens et al., 1992); data reduction: REFLEX (García-Granda et al., 2000); program(s) used to solve structure: DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and SHELXL97.
(C2N3H8)2[CuCl4] | F(000) = 716 |
Mr = 353.57 | Dx = 1.700 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.372 (3) Å | Cell parameters from 25 reflections |
b = 8.042 (2) Å | θ = 15–20° |
c = 15.621 (9) Å | µ = 2.34 mm−1 |
β = 104.71 (2)° | T = 293 K |
V = 1381.8 (9) Å3 | Prismatic, green |
Z = 4 | 0.46 × 0.26 × 0.17 mm |
Nonius CAD-4 diffractometer | 2078 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 35.0°, θmin = 2.7° |
ω–2θ scans | h = −18→17 |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | k = 0→12 |
Tmin = 0.335, Tmax = 0.672 | l = 0→25 |
3302 measured reflections | 3 standard reflections every 200 reflections |
3039 independent reflections | intensity decay: 10.9% |
Refinement on F2 | Primary atom site location: Patterson |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.09 | Calculated w = 1/[σ2(Fo2) + (0.0651P)2 + 0.3729P] where P = (Fo2 + 2Fc2)/3 |
3039 reflections | (Δ/σ)max < 0.001 |
69 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −1.41 e Å−3 |
Experimental. Nonius CAD4 single-crystal diffractometer |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.0000 | 0.15875 (4) | 0.2500 | 0.03172 (10) | |
Cl1 | 0.19436 (5) | 0.24426 (7) | 0.29103 (3) | 0.04420 (14) | |
Cl2 | 0.00624 (5) | 0.07638 (7) | 0.11282 (3) | 0.04416 (14) | |
N1 | 0.7776 (2) | 0.4536 (3) | 0.02025 (14) | 0.0515 (5) | |
H1A | 0.7981 | 0.4278 | 0.0755 | 0.062* | |
H1B | 0.7200 | 0.4003 | −0.0156 | 0.062* | |
N2 | 0.8024 (2) | 0.6138 (3) | −0.09476 (13) | 0.0482 (4) | |
H2A | 0.7446 | 0.5600 | −0.1302 | 0.058* | |
H2B | 0.8391 | 0.6927 | −0.1147 | 0.058* | |
N3 | 0.92352 (18) | 0.6583 (2) | 0.04463 (13) | 0.0440 (4) | |
H3 | 0.9628 | 0.7303 | 0.0221 | 0.053* | |
C1 | 0.83473 (18) | 0.5752 (2) | −0.00962 (13) | 0.0352 (4) | |
C2 | 0.9588 (2) | 0.6354 (3) | 0.14004 (17) | 0.0525 (6) | |
H2C | 1.0250 | 0.7085 | 0.1657 | 0.063* | |
H2D | 0.9836 | 0.5223 | 0.1535 | 0.063* | |
H2E | 0.8909 | 0.6603 | 0.1640 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03675 (17) | 0.03306 (17) | 0.02444 (14) | 0.000 | 0.00611 (11) | 0.000 |
Cl1 | 0.0403 (2) | 0.0565 (3) | 0.0336 (2) | −0.0086 (2) | 0.00535 (18) | −0.0025 (2) |
Cl2 | 0.0503 (3) | 0.0522 (3) | 0.0321 (2) | −0.0133 (2) | 0.01437 (19) | −0.01294 (19) |
N1 | 0.0556 (12) | 0.0516 (11) | 0.0413 (9) | −0.0211 (9) | 0.0010 (8) | 0.0102 (8) |
N2 | 0.0550 (11) | 0.0515 (10) | 0.0363 (8) | −0.0074 (9) | 0.0086 (8) | 0.0064 (8) |
N3 | 0.0449 (9) | 0.0452 (10) | 0.0408 (9) | −0.0111 (8) | 0.0091 (7) | 0.0012 (7) |
C1 | 0.0367 (9) | 0.0339 (9) | 0.0350 (8) | 0.0007 (7) | 0.0092 (7) | 0.0013 (7) |
C2 | 0.0540 (13) | 0.0532 (14) | 0.0438 (11) | −0.0042 (11) | 0.0004 (10) | 0.0002 (10) |
Cu1—Cl1i | 2.2471 (8) | N2—H2A | 0.8600 |
Cu1—Cl1 | 2.2471 (8) | N2—H2B | 0.8600 |
Cu1—Cl2i | 2.2610 (12) | N3—C1 | 1.323 (3) |
Cu1—Cl2 | 2.2611 (12) | N3—C2 | 1.453 (3) |
N1—C1 | 1.323 (3) | N3—H3 | 0.8600 |
N1—H1A | 0.8600 | C2—H2C | 0.9600 |
N1—H1B | 0.8600 | C2—H2D | 0.9600 |
N2—C1 | 1.324 (3) | C2—H2E | 0.9600 |
Cl1i—Cu1—Cl1 | 144.36 (4) | C1—N3—C2 | 124.0 (2) |
Cl1i—Cu1—Cl2i | 95.44 (3) | C1—N3—H3 | 118.0 |
Cl1—Cu1—Cl2i | 94.86 (3) | C2—N3—H3 | 118.0 |
Cl1i—Cu1—Cl2 | 94.85 (3) | N1—C1—N3 | 120.71 (19) |
Cl1—Cu1—Cl2 | 95.43 (3) | N1—C1—N2 | 119.5 (2) |
Cl2i—Cu1—Cl2 | 145.93 (4) | N3—C1—N2 | 119.8 (2) |
C1—N1—H1A | 120.0 | N3—C2—H2C | 109.5 |
C1—N1—H1B | 120.0 | N3—C2—H2D | 109.5 |
H1A—N1—H1B | 120.0 | H2C—C2—H2D | 109.5 |
C1—N2—H2A | 120.0 | N3—C2—H2E | 109.5 |
C1—N2—H2B | 120.0 | H2C—C2—H2E | 109.5 |
H2A—N2—H2B | 120.0 | H2D—C2—H2E | 109.5 |
C2—N3—C1—N1 | −5.5 (4) | C2—N3—C1—N2 | 174.5 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
(C8N4H14)[CuCl4] | F(000) = 748 |
Mr = 371.57 | Dx = 1.793 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.205 (7) Å | Cell parameters from 25 reflections |
b = 16.13 (3) Å | θ = 15–20° |
c = 9.391 (7) Å | µ = 2.35 mm−1 |
β = 99.24 (6)° | T = 293 K |
V = 1376 (3) Å3 | Prismatic, brown |
Z = 4 | 0.28 × 0.23 × 0.20 mm |
Nonius CAD-4 diffractometer | 2756 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 30.0°, θmin = 2.2° |
ω–2θ scans | h = −12→12 |
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995) | k = 0→22 |
Tmin = 0.532, Tmax = 0.626 | l = 0→13 |
4363 measured reflections | 3 standard reflections every 200 reflections |
3994 independent reflections | intensity decay: 3.2% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0669P)2 + 0.6687P] where P = (Fo2 + 2Fc2)/3 |
3994 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.99 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.13591 (5) | 0.05351 (3) | 0.16568 (5) | 0.03290 (14) | |
Cl1 | 0.36211 (10) | 0.05335 (6) | 0.09497 (11) | 0.0375 (2) | |
Cl2 | −0.00591 (11) | 0.12939 (6) | 0.29619 (10) | 0.0392 (2) | |
Cl3 | 0.20705 (10) | −0.03617 (6) | 0.35258 (9) | 0.0331 (2) | |
Cl4 | 0.02347 (12) | 0.10424 (8) | −0.04539 (11) | 0.0496 (3) | |
N1 | −0.6003 (3) | −0.13904 (19) | 0.1105 (3) | 0.0325 (7) | |
H1 | −0.5943 | −0.0865 | 0.1262 | 0.039* | |
N2 | −0.5172 (4) | −0.2725 (2) | 0.1767 (4) | 0.0415 (8) | |
N3 | −0.4186 (3) | −0.16079 (19) | 0.3117 (4) | 0.0363 (7) | |
N4 | −0.1283 (3) | −0.0979 (2) | 0.3738 (3) | 0.0345 (7) | |
H4A | −0.0448 | −0.0837 | 0.3416 | 0.041* | |
H4B | −0.1154 | −0.0877 | 0.4692 | 0.041* | |
C1 | −0.6969 (4) | −0.1673 (3) | −0.0006 (5) | 0.0404 (9) | |
H1A | −0.7554 | −0.1305 | −0.0609 | 0.048* | |
C2 | −0.7088 (5) | −0.2503 (3) | −0.0245 (5) | 0.0474 (11) | |
H2 | −0.7759 | −0.2723 | −0.0995 | 0.057* | |
C3 | −0.6163 (5) | −0.2998 (3) | 0.0681 (5) | 0.0468 (11) | |
H3 | −0.6234 | −0.3568 | 0.0537 | 0.056* | |
C4 | −0.5118 (4) | −0.1905 (2) | 0.1987 (4) | 0.0297 (7) | |
C5 | −0.3006 (4) | −0.2125 (3) | 0.3893 (5) | 0.0408 (9) | |
H5A | −0.3205 | −0.2703 | 0.3655 | 0.049* | |
H5B | −0.2973 | −0.2058 | 0.4924 | 0.049* | |
C6 | −0.1549 (4) | −0.1883 (3) | 0.3493 (5) | 0.0394 (9) | |
H6A | −0.0769 | −0.2197 | 0.4071 | 0.047* | |
H6B | −0.1540 | −0.2014 | 0.2486 | 0.047* | |
C7 | −0.2512 (4) | −0.0450 (2) | 0.3004 (4) | 0.0337 (8) | |
H7A | −0.2577 | −0.0496 | 0.1966 | 0.040* | |
H7B | −0.2326 | 0.0126 | 0.3270 | 0.040* | |
C8 | −0.3937 (4) | −0.0728 (2) | 0.3449 (5) | 0.0354 (8) | |
H8A | −0.3899 | −0.0638 | 0.4475 | 0.042* | |
H8B | −0.4745 | −0.0404 | 0.2940 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0332 (2) | 0.0355 (3) | 0.0303 (2) | 0.00891 (19) | 0.00621 (17) | 0.00798 (19) |
Cl1 | 0.0338 (5) | 0.0301 (5) | 0.0508 (5) | 0.0034 (4) | 0.0132 (4) | 0.0071 (4) |
Cl2 | 0.0448 (5) | 0.0387 (5) | 0.0343 (4) | 0.0119 (4) | 0.0069 (4) | 0.0002 (4) |
Cl3 | 0.0349 (4) | 0.0310 (5) | 0.0314 (4) | 0.0014 (3) | −0.0010 (3) | 0.0063 (3) |
Cl4 | 0.0472 (6) | 0.0695 (8) | 0.0323 (5) | 0.0210 (5) | 0.0069 (4) | 0.0121 (5) |
N1 | 0.0280 (15) | 0.0221 (15) | 0.0453 (18) | −0.0007 (12) | −0.0004 (13) | −0.0024 (13) |
N2 | 0.0436 (19) | 0.0213 (15) | 0.058 (2) | −0.0045 (14) | 0.0029 (16) | −0.0045 (15) |
N3 | 0.0342 (16) | 0.0211 (15) | 0.0489 (18) | −0.0024 (13) | −0.0080 (14) | −0.0006 (14) |
N4 | 0.0302 (15) | 0.0398 (19) | 0.0341 (16) | −0.0050 (13) | 0.0070 (12) | 0.0022 (13) |
C1 | 0.0298 (19) | 0.044 (2) | 0.046 (2) | 0.0006 (17) | 0.0000 (16) | −0.0059 (18) |
C2 | 0.033 (2) | 0.050 (3) | 0.057 (3) | −0.0075 (19) | 0.0015 (19) | −0.019 (2) |
C3 | 0.045 (2) | 0.028 (2) | 0.067 (3) | −0.0122 (18) | 0.009 (2) | −0.016 (2) |
C4 | 0.0253 (16) | 0.0215 (16) | 0.0427 (19) | −0.0042 (13) | 0.0068 (14) | −0.0010 (14) |
C5 | 0.040 (2) | 0.031 (2) | 0.048 (2) | −0.0013 (17) | −0.0054 (17) | 0.0111 (17) |
C6 | 0.039 (2) | 0.035 (2) | 0.044 (2) | 0.0078 (17) | 0.0054 (17) | 0.0033 (17) |
C7 | 0.042 (2) | 0.0229 (18) | 0.0341 (18) | −0.0043 (15) | 0.0008 (15) | −0.0003 (14) |
C8 | 0.0338 (19) | 0.0240 (18) | 0.045 (2) | 0.0005 (15) | −0.0030 (16) | −0.0099 (15) |
Cu1—Cl4 | 2.2386 (19) | C1—C2 | 1.359 (7) |
Cu1—Cl2 | 2.284 (2) | C1—H1A | 0.9300 |
Cu1—Cl1 | 2.2849 (19) | C2—C3 | 1.371 (7) |
Cu1—Cl3 | 2.287 (2) | C2—H2 | 0.9300 |
N1—C1 | 1.338 (5) | C3—H3 | 0.9300 |
N1—C4 | 1.349 (5) | C5—C6 | 1.501 (6) |
N1—H1 | 0.8600 | C5—H5A | 0.9700 |
N2—C3 | 1.330 (6) | C5—H5B | 0.9700 |
N2—C4 | 1.339 (5) | C6—H6A | 0.9700 |
N3—C4 | 1.341 (5) | C6—H6B | 0.9700 |
N3—C8 | 1.464 (5) | C7—C8 | 1.507 (5) |
N3—C5 | 1.467 (5) | C7—H7A | 0.9700 |
N4—C6 | 1.491 (6) | C7—H7B | 0.9700 |
N4—C7 | 1.494 (5) | C8—H8A | 0.9700 |
N4—H4A | 0.9000 | C8—H8B | 0.9700 |
N4—H4B | 0.9000 | ||
Cl4—Cu1—Cl2 | 93.23 (8) | N2—C4—N3 | 118.6 (3) |
Cl4—Cu1—Cl1 | 93.24 (7) | N2—C4—N1 | 120.6 (3) |
Cl2—Cu1—Cl1 | 141.49 (6) | N3—C4—N1 | 120.8 (3) |
Cl4—Cu1—Cl3 | 160.96 (5) | N3—C5—C6 | 110.4 (3) |
Cl2—Cu1—Cl3 | 92.58 (9) | N3—C5—H5A | 109.6 |
Cl1—Cu1—Cl3 | 93.46 (6) | C6—C5—H5A | 109.6 |
C1—N1—C4 | 122.0 (3) | N3—C5—H5B | 109.6 |
C1—N1—H1 | 119.0 | C6—C5—H5B | 109.6 |
C4—N1—H1 | 119.0 | H5A—C5—H5B | 108.1 |
C3—N2—C4 | 116.7 (4) | N4—C6—C5 | 110.3 (3) |
C4—N3—C8 | 125.0 (3) | N4—C6—H6A | 109.6 |
C4—N3—C5 | 121.2 (3) | C5—C6—H6A | 109.6 |
C8—N3—C5 | 111.6 (3) | N4—C6—H6B | 109.6 |
C6—N4—C7 | 113.2 (3) | C5—C6—H6B | 109.6 |
C6—N4—H4A | 108.9 | H6A—C6—H6B | 108.1 |
C7—N4—H4A | 108.9 | N4—C7—C8 | 109.3 (3) |
C6—N4—H4B | 108.9 | N4—C7—H7A | 109.8 |
C7—N4—H4B | 108.9 | C8—C7—H7A | 109.8 |
H4A—N4—H4B | 107.7 | N4—C7—H7B | 109.8 |
N1—C1—C2 | 119.3 (4) | C8—C7—H7B | 109.8 |
N1—C1—H1A | 120.3 | H7A—C7—H7B | 108.3 |
C2—C1—H1A | 120.3 | N3—C8—C7 | 110.1 (3) |
C1—C2—C3 | 116.4 (4) | N3—C8—H8A | 109.6 |
C1—C2—H2 | 121.8 | C7—C8—H8A | 109.6 |
C3—C2—H2 | 121.8 | N3—C8—H8B | 109.6 |
N2—C3—C2 | 125.0 (4) | C7—C8—H8B | 109.6 |
N2—C3—H3 | 117.5 | H8A—C8—H8B | 108.2 |
C2—C3—H3 | 117.5 | ||
C4—N1—C1—C2 | 1.2 (6) | C1—N1—C4—N2 | 0.6 (6) |
N1—C1—C2—C3 | −1.2 (6) | C1—N1—C4—N3 | −178.2 (4) |
C4—N2—C3—C2 | 2.2 (7) | C4—N3—C5—C6 | 104.3 (4) |
C1—C2—C3—N2 | −0.5 (7) | C8—N3—C5—C6 | −59.5 (5) |
C3—N2—C4—N3 | 176.7 (4) | C7—N4—C6—C5 | −53.4 (4) |
C3—N2—C4—N1 | −2.2 (6) | N3—C5—C6—N4 | 54.5 (4) |
C8—N3—C4—N2 | 176.1 (4) | C6—N4—C7—C8 | 54.2 (4) |
C5—N3—C4—N2 | 14.5 (6) | C4—N3—C8—C7 | −102.4 (4) |
C8—N3—C4—N1 | −5.0 (6) | C5—N3—C8—C7 | 60.7 (4) |
C5—N3—C4—N1 | −166.6 (4) | N4—C7—C8—N3 | −56.6 (4) |
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