Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113029533/fm3015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba2pic_100k_1-1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba3pic100k1121apr_0msup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015br3p14jan_0msup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba24lutsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba25lut_100k_11aug_0msup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba_35lutsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba_3br4mepyrsup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba23lutsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113029533/fm3015ba_2br3mepyrsup9.hkl |
CCDC references: 968745; 968746; 968747; 968748; 968749; 968750; 968751; 968752; 968753
For all compounds, data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 (Bruker, 2009); data reduction: APEX2 (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) for ba2pic_100k_1-1, ba24lut, ba_3br4mepyr; SHELXL97 (Sheldrick, 2008) for ba3pic100k1121apr_0m, br3p14jan_0m, ba25lut_100k_11aug_0m, ba_35lut, ba23lut, ba_2br3mepyr.
2C6H8N+·C6Br2O42− | Z = 4 |
Mr = 484.15 | F(000) = 960 |
Monoclinic, P21/c | Dx = 1.799 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.3604 (13) Å | µ = 4.56 mm−1 |
b = 7.7452 (6) Å | T = 100 K |
c = 14.3658 (9) Å | Block, purple |
β = 100.911 (3)° | 0.3 × 0.25 × 0.15 mm |
V = 1787.4 (2) Å3 |
Bruker APEXII CCD area-detector diffractometer | 3506 reflections with I > 2σ(I) |
CCD; rotation images scans | Rint = 0.056 |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | θmax = 29.4°, θmin = 1.3° |
Tmin = 0.567, Tmax = 1.000 | h = −22→22 |
20956 measured reflections | k = −10→10 |
4883 independent reflections | l = −19→17 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
4883 reflections | Δρmax = 0.64 e Å−3 |
245 parameters | Δρmin = −0.45 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C14 | 0.37734 (17) | 0.6533 (4) | 0.6404 (2) | 0.0225 (6) | |
H14 | 0.3549 | 0.6463 | 0.6951 | 0.027* | |
N2 | 0.47738 (15) | 0.7632 (3) | 0.55824 (16) | 0.0154 (5) | |
H2 | 0.5221 (18) | 0.819 (3) | 0.555 (2) | 0.014 (8)* | |
C13 | 0.44575 (17) | 0.7605 (3) | 0.6381 (2) | 0.0182 (6) | |
C16 | 0.37626 (17) | 0.5683 (3) | 0.4798 (2) | 0.0198 (6) | |
H16 | 0.353 | 0.5058 | 0.426 | 0.024* | |
C17 | 0.44378 (18) | 0.6720 (3) | 0.4803 (2) | 0.0190 (6) | |
H17 | 0.467 | 0.6799 | 0.4261 | 0.023* | |
C15 | 0.34340 (18) | 0.5586 (4) | 0.5619 (2) | 0.0228 (6) | |
H15 | 0.298 | 0.4873 | 0.5637 | 0.027* | |
C18 | 0.48453 (18) | 0.8700 (4) | 0.7190 (2) | 0.0233 (6) | |
H18A | 0.518 | 0.7995 | 0.7665 | 0.035* | |
H18B | 0.4418 | 0.9256 | 0.7457 | 0.035* | |
H18C | 0.5189 | 0.956 | 0.6974 | 0.035* | |
Br1 | 0.77406 (2) | 1.20048 (3) | 0.68748 (2) | 0.01821 (8) | |
Br2 | 0.69958 (2) | 0.79178 (3) | 0.26985 (2) | 0.01666 (8) | |
O3 | 0.59107 (12) | 0.8222 (2) | 0.42497 (13) | 0.0183 (4) | |
O1 | 0.87359 (12) | 1.1929 (2) | 0.52699 (13) | 0.0204 (4) | |
O2 | 0.84955 (12) | 1.0180 (3) | 0.36536 (13) | 0.0235 (5) | |
O4 | 0.62485 (11) | 0.9647 (2) | 0.59632 (13) | 0.0184 (4) | |
C5 | 0.65969 (16) | 0.8970 (3) | 0.44594 (18) | 0.0136 (5) | |
C6 | 0.67803 (17) | 0.9850 (3) | 0.54532 (18) | 0.0143 (5) | |
C4 | 0.71999 (16) | 0.9081 (3) | 0.38883 (18) | 0.0147 (5) | |
C2 | 0.80862 (16) | 1.1020 (3) | 0.50893 (18) | 0.0154 (5) | |
C1 | 0.75152 (17) | 1.0828 (3) | 0.56894 (18) | 0.0151 (5) | |
C3 | 0.79362 (16) | 1.0039 (3) | 0.41342 (18) | 0.0151 (5) | |
N1 | 0.96988 (16) | 1.2838 (3) | 0.40231 (18) | 0.0191 (5) | |
H1 | 0.934 (3) | 1.254 (5) | 0.426 (3) | 0.058 (14)* | |
C10 | 1.09443 (19) | 1.2292 (4) | 0.3478 (2) | 0.0225 (6) | |
H10 | 1.1357 | 1.1531 | 0.3371 | 0.027* | |
C9 | 1.09745 (17) | 1.4029 (4) | 0.32392 (18) | 0.0206 (6) | |
H9 | 1.1408 | 1.4444 | 0.2966 | 0.025* | |
C8 | 1.03543 (17) | 1.5140 (3) | 0.34108 (18) | 0.0191 (6) | |
H8 | 1.0379 | 1.6305 | 0.3262 | 0.023* | |
C7 | 0.97025 (17) | 1.4529 (3) | 0.37997 (18) | 0.0166 (5) | |
C11 | 1.02907 (18) | 1.1726 (3) | 0.3874 (2) | 0.0202 (6) | |
H11 | 1.0258 | 1.057 | 0.4039 | 0.024* | |
C12 | 0.89918 (18) | 1.5601 (4) | 0.3976 (2) | 0.0241 (6) | |
H12A | 0.8514 | 1.5385 | 0.3489 | 0.036* | |
H12B | 0.9139 | 1.6801 | 0.397 | 0.036* | |
H12C | 0.8865 | 1.531 | 0.4582 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C14 | 0.0175 (15) | 0.0271 (15) | 0.0244 (16) | 0.0084 (12) | 0.0076 (12) | 0.0078 (13) |
N2 | 0.0142 (12) | 0.0156 (11) | 0.0167 (12) | 0.0021 (9) | 0.0037 (9) | 0.0031 (9) |
C13 | 0.0193 (15) | 0.0181 (13) | 0.0176 (14) | 0.0080 (10) | 0.0046 (11) | 0.0043 (11) |
C16 | 0.0147 (14) | 0.0196 (13) | 0.0248 (15) | 0.0022 (11) | 0.0028 (11) | 0.0003 (11) |
C17 | 0.0188 (15) | 0.0183 (13) | 0.0201 (15) | 0.0065 (11) | 0.0038 (11) | 0.0032 (11) |
C15 | 0.0176 (15) | 0.0217 (14) | 0.0305 (17) | 0.0022 (11) | 0.0081 (12) | 0.0073 (12) |
C18 | 0.0213 (16) | 0.0280 (15) | 0.0206 (15) | 0.0060 (12) | 0.0036 (11) | 0.0019 (13) |
Br1 | 0.02134 (16) | 0.02129 (14) | 0.01274 (14) | −0.00143 (11) | 0.00508 (10) | −0.00220 (11) |
Br2 | 0.01661 (15) | 0.01926 (13) | 0.01452 (14) | −0.00167 (11) | 0.00401 (10) | −0.00316 (11) |
O3 | 0.0170 (10) | 0.0197 (10) | 0.0187 (10) | −0.0032 (8) | 0.0046 (8) | −0.0016 (8) |
O1 | 0.0224 (11) | 0.0223 (10) | 0.0176 (10) | −0.0088 (8) | 0.0069 (8) | −0.0054 (8) |
O2 | 0.0206 (11) | 0.0298 (11) | 0.0226 (11) | −0.0077 (9) | 0.0103 (8) | −0.0060 (9) |
O4 | 0.0168 (10) | 0.0237 (10) | 0.0166 (10) | −0.0008 (8) | 0.0078 (8) | 0.0018 (8) |
C5 | 0.0127 (13) | 0.0112 (11) | 0.0170 (13) | 0.0037 (10) | 0.0028 (10) | 0.0028 (10) |
C6 | 0.0184 (15) | 0.0126 (11) | 0.0127 (13) | 0.0040 (10) | 0.0043 (10) | 0.0039 (10) |
C4 | 0.0160 (14) | 0.0172 (12) | 0.0108 (13) | −0.0002 (10) | 0.0024 (10) | −0.0006 (10) |
C2 | 0.0169 (14) | 0.0139 (12) | 0.0155 (13) | 0.0023 (10) | 0.0030 (10) | 0.0011 (10) |
C1 | 0.0206 (15) | 0.0148 (12) | 0.0111 (13) | 0.0009 (10) | 0.0057 (10) | −0.0010 (10) |
C3 | 0.0159 (14) | 0.0157 (12) | 0.0145 (13) | −0.0005 (10) | 0.0046 (10) | 0.0004 (10) |
N1 | 0.0160 (13) | 0.0221 (12) | 0.0198 (13) | −0.0042 (10) | 0.0050 (10) | 0.0015 (10) |
C10 | 0.0236 (16) | 0.0272 (15) | 0.0156 (14) | 0.0044 (12) | 0.0011 (11) | −0.0013 (12) |
C9 | 0.0181 (15) | 0.0298 (15) | 0.0141 (14) | −0.0074 (12) | 0.0036 (10) | 0.0014 (12) |
C8 | 0.0224 (15) | 0.0179 (13) | 0.0152 (14) | −0.0029 (11) | −0.0005 (11) | −0.0002 (11) |
C7 | 0.0177 (14) | 0.0198 (13) | 0.0109 (13) | −0.0004 (11) | −0.0010 (10) | −0.0002 (10) |
C11 | 0.0210 (15) | 0.0169 (13) | 0.0217 (15) | −0.0009 (11) | 0.0021 (11) | 0.0015 (11) |
C12 | 0.0243 (16) | 0.0285 (15) | 0.0177 (15) | 0.0033 (12) | −0.0005 (12) | −0.0033 (12) |
C14—C15 | 1.371 (4) | C5—C4 | 1.400 (4) |
C14—C13 | 1.399 (4) | C5—C6 | 1.559 (4) |
C14—H14 | 0.93 | C6—C1 | 1.407 (4) |
N2—C13 | 1.346 (3) | C4—C3 | 1.402 (4) |
N2—C17 | 1.350 (4) | C2—C1 | 1.394 (4) |
N2—H2 | 0.86 (3) | C2—C3 | 1.547 (4) |
C13—C18 | 1.481 (4) | N1—C11 | 1.343 (4) |
C16—C17 | 1.365 (4) | N1—C7 | 1.349 (3) |
C16—C15 | 1.388 (4) | N1—H1 | 0.77 (4) |
C16—H16 | 0.93 | C10—C11 | 1.375 (4) |
C17—H17 | 0.93 | C10—C9 | 1.392 (4) |
C15—H15 | 0.93 | C10—H10 | 0.93 |
C18—H18A | 0.96 | C9—C8 | 1.387 (4) |
C18—H18B | 0.96 | C9—H9 | 0.93 |
C18—H18C | 0.96 | C8—C7 | 1.378 (4) |
Br1—C1 | 1.905 (2) | C8—H8 | 0.93 |
Br2—C4 | 1.905 (3) | C7—C12 | 1.489 (4) |
O3—C5 | 1.249 (3) | C11—H11 | 0.93 |
O1—C2 | 1.260 (3) | C12—H12A | 0.96 |
O2—C3 | 1.251 (3) | C12—H12B | 0.96 |
O4—C6 | 1.249 (3) | C12—H12C | 0.96 |
C15—C14—C13 | 120.0 (3) | O1—C2—C1 | 124.8 (2) |
C15—C14—H14 | 120 | O1—C2—C3 | 116.3 (2) |
C13—C14—H14 | 120 | C1—C2—C3 | 118.9 (2) |
C13—N2—C17 | 122.5 (3) | C2—C1—C6 | 123.4 (2) |
C13—N2—H2 | 121.9 (19) | C2—C1—Br1 | 117.56 (19) |
C17—N2—H2 | 115.5 (19) | C6—C1—Br1 | 119.02 (19) |
N2—C13—C14 | 117.9 (3) | O2—C3—C4 | 126.2 (2) |
N2—C13—C18 | 118.9 (3) | O2—C3—C2 | 115.9 (2) |
C14—C13—C18 | 123.2 (3) | C4—C3—C2 | 117.9 (2) |
C17—C16—C15 | 118.1 (3) | C11—N1—C7 | 123.3 (3) |
C17—C16—H16 | 121 | C11—N1—H1 | 121 (3) |
C15—C16—H16 | 121 | C7—N1—H1 | 116 (3) |
N2—C17—C16 | 121.0 (3) | C11—C10—C9 | 118.5 (3) |
N2—C17—H17 | 119.5 | C11—C10—H10 | 120.8 |
C16—C17—H17 | 119.5 | C9—C10—H10 | 120.8 |
C14—C15—C16 | 120.6 (3) | C8—C9—C10 | 119.6 (3) |
C14—C15—H15 | 119.7 | C8—C9—H9 | 120.2 |
C16—C15—H15 | 119.7 | C10—C9—H9 | 120.2 |
C13—C18—H18A | 109.5 | C7—C8—C9 | 120.5 (3) |
C13—C18—H18B | 109.5 | C7—C8—H8 | 119.7 |
H18A—C18—H18B | 109.5 | C9—C8—H8 | 119.7 |
C13—C18—H18C | 109.5 | N1—C7—C8 | 117.9 (3) |
H18A—C18—H18C | 109.5 | N1—C7—C12 | 117.5 (3) |
H18B—C18—H18C | 109.5 | C8—C7—C12 | 124.5 (3) |
O3—C5—C4 | 126.0 (2) | N1—C11—C10 | 120.2 (3) |
O3—C5—C6 | 115.6 (2) | N1—C11—H11 | 119.9 |
C4—C5—C6 | 118.4 (2) | C10—C11—H11 | 119.9 |
O4—C6—C1 | 125.8 (2) | C7—C12—H12A | 109.5 |
O4—C6—C5 | 116.6 (2) | C7—C12—H12B | 109.5 |
C1—C6—C5 | 117.6 (2) | H12A—C12—H12B | 109.5 |
C5—C4—C3 | 123.5 (2) | C7—C12—H12C | 109.5 |
C5—C4—Br2 | 118.27 (19) | H12A—C12—H12C | 109.5 |
C3—C4—Br2 | 118.22 (19) | H12B—C12—H12C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4 | 0.86 (3) | 2.02 (3) | 2.838 (3) | 159 (3) |
N2—H2···O3 | 0.86 (3) | 2.36 (3) | 2.946 (3) | 126 (2) |
N1—H1···O1 | 0.77 (4) | 1.96 (4) | 2.693 (3) | 160 (4) |
N1—H1···O2 | 0.77 (4) | 2.36 (4) | 2.828 (3) | 121 (4) |
2C6H8N+·C6Br2O42− | Z = 2 |
Mr = 484.15 | F(000) = 480 |
Monoclinic, P21/c | Dx = 1.846 Mg m−3 |
a = 8.9526 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6149 (8) Å | µ = 4.68 mm−1 |
c = 10.4275 (8) Å | T = 100 K |
β = 103.935 (4)° | Block, purple |
V = 871.17 (12) Å3 | 0.3 × 0.25 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 2018 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
CCD; rotation images scans | θmax = 28.9°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −12→12 |
Tmin = 0.671, Tmax = 1.000 | k = −13→11 |
9784 measured reflections | l = −11→14 |
2280 independent reflections |
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)] = 0.023 | Hydrogen site location: mixed |
wR(F2) = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0286P)2 + 0.5432P] where P = (Fo2 + 2Fc2)/3 |
2280 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
H5 | 0.893 (4) | 0.515 (3) | 0.285 (3) | 0.057 (10)* | |
Br1 | 0.43444 (2) | 0.23608 (2) | 0.18610 (2) | 0.01678 (7) | |
O1 | 0.71755 (15) | 0.42622 (14) | 0.21943 (13) | 0.0185 (3) | |
O2 | 0.23321 (14) | 0.35789 (14) | −0.07254 (14) | 0.0182 (3) | |
C1 | 0.4732 (2) | 0.38635 (18) | 0.07990 (18) | 0.0137 (3) | |
C3 | 0.3575 (2) | 0.41949 (18) | −0.03428 (18) | 0.0136 (3) | |
C6 | 1.2623 (2) | 0.61801 (19) | 0.47325 (18) | 0.0158 (4) | |
H6 | 1.3581 | 0.6454 | 0.5237 | 0.019* | |
C2 | 0.6123 (2) | 0.45631 (18) | 0.11904 (18) | 0.0135 (3) | |
N1 | 0.98369 (19) | 0.53679 (17) | 0.32431 (16) | 0.0179 (3) | |
C4 | 0.9917 (2) | 0.64850 (19) | 0.40243 (19) | 0.0160 (4) | |
H4 | 0.9021 | 0.6963 | 0.4047 | 0.019* | |
C5 | 1.1315 (2) | 0.69418 (19) | 0.47996 (18) | 0.0141 (3) | |
C7 | 1.2510 (2) | 0.5025 (2) | 0.39267 (19) | 0.0181 (4) | |
H7 | 1.3384 | 0.4521 | 0.3886 | 0.022* | |
C9 | 1.1387 (2) | 0.8178 (2) | 0.5686 (2) | 0.0210 (4) | |
H9A | 1.1519 | 0.9007 | 0.5213 | 0.031* | |
H9B | 1.2239 | 0.8077 | 0.6441 | 0.031* | |
H9C | 1.0448 | 0.8242 | 0.5974 | 0.031* | |
C8 | 1.1086 (2) | 0.4633 (2) | 0.31852 (19) | 0.0195 (4) | |
H8 | 1.0992 | 0.3854 | 0.2642 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01435 (10) | 0.01840 (11) | 0.01676 (11) | −0.00363 (7) | 0.00212 (7) | 0.00366 (7) |
O1 | 0.0149 (6) | 0.0217 (7) | 0.0159 (7) | −0.0044 (5) | −0.0021 (5) | 0.0023 (5) |
O2 | 0.0133 (6) | 0.0184 (7) | 0.0207 (7) | −0.0043 (5) | −0.0004 (5) | 0.0005 (5) |
C1 | 0.0145 (8) | 0.0134 (8) | 0.0136 (9) | −0.0027 (6) | 0.0042 (7) | 0.0001 (7) |
C3 | 0.0129 (8) | 0.0138 (8) | 0.0138 (9) | −0.0005 (6) | 0.0027 (6) | −0.0032 (7) |
C6 | 0.0113 (8) | 0.0192 (9) | 0.0159 (9) | −0.0013 (7) | 0.0011 (7) | 0.0013 (7) |
C2 | 0.0136 (8) | 0.0142 (8) | 0.0127 (8) | −0.0006 (6) | 0.0034 (7) | −0.0025 (7) |
N1 | 0.0150 (8) | 0.0223 (8) | 0.0138 (8) | −0.0055 (6) | −0.0016 (6) | 0.0051 (6) |
C4 | 0.0127 (8) | 0.0177 (9) | 0.0168 (9) | 0.0015 (7) | 0.0023 (7) | 0.0072 (7) |
C5 | 0.0151 (8) | 0.0138 (8) | 0.0140 (9) | −0.0009 (7) | 0.0044 (7) | 0.0035 (7) |
C7 | 0.0175 (9) | 0.0182 (9) | 0.0190 (9) | 0.0034 (7) | 0.0055 (7) | 0.0016 (7) |
C9 | 0.0212 (9) | 0.0177 (9) | 0.0259 (11) | 0.0002 (7) | 0.0091 (8) | −0.0029 (8) |
C8 | 0.0258 (10) | 0.0172 (9) | 0.0151 (9) | −0.0035 (7) | 0.0044 (8) | −0.0009 (7) |
Br1—C1 | 1.9025 (18) | N1—C4 | 1.339 (3) |
O1—C2 | 1.262 (2) | N1—H5 | 0.85 (3) |
O2—C3 | 1.238 (2) | C4—C5 | 1.387 (3) |
C1—C2 | 1.387 (2) | C4—H4 | 0.9300 |
C1—C3 | 1.414 (2) | C5—C9 | 1.498 (3) |
C3—C2i | 1.548 (3) | C7—C8 | 1.375 (3) |
C6—C7 | 1.381 (3) | C7—H7 | 0.9300 |
C6—C5 | 1.397 (3) | C9—H9A | 0.9600 |
C6—H6 | 0.9300 | C9—H9B | 0.9600 |
C2—C3i | 1.548 (3) | C9—H9C | 0.9600 |
N1—C8 | 1.336 (3) | C8—H8 | 0.9300 |
C2—C1—C3 | 124.22 (16) | C5—C4—H4 | 119.4 |
C2—C1—Br1 | 118.27 (13) | C4—C5—C6 | 117.00 (17) |
C3—C1—Br1 | 117.51 (13) | C4—C5—C9 | 120.62 (17) |
O2—C3—C1 | 125.66 (17) | C6—C5—C9 | 122.36 (16) |
O2—C3—C2i | 116.88 (16) | C8—C7—C6 | 118.99 (18) |
C1—C3—C2i | 117.47 (15) | C8—C7—H7 | 120.5 |
C7—C6—C5 | 120.83 (17) | C6—C7—H7 | 120.5 |
C7—C6—H6 | 119.6 | C5—C9—H9A | 109.5 |
C5—C6—H6 | 119.6 | C5—C9—H9B | 109.5 |
O1—C2—C1 | 124.82 (17) | H9A—C9—H9B | 109.5 |
O1—C2—C3i | 116.88 (15) | C5—C9—H9C | 109.5 |
C1—C2—C3i | 118.30 (15) | H9A—C9—H9C | 109.5 |
C8—N1—C4 | 121.90 (16) | H9B—C9—H9C | 109.5 |
C8—N1—H5 | 124 (2) | N1—C8—C7 | 120.14 (18) |
C4—N1—H5 | 114 (2) | N1—C8—H8 | 119.9 |
N1—C4—C5 | 121.13 (17) | C7—C8—H8 | 119.9 |
N1—C4—H4 | 119.4 | ||
C2—C1—C3—O2 | 179.04 (18) | C8—N1—C4—C5 | 0.9 (3) |
Br1—C1—C3—O2 | −1.0 (3) | N1—C4—C5—C6 | −0.4 (3) |
C2—C1—C3—C2i | −1.2 (3) | N1—C4—C5—C9 | −178.95 (17) |
Br1—C1—C3—C2i | 178.77 (12) | C7—C6—C5—C4 | −0.1 (3) |
C3—C1—C2—O1 | −178.72 (18) | C7—C6—C5—C9 | 178.45 (18) |
Br1—C1—C2—O1 | 1.4 (3) | C5—C6—C7—C8 | 0.1 (3) |
C3—C1—C2—C3i | 1.2 (3) | C4—N1—C8—C7 | −0.9 (3) |
Br1—C1—C2—C3i | −178.76 (12) | C6—C7—C8—N1 | 0.4 (3) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H5···O1 | 0.84 (3) | 1.78 (3) | 2.598 (2) | 165 (3) |
N1—H5···O2i | 0.84 (3) | 2.54 (3) | 3.039 (2) | 119 (3) |
C4—H4···Br1ii | 0.93 | 2.96 | 3.7977 (18) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2. |
2C6H8N+·C6Br2O42− | Z = 2 |
Mr = 484.15 | F(000) = 480 |
Monoclinic, P21/c | Dx = 1.817 Mg m−3 |
a = 8.1345 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.1517 (6) Å | µ = 4.61 mm−1 |
c = 17.7868 (17) Å | T = 100 K |
β = 96.177 (7)° | Block, purple |
V = 884.90 (15) Å3 | 0.35 × 0.25 × 0.2 mm |
Bruker APEXII CCD area-detector diffractometer | 2464 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
CCD; rotation images scans | θmax = 32.8°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −11→12 |
Tmin = 0.576, Tmax = 1.000 | k = −9→8 |
14105 measured reflections | l = −26→25 |
3234 independent reflections |
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)] = 0.034 | Hydrogen site location: mixed |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.040P)2 + 0.2356P] where P = (Fo2 + 2Fc2)/3 |
3234 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
H3 | −0.105 (4) | 0.310 (6) | −0.2171 (19) | 0.047 (10)* | |
Br1 | 0.25110 (3) | 0.07121 (3) | 0.02493 (2) | 0.01863 (8) | |
O1 | 0.07011 (19) | 0.2668 (2) | −0.12123 (8) | 0.0186 (3) | |
O2 | −0.1218 (2) | 0.6144 (3) | −0.14197 (9) | 0.0189 (3) | |
C3 | −0.0715 (3) | 0.5690 (3) | −0.07520 (12) | 0.0154 (4) | |
C5 | −0.3229 (3) | −0.0633 (3) | −0.26829 (13) | 0.0196 (4) | |
H5 | −0.3546 | −0.2000 | −0.2528 | 0.024* | |
C6 | −0.2127 (3) | 0.0570 (4) | −0.22235 (13) | 0.0215 (5) | |
H6 | −0.1685 | 0.0014 | −0.1759 | 0.026* | |
C2 | 0.0452 (2) | 0.3690 (3) | −0.06305 (12) | 0.0146 (4) | |
N1 | −0.1680 (3) | 0.2553 (3) | −0.24406 (11) | 0.0214 (4) | |
C4 | −0.3880 (3) | 0.0175 (4) | −0.33817 (13) | 0.0176 (4) | |
C1 | 0.1120 (3) | 0.3196 (3) | 0.01073 (12) | 0.0157 (4) | |
C7 | −0.2265 (3) | 0.3409 (4) | −0.31087 (13) | 0.0213 (4) | |
H7 | −0.1925 | 0.4781 | −0.3247 | 0.026* | |
C8 | −0.3370 (3) | 0.2240 (4) | −0.35860 (12) | 0.0195 (4) | |
H8 | −0.3783 | 0.2827 | −0.4050 | 0.023* | |
C9 | −0.5047 (3) | −0.1147 (4) | −0.39065 (15) | 0.0275 (5) | |
H9A | −0.4464 | −0.1745 | −0.4300 | 0.041* | |
H9B | −0.5930 | −0.0237 | −0.4126 | 0.041* | |
H9C | −0.5494 | −0.2306 | −0.3630 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02148 (12) | 0.01545 (11) | 0.01885 (12) | 0.00438 (8) | 0.00160 (8) | 0.00058 (8) |
O1 | 0.0216 (8) | 0.0192 (7) | 0.0148 (7) | 0.0018 (6) | 0.0013 (6) | −0.0037 (6) |
O2 | 0.0247 (8) | 0.0181 (7) | 0.0134 (7) | 0.0011 (6) | −0.0003 (6) | 0.0014 (6) |
C3 | 0.0152 (10) | 0.0133 (9) | 0.0176 (10) | −0.0028 (7) | 0.0019 (8) | 0.0003 (8) |
C5 | 0.0230 (11) | 0.0147 (10) | 0.0222 (11) | 0.0006 (8) | 0.0080 (9) | 0.0022 (8) |
C6 | 0.0255 (12) | 0.0250 (12) | 0.0141 (10) | 0.0041 (9) | 0.0021 (9) | 0.0035 (8) |
C2 | 0.0130 (9) | 0.0139 (9) | 0.0168 (9) | −0.0020 (7) | 0.0015 (8) | −0.0001 (8) |
N1 | 0.0219 (10) | 0.0261 (11) | 0.0165 (9) | −0.0058 (8) | 0.0030 (8) | −0.0047 (8) |
C4 | 0.0155 (10) | 0.0185 (10) | 0.0196 (10) | 0.0018 (8) | 0.0048 (8) | −0.0046 (8) |
C1 | 0.0151 (10) | 0.0125 (9) | 0.0193 (10) | 0.0015 (7) | 0.0001 (8) | 0.0000 (8) |
C7 | 0.0251 (11) | 0.0171 (11) | 0.0221 (11) | −0.0041 (9) | 0.0045 (9) | 0.0014 (9) |
C8 | 0.0212 (11) | 0.0211 (11) | 0.0160 (10) | 0.0010 (8) | 0.0016 (8) | 0.0039 (8) |
C9 | 0.0214 (12) | 0.0289 (12) | 0.0319 (13) | −0.0045 (9) | 0.0015 (10) | −0.0092 (10) |
Br1—C1 | 1.902 (2) | N1—C7 | 1.339 (3) |
O1—C2 | 1.246 (2) | N1—H3 | 0.74 (3) |
O2—C3 | 1.246 (3) | C4—C8 | 1.396 (3) |
C3—C1i | 1.405 (3) | C4—C9 | 1.498 (3) |
C3—C2 | 1.554 (3) | C1—C3i | 1.405 (3) |
C5—C6 | 1.364 (3) | C7—C8 | 1.372 (3) |
C5—C4 | 1.390 (3) | C7—H7 | 0.9300 |
C5—H5 | 0.9300 | C8—H8 | 0.9300 |
C6—N1 | 1.341 (3) | C9—H9A | 0.9600 |
C6—H6 | 0.9300 | C9—H9B | 0.9600 |
C2—C1 | 1.399 (3) | C9—H9C | 0.9600 |
O2—C3—C1i | 125.9 (2) | C8—C4—C9 | 121.2 (2) |
O2—C3—C2 | 116.31 (18) | C2—C1—C3i | 123.93 (19) |
C1i—C3—C2 | 117.75 (18) | C2—C1—Br1 | 117.69 (15) |
C6—C5—C4 | 120.3 (2) | C3i—C1—Br1 | 118.15 (15) |
C6—C5—H5 | 119.9 | N1—C7—C8 | 119.3 (2) |
C4—C5—H5 | 119.9 | N1—C7—H7 | 120.3 |
N1—C6—C5 | 120.1 (2) | C8—C7—H7 | 120.3 |
N1—C6—H6 | 119.9 | C7—C8—C4 | 120.6 (2) |
C5—C6—H6 | 119.9 | C7—C8—H8 | 119.7 |
O1—C2—C1 | 126.0 (2) | C4—C8—H8 | 119.7 |
O1—C2—C3 | 115.80 (18) | C4—C9—H9A | 109.5 |
C1—C2—C3 | 118.17 (18) | C4—C9—H9B | 109.5 |
C7—N1—C6 | 122.1 (2) | H9A—C9—H9B | 109.5 |
C7—N1—H3 | 123 (3) | C4—C9—H9C | 109.5 |
C6—N1—H3 | 115 (3) | H9A—C9—H9C | 109.5 |
C5—C4—C8 | 117.6 (2) | H9B—C9—H9C | 109.5 |
C5—C4—C9 | 121.2 (2) | ||
C4—C5—C6—N1 | 0.8 (3) | O1—C2—C1—C3i | −175.6 (2) |
O2—C3—C2—O1 | −3.6 (3) | C3—C2—C1—C3i | 4.4 (3) |
C1i—C3—C2—O1 | 175.83 (19) | O1—C2—C1—Br1 | −1.1 (3) |
O2—C3—C2—C1 | 176.4 (2) | C3—C2—C1—Br1 | 178.82 (14) |
C1i—C3—C2—C1 | −4.1 (3) | C6—N1—C7—C8 | 0.7 (3) |
C5—C6—N1—C7 | −1.0 (3) | N1—C7—C8—C4 | −0.2 (3) |
C6—C5—C4—C8 | −0.3 (3) | C5—C4—C8—C7 | 0.0 (3) |
C6—C5—C4—C9 | 177.9 (2) | C9—C4—C8—C7 | −178.2 (2) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H3···O1 | 0.74 (3) | 2.12 (3) | 2.760 (3) | 145 (4) |
N1—H3···O2 | 0.74 (3) | 2.31 (3) | 2.859 (3) | 131 (3) |
C7H10N+·C6HBr2O4− | Z = 4 |
Mr = 405.04 | F(000) = 792 |
Monoclinic, P21/c | Dx = 1.962 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2948 (2) Å | µ = 5.92 mm−1 |
b = 12.1560 (4) Å | T = 100 K |
c = 13.9544 (5) Å | Block, purple |
β = 102.966 (2)° | 0.25 × 0.2 × 0.1 mm |
V = 1371.17 (8) Å3 |
Bruker APEXII CCD area-detector diffractometer | 4537 reflections with I > 2σ(I) |
CCD; rotation images scans | Rint = 0.042 |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | θmax = 36.0°, θmin = 2.3° |
Tmin = 0.631, Tmax = 1.000 | h = −13→12 |
22482 measured reflections | k = −20→19 |
6064 independent reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
6064 reflections | Δρmax = 0.85 e Å−3 |
191 parameters | Δρmin = −0.56 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9045 (2) | 0.19237 (15) | 0.55371 (13) | 0.0139 (3) | |
C6 | 1.0303 (2) | 0.18822 (15) | 0.49598 (13) | 0.0143 (3) | |
C5 | 1.00553 (19) | 0.10938 (15) | 0.40704 (12) | 0.0128 (3) | |
C4 | 0.8566 (2) | 0.05013 (15) | 0.38346 (12) | 0.0128 (3) | |
C3 | 0.73806 (19) | 0.05285 (15) | 0.44130 (12) | 0.0124 (3) | |
C2 | 0.77015 (19) | 0.12614 (15) | 0.53102 (12) | 0.0122 (3) | |
O1 | 0.65618 (16) | 0.12722 (12) | 0.58359 (10) | 0.0172 (3) | |
O2 | 0.60467 (15) | 0.00124 (12) | 0.42410 (9) | 0.0180 (3) | |
Br2 | 0.81175 (2) | −0.03915 (2) | 0.26962 (2) | 0.01608 (5) | |
O3 | 1.12026 (14) | 0.10678 (11) | 0.36234 (9) | 0.0160 (3) | |
O4 | 1.15299 (15) | 0.24626 (13) | 0.51291 (10) | 0.0211 (3) | |
Br1 | 0.93387 (2) | 0.29327 (2) | 0.65786 (2) | 0.01894 (5) | |
C7 | 0.4727 (2) | 0.23284 (18) | 0.31075 (13) | 0.0184 (4) | |
C8 | 0.6120 (2) | 0.29544 (18) | 0.30788 (15) | 0.0226 (4) | |
H8 | 0.6627 | 0.2868 | 0.2553 | 0.027* | |
C9 | 0.6772 (2) | 0.37030 (18) | 0.38125 (17) | 0.0246 (4) | |
C10 | 0.5959 (2) | 0.38279 (17) | 0.45817 (17) | 0.0233 (4) | |
H10 | 0.6353 | 0.4328 | 0.5084 | 0.028* | |
C11 | 0.4577 (2) | 0.32110 (17) | 0.45937 (15) | 0.0195 (4) | |
H11 | 0.4038 | 0.3295 | 0.5106 | 0.023* | |
N1 | 0.39987 (18) | 0.24877 (15) | 0.38719 (12) | 0.0157 (3) | |
C13 | 0.8327 (3) | 0.4343 (2) | 0.3811 (2) | 0.0379 (6) | |
H13A | 0.9259 | 0.3972 | 0.4213 | 0.057* | |
H13B | 0.8235 | 0.5067 | 0.4068 | 0.057* | |
H13C | 0.8478 | 0.4397 | 0.315 | 0.057* | |
C12 | 0.4002 (2) | 0.1503 (2) | 0.23501 (14) | 0.0271 (5) | |
H12A | 0.352 | 0.0916 | 0.2651 | 0.041* | |
H12B | 0.4854 | 0.1214 | 0.2056 | 0.041* | |
H12C | 0.3164 | 0.1846 | 0.1853 | 0.041* | |
H1 | 0.595 (4) | 0.091 (3) | 0.565 (2) | 0.050 (10)* | |
H2 | 0.332 (3) | 0.211 (2) | 0.3888 (18) | 0.023 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0158 (7) | 0.0135 (9) | 0.0136 (7) | −0.0006 (6) | 0.0059 (6) | −0.0020 (6) |
C6 | 0.0143 (7) | 0.0151 (9) | 0.0141 (7) | −0.0005 (6) | 0.0046 (6) | −0.0010 (6) |
C5 | 0.0135 (6) | 0.0135 (9) | 0.0117 (7) | 0.0013 (6) | 0.0030 (5) | 0.0020 (6) |
C4 | 0.0152 (6) | 0.0128 (9) | 0.0107 (7) | −0.0010 (6) | 0.0034 (5) | −0.0008 (6) |
C3 | 0.0147 (7) | 0.0115 (8) | 0.0113 (7) | −0.0002 (6) | 0.0032 (5) | 0.0006 (6) |
C2 | 0.0130 (6) | 0.0113 (8) | 0.0134 (7) | −0.0007 (6) | 0.0055 (5) | 0.0000 (6) |
O1 | 0.0162 (5) | 0.0178 (7) | 0.0205 (6) | −0.0055 (5) | 0.0100 (5) | −0.0057 (6) |
O2 | 0.0168 (5) | 0.0204 (7) | 0.0178 (6) | −0.0071 (5) | 0.0060 (5) | −0.0027 (5) |
Br2 | 0.01998 (8) | 0.01664 (10) | 0.01232 (8) | −0.00307 (6) | 0.00512 (6) | −0.00285 (6) |
O3 | 0.0151 (5) | 0.0199 (7) | 0.0146 (6) | −0.0007 (5) | 0.0065 (4) | −0.0012 (5) |
O4 | 0.0179 (6) | 0.0250 (8) | 0.0229 (7) | −0.0080 (5) | 0.0097 (5) | −0.0073 (6) |
Br1 | 0.02109 (9) | 0.01842 (10) | 0.02018 (9) | −0.00729 (7) | 0.01073 (7) | −0.00876 (7) |
C7 | 0.0149 (7) | 0.0253 (11) | 0.0158 (8) | 0.0077 (7) | 0.0052 (6) | 0.0057 (7) |
C8 | 0.0162 (7) | 0.0307 (12) | 0.0236 (9) | 0.0079 (7) | 0.0103 (7) | 0.0126 (8) |
C9 | 0.0157 (7) | 0.0214 (11) | 0.0390 (11) | 0.0032 (7) | 0.0109 (7) | 0.0132 (9) |
C10 | 0.0179 (8) | 0.0169 (10) | 0.0365 (11) | −0.0020 (7) | 0.0091 (7) | −0.0020 (9) |
C11 | 0.0191 (7) | 0.0170 (10) | 0.0251 (9) | 0.0001 (7) | 0.0107 (7) | −0.0008 (8) |
N1 | 0.0138 (6) | 0.0166 (8) | 0.0181 (7) | −0.0002 (6) | 0.0065 (5) | 0.0023 (6) |
C13 | 0.0202 (9) | 0.0312 (14) | 0.0657 (18) | 0.0011 (9) | 0.0168 (10) | 0.0192 (13) |
C12 | 0.0233 (9) | 0.0417 (14) | 0.0159 (8) | 0.0069 (9) | 0.0037 (7) | −0.0048 (9) |
C1—C2 | 1.353 (2) | C3—C2 | 1.511 (2) |
C1—C6 | 1.455 (2) | C2—O1 | 1.3204 (19) |
C1—Br1 | 1.8753 (18) | C7—N1 | 1.352 (2) |
C6—O4 | 1.217 (2) | C7—C8 | 1.392 (3) |
C6—C5 | 1.545 (2) | C7—C12 | 1.483 (3) |
C5—O3 | 1.2499 (19) | C8—C9 | 1.386 (3) |
C5—C4 | 1.404 (2) | C9—C10 | 1.398 (3) |
C4—C3 | 1.405 (2) | C9—C13 | 1.506 (3) |
C4—Br2 | 1.8907 (17) | C10—C11 | 1.373 (3) |
C3—O2 | 1.248 (2) | C11—N1 | 1.342 (3) |
C2—C1—C6 | 120.32 (16) | C4—C3—C2 | 118.29 (14) |
C2—C1—Br1 | 121.83 (12) | O1—C2—C1 | 121.24 (16) |
C6—C1—Br1 | 117.85 (12) | O1—C2—C3 | 116.83 (14) |
O4—C6—C1 | 123.00 (16) | C1—C2—C3 | 121.83 (14) |
O4—C6—C5 | 118.05 (14) | N1—C7—C8 | 117.71 (19) |
C1—C6—C5 | 118.92 (14) | N1—C7—C12 | 118.54 (17) |
O3—C5—C4 | 126.77 (16) | C8—C7—C12 | 123.75 (17) |
O3—C5—C6 | 115.96 (14) | C9—C8—C7 | 121.78 (17) |
C4—C5—C6 | 117.26 (14) | C8—C9—C10 | 117.57 (17) |
C5—C4—C3 | 123.06 (15) | C8—C9—C13 | 122.0 (2) |
C5—C4—Br2 | 119.22 (12) | C10—C9—C13 | 120.4 (2) |
C3—C4—Br2 | 117.72 (12) | C11—C10—C9 | 119.9 (2) |
O2—C3—C4 | 125.60 (16) | N1—C11—C10 | 120.51 (18) |
O2—C3—C2 | 116.09 (14) | C11—N1—C7 | 122.55 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.68 (3) | 2.03 (3) | 2.6509 (18) | 151 (3) |
O1—H1···O2 | 0.68 (3) | 2.26 (3) | 2.6559 (19) | 119 (3) |
N1—H2···O3ii | 0.72 (2) | 2.14 (2) | 2.849 (2) | 168 (3) |
N1—H2···O4ii | 0.72 (2) | 2.56 (2) | 2.9807 (18) | 119 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z. |
C7H10N+·C6HBr2O4− | Z = 4 |
Mr = 405.05 | F(000) = 792 |
Monoclinic, P21/c | Dx = 1.981 Mg m−3 |
a = 7.7357 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1416 (6) Å | µ = 5.98 mm−1 |
c = 15.8011 (9) Å | T = 100 K |
β = 94.269 (3)° | Block, purple |
V = 1358.09 (13) Å3 | 0.35 × 0.25 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 6083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
CCD; rotation images scans | θmax = 42.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −14→14 |
Tmin = 0.404, Tmax = 1.000 | k = −20→20 |
38096 measured reflections | l = −28→29 |
9404 independent reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.0632P] where P = (Fo2 + 2Fc2)/3 |
9404 reflections | (Δ/σ)max = 0.001 |
184 parameters | Δρmax = 1.34 e Å−3 |
0 restraints | Δρmin = −1.29 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
Br1 | 0.47843 (2) | 0.233106 (16) | 0.109383 (11) | 0.01484 (4) | |
Br2 | 0.31634 (2) | −0.007081 (16) | −0.274211 (11) | 0.01501 (4) | |
C3 | 0.2818 (2) | 0.10008 (15) | −0.01690 (11) | 0.0119 (3) | |
C6 | 0.5275 (2) | 0.11978 (14) | −0.14671 (11) | 0.0123 (3) | |
O1 | 0.09913 (16) | −0.00774 (12) | −0.12129 (9) | 0.0173 (3) | |
H1 | 0.0473 | −0.01 | −0.0779 | 0.026* | |
C4 | 0.4370 (2) | 0.16251 (15) | 0.00124 (11) | 0.0122 (3) | |
N1 | 0.96656 (18) | 0.26704 (13) | −0.16218 (11) | 0.0155 (3) | |
H1A | 0.8804 | 0.2191 | −0.1584 | 0.019* | |
O3 | 0.70419 (18) | 0.22877 (14) | −0.04465 (10) | 0.0258 (3) | |
O2 | 0.16434 (16) | 0.08351 (13) | 0.03197 (9) | 0.0195 (3) | |
C1 | 0.3631 (2) | 0.05998 (14) | −0.16580 (10) | 0.0117 (3) | |
C2 | 0.24886 (19) | 0.04840 (14) | −0.10558 (11) | 0.0117 (3) | |
C5 | 0.5638 (2) | 0.17603 (16) | −0.05714 (11) | 0.0141 (3) | |
O4 | 0.63921 (16) | 0.12894 (12) | −0.19711 (9) | 0.0187 (3) | |
C7 | 1.0291 (2) | 0.28251 (16) | −0.23903 (12) | 0.0156 (3) | |
C8 | 1.1653 (2) | 0.36261 (16) | −0.24409 (13) | 0.0177 (3) | |
H8 | 1.2113 | 0.3762 | −0.296 | 0.021* | |
C10 | 1.1676 (2) | 0.40233 (16) | −0.09342 (12) | 0.0165 (3) | |
C11 | 1.0320 (2) | 0.32284 (16) | −0.09082 (12) | 0.0162 (3) | |
H11 | 0.9849 | 0.3073 | −0.0395 | 0.019* | |
C12 | 0.9487 (3) | 0.21602 (18) | −0.31284 (13) | 0.0212 (4) | |
H12A | 0.9596 | 0.1313 | −0.3026 | 0.032* | |
H12B | 1.0061 | 0.2367 | −0.3626 | 0.032* | |
H12C | 0.8282 | 0.2369 | −0.3212 | 0.032* | |
C13 | 1.2407 (3) | 0.46639 (19) | −0.01483 (14) | 0.0233 (4) | |
H13A | 1.1682 | 0.4516 | 0.0308 | 0.035* | |
H13B | 1.245 | 0.5511 | −0.0258 | 0.035* | |
H13C | 1.3556 | 0.4373 | 0.0006 | 0.035* | |
C9 | 1.2329 (2) | 0.42230 (17) | −0.17244 (12) | 0.0173 (3) | |
H9 | 1.3231 | 0.4766 | −0.1768 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01520 (7) | 0.01706 (8) | 0.01267 (8) | −0.00345 (6) | 0.00383 (5) | −0.00279 (6) |
Br2 | 0.01336 (7) | 0.02117 (9) | 0.01085 (8) | −0.00387 (6) | 0.00315 (5) | −0.00109 (6) |
C3 | 0.0101 (6) | 0.0137 (7) | 0.0126 (7) | −0.0014 (5) | 0.0046 (5) | −0.0004 (5) |
C6 | 0.0107 (6) | 0.0128 (7) | 0.0139 (7) | −0.0009 (5) | 0.0047 (5) | −0.0004 (5) |
O1 | 0.0122 (5) | 0.0264 (7) | 0.0141 (6) | −0.0088 (5) | 0.0056 (4) | −0.0027 (5) |
C4 | 0.0106 (6) | 0.0134 (7) | 0.0130 (7) | −0.0015 (5) | 0.0033 (5) | −0.0013 (5) |
N1 | 0.0104 (5) | 0.0156 (6) | 0.0206 (7) | −0.0011 (5) | 0.0030 (5) | 0.0043 (5) |
O3 | 0.0161 (6) | 0.0394 (8) | 0.0232 (7) | −0.0155 (6) | 0.0089 (5) | −0.0115 (6) |
O2 | 0.0149 (5) | 0.0284 (7) | 0.0164 (6) | −0.0087 (5) | 0.0086 (4) | −0.0036 (5) |
C1 | 0.0102 (6) | 0.0125 (7) | 0.0126 (7) | −0.0016 (5) | 0.0034 (5) | −0.0008 (5) |
C2 | 0.0089 (6) | 0.0122 (7) | 0.0144 (7) | −0.0015 (5) | 0.0037 (5) | 0.0007 (5) |
C5 | 0.0112 (6) | 0.0163 (7) | 0.0154 (8) | −0.0030 (5) | 0.0049 (5) | −0.0018 (6) |
O4 | 0.0137 (5) | 0.0258 (7) | 0.0179 (6) | −0.0056 (5) | 0.0098 (4) | −0.0045 (5) |
C7 | 0.0117 (6) | 0.0160 (7) | 0.0195 (8) | 0.0045 (5) | 0.0048 (6) | 0.0026 (6) |
C8 | 0.0133 (7) | 0.0199 (8) | 0.0211 (9) | 0.0024 (6) | 0.0094 (6) | 0.0057 (7) |
C10 | 0.0098 (6) | 0.0179 (8) | 0.0220 (9) | 0.0013 (6) | 0.0013 (6) | 0.0051 (6) |
C11 | 0.0118 (6) | 0.0193 (8) | 0.0178 (8) | −0.0002 (6) | 0.0033 (6) | 0.0051 (6) |
C12 | 0.0208 (8) | 0.0214 (9) | 0.0216 (9) | 0.0021 (7) | 0.0040 (7) | −0.0025 (7) |
C13 | 0.0202 (8) | 0.0280 (10) | 0.0214 (9) | −0.0036 (7) | −0.0010 (7) | 0.0036 (8) |
C9 | 0.0111 (6) | 0.0178 (8) | 0.0236 (9) | −0.0003 (6) | 0.0043 (6) | 0.0054 (6) |
Br1—C4 | 1.8868 (17) | C7—C8 | 1.387 (2) |
Br2—C1 | 1.8792 (17) | C7—C12 | 1.479 (3) |
C3—O2 | 1.2495 (19) | C8—C9 | 1.382 (3) |
C3—C4 | 1.398 (2) | C8—H8 | 0.93 |
C3—C2 | 1.519 (2) | C10—C11 | 1.376 (2) |
C6—O4 | 1.2224 (19) | C10—C9 | 1.399 (3) |
C6—C1 | 1.447 (2) | C10—C13 | 1.506 (3) |
C6—C5 | 1.554 (2) | C11—H11 | 0.93 |
O1—C2 | 1.3235 (19) | C12—H12A | 0.96 |
O1—H1 | 0.82 | C12—H12B | 0.96 |
C4—C5 | 1.403 (2) | C12—H12C | 0.96 |
N1—C7 | 1.351 (2) | C13—H13A | 0.96 |
N1—C11 | 1.352 (2) | C13—H13B | 0.96 |
N1—H1A | 0.86 | C13—H13C | 0.96 |
O3—C5 | 1.238 (2) | C9—H9 | 0.93 |
C1—C2 | 1.352 (2) | ||
O2—C3—C4 | 126.84 (16) | C9—C8—C7 | 120.33 (17) |
O2—C3—C2 | 115.73 (14) | C9—C8—H8 | 119.8 |
C4—C3—C2 | 117.41 (14) | C7—C8—H8 | 119.8 |
O4—C6—C1 | 123.74 (16) | C11—C10—C9 | 117.11 (17) |
O4—C6—C5 | 118.11 (14) | C11—C10—C13 | 121.42 (17) |
C1—C6—C5 | 118.15 (13) | C9—C10—C13 | 121.47 (16) |
C2—O1—H1 | 109.5 | N1—C11—C10 | 120.66 (16) |
C3—C4—C5 | 123.35 (15) | N1—C11—H11 | 119.7 |
C3—C4—Br1 | 118.58 (12) | C10—C11—H11 | 119.7 |
C5—C4—Br1 | 118.07 (12) | C7—C12—H12A | 109.5 |
C7—N1—C11 | 123.63 (15) | C7—C12—H12B | 109.5 |
C7—N1—H1A | 118.2 | H12A—C12—H12B | 109.5 |
C11—N1—H1A | 118.2 | C7—C12—H12C | 109.5 |
C2—C1—C6 | 120.49 (15) | H12A—C12—H12C | 109.5 |
C2—C1—Br2 | 120.78 (12) | H12B—C12—H12C | 109.5 |
C6—C1—Br2 | 118.67 (11) | C10—C13—H13A | 109.5 |
O1—C2—C1 | 121.46 (15) | C10—C13—H13B | 109.5 |
O1—C2—C3 | 115.90 (13) | H13A—C13—H13B | 109.5 |
C1—C2—C3 | 122.63 (14) | C10—C13—H13C | 109.5 |
O3—C5—C4 | 126.44 (16) | H13A—C13—H13C | 109.5 |
O3—C5—C6 | 115.69 (14) | H13B—C13—H13C | 109.5 |
C4—C5—C6 | 117.88 (14) | C8—C9—C10 | 120.99 (16) |
N1—C7—C8 | 117.26 (17) | C8—C9—H9 | 119.5 |
N1—C7—C12 | 119.15 (16) | C10—C9—H9 | 119.5 |
C8—C7—C12 | 123.59 (17) | ||
O2—C3—C4—C5 | 179.27 (17) | Br1—C4—C5—O3 | 1.3 (3) |
C2—C3—C4—C5 | −2.0 (2) | C3—C4—C5—C6 | 0.8 (3) |
O2—C3—C4—Br1 | −1.1 (2) | Br1—C4—C5—C6 | −178.86 (12) |
C2—C3—C4—Br1 | 177.66 (11) | O4—C6—C5—O3 | 1.5 (3) |
O4—C6—C1—C2 | 176.91 (17) | C1—C6—C5—O3 | −178.24 (16) |
C5—C6—C1—C2 | −3.3 (2) | O4—C6—C5—C4 | −178.34 (16) |
O4—C6—C1—Br2 | −0.4 (2) | C1—C6—C5—C4 | 1.9 (2) |
C5—C6—C1—Br2 | 179.37 (12) | C11—N1—C7—C8 | −1.6 (2) |
C6—C1—C2—O1 | −178.85 (15) | C11—N1—C7—C12 | 179.42 (16) |
Br2—C1—C2—O1 | −1.6 (2) | N1—C7—C8—C9 | 0.5 (2) |
C6—C1—C2—C3 | 2.2 (2) | C12—C7—C8—C9 | 179.45 (17) |
Br2—C1—C2—C3 | 179.44 (12) | C7—N1—C11—C10 | 1.3 (3) |
O2—C3—C2—O1 | 0.4 (2) | C9—C10—C11—N1 | 0.1 (3) |
C4—C3—C2—O1 | −178.49 (15) | C13—C10—C11—N1 | 179.28 (16) |
O2—C3—C2—C1 | 179.37 (16) | C7—C8—C9—C10 | 0.8 (3) |
C4—C3—C2—C1 | 0.5 (2) | C11—C10—C9—C8 | −1.2 (3) |
C3—C4—C5—O3 | −179.05 (18) | C13—C10—C9—C8 | 179.70 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.82 | 2.01 | 2.6994 (17) | 141 |
O1—H1···O2 | 0.82 | 2.16 | 2.6403 (19) | 117 |
N1—H1A···O4 | 0.86 | 2.17 | 2.9794 (19) | 158 |
N1—H1A···O3 | 0.86 | 2.34 | 2.883 (2) | 122 |
Symmetry code: (i) −x, −y, −z. |
C7H10N+·C6HBr2O4− | Z = 4 |
Mr = 405.04 | F(000) = 792 |
Monoclinic, P21/c | Dx = 1.929 Mg m−3 |
a = 11.6766 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4926 (5) Å | µ = 5.82 mm−1 |
c = 11.5221 (5) Å | T = 100 K |
β = 98.834 (2)° | Block, purple |
V = 1394.92 (11) Å3 | 0.25 × 0.2 × 0.1 mm |
Bruker APEXII CCD area-detector diffractometer | 3131 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
CCD; rotation images scans | θmax = 31.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −13→12 |
Tmin = 0.684, Tmax = 1.000 | k = −14→15 |
14020 measured reflections | l = −16→16 |
3817 independent reflections |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0335P)2 + 0.6408P] where P = (Fo2 + 2Fc2)/3 |
3817 reflections | (Δ/σ)max = 0.001 |
191 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. H atoms were placed on calculated positions modelled as riding on the atoms to which they were bonded except those involved in hydrogen bonding H1 and H2 (bonded to O1 and N1, respectively) which were identified in a Fourier difference map and the position and isotropic thermal parameters allowed to freely refine. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1510 (2) | 0.0322 (2) | 0.38903 (18) | 0.0123 (5) | |
C6 | 0.0825 (2) | 0.1413 (2) | 0.41310 (18) | 0.0123 (4) | |
C5 | 0.1428 (2) | 0.2483 (2) | 0.49363 (18) | 0.0123 (4) | |
C4 | 0.2597 (2) | 0.2332 (2) | 0.53947 (18) | 0.0112 (4) | |
C3 | 0.3269 (2) | 0.1288 (2) | 0.51195 (18) | 0.0120 (5) | |
C2 | 0.2658 (2) | 0.0288 (2) | 0.42894 (18) | 0.0122 (5) | |
O1 | 0.33345 (18) | −0.06415 (16) | 0.40007 (15) | 0.0165 (4) | |
O2 | 0.43032 (15) | 0.10769 (16) | 0.55024 (13) | 0.0158 (3) | |
Br2 | 0.32803 (2) | 0.35454 (2) | 0.649891 (18) | 0.01431 (7) | |
O3 | 0.08053 (15) | 0.33992 (15) | 0.51253 (15) | 0.0173 (4) | |
O4 | −0.01960 (15) | 0.15499 (16) | 0.37320 (14) | 0.0183 (4) | |
Br1 | 0.07565 (2) | −0.09875 (2) | 0.295328 (19) | 0.01606 (7) | |
C10 | 0.3537 (2) | 0.6732 (2) | 0.55142 (19) | 0.0144 (5) | |
C9 | 0.3628 (2) | 0.6104 (2) | 0.44682 (19) | 0.0155 (5) | |
H9 | 0.4359 | 0.5971 | 0.4263 | 0.019* | |
C8 | 0.2654 (2) | 0.5670 (2) | 0.37211 (18) | 0.0151 (5) | |
C7 | 0.1590 (2) | 0.5907 (2) | 0.40512 (19) | 0.0144 (5) | |
H7 | 0.092 | 0.5631 | 0.3574 | 0.017* | |
N1 | 0.15066 (19) | 0.65280 (18) | 0.50482 (16) | 0.0137 (4) | |
C11 | 0.2440 (2) | 0.6936 (2) | 0.57811 (19) | 0.0142 (5) | |
H11 | 0.2347 | 0.7358 | 0.647 | 0.017* | |
C12 | 0.2730 (2) | 0.4943 (3) | 0.2616 (2) | 0.0239 (6) | |
H12A | 0.2701 | 0.4045 | 0.277 | 0.036* | |
H12B | 0.3446 | 0.5144 | 0.2344 | 0.036* | |
H12C | 0.2092 | 0.5174 | 0.2025 | 0.036* | |
C13 | 0.4582 (2) | 0.7162 (3) | 0.6358 (2) | 0.0230 (6) | |
H13A | 0.4606 | 0.8076 | 0.6379 | 0.034* | |
H13B | 0.5273 | 0.6842 | 0.6104 | 0.034* | |
H13C | 0.4531 | 0.684 | 0.7129 | 0.034* | |
H2 | 0.078 (3) | 0.664 (3) | 0.528 (3) | 0.037 (9)* | |
H1 | 0.393 (3) | −0.058 (3) | 0.428 (3) | 0.026 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0128 (14) | 0.0138 (10) | 0.0105 (9) | 0.0014 (8) | 0.0030 (8) | 0.0005 (7) |
C6 | 0.0116 (14) | 0.0143 (10) | 0.0115 (9) | 0.0005 (9) | 0.0030 (8) | 0.0019 (8) |
C5 | 0.0120 (13) | 0.0126 (10) | 0.0132 (9) | 0.0006 (8) | 0.0045 (8) | 0.0022 (8) |
C4 | 0.0086 (13) | 0.0133 (10) | 0.0120 (9) | 0.0000 (8) | 0.0023 (8) | −0.0001 (7) |
C3 | 0.0101 (14) | 0.0153 (10) | 0.0114 (9) | 0.0018 (8) | 0.0044 (8) | 0.0050 (8) |
C2 | 0.0143 (14) | 0.0112 (10) | 0.0118 (9) | 0.0040 (8) | 0.0046 (8) | 0.0035 (7) |
O1 | 0.0109 (11) | 0.0174 (8) | 0.0212 (8) | 0.0056 (7) | 0.0021 (7) | −0.0023 (6) |
O2 | 0.0097 (10) | 0.0202 (8) | 0.0177 (7) | 0.0050 (7) | 0.0024 (6) | 0.0006 (6) |
Br2 | 0.01108 (15) | 0.01456 (11) | 0.01695 (11) | 0.00013 (8) | 0.00107 (8) | −0.00140 (8) |
O3 | 0.0115 (10) | 0.0145 (8) | 0.0259 (8) | 0.0028 (6) | 0.0028 (7) | −0.0038 (6) |
O4 | 0.0117 (10) | 0.0202 (8) | 0.0220 (8) | 0.0041 (7) | −0.0012 (7) | −0.0033 (7) |
Br1 | 0.01622 (16) | 0.01440 (11) | 0.01679 (11) | 0.00185 (9) | 0.00011 (9) | −0.00278 (8) |
C10 | 0.0115 (14) | 0.0145 (10) | 0.0165 (10) | −0.0007 (9) | −0.0003 (9) | 0.0033 (8) |
C9 | 0.0094 (14) | 0.0203 (11) | 0.0175 (10) | 0.0042 (9) | 0.0043 (9) | 0.0052 (9) |
C8 | 0.0182 (15) | 0.0146 (10) | 0.0126 (9) | 0.0049 (9) | 0.0028 (9) | 0.0020 (8) |
C7 | 0.0138 (14) | 0.0128 (10) | 0.0156 (10) | 0.0014 (9) | −0.0012 (9) | −0.0005 (8) |
N1 | 0.0077 (12) | 0.0167 (9) | 0.0171 (9) | 0.0023 (8) | 0.0034 (8) | 0.0004 (7) |
C11 | 0.0149 (14) | 0.0132 (10) | 0.0149 (9) | 0.0002 (9) | 0.0037 (9) | −0.0010 (8) |
C12 | 0.0264 (16) | 0.0267 (13) | 0.0187 (11) | 0.0071 (11) | 0.0036 (10) | −0.0055 (10) |
C13 | 0.0160 (15) | 0.0315 (14) | 0.0204 (11) | −0.0066 (11) | −0.0008 (10) | 0.0020 (10) |
C1—C2 | 1.349 (3) | C3—C2 | 1.522 (3) |
C1—C6 | 1.447 (3) | C2—O1 | 1.329 (3) |
C1—Br1 | 1.881 (2) | C10—C11 | 1.379 (3) |
C6—O4 | 1.219 (3) | C10—C9 | 1.392 (3) |
C6—C5 | 1.554 (3) | C10—C13 | 1.507 (3) |
C5—O3 | 1.245 (3) | C9—C8 | 1.394 (3) |
C5—C4 | 1.395 (3) | C8—C7 | 1.376 (4) |
C4—C3 | 1.412 (3) | C8—C12 | 1.499 (3) |
C4—Br2 | 1.888 (2) | C7—N1 | 1.337 (3) |
C3—O2 | 1.240 (3) | N1—C11 | 1.343 (3) |
C2—C1—C6 | 120.4 (2) | C4—C3—C2 | 116.9 (2) |
C2—C1—Br1 | 121.94 (17) | O1—C2—C1 | 122.1 (2) |
C6—C1—Br1 | 117.65 (17) | O1—C2—C3 | 115.1 (2) |
O4—C6—C1 | 124.0 (2) | C1—C2—C3 | 122.8 (2) |
O4—C6—C5 | 117.8 (2) | C11—C10—C9 | 117.6 (2) |
C1—C6—C5 | 118.2 (2) | C11—C10—C13 | 119.8 (2) |
O3—C5—C4 | 125.8 (2) | C9—C10—C13 | 122.6 (2) |
O3—C5—C6 | 116.0 (2) | C10—C9—C8 | 121.7 (2) |
C4—C5—C6 | 118.1 (2) | C7—C8—C9 | 117.1 (2) |
C5—C4—C3 | 123.3 (2) | C7—C8—C12 | 120.0 (2) |
C5—C4—Br2 | 117.77 (16) | C9—C8—C12 | 122.8 (2) |
C3—C4—Br2 | 118.86 (17) | N1—C7—C8 | 120.9 (2) |
O2—C3—C4 | 127.1 (2) | C7—N1—C11 | 122.5 (2) |
O2—C3—C2 | 115.96 (19) | N1—C11—C10 | 120.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H2···O3i | 0.93 (3) | 1.84 (3) | 2.677 (3) | 148 (3) |
N1—H2···O4i | 0.93 (3) | 2.37 (3) | 3.008 (3) | 125 (3) |
O1—H1···O2ii | 0.72 (3) | 2.11 (3) | 2.768 (3) | 152 (3) |
O1—H1···O2 | 0.72 (3) | 2.23 (3) | 2.631 (2) | 116 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
C6H7BrN+·C6HBr2O4− | Z = 4 |
Mr = 469.91 | F(000) = 896 |
Monoclinic, P21/c | Dx = 2.244 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2229 (4) Å | µ = 8.71 mm−1 |
b = 5.5760 (2) Å | T = 100 K |
c = 24.5300 (9) Å | Block, purple |
β = 95.802 (3)° | 0.25 × 0.15 × 0.1 mm |
V = 1391.12 (9) Å3 |
Bruker APEXII CCD area-detector diffractometer | 3311 reflections with I > 2σ(I) |
CCD; rotation images scans | Rint = 0.057 |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | θmax = 32.2°, θmin = 1.7° |
Tmin = 0.499, Tmax = 1.000 | h = −15→15 |
19916 measured reflections | k = −8→6 |
4796 independent reflections | l = −36→36 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0482P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
4796 reflections | Δρmax = 1.23 e Å−3 |
190 parameters | Δρmin = −1.13 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C4 | 0.2394 (3) | 0.2669 (7) | 0.91013 (13) | 0.0159 (7) | |
C3 | 0.1456 (3) | 0.1217 (7) | 0.93350 (13) | 0.0167 (7) | |
C2 | 0.0747 (3) | −0.0693 (7) | 0.89770 (13) | 0.0168 (7) | |
C1 | 0.1034 (3) | −0.1083 (7) | 0.84602 (13) | 0.0157 (7) | |
C6 | 0.2048 (3) | 0.0288 (7) | 0.82360 (13) | 0.0158 (7) | |
C5 | 0.2691 (3) | 0.2388 (7) | 0.85643 (13) | 0.0158 (7) | |
O3 | 0.3444 (3) | 0.3718 (5) | 0.83178 (9) | 0.0205 (6) | |
O4 | 0.2426 (3) | −0.0150 (5) | 0.77843 (9) | 0.0200 (6) | |
Br1 | 0.01728 (3) | −0.34997 (7) | 0.80172 (2) | 0.01880 (10) | |
O1 | −0.0141 (3) | −0.1955 (5) | 0.92133 (10) | 0.0217 (6) | |
O2 | 0.1142 (2) | 0.1390 (5) | 0.98099 (9) | 0.0203 (6) | |
Br2 | 0.31926 (4) | 0.51666 (7) | 0.95403 (2) | 0.01953 (10) | |
C8 | 0.7096 (3) | 0.1138 (7) | 0.86016 (14) | 0.0171 (7) | |
C9 | 0.6171 (3) | −0.0257 (7) | 0.88470 (13) | 0.0174 (7) | |
C10 | 0.5522 (4) | −0.2030 (7) | 0.85268 (14) | 0.0201 (8) | |
H10 | 0.49 | −0.2991 | 0.8673 | 0.024* | |
C11 | 0.5796 (4) | −0.2372 (7) | 0.79908 (14) | 0.0211 (8) | |
H11 | 0.538 | −0.3595 | 0.7782 | 0.025* | |
N1 | 0.6657 (3) | −0.0950 (6) | 0.77734 (13) | 0.0208 (7) | |
C7 | 0.7321 (4) | 0.0788 (7) | 0.80625 (14) | 0.0194 (8) | |
H7 | 0.7924 | 0.1739 | 0.7902 | 0.023* | |
C12 | 0.5888 (4) | 0.0144 (8) | 0.94276 (14) | 0.0240 (9) | |
H12A | 0.5601 | 0.1767 | 0.947 | 0.036* | |
H12B | 0.6671 | −0.0138 | 0.9669 | 0.036* | |
H12C | 0.521 | −0.0939 | 0.9516 | 0.036* | |
Br3 | 0.80539 (4) | 0.35718 (7) | 0.89969 (2) | 0.02332 (10) | |
H1 | −0.027 (4) | −0.120 (8) | 0.9513 (18) | 0.031 (13)* | |
H5 | 0.681 (5) | −0.102 (9) | 0.746 (2) | 0.039 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4 | 0.0167 (16) | 0.020 (2) | 0.0113 (15) | −0.0020 (14) | 0.0024 (11) | −0.0030 (13) |
C3 | 0.0160 (16) | 0.024 (2) | 0.0099 (14) | 0.0002 (14) | 0.0005 (11) | 0.0011 (13) |
C2 | 0.0186 (17) | 0.017 (2) | 0.0146 (16) | 0.0008 (14) | 0.0012 (12) | 0.0012 (13) |
C1 | 0.0190 (17) | 0.015 (2) | 0.0127 (15) | −0.0025 (14) | 0.0012 (12) | −0.0008 (13) |
C6 | 0.0162 (16) | 0.020 (2) | 0.0117 (15) | 0.0027 (14) | 0.0027 (12) | 0.0014 (13) |
C5 | 0.0174 (16) | 0.017 (2) | 0.0130 (15) | −0.0007 (14) | 0.0032 (12) | 0.0012 (13) |
O3 | 0.0263 (14) | 0.0234 (16) | 0.0124 (11) | −0.0063 (11) | 0.0055 (9) | 0.0011 (10) |
O4 | 0.0253 (13) | 0.0241 (16) | 0.0116 (11) | −0.0030 (11) | 0.0069 (9) | −0.0005 (10) |
Br1 | 0.02324 (18) | 0.0218 (2) | 0.01161 (15) | −0.00572 (15) | 0.00313 (12) | −0.00253 (13) |
O1 | 0.0270 (14) | 0.0285 (17) | 0.0109 (11) | −0.0101 (12) | 0.0085 (10) | −0.0047 (11) |
O2 | 0.0224 (13) | 0.0304 (17) | 0.0088 (11) | −0.0073 (11) | 0.0052 (9) | −0.0036 (10) |
Br2 | 0.02441 (18) | 0.0226 (2) | 0.01180 (15) | −0.00683 (15) | 0.00318 (12) | −0.00302 (14) |
C8 | 0.0183 (17) | 0.019 (2) | 0.0146 (15) | −0.0029 (14) | 0.0028 (12) | 0.0006 (13) |
C9 | 0.0184 (17) | 0.020 (2) | 0.0132 (15) | −0.0006 (14) | 0.0009 (12) | 0.0007 (14) |
C10 | 0.0229 (18) | 0.023 (2) | 0.0154 (16) | −0.0045 (15) | 0.0065 (13) | −0.0004 (14) |
C11 | 0.0223 (18) | 0.023 (2) | 0.0178 (17) | 0.0000 (16) | 0.0008 (13) | −0.0060 (15) |
N1 | 0.0246 (16) | 0.025 (2) | 0.0134 (14) | 0.0067 (14) | 0.0058 (12) | 0.0001 (13) |
C7 | 0.0212 (18) | 0.021 (2) | 0.0162 (16) | 0.0007 (15) | 0.0044 (13) | 0.0009 (14) |
C12 | 0.029 (2) | 0.033 (3) | 0.0117 (15) | −0.0061 (17) | 0.0074 (13) | −0.0020 (15) |
Br3 | 0.0249 (2) | 0.0231 (2) | 0.02254 (19) | −0.00646 (16) | 0.00484 (14) | −0.00396 (15) |
C4—C5 | 1.390 (4) | C6—C5 | 1.531 (5) |
C4—C3 | 1.420 (5) | C5—O3 | 1.266 (4) |
C4—Br2 | 1.894 (4) | C8—C7 | 1.379 (5) |
C3—O2 | 1.243 (4) | C8—C9 | 1.406 (5) |
C3—C2 | 1.517 (5) | C8—Br3 | 1.884 (4) |
C2—O1 | 1.327 (4) | C9—C10 | 1.389 (5) |
C2—C1 | 1.347 (5) | C9—C12 | 1.499 (5) |
C1—C6 | 1.442 (5) | C10—C11 | 1.385 (5) |
C1—Br1 | 1.892 (3) | C11—N1 | 1.335 (5) |
C6—O4 | 1.234 (4) | N1—C7 | 1.344 (5) |
C5—C4—C3 | 122.7 (3) | C1—C6—C5 | 119.5 (3) |
C5—C4—Br2 | 119.9 (3) | O3—C5—C4 | 126.0 (3) |
C3—C4—Br2 | 117.4 (2) | O3—C5—C6 | 116.5 (3) |
O2—C3—C4 | 125.7 (3) | C4—C5—C6 | 117.5 (3) |
O2—C3—C2 | 116.3 (3) | C7—C8—C9 | 121.2 (3) |
C4—C3—C2 | 118.0 (3) | C7—C8—Br3 | 117.8 (3) |
O1—C2—C1 | 123.3 (3) | C9—C8—Br3 | 121.0 (3) |
O1—C2—C3 | 115.3 (3) | C10—C9—C8 | 117.1 (3) |
C1—C2—C3 | 121.4 (3) | C10—C9—C12 | 121.1 (3) |
C2—C1—C6 | 120.4 (3) | C8—C9—C12 | 121.8 (3) |
C2—C1—Br1 | 121.5 (3) | C11—C10—C9 | 120.3 (3) |
C6—C1—Br1 | 118.0 (2) | N1—C11—C10 | 120.2 (4) |
O4—C6—C1 | 122.7 (3) | C11—N1—C7 | 122.4 (3) |
O4—C6—C5 | 117.9 (3) | N1—C7—C8 | 118.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.87 (5) | 1.97 (5) | 2.717 (3) | 144 (4) |
O1—H1···O2 | 0.87 (5) | 2.12 (4) | 2.637 (4) | 118 (4) |
N1—H5···O3ii | 0.79 (5) | 1.91 (5) | 2.675 (4) | 161 (5) |
N1—H5···O4ii | 0.79 (5) | 2.53 (5) | 2.915 (4) | 112 (4) |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, y−1/2, −z+3/2. |
C7H10N+·C6HBr2O4− | Z = 4 |
Mr = 405.04 | F(000) = 792 |
Monoclinic, P21/n | Dx = 1.932 Mg m−3 |
a = 4.9786 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 23.181 (3) Å | µ = 5.83 mm−1 |
c = 12.2811 (13) Å | T = 100 K |
β = 100.794 (3)° | Block, purple |
V = 1392.3 (2) Å3 | 0.2 × 0.1 × 0.05 mm |
Bruker APEXII CCD area-detector diffractometer | 1664 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
CCD; rotation images scans | θmax = 23.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −5→5 |
Tmin = 0.791, Tmax = 1.000 | k = −26→25 |
9783 measured reflections | l = −13→13 |
2053 independent reflections |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0301P)2 + 0.8134P] where P = (Fo2 + 2Fc2)/3 |
2053 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. All H atoms were placed on calculated positions and refined as riding on the atom to which they were bonded with the exception of H1 where the position was allowed to freely refine but the thermal parameter was constrained to take a value of 1.2 times the Ueq of the atom to which it was bonded (O1). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6253 (8) | 0.29473 (17) | 0.0801 (3) | 0.0161 (9) | |
C2 | 0.6786 (8) | 0.29433 (17) | 0.1910 (3) | 0.0163 (9) | |
C3 | 0.5234 (8) | 0.33215 (18) | 0.2594 (3) | 0.0182 (10) | |
C4 | 0.3191 (8) | 0.36859 (17) | 0.2012 (3) | 0.0174 (10) | |
C5 | 0.2523 (8) | 0.37123 (17) | 0.0857 (3) | 0.0173 (9) | |
C6 | 0.4239 (8) | 0.33427 (17) | 0.0198 (3) | 0.0174 (10) | |
O4 | 0.3842 (6) | 0.33949 (12) | −0.0808 (2) | 0.0226 (7) | |
O3 | 0.0655 (6) | 0.40095 (12) | 0.0294 (2) | 0.0232 (7) | |
Br2 | 0.11288 (8) | 0.413330 (18) | 0.28551 (3) | 0.02328 (15) | |
O2 | 0.5924 (6) | 0.32675 (12) | 0.3614 (2) | 0.0226 (7) | |
O1 | 0.8656 (6) | 0.25996 (12) | 0.2500 (2) | 0.0222 (7) | |
H1 | 0.8817 | 0.2679 | 0.316 | 0.033* | |
Br1 | 0.81832 (8) | 0.247086 (17) | −0.00350 (3) | 0.01960 (14) | |
C7 | 0.6455 (8) | 0.43225 (18) | −0.2235 (3) | 0.0188 (10) | |
C8 | 0.5129 (8) | 0.43486 (17) | −0.3345 (3) | 0.0179 (9) | |
C9 | 0.5929 (9) | 0.39720 (18) | −0.4105 (3) | 0.0226 (10) | |
H9 | 0.5042 | 0.3981 | −0.4842 | 0.027* | |
C10 | 0.8046 (8) | 0.35822 (19) | −0.3772 (3) | 0.0260 (11) | |
H10 | 0.8596 | 0.3333 | −0.4281 | 0.031* | |
C11 | 0.9303 (8) | 0.35721 (18) | −0.2685 (3) | 0.0220 (10) | |
H11 | 1.0725 | 0.3315 | −0.2447 | 0.026* | |
N1 | 0.8484 (7) | 0.39346 (15) | −0.1956 (3) | 0.0211 (8) | |
H1A | 0.93 | 0.3918 | −0.1274 | 0.025* | |
C13 | 0.2859 (9) | 0.47821 (18) | −0.3707 (4) | 0.0270 (11) | |
H13A | 0.2121 | 0.473 | −0.4481 | 0.041* | |
H13B | 0.3577 | 0.5166 | −0.3586 | 0.041* | |
H13C | 0.1441 | 0.4725 | −0.3285 | 0.041* | |
C12 | 0.5747 (9) | 0.46959 (18) | −0.1333 (3) | 0.0244 (10) | |
H12A | 0.6972 | 0.4613 | −0.0649 | 0.037* | |
H12B | 0.3902 | 0.4619 | −0.125 | 0.037* | |
H12C | 0.5915 | 0.5094 | −0.1522 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.017 (2) | 0.016 (2) | 0.016 (2) | −0.0026 (18) | 0.0050 (18) | −0.0026 (18) |
C2 | 0.015 (2) | 0.015 (2) | 0.019 (2) | −0.0042 (19) | 0.0012 (18) | 0.0037 (19) |
C3 | 0.018 (2) | 0.019 (2) | 0.019 (3) | −0.0088 (19) | 0.0044 (19) | −0.0001 (19) |
C4 | 0.015 (2) | 0.017 (2) | 0.021 (2) | −0.0028 (18) | 0.0053 (18) | −0.0057 (19) |
C5 | 0.014 (2) | 0.018 (2) | 0.020 (2) | −0.0024 (19) | 0.0030 (18) | −0.001 (2) |
C6 | 0.018 (2) | 0.013 (2) | 0.020 (3) | −0.0045 (18) | 0.0005 (19) | −0.0008 (19) |
O4 | 0.0213 (17) | 0.0315 (18) | 0.0144 (17) | 0.0028 (13) | 0.0022 (12) | 0.0009 (13) |
O3 | 0.0213 (17) | 0.0252 (17) | 0.0208 (16) | 0.0035 (14) | −0.0015 (13) | −0.0016 (14) |
Br2 | 0.0204 (3) | 0.0277 (3) | 0.0230 (3) | −0.0018 (2) | 0.00735 (18) | −0.0073 (2) |
O2 | 0.0240 (17) | 0.0306 (18) | 0.0128 (16) | −0.0069 (14) | 0.0021 (13) | 0.0015 (13) |
O1 | 0.0238 (17) | 0.0273 (18) | 0.0137 (15) | 0.0049 (14) | −0.0008 (13) | 0.0021 (14) |
Br1 | 0.0197 (3) | 0.0216 (3) | 0.0173 (2) | 0.00247 (19) | 0.00311 (17) | −0.0020 (2) |
C7 | 0.015 (2) | 0.019 (2) | 0.024 (2) | −0.0028 (19) | 0.0073 (18) | −0.001 (2) |
C8 | 0.014 (2) | 0.016 (2) | 0.022 (2) | −0.0031 (18) | −0.0009 (18) | −0.0011 (19) |
C9 | 0.023 (3) | 0.026 (3) | 0.017 (2) | −0.001 (2) | −0.0019 (18) | −0.001 (2) |
C10 | 0.024 (3) | 0.031 (3) | 0.022 (3) | 0.001 (2) | 0.003 (2) | −0.006 (2) |
C11 | 0.021 (3) | 0.023 (3) | 0.020 (2) | 0.006 (2) | −0.0002 (19) | 0.001 (2) |
N1 | 0.018 (2) | 0.027 (2) | 0.0167 (19) | −0.0008 (17) | −0.0005 (15) | −0.0006 (17) |
C13 | 0.022 (3) | 0.028 (3) | 0.029 (3) | 0.005 (2) | 0.002 (2) | 0.000 (2) |
C12 | 0.026 (3) | 0.023 (3) | 0.026 (2) | 0.002 (2) | 0.009 (2) | −0.002 (2) |
C1—C2 | 1.338 (5) | C5—C6 | 1.542 (6) |
C1—C6 | 1.455 (6) | C6—O4 | 1.220 (5) |
C1—Br1 | 1.889 (4) | C7—N1 | 1.348 (5) |
C2—O1 | 1.332 (4) | C7—C8 | 1.399 (6) |
C2—C3 | 1.522 (6) | C7—C12 | 1.499 (5) |
C3—O2 | 1.242 (4) | C8—C9 | 1.390 (6) |
C3—C4 | 1.409 (6) | C8—C13 | 1.515 (6) |
C4—C5 | 1.397 (5) | C9—C10 | 1.391 (6) |
C4—Br2 | 1.897 (4) | C10—C11 | 1.364 (5) |
C5—O3 | 1.255 (5) | C11—N1 | 1.346 (5) |
C2—C1—C6 | 120.6 (4) | C4—C5—C6 | 117.3 (4) |
C2—C1—Br1 | 121.7 (3) | O4—C6—C1 | 122.9 (4) |
C6—C1—Br1 | 117.7 (3) | O4—C6—C5 | 118.4 (4) |
O1—C2—C1 | 122.9 (4) | C1—C6—C5 | 118.7 (3) |
O1—C2—C3 | 114.8 (3) | N1—C7—C8 | 118.1 (4) |
C1—C2—C3 | 122.3 (4) | N1—C7—C12 | 117.7 (4) |
O2—C3—C4 | 127.5 (4) | C8—C7—C12 | 124.1 (4) |
O2—C3—C2 | 115.2 (4) | C9—C8—C7 | 119.0 (4) |
C4—C3—C2 | 117.3 (3) | C9—C8—C13 | 120.7 (4) |
C5—C4—C3 | 123.6 (4) | C7—C8—C13 | 120.3 (4) |
C5—C4—Br2 | 118.7 (3) | C8—C9—C10 | 120.5 (4) |
C3—C4—Br2 | 117.6 (3) | C11—C10—C9 | 118.9 (4) |
O3—C5—C4 | 126.4 (4) | N1—C11—C10 | 120.0 (4) |
O3—C5—C6 | 116.2 (3) | C11—N1—C7 | 123.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 2.13 | 2.611 (4) | 117 |
O1—H1···Br1i | 0.82 | 2.82 | 3.423 (3) | 132 |
N1—H1A···O3ii | 0.86 | 1.93 | 2.777 (4) | 168 |
N1—H1A···O4ii | 0.86 | 2.54 | 3.043 (4) | 119 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1, y, z. |
C6H6BrN·C6H2Br2O4 | Z = 4 |
Mr = 469.91 | F(000) = 896 |
Monoclinic, P21/c | Dx = 2.168 Mg m−3 |
a = 5.2866 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.3814 (8) Å | µ = 8.42 mm−1 |
c = 20.3576 (13) Å | T = 100 K |
β = 91.556 (4)° | Block, red |
V = 1439.61 (15) Å3 | 0.25 × 0.2 × 0.1 mm |
Bruker APEXII CCD area-detector diffractometer | 2267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
CCD; rotation images scans | θmax = 27.2°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −6→5 |
Tmin = 0.465, Tmax = 1.000 | k = −17→17 |
14350 measured reflections | l = −26→26 |
3202 independent reflections |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0324P)2] where P = (Fo2 + 2Fc2)/3 |
3202 reflections | (Δ/σ)max = 0.001 |
188 parameters | Δρmax = 0.77 e Å−3 |
1 restraint | Δρmin = −0.67 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. All H atoms were placed on calculated positions and modelled as riding on the atoms to which they were bonded except H1 and H2. H1 was constrained to take a thermal parameter 1.2 times the Ueq of the atom to which it was bonded (O1) to ensure that a sensible thermal parameter was obtained. The methyl group positons were based on the electron density but with the bond lengths and angles constrained to take standard values for a methyl group. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6951 (8) | 0.5218 (3) | 0.4532 (2) | 0.0142 (10) | |
C3 | 0.6017 (8) | 0.5990 (3) | 0.4964 (2) | 0.0153 (10) | |
C2 | 0.6005 (8) | 0.4285 (3) | 0.4553 (2) | 0.0134 (10) | |
O1 | 0.6758 (6) | 0.3552 (2) | 0.41693 (17) | 0.0226 (8) | |
O2 | 0.6701 (6) | 0.6863 (2) | 0.49613 (16) | 0.0244 (8) | |
Br1 | 0.95526 (9) | 0.55598 (3) | 0.39596 (2) | 0.01783 (14) | |
C4 | 0.6894 (8) | 0.0737 (3) | 0.5152 (2) | 0.0149 (10) | |
C6 | 0.5333 (8) | 0.0834 (3) | 0.4566 (2) | 0.0148 (10) | |
C5 | 0.3339 (8) | 0.0032 (3) | 0.4423 (2) | 0.0141 (10) | |
O3 | 0.1920 (6) | 0.0119 (2) | 0.38894 (16) | 0.0188 (8) | |
O4 | 0.5461 (6) | 0.1528 (2) | 0.41714 (16) | 0.0190 (7) | |
Br2 | 0.93951 (9) | 0.17269 (3) | 0.52850 (2) | 0.01781 (14) | |
C7 | 0.3385 (8) | 0.1755 (3) | 0.2548 (2) | 0.0169 (11) | |
C8 | 0.3281 (9) | 0.2589 (4) | 0.2135 (2) | 0.0205 (11) | |
C9 | 0.1496 (9) | 0.3294 (4) | 0.2290 (2) | 0.0244 (12) | |
H9 | 0.1296 | 0.3858 | 0.2027 | 0.029* | |
C10 | 0.0000 (9) | 0.3180 (3) | 0.2830 (2) | 0.0239 (12) | |
H10 | −0.1194 | 0.3661 | 0.2933 | 0.029* | |
C11 | 0.0310 (9) | 0.2333 (4) | 0.3214 (2) | 0.0233 (12) | |
H11 | −0.0658 | 0.2259 | 0.3586 | 0.028* | |
N1 | 0.1966 (7) | 0.1620 (3) | 0.30642 (18) | 0.0161 (9) | |
C12 | 0.4994 (9) | 0.2719 (4) | 0.1563 (2) | 0.0308 (13) | |
H12A | 0.4070 | 0.2577 | 0.1162 | 0.046* | |
H12B | 0.6400 | 0.2268 | 0.1609 | 0.046* | |
H12C | 0.5604 | 0.3394 | 0.1554 | 0.046* | |
Br3 | 0.56870 (10) | 0.06825 (4) | 0.23905 (3) | 0.02778 (16) | |
H1 | 0.601 (8) | 0.301 (2) | 0.427 (2) | 0.033* | |
H2 | 0.227 (10) | 0.064 (4) | 0.361 (3) | 0.042 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.013 (3) | 0.018 (2) | 0.012 (2) | −0.0009 (19) | 0.0048 (19) | 0.0018 (19) |
C3 | 0.014 (3) | 0.015 (2) | 0.018 (3) | 0.0006 (19) | 0.001 (2) | 0.005 (2) |
C2 | 0.012 (3) | 0.013 (2) | 0.015 (2) | −0.0030 (18) | 0.0001 (19) | 0.0026 (19) |
O1 | 0.028 (2) | 0.0113 (17) | 0.029 (2) | −0.0051 (15) | 0.0139 (16) | −0.0011 (15) |
O2 | 0.029 (2) | 0.0144 (19) | 0.030 (2) | −0.0055 (15) | 0.0083 (16) | −0.0055 (15) |
Br1 | 0.0156 (3) | 0.0173 (3) | 0.0208 (3) | −0.00355 (18) | 0.0055 (2) | 0.0019 (2) |
C4 | 0.015 (3) | 0.013 (2) | 0.017 (2) | −0.0071 (18) | 0.004 (2) | −0.0015 (19) |
C6 | 0.009 (3) | 0.013 (2) | 0.022 (3) | 0.0018 (18) | 0.005 (2) | −0.001 (2) |
C5 | 0.015 (3) | 0.011 (2) | 0.017 (3) | −0.0012 (19) | 0.005 (2) | −0.002 (2) |
O3 | 0.021 (2) | 0.0135 (18) | 0.022 (2) | −0.0048 (14) | −0.0002 (16) | 0.0040 (15) |
O4 | 0.023 (2) | 0.0131 (17) | 0.0206 (18) | −0.0049 (14) | 0.0025 (15) | 0.0047 (14) |
Br2 | 0.0172 (3) | 0.0130 (2) | 0.0234 (3) | −0.00624 (19) | 0.0034 (2) | −0.0012 (2) |
C7 | 0.011 (3) | 0.018 (3) | 0.022 (3) | −0.0001 (19) | −0.002 (2) | −0.002 (2) |
C8 | 0.021 (3) | 0.026 (3) | 0.014 (3) | −0.007 (2) | −0.004 (2) | −0.003 (2) |
C9 | 0.030 (3) | 0.019 (3) | 0.024 (3) | −0.008 (2) | −0.001 (2) | 0.004 (2) |
C10 | 0.025 (3) | 0.017 (3) | 0.029 (3) | 0.003 (2) | 0.003 (2) | −0.004 (2) |
C11 | 0.025 (3) | 0.025 (3) | 0.020 (3) | −0.001 (2) | 0.007 (2) | 0.001 (2) |
N1 | 0.019 (2) | 0.013 (2) | 0.017 (2) | −0.0002 (16) | −0.0008 (17) | −0.0014 (17) |
C12 | 0.029 (3) | 0.044 (3) | 0.019 (3) | −0.008 (3) | 0.001 (2) | 0.014 (3) |
Br3 | 0.0233 (3) | 0.0317 (3) | 0.0284 (3) | 0.0097 (2) | 0.0017 (2) | −0.0022 (2) |
C1—C2 | 1.346 (6) | O3—H2 | 0.92 (5) |
C1—C3 | 1.453 (6) | C7—N1 | 1.321 (6) |
C1—Br1 | 1.882 (4) | C7—C8 | 1.397 (6) |
C3—O2 | 1.223 (5) | C7—Br3 | 1.914 (4) |
C3—C2i | 1.517 (6) | C8—C9 | 1.378 (7) |
C2—O1 | 1.322 (5) | C8—C12 | 1.504 (7) |
C2—C3i | 1.517 (6) | C9—C10 | 1.379 (7) |
O1—H1 | 0.857 (19) | C9—H9 | 0.9300 |
C4—C5ii | 1.353 (6) | C10—C11 | 1.384 (6) |
C4—C6 | 1.437 (6) | C10—H10 | 0.9300 |
C4—Br2 | 1.886 (4) | C11—N1 | 1.336 (6) |
C6—O4 | 1.230 (5) | C11—H11 | 0.9300 |
C6—C5 | 1.527 (6) | C12—H12A | 0.9600 |
C5—O3 | 1.308 (5) | C12—H12B | 0.9600 |
C5—C4ii | 1.353 (6) | C12—H12C | 0.9600 |
C2—C1—C3 | 120.5 (4) | N1—C7—Br3 | 114.1 (3) |
C2—C1—Br1 | 121.6 (3) | C8—C7—Br3 | 120.9 (4) |
C3—C1—Br1 | 117.9 (3) | C9—C8—C7 | 115.2 (4) |
O2—C3—C1 | 124.9 (4) | C9—C8—C12 | 121.9 (4) |
O2—C3—C2i | 116.6 (4) | C7—C8—C12 | 122.9 (4) |
C1—C3—C2i | 118.5 (4) | C8—C9—C10 | 121.2 (5) |
O1—C2—C1 | 123.4 (4) | C8—C9—H9 | 119.4 |
O1—C2—C3i | 115.6 (4) | C10—C9—H9 | 119.4 |
C1—C2—C3i | 121.0 (4) | C9—C10—C11 | 118.7 (5) |
C2—O1—H1 | 110 (4) | C9—C10—H10 | 120.7 |
C5ii—C4—C6 | 122.7 (4) | C11—C10—H10 | 120.7 |
C5ii—C4—Br2 | 121.2 (3) | N1—C11—C10 | 121.6 (5) |
C6—C4—Br2 | 116.1 (3) | N1—C11—H11 | 119.2 |
O4—C6—C4 | 124.7 (4) | C10—C11—H11 | 119.2 |
O4—C6—C5 | 117.1 (4) | C7—N1—C11 | 118.3 (4) |
C4—C6—C5 | 118.2 (4) | C8—C12—H12A | 109.5 |
O3—C5—C4ii | 122.6 (4) | C8—C12—H12B | 109.5 |
O3—C5—C6 | 118.3 (4) | H12A—C12—H12B | 109.5 |
C4ii—C5—C6 | 119.1 (4) | C8—C12—H12C | 109.5 |
C5—O3—H2 | 117 (3) | H12A—C12—H12C | 109.5 |
N1—C7—C8 | 125.1 (4) | H12B—C12—H12C | 109.5 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4 | 0.86 (2) | 2.01 (3) | 2.794 (4) | 151 (5) |
O1—H1···O2i | 0.86 (2) | 2.15 (5) | 2.638 (5) | 115 (4) |
O3—H2···N1 | 0.92 (5) | 1.73 (5) | 2.619 (5) | 163 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
The numbering scheme is as in Fig. 5 and does not necessarily relate to the CIF entries as some molecules have internal inversion symmetry. |
VAGTUS BAH2 | 2-picoline BA2- | 3-picoline BA2- | 4-picoline BA2- | |
C1-Br1 | 1.868 (4) | 1.905 (2) | 1.902 (2) | 1.902 (2) |
C1-C2 | 1.347 (6) | 1.394 (4) | 1.387 (2) | 1.399 (3) |
C2-O1 | 1.323 (5) | 1.260 (3) | 1.262 (2) | 1.246 (3) |
C2-C3 | 1.504 (5) | 1.547 (4) | 1.548 (3) | 1.555 (3) |
C3-O2 | 1.225 (5) | 1.251 (4) | 1.239 (2) | 1.246 (3) |
C3-C4 | 1.449 (5) | 1.402 (3) | 1.414 (2) | 1.405 (3) |
C4-Br2 | 1.868 (4)* | 1.905 (3) | 1.902 (2)* | 1.902 (2)* |
C4-C5 | 1.347 (6)* | 1.400 (4) | 1.387 (2)* | 1.399 (3)* |
C5-O3 | 1.323 (5)* | 1.249 (3) | 1.262 (2)* | 1.246 (3)* |
C5-C6 | 1.504 (5)* | 1.559 (4) | 1.548 (3)* | 1.555 (3)* |
C6-O4 | 1.225 (5)* | 1.249 (4) | 1.239 (2)* | 1.246 (3)* |
C1-C6 | 1.449 (5)* | 1.407 (4) | 1.414 (2)* | 1.405 (3)* |
* Related by inversion symmetry to the other half of the bromanilic acid molecule |
The numbering scheme is as in Fig. 5 and does not necessarily relate to the CIF entries as some molecules have internal inversion symmetry. |
VAGTUS BAH2 | 2,3-lutidine BAH- | 2,4-lutidine BAH- | 2,5-lutidine BAH- | 3,5-lutidine BAH- | |
C1-Br1 | 1.868 (4) | 1.889 (4) | 1.875 (2) | 1.879 (2) | 1.879 (2) |
C1-C2 | 1.347 (6) | 1.338 (5) | 1.354 (2) | 1.352 (2) | 1.352 (2) |
C2-O1 | 1.323 (5) | 1.332 (5) | 1.320 (2) | 1.323 (2) | 1.323 (2) |
C2-C3 | 1.504 (5) | 1.521 (6) | 1.511 (2) | 1.519 (2) | 1.519 (2) |
C3-O2 | 1.225 (5) | 1.242 (4) | 1.247 (2) | 1.249 (2) | 1.249 (2) |
C3-C4 | 1.449 (5) | 1.409 (5) | 1.406 (3) | 1.399 (2) | 1.399 (2) |
C4-Br2 | 1.868 (4)* | 1.897 (4) | 1.891 (2) | 1.887 (2) | 1.887 (2) |
C4-C5 | 1.347 (6)* | 1.396 (5) | 1.404 (2) | 1.404 (2) | 1.404 (2) |
C5-O3 | 1.323 (5)* | 1.256 (5) | 1.250 (2) | 1.238 (2) | 1.238 (2) |
C5-C6 | 1.504 (5)* | 1.542 (6) | 1.545 (2) | 1.554 (2) | 1.554 (2) |
C6-O4 | 1.225 (5)* | 1.220 (4) | 1.217 (2) | 1.222 (2) | 1.222 (2) |
C1-C6 | 1.449 (5)* | 1.455 (5) | 1.455 (3) | 1.447 (2) | 1.447 (2) |
* Related by inversion symmetry to the other half of the bromanilic acid molecule. |
The numbering scheme is as in Fig. 5 and does not necessarily relate to the CIF entries as some molecules have internal inversion symmetry. |
VAGTUS BAH2 | 2-bromo-3-methylpyridine (i) BAH2 | 2-bromo-3-methylpyridine (ii) BAH2 | 3-bromo-4-methylpyridine BAH- | |
C1-Br1 | 1.868 (4) | 1.883 (4) | 1.886 (4) | 1.892 (3) |
C1-C2 | 1.347 (6) | 1.346 (6) | 1.352 (6) | 1.347 (5) |
C2-O1 | 1.323 (5) | 1.322 (5) | 1.308 (5) | 1.327 (5) |
C2-C3 | 1.504 (5) | 1.517 (6) | 1.527 (6) | 1.517 (5) |
C3-O2 | 1.225 (5) | 1.223 (5) | 1.231 (5) | 1.243 (4) |
C3-C4 | 1.449 (5) | 1.452 (6) | 1.438 (6) | 1.419 (5) |
C4-Br2 | 1.868 (4)* | 1.883 (4)* | 1.886 (4)* | 1.894 (4) |
C4-C5 | 1.347 (6)* | 1.346 (6)* | 1.352 (6)* | 1.390 (5) |
C5-O3 | 1.323 (5)* | 1.322 (5)* | 1.308 (5)* | 1.266 (5) |
C5-C6 | 1.504 (5)* | 1.517 (6)* | 1.527 (6)* | 1.531 (5) |
C6-O4 | 1.225 (5)* | 1.223 (5)* | 1.231 (5)* | 1.234 (4) |
C1-C6 | 1.449 (5)* | 1.452 (6)* | 1.438 (6)* | 1.441 (5) |
* Related by inversion symmetry to the other half of the bromanilic acid molecule. (i) and (ii) represent the two independent bromanilic acid molecules in the 2-bromo-3-methylpyridine molecular complex. |
D—H···A | D—H (Å) | H···A (Å) | D···A (Å) | D—H···A (°) |
2-picoline | ||||
N2—H2···O4 | 0.86 (3) | 2.02 (3) | 2.838 (3) | 159 (3) |
N2—H2···O3 | 0.86 (3) | 2.36 (3) | 2.946 (3) | 126 (2) |
N1—H1···O1 | 0.77 (4) | 1.96 (4) | 2.693 (3) | 160 (4) |
N1—H1···O2 | 0.77 (4) | 2.36 (4) | 2.828 (3) | 121 (4) |
3-picoline | ||||
N1—H5···O1 | 0.84 (3) | 1.78 (3) | 2.598 (2) | 165 (3) |
N1—H5···O2i | 0.84 (3) | 2.54 (3) | 3.039 (2) | 119 (3) |
C4—H4···Br1ii | 0.93 | 2.96 | 3.7977 (18) | 151.0 |
4-picoline | ||||
N1—H3···O1 | 0.74 (3) | 2.12 (3) | 2.760 (3) | 145 (4) |
N1—H3···O2 | 0.74 (3) | 2.31 (3) | 2.859 (3) | 131 (3) |
2,4-lutidine | ||||
O1—H1···O2iii | 0.68 (3) | 2.03 (3) | 2.6509 (18) | 151 (3) |
O1—H1···O2 | 0.68 (3) | 2.26 (3) | 2.6559 (19) | 119 (3) |
N1—H2···O3iv | 0.72 (2) | 2.14 (2) | 2.849 (2) | 168 (3) |
N1—H2···O4iv | 0.72 (2) | 2.56 (2) | 2.9807 (18) | 119 (2) |
2,5-lutidine | ||||
O1—H1···O2v | 0.82 | 2.01 | 2.6994 (17) | 140.8 |
O1—H1···O2 | 0.82 | 2.16 | 2.6403 (19) | 117 |
N1—H1A···O4 | 0.86 | 2.17 | 2.9794 (19) | 157.6 |
N1—H1A···O3 | 0.86 | 2.34 | 2.883 (2) | 121.6 |
3,5-lutidine | ||||
N1—H2···O3vi | 0.93 (3) | 1.84 (3) | 2.677 (3) | 148 (3) |
N1—H2···O4vi | 0.93 (3) | 2.37 (3) | 3.008 (3) | 125 (3) |
O1—H1···O2iii | 0.72 (3) | 2.11 (3) | 2.768 (3) | 152 (3) |
O1—H1···O2 | 0.72 (3) | 2.23 (3) | 2.631 (2) | 116 (3) |
3-bromo-4-methylpyridine | ||||
O1—H1···O2vii | 0.87 (5) | 1.97 (5) | 2.717 (3) | 144 (4) |
O1—H1···O2 | 0.87 (5) | 2.12 (4) | 2.637 (4) | 118 (4) |
N1—H5···O3viii | 0.79 (5) | 1.91 (5) | 2.675 (4) | 161 (5) |
N1—H5···O4viii | 0.79 (5) | 2.53 (5) | 2.915 (4) | 112 (4) |
2,3-lutidine | ||||
O1—H1···O2 | 0.82 | 2.13 | 2.611 (4) | 117.1 |
O1—H1···Br1ix | 0.82 | 2.82 | 3.423 (3) | 131.9 |
N1—H1A···O3x | 0.86 | 1.93 | 2.777 (4) | 168.4 |
N1—H1A···O4x | 0.86 | 2.54 | 3.043 (4) | 118.7 |
2-bromo-3-methylpyridine | ||||
O1—H1···O4 | 0.857 (19) | 2.01 (3) | 2.794 (4) | 151 (5) |
O1—H1···O2xi | 0.857 (19) | 2.15 (5) | 2.638 (5) | 115 (4) |
O3—H2···N1 | 0.92 (5) | 1.73 (5) | 2.619 (5) | 163 (5) |
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, y+1/2, -z+1/2; (iii) -x+1, -y, -z+1; (iv) x-1, y, z; (v) -x, -y, -z; (vi) -x, -y+1, -z+1; (vii) -x, -y, -z+2; (viii) -x+1, y-1/2, -z+3/2; (ix) x+1/2, -y+1/2, z+1/2; (x) x+1, y, z; (xi) -x+1, -y+1, -z+1. |
No data available in manuscript - please supply missing values. |
Br···Br | Br···O | C-H···Br | Br···π | O-H···Br | |
VAGTUS (Robl, 1987) | |||||
2-picoline | |||||
3-picoline | |||||
4-picoline | ?(x2) | ||||
2,3-lutidine | ?(x2) | ||||
2,4-lutidine | |||||
2,5-lutidine | ?(x4) | ||||
3,5-lutidine | ?(x2) | ||||
2-bromo-3-methylpyridine | |||||
3-bromo-4-methylpyridine | ?(x2) |
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