Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617017648/ky3133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017648/ky3133Eacrylsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617017648/ky3133Zacrylsup3.hkl |
CCDC references: 1567601; 1567602
Data collection: SAINT (Bruker, 2012) for Eacryl; APEX2 (Bruker, 2012) for Zacryl. Cell refinement: APEX2 (Bruker, 2012) for Eacryl; SAINT (Bruker, 2012) for Zacryl. For both structures, data reduction: SAINT (Bruker, 2012). Program(s) used to solve structure: SIR2004 (Burla et al., 2003) for Eacryl; SHELXT (Sheldrick, 2015a) for Zacryl. Program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b) for Eacryl; SHELXL (Sheldrick, 2015b) for Zacryl. Molecular graphics: OLEX2 (Dolomanov et al., 2009) for Eacryl; SHELXTL (Bruker, 2012) for Zacryl. Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for Eacryl; SHELXTL (Bruker, 2012) for Zacryl.
C17H13Br3N2 | Z = 4 |
Mr = 485.02 | F(000) = 936 |
Triclinic, P1 | Dx = 1.830 Mg m−3 |
a = 11.965 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.595 (2) Å | Cell parameters from 4669 reflections |
c = 13.667 (3) Å | θ = 2.5–26.8° |
α = 114.497 (3)° | µ = 6.87 mm−1 |
β = 106.139 (4)° | T = 100 K |
γ = 93.912 (4)° | Plate, yellow |
V = 1760.3 (8) Å3 | 0.4 × 0.2 × 0.06 mm |
Bruker APEXII CCD diffractometer | 4214 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | θmax = 25.0°, θmin = 1.8° |
Tmin = 0.047, Tmax = 0.154 | h = −14→14 |
13968 measured reflections | k = −14→14 |
6178 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0409P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.001 |
6178 reflections | Δρmax = 0.66 e Å−3 |
401 parameters | Δρmin = −0.55 e Å−3 |
0 restraints |
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 | ||
Br1 | 0.98998 (4) | 0.89059 (4) | 0.15948 (4) | 0.05443 (14) | |
Br2 | 0.81943 (6) | 0.40862 (5) | −0.15987 (5) | 0.08624 (19) | |
Br3 | 0.61195 (4) | 0.61348 (4) | 0.18038 (5) | 0.07006 (17) | |
N1 | 0.6910 (3) | 0.9993 (3) | 0.2473 (3) | 0.0616 (10) | |
N2 | 1.1546 (3) | 0.6158 (3) | 0.5775 (3) | 0.0576 (9) | |
C1 | 0.7418 (4) | 0.9285 (3) | 0.2554 (3) | 0.0448 (10) | |
C2 | 0.8071 (3) | 0.8404 (3) | 0.2675 (3) | 0.0347 (9) | |
C3 | 0.8666 (3) | 0.8583 (3) | 0.3743 (3) | 0.0368 (9) | |
H3 | 0.860603 | 0.930628 | 0.432105 | 0.044* | |
C4 | 0.8047 (3) | 0.7380 (3) | 0.1606 (3) | 0.0345 (8) | |
C5 | 0.8829 (3) | 0.7449 (3) | 0.1048 (3) | 0.0368 (9) | |
C6 | 0.8890 (3) | 0.6487 (3) | 0.0098 (3) | 0.0462 (10) | |
H6 | 0.945231 | 0.655996 | −0.025495 | 0.055* | |
C7 | 0.8112 (4) | 0.5426 (3) | −0.0317 (3) | 0.0496 (10) | |
C8 | 0.7277 (4) | 0.5312 (3) | 0.0173 (4) | 0.0510 (11) | |
H8 | 0.672915 | 0.457761 | −0.013605 | 0.061* | |
C9 | 0.7257 (3) | 0.6288 (3) | 0.1118 (4) | 0.0444 (10) | |
C10 | 0.9377 (3) | 0.7896 (3) | 0.4187 (3) | 0.0352 (9) | |
C11 | 0.9874 (3) | 0.8364 (3) | 0.5385 (3) | 0.0430 (10) | |
H11 | 0.971582 | 0.910179 | 0.584838 | 0.052* | |
C12 | 1.0571 (3) | 0.7808 (3) | 0.5908 (3) | 0.0435 (10) | |
H12 | 1.087782 | 0.815862 | 0.671790 | 0.052* | |
C13 | 1.0843 (3) | 0.6710 (3) | 0.5253 (4) | 0.0445 (10) | |
C14 | 1.0346 (3) | 0.6234 (3) | 0.4059 (3) | 0.0445 (10) | |
H14 | 1.050264 | 0.549720 | 0.359228 | 0.053* | |
C15 | 0.9640 (3) | 0.6804 (3) | 0.3550 (3) | 0.0429 (10) | |
H15 | 0.932054 | 0.644880 | 0.273950 | 0.051* | |
C16 | 1.2096 (4) | 0.6691 (5) | 0.7008 (4) | 0.0730 (14) | |
H16A | 1.147855 | 0.683826 | 0.736332 | 0.110* | |
H16B | 1.264083 | 0.744801 | 0.727575 | 0.110* | |
H16C | 1.254085 | 0.614745 | 0.721586 | 0.110* | |
C17 | 1.1921 (4) | 0.5093 (4) | 0.5104 (4) | 0.0699 (14) | |
H17A | 1.121910 | 0.445356 | 0.458370 | 0.105* | |
H17B | 1.244237 | 0.483582 | 0.561782 | 0.105* | |
H17C | 1.235231 | 0.527610 | 0.466086 | 0.105* | |
Br4 | 0.42342 (5) | 0.48532 (4) | 0.33567 (5) | 0.07571 (18) | |
Br5 | 0.57610 (4) | 0.19548 (4) | −0.01856 (4) | 0.06937 (16) | |
Br6 | 0.18828 (4) | −0.00305 (4) | 0.05300 (4) | 0.05723 (14) | |
N3 | 0.0283 (4) | 0.2885 (4) | 0.1784 (4) | 0.0813 (13) | |
N4 | 0.6575 (3) | 0.1389 (3) | 0.6178 (3) | 0.0461 (8) | |
C18 | 0.1202 (4) | 0.2712 (4) | 0.2135 (4) | 0.0558 (11) | |
C19 | 0.2362 (3) | 0.2501 (3) | 0.2580 (4) | 0.0446 (10) | |
C20 | 0.2635 (3) | 0.2411 (3) | 0.3556 (4) | 0.0439 (10) | |
H20 | 0.202042 | 0.250391 | 0.388059 | 0.053* | |
C21 | 0.3151 (3) | 0.2390 (3) | 0.1877 (3) | 0.0390 (9) | |
C22 | 0.4013 (3) | 0.3342 (3) | 0.2113 (4) | 0.0443 (10) | |
C23 | 0.4770 (3) | 0.3209 (3) | 0.1486 (4) | 0.0449 (10) | |
H23 | 0.535806 | 0.386991 | 0.166671 | 0.054* | |
C24 | 0.4667 (3) | 0.2131 (3) | 0.0613 (3) | 0.0424 (10) | |
C25 | 0.3811 (3) | 0.1156 (3) | 0.0311 (3) | 0.0434 (10) | |
H25 | 0.373643 | 0.040537 | −0.030950 | 0.052* | |
C26 | 0.3061 (3) | 0.1319 (3) | 0.0959 (3) | 0.0404 (9) | |
C27 | 0.3697 (3) | 0.2197 (3) | 0.4208 (3) | 0.0389 (9) | |
C28 | 0.3665 (3) | 0.2047 (3) | 0.5152 (3) | 0.0435 (10) | |
H28 | 0.296719 | 0.213284 | 0.535530 | 0.052* | |
C29 | 0.4585 (3) | 0.1783 (3) | 0.5804 (3) | 0.0429 (10) | |
H29 | 0.450666 | 0.167619 | 0.643161 | 0.052* | |
C30 | 0.5651 (3) | 0.1667 (3) | 0.5552 (3) | 0.0387 (9) | |
C31 | 0.5706 (3) | 0.1864 (3) | 0.4623 (3) | 0.0428 (10) | |
H31 | 0.641828 | 0.182516 | 0.444196 | 0.051* | |
C32 | 0.4763 (3) | 0.2110 (3) | 0.3973 (3) | 0.0446 (10) | |
H32 | 0.483402 | 0.222403 | 0.334674 | 0.054* | |
C33 | 0.6464 (4) | 0.1123 (4) | 0.7093 (4) | 0.0554 (11) | |
H33A | 0.626324 | 0.180228 | 0.765152 | 0.083* | |
H33B | 0.722035 | 0.097663 | 0.746960 | 0.083* | |
H33C | 0.583458 | 0.041247 | 0.677308 | 0.083* | |
C34 | 0.7615 (4) | 0.1172 (4) | 0.5841 (4) | 0.0570 (11) | |
H34A | 0.805099 | 0.191839 | 0.594258 | 0.085* | |
H34B | 0.736643 | 0.058036 | 0.503724 | 0.085* | |
H34C | 0.813099 | 0.087035 | 0.631605 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0559 (3) | 0.0553 (3) | 0.0536 (3) | −0.00597 (19) | 0.0264 (2) | 0.0237 (2) |
Br2 | 0.1163 (5) | 0.0646 (3) | 0.0535 (3) | 0.0245 (3) | 0.0357 (3) | −0.0009 (3) |
Br3 | 0.0679 (3) | 0.0526 (3) | 0.0891 (4) | −0.0066 (2) | 0.0488 (3) | 0.0202 (3) |
N1 | 0.076 (3) | 0.058 (2) | 0.050 (3) | 0.023 (2) | 0.019 (2) | 0.023 (2) |
N2 | 0.056 (2) | 0.069 (2) | 0.053 (3) | 0.0241 (19) | 0.020 (2) | 0.029 (2) |
C1 | 0.058 (3) | 0.040 (2) | 0.032 (2) | 0.003 (2) | 0.018 (2) | 0.011 (2) |
C2 | 0.036 (2) | 0.034 (2) | 0.034 (2) | 0.0031 (16) | 0.0176 (19) | 0.0116 (18) |
C3 | 0.039 (2) | 0.033 (2) | 0.037 (2) | 0.0044 (16) | 0.021 (2) | 0.0087 (18) |
C4 | 0.039 (2) | 0.035 (2) | 0.030 (2) | 0.0058 (16) | 0.0126 (18) | 0.0153 (18) |
C5 | 0.037 (2) | 0.040 (2) | 0.031 (2) | 0.0024 (16) | 0.0088 (19) | 0.0167 (19) |
C6 | 0.048 (3) | 0.061 (3) | 0.036 (2) | 0.013 (2) | 0.019 (2) | 0.025 (2) |
C7 | 0.061 (3) | 0.047 (2) | 0.030 (2) | 0.013 (2) | 0.016 (2) | 0.007 (2) |
C8 | 0.052 (3) | 0.034 (2) | 0.049 (3) | 0.0000 (18) | 0.012 (2) | 0.007 (2) |
C9 | 0.045 (2) | 0.042 (2) | 0.051 (3) | 0.0046 (18) | 0.023 (2) | 0.022 (2) |
C10 | 0.035 (2) | 0.039 (2) | 0.033 (2) | 0.0057 (16) | 0.0173 (19) | 0.0141 (18) |
C11 | 0.048 (2) | 0.037 (2) | 0.042 (3) | 0.0056 (17) | 0.021 (2) | 0.013 (2) |
C12 | 0.038 (2) | 0.055 (2) | 0.033 (2) | 0.0036 (18) | 0.012 (2) | 0.017 (2) |
C13 | 0.037 (2) | 0.050 (2) | 0.049 (3) | 0.0086 (18) | 0.018 (2) | 0.023 (2) |
C14 | 0.048 (2) | 0.044 (2) | 0.044 (3) | 0.0132 (18) | 0.024 (2) | 0.016 (2) |
C15 | 0.048 (2) | 0.045 (2) | 0.034 (2) | 0.0066 (18) | 0.019 (2) | 0.013 (2) |
C16 | 0.066 (3) | 0.097 (4) | 0.056 (4) | 0.032 (3) | 0.012 (3) | 0.038 (3) |
C17 | 0.072 (3) | 0.084 (3) | 0.074 (4) | 0.040 (3) | 0.038 (3) | 0.042 (3) |
Br4 | 0.0849 (4) | 0.0501 (3) | 0.0893 (4) | 0.0049 (2) | 0.0508 (3) | 0.0166 (3) |
Br5 | 0.0702 (3) | 0.0830 (3) | 0.0722 (4) | 0.0076 (2) | 0.0489 (3) | 0.0365 (3) |
Br6 | 0.0465 (3) | 0.0572 (3) | 0.0723 (3) | −0.00078 (19) | 0.0232 (2) | 0.0330 (2) |
N3 | 0.054 (3) | 0.143 (4) | 0.093 (4) | 0.042 (3) | 0.038 (3) | 0.083 (3) |
N4 | 0.050 (2) | 0.054 (2) | 0.043 (2) | 0.0178 (16) | 0.0235 (18) | 0.0244 (18) |
C18 | 0.050 (3) | 0.083 (3) | 0.058 (3) | 0.021 (2) | 0.032 (3) | 0.045 (3) |
C19 | 0.041 (2) | 0.052 (2) | 0.055 (3) | 0.0143 (18) | 0.024 (2) | 0.031 (2) |
C20 | 0.047 (2) | 0.045 (2) | 0.058 (3) | 0.0164 (18) | 0.036 (2) | 0.028 (2) |
C21 | 0.036 (2) | 0.050 (2) | 0.045 (3) | 0.0114 (17) | 0.018 (2) | 0.031 (2) |
C22 | 0.043 (2) | 0.044 (2) | 0.052 (3) | 0.0109 (18) | 0.021 (2) | 0.025 (2) |
C23 | 0.037 (2) | 0.055 (3) | 0.057 (3) | 0.0037 (18) | 0.017 (2) | 0.038 (2) |
C24 | 0.045 (2) | 0.055 (3) | 0.043 (3) | 0.0101 (19) | 0.024 (2) | 0.030 (2) |
C25 | 0.049 (2) | 0.049 (2) | 0.037 (3) | 0.0081 (18) | 0.018 (2) | 0.023 (2) |
C26 | 0.033 (2) | 0.049 (2) | 0.048 (3) | 0.0021 (17) | 0.014 (2) | 0.032 (2) |
C27 | 0.041 (2) | 0.039 (2) | 0.043 (3) | 0.0082 (16) | 0.020 (2) | 0.0205 (19) |
C28 | 0.047 (2) | 0.048 (2) | 0.051 (3) | 0.0164 (19) | 0.033 (2) | 0.025 (2) |
C29 | 0.053 (3) | 0.046 (2) | 0.044 (3) | 0.0152 (19) | 0.030 (2) | 0.024 (2) |
C30 | 0.046 (2) | 0.0319 (19) | 0.038 (2) | 0.0077 (16) | 0.019 (2) | 0.0119 (18) |
C31 | 0.040 (2) | 0.055 (2) | 0.045 (3) | 0.0151 (18) | 0.025 (2) | 0.026 (2) |
C32 | 0.051 (3) | 0.054 (2) | 0.046 (3) | 0.0161 (19) | 0.031 (2) | 0.028 (2) |
C33 | 0.060 (3) | 0.065 (3) | 0.053 (3) | 0.011 (2) | 0.022 (2) | 0.037 (2) |
C34 | 0.051 (3) | 0.070 (3) | 0.055 (3) | 0.021 (2) | 0.023 (2) | 0.028 (2) |
Br1—C5 | 1.892 (3) | Br4—C22 | 1.892 (4) |
Br2—C7 | 1.895 (4) | Br5—C24 | 1.894 (4) |
Br3—C9 | 1.895 (4) | Br6—C26 | 1.899 (3) |
N1—C1 | 1.139 (5) | N3—C18 | 1.146 (5) |
N2—C13 | 1.363 (5) | N4—C30 | 1.361 (5) |
N2—C16 | 1.451 (5) | N4—C33 | 1.458 (5) |
N2—C17 | 1.460 (5) | N4—C34 | 1.448 (5) |
C1—C2 | 1.438 (5) | C18—C19 | 1.443 (6) |
C2—C3 | 1.347 (5) | C19—C20 | 1.337 (5) |
C2—C4 | 1.486 (5) | C19—C21 | 1.498 (5) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C3—C10 | 1.446 (5) | C20—C27 | 1.448 (5) |
C4—C5 | 1.381 (5) | C21—C22 | 1.390 (5) |
C4—C9 | 1.394 (5) | C21—C26 | 1.381 (5) |
C5—C6 | 1.385 (5) | C22—C23 | 1.384 (5) |
C6—H6 | 0.9500 | C23—H23 | 0.9500 |
C6—C7 | 1.372 (5) | C23—C24 | 1.354 (5) |
C7—C8 | 1.379 (5) | C24—C25 | 1.379 (5) |
C8—H8 | 0.9500 | C25—H25 | 0.9500 |
C8—C9 | 1.373 (5) | C25—C26 | 1.396 (5) |
C10—C11 | 1.411 (5) | C27—C28 | 1.390 (5) |
C10—C15 | 1.402 (5) | C27—C32 | 1.399 (5) |
C11—H11 | 0.9500 | C28—H28 | 0.9500 |
C11—C12 | 1.364 (5) | C28—C29 | 1.366 (5) |
C12—H12 | 0.9500 | C29—H29 | 0.9500 |
C12—C13 | 1.419 (5) | C29—C30 | 1.412 (5) |
C13—C14 | 1.406 (5) | C30—C31 | 1.408 (5) |
C14—H14 | 0.9500 | C31—H31 | 0.9500 |
C14—C15 | 1.373 (5) | C31—C32 | 1.370 (5) |
C15—H15 | 0.9500 | C32—H32 | 0.9500 |
C16—H16A | 0.9800 | C33—H33A | 0.9800 |
C16—H16B | 0.9800 | C33—H33B | 0.9800 |
C16—H16C | 0.9800 | C33—H33C | 0.9800 |
C17—H17A | 0.9800 | C34—H34A | 0.9800 |
C17—H17B | 0.9800 | C34—H34B | 0.9800 |
C17—H17C | 0.9800 | C34—H34C | 0.9800 |
C13—N2—C16 | 121.9 (4) | C30—N4—C33 | 120.6 (3) |
C13—N2—C17 | 120.5 (4) | C30—N4—C34 | 120.6 (3) |
C16—N2—C17 | 116.9 (3) | C34—N4—C33 | 118.1 (3) |
N1—C1—C2 | 179.1 (5) | N3—C18—C19 | 179.7 (7) |
C1—C2—C4 | 116.9 (3) | C18—C19—C21 | 115.6 (4) |
C3—C2—C1 | 117.5 (3) | C20—C19—C18 | 118.4 (4) |
C3—C2—C4 | 125.5 (3) | C20—C19—C21 | 126.0 (3) |
C2—C3—H3 | 113.5 | C19—C20—H20 | 114.1 |
C2—C3—C10 | 132.9 (3) | C19—C20—C27 | 131.8 (4) |
C10—C3—H3 | 113.5 | C27—C20—H20 | 114.1 |
C5—C4—C2 | 121.7 (3) | C22—C21—C19 | 122.4 (4) |
C5—C4—C9 | 115.8 (3) | C26—C21—C19 | 121.1 (3) |
C9—C4—C2 | 122.5 (3) | C26—C21—C22 | 116.5 (3) |
C4—C5—Br1 | 119.7 (3) | C21—C22—Br4 | 120.5 (3) |
C4—C5—C6 | 123.2 (3) | C23—C22—Br4 | 117.8 (3) |
C6—C5—Br1 | 117.1 (3) | C23—C22—C21 | 121.6 (4) |
C5—C6—H6 | 121.1 | C22—C23—H23 | 120.2 |
C7—C6—C5 | 117.9 (4) | C24—C23—C22 | 119.7 (3) |
C7—C6—H6 | 121.1 | C24—C23—H23 | 120.2 |
C6—C7—Br2 | 118.9 (3) | C23—C24—Br5 | 118.8 (3) |
C6—C7—C8 | 121.7 (4) | C23—C24—C25 | 121.9 (4) |
C8—C7—Br2 | 119.4 (3) | C25—C24—Br5 | 119.3 (3) |
C7—C8—H8 | 120.9 | C24—C25—H25 | 121.5 |
C9—C8—C7 | 118.2 (3) | C24—C25—C26 | 117.1 (4) |
C9—C8—H8 | 120.9 | C26—C25—H25 | 121.5 |
C4—C9—Br3 | 118.5 (3) | C21—C26—Br6 | 120.1 (3) |
C8—C9—Br3 | 118.5 (3) | C21—C26—C25 | 123.3 (3) |
C8—C9—C4 | 123.0 (4) | C25—C26—Br6 | 116.6 (3) |
C11—C10—C3 | 117.4 (3) | C28—C27—C20 | 117.7 (3) |
C15—C10—C3 | 126.7 (3) | C28—C27—C32 | 116.0 (3) |
C15—C10—C11 | 115.8 (3) | C32—C27—C20 | 126.2 (3) |
C10—C11—H11 | 118.5 | C27—C28—H28 | 118.3 |
C12—C11—C10 | 123.0 (3) | C29—C28—C27 | 123.4 (3) |
C12—C11—H11 | 118.5 | C29—C28—H28 | 118.3 |
C11—C12—H12 | 119.7 | C28—C29—H29 | 119.7 |
C11—C12—C13 | 120.7 (4) | C28—C29—C30 | 120.6 (3) |
C13—C12—H12 | 119.7 | C30—C29—H29 | 119.7 |
N2—C13—C12 | 120.7 (4) | N4—C30—C29 | 121.8 (3) |
N2—C13—C14 | 122.7 (4) | N4—C30—C31 | 122.0 (3) |
C14—C13—C12 | 116.6 (4) | C31—C30—C29 | 116.2 (3) |
C13—C14—H14 | 119.1 | C30—C31—H31 | 119.0 |
C15—C14—C13 | 121.8 (4) | C32—C31—C30 | 121.9 (3) |
C15—C14—H14 | 119.1 | C32—C31—H31 | 119.0 |
C10—C15—H15 | 119.0 | C27—C32—H32 | 119.1 |
C14—C15—C10 | 122.0 (4) | C31—C32—C27 | 121.7 (4) |
C14—C15—H15 | 119.0 | C31—C32—H32 | 119.1 |
N2—C16—H16A | 109.5 | N4—C33—H33A | 109.5 |
N2—C16—H16B | 109.5 | N4—C33—H33B | 109.5 |
N2—C16—H16C | 109.5 | N4—C33—H33C | 109.5 |
H16A—C16—H16B | 109.5 | H33A—C33—H33B | 109.5 |
H16A—C16—H16C | 109.5 | H33A—C33—H33C | 109.5 |
H16B—C16—H16C | 109.5 | H33B—C33—H33C | 109.5 |
N2—C17—H17A | 109.5 | N4—C34—H34A | 109.5 |
N2—C17—H17B | 109.5 | N4—C34—H34B | 109.5 |
N2—C17—H17C | 109.5 | N4—C34—H34C | 109.5 |
H17A—C17—H17B | 109.5 | H34A—C34—H34B | 109.5 |
H17A—C17—H17C | 109.5 | H34A—C34—H34C | 109.5 |
H17B—C17—H17C | 109.5 | H34B—C34—H34C | 109.5 |
Br1—C5—C6—C7 | −179.4 (3) | Br4—C22—C23—C24 | 177.8 (3) |
Br2—C7—C8—C9 | 178.3 (3) | Br5—C24—C25—C26 | 177.2 (3) |
N2—C13—C14—C15 | −180.0 (4) | N4—C30—C31—C32 | 178.1 (3) |
C1—C2—C3—C10 | 178.4 (4) | C18—C19—C20—C27 | 179.5 (4) |
C1—C2—C4—C5 | 85.0 (4) | C18—C19—C21—C22 | 97.0 (5) |
C1—C2—C4—C9 | −96.4 (4) | C18—C19—C21—C26 | −83.8 (5) |
C2—C3—C10—C11 | −179.7 (4) | C19—C20—C27—C28 | −174.4 (4) |
C2—C3—C10—C15 | 1.0 (6) | C19—C20—C27—C32 | 4.7 (7) |
C2—C4—C5—Br1 | −3.9 (5) | C19—C21—C22—Br4 | −0.1 (5) |
C2—C4—C5—C6 | 175.1 (3) | C19—C21—C22—C23 | 177.0 (4) |
C2—C4—C9—Br3 | 3.4 (5) | C19—C21—C26—Br6 | 2.5 (5) |
C2—C4—C9—C8 | −175.7 (4) | C19—C21—C26—C25 | −176.9 (3) |
C3—C2—C4—C5 | −94.0 (4) | C20—C19—C21—C22 | −83.7 (5) |
C3—C2—C4—C9 | 84.6 (5) | C20—C19—C21—C26 | 95.6 (5) |
C3—C10—C11—C12 | −179.3 (3) | C20—C27—C28—C29 | 176.7 (3) |
C3—C10—C15—C14 | 178.8 (3) | C20—C27—C32—C31 | −177.7 (4) |
C4—C2—C3—C10 | −2.7 (6) | C21—C19—C20—C27 | 0.2 (7) |
C4—C5—C6—C7 | 1.6 (6) | C21—C22—C23—C24 | 0.6 (6) |
C5—C4—C9—Br3 | −178.0 (3) | C22—C21—C26—Br6 | −178.2 (3) |
C5—C4—C9—C8 | 3.0 (6) | C22—C21—C26—C25 | 2.4 (6) |
C5—C6—C7—Br2 | −178.8 (3) | C22—C23—C24—Br5 | −177.0 (3) |
C5—C6—C7—C8 | 1.2 (6) | C22—C23—C24—C25 | 1.1 (6) |
C6—C7—C8—C9 | −1.7 (6) | C23—C24—C25—C26 | −1.0 (6) |
C7—C8—C9—Br3 | −179.5 (3) | C24—C25—C26—Br6 | 179.7 (3) |
C7—C8—C9—C4 | −0.4 (6) | C24—C25—C26—C21 | −0.9 (6) |
C9—C4—C5—Br1 | 177.5 (3) | C26—C21—C22—Br4 | −179.4 (3) |
C9—C4—C5—C6 | −3.5 (6) | C26—C21—C22—C23 | −2.3 (6) |
C10—C11—C12—C13 | 0.6 (6) | C27—C28—C29—C30 | 1.1 (6) |
C11—C10—C15—C14 | −0.5 (5) | C28—C27—C32—C31 | 1.4 (5) |
C11—C12—C13—N2 | 179.6 (4) | C28—C29—C30—N4 | −179.1 (3) |
C11—C12—C13—C14 | −0.9 (5) | C28—C29—C30—C31 | 1.3 (5) |
C12—C13—C14—C15 | 0.5 (5) | C29—C30—C31—C32 | −2.4 (5) |
C13—C14—C15—C10 | 0.2 (6) | C30—C31—C32—C27 | 1.0 (6) |
C15—C10—C11—C12 | 0.1 (5) | C32—C27—C28—C29 | −2.5 (6) |
C16—N2—C13—C12 | −3.4 (6) | C33—N4—C30—C29 | 4.0 (5) |
C16—N2—C13—C14 | 177.0 (4) | C33—N4—C30—C31 | −176.5 (3) |
C17—N2—C13—C12 | −173.9 (4) | C34—N4—C30—C29 | 174.5 (3) |
C17—N2—C13—C14 | 6.6 (6) | C34—N4—C30—C31 | −6.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···C4 | 0.95 | 2.56 | 3.191 (5) | 124 |
C15—H15···C9 | 0.95 | 2.75 | 3.504 (6) | 137 |
C32—H32···C21 | 0.95 | 2.51 | 3.149 (5) | 125 |
C32—H32···C22 | 0.95 | 2.65 | 3.446 (5) | 142 |
C17H13Br3N2 | F(000) = 936 |
Mr = 484.99 | Dx = 1.948 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.082 (2) Å | Cell parameters from 7150 reflections |
b = 13.024 (3) Å | θ = 2.5–30.4° |
c = 14.266 (3) Å | µ = 7.32 mm−1 |
β = 101.467 (3)° | T = 100 K |
V = 1653.8 (6) Å3 | Prism, yellow |
Z = 4 | 0.30 × 0.30 × 0.20 mm |
Bruker APEXII CCD diffractometer | 3954 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
φ and ω scans | θmax = 30.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→12 |
Tmin = 0.120, Tmax = 0.222 | k = −18→18 |
25670 measured reflections | l = −20→20 |
5071 independent reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.4374P] where P = (Fo2 + 2Fc2)/3 |
5071 reflections | (Δ/σ)max = 0.001 |
201 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −1.07 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 | ||
Br1 | 0.54668 (3) | 0.59083 (2) | 0.76907 (2) | 0.01443 (7) | |
Br2 | −0.02660 (3) | 0.73745 (2) | 0.79072 (2) | 0.02085 (8) | |
Br3 | 0.29258 (3) | 0.93565 (2) | 0.54218 (2) | 0.02020 (7) | |
N1 | 0.7073 (3) | 0.93211 (17) | 0.64818 (18) | 0.0194 (5) | |
N2 | 1.0562 (2) | 0.59048 (16) | 0.37878 (16) | 0.0150 (4) | |
C1 | 0.6333 (3) | 0.8607 (2) | 0.63280 (18) | 0.0139 (5) | |
C2 | 0.5420 (3) | 0.76963 (19) | 0.61470 (18) | 0.0119 (5) | |
C3 | 0.5751 (3) | 0.69145 (18) | 0.55982 (18) | 0.0115 (5) | |
H3 | 0.5027 | 0.6379 | 0.5509 | 0.014* | |
C4 | 0.4078 (3) | 0.76454 (18) | 0.66008 (17) | 0.0110 (5) | |
C5 | 0.3918 (3) | 0.68805 (19) | 0.72655 (18) | 0.0117 (5) | |
C6 | 0.2643 (3) | 0.6797 (2) | 0.76624 (18) | 0.0143 (5) | |
H6 | 0.2560 | 0.6267 | 0.8106 | 0.017* | |
C7 | 0.1494 (3) | 0.7505 (2) | 0.73972 (19) | 0.0152 (5) | |
C8 | 0.1603 (3) | 0.8291 (2) | 0.67671 (19) | 0.0154 (5) | |
H8 | 0.0825 | 0.8786 | 0.6609 | 0.018* | |
C9 | 0.2879 (3) | 0.83430 (19) | 0.63691 (18) | 0.0138 (5) | |
C10 | 0.6993 (3) | 0.67368 (18) | 0.51219 (17) | 0.0111 (5) | |
C11 | 0.6945 (3) | 0.58412 (19) | 0.45657 (18) | 0.0137 (5) | |
H11 | 0.6087 | 0.5410 | 0.4499 | 0.016* | |
C12 | 0.8091 (3) | 0.55636 (19) | 0.41134 (18) | 0.0135 (5) | |
H12 | 0.8009 | 0.4954 | 0.3741 | 0.016* | |
C13 | 0.9394 (3) | 0.61878 (19) | 0.42019 (17) | 0.0124 (5) | |
C14 | 0.9425 (3) | 0.71067 (19) | 0.47314 (18) | 0.0131 (5) | |
H14 | 1.0265 | 0.7553 | 0.4782 | 0.016* | |
C15 | 0.8263 (3) | 0.7370 (2) | 0.51759 (19) | 0.0149 (5) | |
H15 | 0.8320 | 0.7994 | 0.5527 | 0.018* | |
C16 | 1.0513 (3) | 0.4934 (2) | 0.32853 (19) | 0.0157 (5) | |
H16A | 0.9681 | 0.4942 | 0.2730 | 0.024* | |
H16B | 1.0362 | 0.4374 | 0.3716 | 0.024* | |
H16C | 1.1462 | 0.4829 | 0.3071 | 0.024* | |
C17 | 1.1968 (3) | 0.6475 (2) | 0.3997 (2) | 0.0193 (6) | |
H17A | 1.1806 | 0.7169 | 0.3732 | 0.029* | |
H17B | 1.2723 | 0.6123 | 0.3710 | 0.029* | |
H17C | 1.2321 | 0.6517 | 0.4692 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01162 (12) | 0.01344 (13) | 0.01844 (13) | 0.00250 (9) | 0.00348 (9) | 0.00418 (9) |
Br2 | 0.01221 (12) | 0.03001 (16) | 0.02206 (15) | −0.00045 (10) | 0.00760 (10) | −0.00982 (11) |
Br3 | 0.02015 (14) | 0.01703 (14) | 0.02199 (14) | 0.00415 (10) | 0.00073 (11) | 0.00642 (10) |
N1 | 0.0199 (11) | 0.0173 (11) | 0.0227 (12) | −0.0032 (9) | 0.0081 (10) | −0.0033 (9) |
N2 | 0.0145 (10) | 0.0150 (11) | 0.0166 (11) | −0.0008 (8) | 0.0054 (9) | −0.0010 (9) |
C1 | 0.0148 (12) | 0.0161 (12) | 0.0114 (12) | 0.0021 (10) | 0.0036 (10) | −0.0007 (9) |
C2 | 0.0105 (11) | 0.0133 (12) | 0.0115 (12) | −0.0004 (9) | 0.0012 (9) | −0.0001 (9) |
C3 | 0.0108 (11) | 0.0100 (11) | 0.0131 (11) | −0.0018 (9) | 0.0009 (9) | 0.0006 (9) |
C4 | 0.0095 (11) | 0.0123 (11) | 0.0106 (12) | −0.0013 (9) | 0.0006 (9) | −0.0033 (9) |
C5 | 0.0083 (10) | 0.0123 (11) | 0.0134 (11) | 0.0015 (9) | −0.0001 (9) | −0.0027 (9) |
C6 | 0.0122 (11) | 0.0167 (12) | 0.0141 (12) | −0.0011 (9) | 0.0027 (10) | −0.0015 (9) |
C7 | 0.0109 (11) | 0.0194 (13) | 0.0155 (13) | 0.0000 (9) | 0.0033 (9) | −0.0080 (10) |
C8 | 0.0103 (11) | 0.0153 (13) | 0.0186 (13) | 0.0028 (9) | −0.0018 (10) | −0.0070 (10) |
C9 | 0.0143 (12) | 0.0129 (12) | 0.0127 (12) | −0.0001 (9) | −0.0007 (9) | 0.0000 (9) |
C10 | 0.0100 (11) | 0.0131 (12) | 0.0095 (11) | −0.0006 (9) | 0.0004 (9) | −0.0008 (9) |
C11 | 0.0102 (11) | 0.0130 (12) | 0.0177 (12) | −0.0026 (9) | 0.0019 (9) | 0.0001 (10) |
C12 | 0.0137 (12) | 0.0125 (12) | 0.0143 (12) | −0.0003 (9) | 0.0027 (10) | −0.0017 (9) |
C13 | 0.0121 (11) | 0.0153 (12) | 0.0096 (11) | −0.0001 (9) | 0.0014 (9) | 0.0015 (9) |
C14 | 0.0116 (11) | 0.0139 (12) | 0.0132 (12) | −0.0042 (9) | 0.0010 (9) | −0.0002 (9) |
C15 | 0.0164 (12) | 0.0124 (12) | 0.0148 (12) | −0.0032 (9) | 0.0005 (10) | −0.0020 (9) |
C16 | 0.0162 (12) | 0.0169 (13) | 0.0147 (12) | 0.0005 (10) | 0.0051 (10) | 0.0001 (10) |
C17 | 0.0119 (12) | 0.0210 (14) | 0.0265 (15) | −0.0020 (10) | 0.0076 (11) | 0.0035 (11) |
Br1—C5 | 1.900 (2) | C8—C9 | 1.390 (4) |
Br2—C7 | 1.891 (3) | C8—H8 | 0.9500 |
Br3—C9 | 1.896 (3) | C10—C11 | 1.407 (3) |
N1—C1 | 1.143 (3) | C10—C15 | 1.408 (3) |
N2—C13 | 1.364 (3) | C11—C12 | 1.377 (3) |
N2—C16 | 1.450 (3) | C11—H11 | 0.9500 |
N2—C17 | 1.456 (3) | C12—C13 | 1.421 (3) |
C1—C2 | 1.440 (4) | C12—H12 | 0.9500 |
C2—C3 | 1.354 (3) | C13—C14 | 1.413 (3) |
C2—C4 | 1.491 (3) | C14—C15 | 1.378 (4) |
C3—C10 | 1.446 (3) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.403 (3) | C16—H16A | 0.9800 |
C4—C9 | 1.406 (3) | C16—H16B | 0.9800 |
C5—C6 | 1.391 (3) | C16—H16C | 0.9800 |
C6—C7 | 1.387 (4) | C17—H17A | 0.9800 |
C6—H6 | 0.9500 | C17—H17B | 0.9800 |
C7—C8 | 1.379 (4) | C17—H17C | 0.9800 |
C13—N2—C16 | 120.0 (2) | C11—C10—C3 | 117.3 (2) |
C13—N2—C17 | 120.0 (2) | C15—C10—C3 | 126.0 (2) |
C16—N2—C17 | 119.1 (2) | C12—C11—C10 | 122.7 (2) |
N1—C1—C2 | 178.9 (3) | C12—C11—H11 | 118.6 |
C3—C2—C1 | 122.5 (2) | C10—C11—H11 | 118.6 |
C3—C2—C4 | 120.8 (2) | C11—C12—C13 | 120.1 (2) |
C1—C2—C4 | 116.7 (2) | C11—C12—H12 | 119.9 |
C2—C3—C10 | 132.5 (2) | C13—C12—H12 | 119.9 |
C2—C3—H3 | 113.8 | N2—C13—C14 | 121.7 (2) |
C10—C3—H3 | 113.8 | N2—C13—C12 | 120.9 (2) |
C5—C4—C9 | 116.0 (2) | C14—C13—C12 | 117.4 (2) |
C5—C4—C2 | 121.9 (2) | C15—C14—C13 | 121.4 (2) |
C9—C4—C2 | 122.1 (2) | C15—C14—H14 | 119.3 |
C6—C5—C4 | 122.5 (2) | C13—C14—H14 | 119.3 |
C6—C5—Br1 | 116.22 (19) | C14—C15—C10 | 121.5 (2) |
C4—C5—Br1 | 121.28 (18) | C14—C15—H15 | 119.2 |
C7—C6—C5 | 118.7 (2) | C10—C15—H15 | 119.2 |
C7—C6—H6 | 120.7 | N2—C16—H16A | 109.5 |
C5—C6—H6 | 120.7 | N2—C16—H16B | 109.5 |
C8—C7—C6 | 121.5 (2) | H16A—C16—H16B | 109.5 |
C8—C7—Br2 | 119.55 (19) | N2—C16—H16C | 109.5 |
C6—C7—Br2 | 118.9 (2) | H16A—C16—H16C | 109.5 |
C7—C8—C9 | 118.4 (2) | H16B—C16—H16C | 109.5 |
C7—C8—H8 | 120.8 | N2—C17—H17A | 109.5 |
C9—C8—H8 | 120.8 | N2—C17—H17B | 109.5 |
C8—C9—C4 | 122.8 (2) | H17A—C17—H17B | 109.5 |
C8—C9—Br3 | 117.61 (19) | N2—C17—H17C | 109.5 |
C4—C9—Br3 | 119.44 (19) | H17A—C17—H17C | 109.5 |
C11—C10—C15 | 116.7 (2) | H17B—C17—H17C | 109.5 |
C1—C2—C3—C10 | 3.3 (4) | C2—C4—C9—C8 | 178.3 (2) |
C4—C2—C3—C10 | −176.3 (2) | C5—C4—C9—Br3 | −176.24 (18) |
C3—C2—C4—C5 | 61.4 (3) | C2—C4—C9—Br3 | 2.1 (3) |
C1—C2—C4—C5 | −118.3 (3) | C2—C3—C10—C11 | −177.3 (3) |
C3—C2—C4—C9 | −116.8 (3) | C2—C3—C10—C15 | 3.8 (5) |
C1—C2—C4—C9 | 63.5 (3) | C15—C10—C11—C12 | 2.0 (4) |
C9—C4—C5—C6 | 1.2 (4) | C3—C10—C11—C12 | −177.0 (2) |
C2—C4—C5—C6 | −177.1 (2) | C10—C11—C12—C13 | 0.4 (4) |
C9—C4—C5—Br1 | −177.69 (17) | C16—N2—C13—C14 | 177.3 (2) |
C2—C4—C5—Br1 | 4.0 (3) | C17—N2—C13—C14 | 8.8 (4) |
C4—C5—C6—C7 | −0.6 (4) | C16—N2—C13—C12 | −2.8 (4) |
Br1—C5—C6—C7 | 178.28 (19) | C17—N2—C13—C12 | −171.3 (2) |
C5—C6—C7—C8 | −1.2 (4) | C11—C12—C13—N2 | 177.6 (2) |
C5—C6—C7—Br2 | 178.31 (18) | C11—C12—C13—C14 | −2.5 (4) |
C6—C7—C8—C9 | 2.3 (4) | N2—C13—C14—C15 | −177.7 (2) |
Br2—C7—C8—C9 | −177.15 (18) | C12—C13—C14—C15 | 2.4 (4) |
C7—C8—C9—C4 | −1.8 (4) | C13—C14—C15—C10 | 0.0 (4) |
C7—C8—C9—Br3 | 174.57 (19) | C11—C10—C15—C14 | −2.1 (4) |
C5—C4—C9—C8 | 0.0 (4) | C3—C10—C15—C14 | 176.7 (2) |