Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620002772/xk5067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067100K_v2_asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067120K_v2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067150Ksup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067180Ksup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067210Ksup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067240Ksup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067270Ksup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067293Ksup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067310Ksup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067340Ksup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067370Ksup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_ddq_4cnsup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.25GPasup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.49GPasup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.86GPasup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_1.42GPasup17.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_1.85GPasup18.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_2.55GPasup19.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_3.09GPasup20.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_3.95GPasup21.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_4.80GPasup22.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_5.48GPasup23.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_6.00GPasup24.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620002772/xk5067sup25.pdf |
CCDC references: 1986892; 1986893; 1986894; 1986895; 1986896; 1986897; 1986898; 1986899; 1986900; 1986901; 1986902; 1986903; 1986904; 1986905; 1986906; 1986907; 1986908; 1986909; 1986910; 1986911; 1986912; 1986913; 1986914
Data collection: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019) for 100K_v2_a, 120K_v2, 150K, 180K, 210K, 240K, 270K, 293K, 310K, 340K, 370K; CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for test3_ddq_4cn, test3_0.25GPa, test3_0.49GPa, test3_0.86GPa, test3_1.42GPa, test3_1.85GPa, test3_2.55GPa, test3_3.09GPa, test3_3.95GPa, test3_4.80GPa, test3_5.48GPa, test3_6.00GPa. Cell refinement: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019) for 100K_v2_a, 120K_v2, 150K, 180K, 210K, 240K, 270K, 293K, 310K, 340K, 370K; CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for test3_ddq_4cn, test3_0.25GPa, test3_0.49GPa, test3_0.86GPa, test3_1.42GPa, test3_1.85GPa, test3_2.55GPa, test3_3.09GPa, test3_3.95GPa, test3_4.80GPa, test3_5.48GPa, test3_6.00GPa. Data reduction: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019) for 100K_v2_a, 120K_v2, 150K, 180K, 210K, 240K, 270K, 293K, 310K, 340K, 370K; CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for test3_ddq_4cn, test3_0.25GPa, test3_0.49GPa, test3_0.86GPa, test3_1.42GPa, test3_1.85GPa, test3_2.55GPa, test3_3.09GPa, test3_3.95GPa, test3_4.80GPa, test3_5.48GPa, test3_6.00GPa. For all structures, program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018).
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.665 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7437 (1) Å | Cell parameters from 4986 reflections |
b = 10.0558 (2) Å | θ = 2.0–28.1° |
c = 20.4325 (4) Å | µ = 0.49 mm−1 |
β = 94.828 (2)° | T = 100 K |
V = 1380.68 (4) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3025 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2616 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 27.1°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −7→8 |
Tmin = 0.958, Tmax = 1.000 | k = −12→12 |
8958 measured reflections | l = −26→25 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0318P)2 + 1.1138P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
3025 reflections | Δρmax = 0.42 e Å−3 |
209 parameters | Δρmin = −0.24 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 | ||
Cl1 | 0.20839 (6) | 0.11213 (4) | −0.00692 (2) | 0.01412 (10) | |
N4 | 0.9971 (2) | 1.20526 (15) | 0.24921 (7) | 0.0199 (3) | |
Cl2 | 0.11858 (6) | 0.28111 (4) | 0.11765 (2) | 0.01427 (10) | |
C15 | 0.8453 (3) | 1.15719 (16) | 0.23625 (8) | 0.0160 (3) | |
O1 | 0.13549 (16) | 0.56748 (11) | 0.09454 (5) | 0.0141 (2) | |
O2 | 0.29019 (17) | 0.27739 (11) | −0.11898 (5) | 0.0157 (2) | |
N1 | 0.2964 (2) | 0.81495 (14) | −0.00674 (7) | 0.0171 (3) | |
N2 | 0.4174 (2) | 0.59870 (14) | −0.16878 (7) | 0.0173 (3) | |
C1 | 0.1808 (2) | 0.50059 (16) | 0.04682 (7) | 0.0110 (3) | |
C2 | 0.2475 (2) | 0.56100 (15) | −0.01202 (7) | 0.0112 (3) | |
C3 | 0.2886 (2) | 0.48723 (16) | −0.06644 (7) | 0.0117 (3) | |
C4 | 0.2644 (2) | 0.34343 (16) | −0.06915 (7) | 0.0119 (3) | |
C5 | 0.2144 (2) | 0.28256 (15) | −0.00757 (7) | 0.0115 (3) | |
C6 | 0.1752 (2) | 0.35472 (16) | 0.04580 (7) | 0.0116 (3) | |
C7 | 0.2746 (2) | 0.70222 (16) | −0.00955 (7) | 0.0123 (3) | |
C8 | 0.3593 (2) | 0.55030 (16) | −0.12323 (8) | 0.0128 (3) | |
N3 | 0.3182 (2) | 0.95368 (13) | 0.18261 (7) | 0.0149 (3) | |
C9 | 0.3503 (2) | 0.99969 (16) | 0.24440 (8) | 0.0149 (3) | |
H9 | 0.254226 | 0.984262 | 0.275001 | 0.018* | |
C10 | 0.5213 (2) | 1.06895 (16) | 0.26355 (8) | 0.0143 (3) | |
H10 | 0.544576 | 1.101418 | 0.307181 | 0.017* | |
C11 | 0.6593 (2) | 1.09053 (15) | 0.21786 (8) | 0.0138 (3) | |
C12 | 0.6227 (3) | 1.04289 (17) | 0.15402 (8) | 0.0164 (3) | |
H12 | 0.715077 | 1.058297 | 0.122233 | 0.020* | |
C13 | 0.4509 (3) | 0.97341 (16) | 0.13793 (8) | 0.0171 (3) | |
H13 | 0.425139 | 0.938772 | 0.094799 | 0.021* | |
C14 | 0.1367 (3) | 0.87596 (19) | 0.16300 (9) | 0.0241 (4) | |
H14A | 0.060501 | 0.920636 | 0.126391 | 0.036* | |
H14B | 0.054963 | 0.869076 | 0.200313 | 0.036* | |
H14C | 0.174236 | 0.786692 | 0.149296 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0199 (2) | 0.00834 (18) | 0.01423 (19) | 0.00039 (14) | 0.00207 (15) | 0.00020 (13) |
N4 | 0.0230 (8) | 0.0209 (8) | 0.0163 (7) | −0.0036 (6) | 0.0038 (6) | 0.0025 (6) |
Cl2 | 0.0189 (2) | 0.01392 (19) | 0.01031 (18) | −0.00114 (14) | 0.00294 (14) | 0.00226 (13) |
C15 | 0.0226 (9) | 0.0146 (8) | 0.0115 (8) | 0.0017 (7) | 0.0052 (6) | 0.0017 (6) |
O1 | 0.0166 (6) | 0.0145 (6) | 0.0116 (5) | 0.0010 (4) | 0.0023 (4) | −0.0032 (4) |
O2 | 0.0227 (6) | 0.0134 (6) | 0.0114 (5) | 0.0022 (5) | 0.0037 (5) | −0.0016 (4) |
N1 | 0.0186 (7) | 0.0136 (8) | 0.0191 (7) | −0.0011 (6) | 0.0007 (6) | −0.0003 (6) |
N2 | 0.0202 (7) | 0.0170 (7) | 0.0149 (7) | −0.0025 (6) | 0.0027 (6) | 0.0006 (6) |
C1 | 0.0090 (7) | 0.0121 (8) | 0.0118 (7) | 0.0002 (6) | −0.0003 (6) | 0.0003 (6) |
C2 | 0.0102 (7) | 0.0097 (7) | 0.0134 (7) | 0.0006 (6) | −0.0009 (6) | 0.0005 (6) |
C3 | 0.0110 (7) | 0.0137 (8) | 0.0105 (7) | −0.0009 (6) | 0.0007 (6) | 0.0011 (6) |
C4 | 0.0110 (7) | 0.0123 (8) | 0.0123 (7) | 0.0021 (6) | 0.0001 (6) | 0.0000 (6) |
C5 | 0.0127 (7) | 0.0081 (7) | 0.0132 (7) | 0.0007 (6) | −0.0008 (6) | 0.0014 (6) |
C6 | 0.0121 (8) | 0.0128 (8) | 0.0099 (7) | −0.0004 (6) | 0.0013 (6) | 0.0028 (6) |
C7 | 0.0102 (7) | 0.0167 (9) | 0.0099 (7) | 0.0002 (6) | 0.0012 (6) | −0.0004 (6) |
C8 | 0.0139 (8) | 0.0103 (7) | 0.0141 (8) | 0.0012 (6) | 0.0000 (6) | −0.0026 (6) |
N3 | 0.0167 (7) | 0.0109 (7) | 0.0166 (7) | 0.0017 (5) | −0.0025 (5) | 0.0000 (5) |
C9 | 0.0171 (8) | 0.0132 (8) | 0.0145 (8) | 0.0030 (6) | 0.0016 (6) | 0.0022 (6) |
C10 | 0.0189 (8) | 0.0128 (8) | 0.0112 (7) | 0.0031 (6) | 0.0007 (6) | −0.0001 (6) |
C11 | 0.0168 (8) | 0.0100 (7) | 0.0145 (8) | 0.0024 (6) | 0.0001 (6) | 0.0017 (6) |
C12 | 0.0210 (9) | 0.0167 (8) | 0.0118 (8) | 0.0022 (7) | 0.0036 (6) | 0.0019 (6) |
C13 | 0.0254 (9) | 0.0141 (8) | 0.0115 (8) | 0.0055 (7) | −0.0007 (6) | −0.0006 (6) |
C14 | 0.0219 (9) | 0.0220 (9) | 0.0272 (10) | −0.0037 (7) | −0.0051 (7) | −0.0026 (7) |
Cl1—C5 | 1.7145 (15) | C5—C6 | 1.354 (2) |
N4—C15 | 1.143 (2) | N3—C9 | 1.345 (2) |
Cl2—C6 | 1.7157 (15) | N3—C13 | 1.346 (2) |
C15—C11 | 1.444 (2) | N3—C14 | 1.479 (2) |
O1—C1 | 1.2437 (18) | C9—C10 | 1.376 (2) |
O2—C4 | 1.2402 (19) | C9—H9 | 0.9500 |
N1—C7 | 1.144 (2) | C10—C11 | 1.390 (2) |
N2—C8 | 1.148 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.452 (2) | C11—C12 | 1.392 (2) |
C1—C6 | 1.467 (2) | C12—C13 | 1.369 (2) |
C2—C3 | 1.384 (2) | C12—H12 | 0.9500 |
C2—C7 | 1.432 (2) | C13—H13 | 0.9500 |
C3—C8 | 1.438 (2) | C14—H14A | 0.9800 |
C3—C4 | 1.456 (2) | C14—H14B | 0.9800 |
C4—C5 | 1.464 (2) | C14—H14C | 0.9800 |
N4—C15—C11 | 176.66 (18) | C13—N3—C14 | 118.46 (14) |
O1—C1—C2 | 122.45 (14) | N3—C9—C10 | 120.37 (15) |
O1—C1—C6 | 122.96 (14) | N3—C9—H9 | 119.8 |
C2—C1—C6 | 114.58 (13) | C10—C9—H9 | 119.8 |
C3—C2—C7 | 121.75 (14) | C9—C10—C11 | 118.75 (15) |
C3—C2—C1 | 122.55 (14) | C9—C10—H10 | 120.6 |
C7—C2—C1 | 115.67 (14) | C11—C10—H10 | 120.6 |
C2—C3—C8 | 120.95 (14) | C10—C11—C12 | 119.96 (15) |
C2—C3—C4 | 122.24 (14) | C10—C11—C15 | 120.93 (14) |
C8—C3—C4 | 116.81 (14) | C12—C11—C15 | 119.05 (15) |
O2—C4—C3 | 122.68 (14) | C13—C12—C11 | 118.73 (15) |
O2—C4—C5 | 122.70 (14) | C13—C12—H12 | 120.6 |
C3—C4—C5 | 114.58 (13) | C11—C12—H12 | 120.6 |
C6—C5—C4 | 122.87 (14) | N3—C13—C12 | 120.65 (15) |
C6—C5—Cl1 | 121.54 (12) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.59 (11) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.72 (14) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.04 (12) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.24 (11) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.14 (17) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 178.86 (17) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.52 (15) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 119.99 (14) | ||
O1—C1—C2—C3 | −176.73 (15) | Cl1—C5—C6—C1 | 179.51 (12) |
C6—C1—C2—C3 | 4.4 (2) | C4—C5—C6—Cl2 | −179.56 (12) |
O1—C1—C2—C7 | 5.2 (2) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.62 (13) | O1—C1—C6—C5 | 176.38 (15) |
C7—C2—C3—C8 | −0.4 (2) | C2—C1—C6—C5 | −4.8 (2) |
C1—C2—C3—C8 | −178.39 (14) | O1—C1—C6—Cl2 | −4.5 (2) |
C7—C2—C3—C4 | 179.11 (14) | C2—C1—C6—Cl2 | 174.34 (11) |
C1—C2—C3—C4 | 1.2 (2) | C13—N3—C9—C10 | 0.1 (2) |
C2—C3—C4—O2 | 175.89 (15) | C14—N3—C9—C10 | 178.23 (15) |
C8—C3—C4—O2 | −4.5 (2) | N3—C9—C10—C11 | 0.2 (2) |
C2—C3—C4—C5 | −6.3 (2) | C9—C10—C11—C12 | 0.3 (2) |
C8—C3—C4—C5 | 173.27 (13) | C9—C10—C11—C15 | −177.09 (15) |
O2—C4—C5—C6 | −176.20 (15) | C10—C11—C12—C13 | −1.0 (2) |
C3—C4—C5—C6 | 6.0 (2) | C15—C11—C12—C13 | 176.46 (15) |
O2—C4—C5—Cl1 | 3.8 (2) | C9—N3—C13—C12 | −0.8 (2) |
C3—C4—C5—Cl1 | −174.00 (11) | C14—N3—C13—C12 | −178.98 (15) |
C4—C5—C6—C1 | −0.5 (2) | C11—C12—C13—N3 | 1.2 (2) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.659 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.75559 (15) Å | Cell parameters from 4912 reflections |
b = 10.0647 (2) Å | θ = 2.0–28.1° |
c = 20.4519 (4) Å | µ = 0.48 mm−1 |
β = 94.8065 (19)° | T = 120 K |
V = 1385.70 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 2682 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −8→7 |
Tmin = 0.928, Tmax = 1.000 | k = −13→12 |
9214 measured reflections | l = −26→27 |
3171 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0318P)2 + 0.8587P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
3171 reflections | Δρmax = 0.34 e Å−3 |
209 parameters | Δρmin = −0.24 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 | ||
Cl1 | 0.20801 (6) | 0.11224 (4) | −0.00695 (2) | 0.01622 (10) | |
N4 | 0.9964 (2) | 1.20498 (16) | 0.24907 (7) | 0.0231 (3) | |
Cl2 | 0.11839 (6) | 0.28113 (4) | 0.11756 (2) | 0.01644 (10) | |
C15 | 0.8447 (3) | 1.15698 (17) | 0.23615 (8) | 0.0182 (3) | |
O1 | 0.13554 (16) | 0.56741 (11) | 0.09448 (5) | 0.0160 (2) | |
O2 | 0.29025 (18) | 0.27754 (11) | −0.11887 (5) | 0.0180 (3) | |
N1 | 0.2964 (2) | 0.81469 (14) | −0.00683 (7) | 0.0193 (3) | |
N2 | 0.4171 (2) | 0.59868 (14) | −0.16860 (7) | 0.0195 (3) | |
C1 | 0.1807 (2) | 0.50043 (16) | 0.04676 (7) | 0.0125 (3) | |
C2 | 0.2471 (2) | 0.56082 (15) | −0.01188 (7) | 0.0124 (3) | |
C3 | 0.2887 (2) | 0.48719 (16) | −0.06634 (7) | 0.0125 (3) | |
C4 | 0.2643 (2) | 0.34338 (16) | −0.06908 (7) | 0.0128 (3) | |
C5 | 0.2140 (2) | 0.28270 (15) | −0.00759 (7) | 0.0124 (3) | |
C6 | 0.1751 (2) | 0.35481 (16) | 0.04578 (7) | 0.0126 (3) | |
C7 | 0.2751 (2) | 0.70206 (16) | −0.00946 (7) | 0.0138 (3) | |
C8 | 0.3594 (2) | 0.55007 (16) | −0.12305 (8) | 0.0139 (3) | |
N3 | 0.3181 (2) | 0.95345 (13) | 0.18273 (7) | 0.0169 (3) | |
C9 | 0.3504 (2) | 0.99976 (16) | 0.24430 (8) | 0.0170 (3) | |
H9 | 0.254473 | 0.984556 | 0.274875 | 0.020* | |
C10 | 0.5207 (2) | 1.06883 (16) | 0.26352 (8) | 0.0158 (3) | |
H10 | 0.543986 | 1.101287 | 0.307107 | 0.019* | |
C11 | 0.6587 (2) | 1.09025 (16) | 0.21764 (8) | 0.0156 (3) | |
C12 | 0.6221 (3) | 1.04258 (17) | 0.15410 (8) | 0.0189 (4) | |
H12 | 0.714517 | 1.057795 | 0.122357 | 0.023* | |
C13 | 0.4507 (3) | 0.97332 (17) | 0.13796 (8) | 0.0193 (4) | |
H13 | 0.424936 | 0.938901 | 0.094835 | 0.023* | |
C14 | 0.1370 (3) | 0.87598 (19) | 0.16316 (10) | 0.0273 (4) | |
H14A | 0.055613 | 0.868872 | 0.200485 | 0.041* | |
H14B | 0.174424 | 0.786869 | 0.149322 | 0.041* | |
H14C | 0.060813 | 0.920809 | 0.126692 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0224 (2) | 0.00946 (19) | 0.0170 (2) | 0.00043 (15) | 0.00266 (15) | 0.00033 (14) |
N4 | 0.0258 (8) | 0.0250 (8) | 0.0188 (7) | −0.0050 (7) | 0.0036 (6) | 0.0023 (6) |
Cl2 | 0.0214 (2) | 0.0161 (2) | 0.01220 (19) | −0.00100 (15) | 0.00350 (14) | 0.00277 (14) |
C15 | 0.0243 (9) | 0.0171 (8) | 0.0137 (8) | 0.0006 (7) | 0.0052 (7) | 0.0024 (6) |
O1 | 0.0185 (6) | 0.0167 (6) | 0.0130 (5) | 0.0003 (5) | 0.0029 (4) | −0.0040 (4) |
O2 | 0.0262 (6) | 0.0142 (6) | 0.0140 (6) | 0.0029 (5) | 0.0040 (5) | −0.0020 (4) |
N1 | 0.0209 (8) | 0.0159 (8) | 0.0211 (7) | −0.0013 (6) | 0.0013 (6) | −0.0010 (6) |
N2 | 0.0223 (8) | 0.0191 (8) | 0.0173 (7) | −0.0016 (6) | 0.0027 (6) | 0.0015 (6) |
C1 | 0.0117 (7) | 0.0130 (8) | 0.0126 (7) | 0.0005 (6) | 0.0000 (6) | 0.0006 (6) |
C2 | 0.0118 (7) | 0.0117 (7) | 0.0137 (7) | 0.0001 (6) | 0.0008 (6) | −0.0004 (6) |
C3 | 0.0120 (7) | 0.0137 (8) | 0.0119 (7) | −0.0002 (6) | 0.0009 (6) | 0.0018 (6) |
C4 | 0.0121 (7) | 0.0136 (8) | 0.0127 (7) | 0.0027 (6) | 0.0007 (6) | 0.0000 (6) |
C5 | 0.0129 (7) | 0.0093 (7) | 0.0147 (8) | −0.0001 (6) | −0.0003 (6) | 0.0006 (6) |
C6 | 0.0125 (7) | 0.0139 (8) | 0.0115 (7) | −0.0005 (6) | 0.0019 (6) | 0.0023 (6) |
C7 | 0.0128 (8) | 0.0171 (9) | 0.0118 (7) | −0.0002 (6) | 0.0017 (6) | 0.0000 (6) |
C8 | 0.0144 (8) | 0.0121 (8) | 0.0150 (8) | 0.0012 (6) | −0.0005 (6) | −0.0028 (6) |
N3 | 0.0187 (7) | 0.0128 (7) | 0.0184 (7) | 0.0015 (6) | −0.0031 (5) | −0.0004 (5) |
C9 | 0.0191 (8) | 0.0161 (8) | 0.0160 (8) | 0.0034 (7) | 0.0026 (6) | 0.0020 (6) |
C10 | 0.0193 (8) | 0.0162 (8) | 0.0120 (7) | 0.0038 (6) | 0.0015 (6) | 0.0002 (6) |
C11 | 0.0184 (8) | 0.0118 (8) | 0.0167 (8) | 0.0022 (6) | 0.0014 (6) | 0.0023 (6) |
C12 | 0.0237 (9) | 0.0185 (9) | 0.0148 (8) | 0.0041 (7) | 0.0035 (7) | 0.0015 (6) |
C13 | 0.0275 (9) | 0.0169 (8) | 0.0128 (8) | 0.0049 (7) | −0.0017 (7) | −0.0012 (6) |
C14 | 0.0243 (10) | 0.0249 (10) | 0.0313 (10) | −0.0049 (8) | −0.0063 (8) | −0.0043 (8) |
Cl1—C5 | 1.7161 (16) | C5—C6 | 1.355 (2) |
N4—C15 | 1.144 (2) | N3—C9 | 1.343 (2) |
Cl2—C6 | 1.7163 (15) | N3—C13 | 1.349 (2) |
C15—C11 | 1.447 (2) | N3—C14 | 1.478 (2) |
O1—C1 | 1.2448 (18) | C9—C10 | 1.373 (2) |
O2—C4 | 1.2396 (19) | C9—H9 | 0.9500 |
N1—C7 | 1.143 (2) | C10—C11 | 1.394 (2) |
N2—C8 | 1.149 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.449 (2) | C11—C12 | 1.388 (2) |
C1—C6 | 1.466 (2) | C12—C13 | 1.368 (2) |
C2—C3 | 1.386 (2) | C12—H12 | 0.9500 |
C2—C7 | 1.434 (2) | C13—H13 | 0.9500 |
C3—C8 | 1.438 (2) | C14—H14A | 0.9800 |
C3—C4 | 1.457 (2) | C14—H14B | 0.9800 |
C4—C5 | 1.463 (2) | C14—H14C | 0.9800 |
N4—C15—C11 | 176.56 (18) | C13—N3—C14 | 118.45 (14) |
O1—C1—C2 | 122.34 (14) | N3—C9—C10 | 120.69 (15) |
O1—C1—C6 | 122.98 (14) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.66 (13) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.51 (14) | C9—C10—C11 | 118.50 (15) |
C3—C2—C1 | 122.59 (14) | C9—C10—H10 | 120.8 |
C7—C2—C1 | 115.86 (14) | C11—C10—H10 | 120.8 |
C2—C3—C8 | 121.09 (14) | C12—C11—C10 | 120.02 (16) |
C2—C3—C4 | 122.15 (14) | C12—C11—C15 | 119.22 (15) |
C8—C3—C4 | 116.76 (14) | C10—C11—C15 | 120.71 (15) |
O2—C4—C3 | 122.63 (14) | C13—C12—C11 | 118.87 (16) |
O2—C4—C5 | 122.80 (14) | C13—C12—H12 | 120.6 |
C3—C4—C5 | 114.53 (13) | C11—C12—H12 | 120.6 |
C6—C5—C4 | 122.92 (14) | N3—C13—C12 | 120.58 (15) |
C6—C5—Cl1 | 121.53 (12) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.55 (11) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.68 (14) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.00 (13) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.31 (11) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.17 (18) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.05 (18) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.33 (15) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.19 (14) | ||
O1—C1—C2—C3 | −176.93 (15) | Cl1—C5—C6—C1 | 179.52 (12) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.47 (12) |
O1—C1—C2—C7 | 5.4 (2) | Cl1—C5—C6—Cl2 | 0.3 (2) |
C6—C1—C2—C7 | −173.35 (13) | O1—C1—C6—C5 | 176.36 (15) |
C7—C2—C3—C8 | −0.8 (2) | C2—C1—C6—C5 | −4.9 (2) |
C1—C2—C3—C8 | −178.32 (14) | O1—C1—C6—Cl2 | −4.4 (2) |
C7—C2—C3—C4 | 178.88 (14) | C2—C1—C6—Cl2 | 174.38 (11) |
C1—C2—C3—C4 | 1.4 (2) | C13—N3—C9—C10 | −0.1 (2) |
C2—C3—C4—O2 | 175.79 (15) | C14—N3—C9—C10 | 178.26 (15) |
C8—C3—C4—O2 | −4.5 (2) | N3—C9—C10—C11 | 0.3 (2) |
C2—C3—C4—C5 | −6.3 (2) | C9—C10—C11—C12 | 0.2 (2) |
C8—C3—C4—C5 | 173.35 (13) | C9—C10—C11—C15 | −177.09 (15) |
O2—C4—C5—C6 | −176.31 (15) | C10—C11—C12—C13 | −0.9 (2) |
C3—C4—C5—C6 | 5.8 (2) | C15—C11—C12—C13 | 176.50 (15) |
O2—C4—C5—Cl1 | 3.9 (2) | C9—N3—C13—C12 | −0.5 (2) |
C3—C4—C5—Cl1 | −173.96 (11) | C14—N3—C13—C12 | −178.95 (16) |
C4—C5—C6—C1 | −0.3 (2) | C11—C12—C13—N3 | 1.0 (2) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.654 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.77203 (15) Å | Cell parameters from 4725 reflections |
b = 10.0679 (2) Å | θ = 2.0–28.1° |
c = 20.4627 (4) Å | µ = 0.48 mm−1 |
β = 94.7855 (19)° | T = 150 K |
V = 1390.28 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3178 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2695 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −8→7 |
Tmin = 0.955, Tmax = 1.000 | k = −13→12 |
9239 measured reflections | l = −26→27 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0324P)2 + 0.5503P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3178 reflections | Δρmax = 0.34 e Å−3 |
209 parameters | Δρmin = −0.26 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 | ||
Cl1 | 0.20742 (6) | 0.11236 (4) | −0.00699 (2) | 0.01950 (11) | |
N4 | 0.9950 (2) | 1.20447 (16) | 0.24893 (7) | 0.0275 (3) | |
Cl2 | 0.11795 (6) | 0.28112 (4) | 0.11743 (2) | 0.01970 (11) | |
C15 | 0.8438 (3) | 1.15665 (17) | 0.23606 (8) | 0.0217 (4) | |
O1 | 0.13550 (16) | 0.56728 (11) | 0.09448 (5) | 0.0188 (2) | |
O2 | 0.29016 (18) | 0.27743 (11) | −0.11873 (5) | 0.0215 (3) | |
N1 | 0.2973 (2) | 0.81416 (14) | −0.00682 (7) | 0.0233 (3) | |
N2 | 0.4170 (2) | 0.59857 (14) | −0.16819 (7) | 0.0231 (3) | |
C1 | 0.1807 (2) | 0.50057 (15) | 0.04683 (7) | 0.0143 (3) | |
C2 | 0.2472 (2) | 0.56055 (15) | −0.01192 (7) | 0.0145 (3) | |
C3 | 0.2884 (2) | 0.48710 (16) | −0.06628 (7) | 0.0146 (3) | |
C4 | 0.2646 (2) | 0.34355 (16) | −0.06889 (7) | 0.0154 (3) | |
C5 | 0.2143 (2) | 0.28288 (15) | −0.00756 (7) | 0.0146 (3) | |
C6 | 0.1748 (2) | 0.35486 (16) | 0.04581 (7) | 0.0148 (3) | |
C7 | 0.2752 (2) | 0.70175 (16) | −0.00939 (7) | 0.0162 (3) | |
C8 | 0.3598 (2) | 0.54994 (15) | −0.12282 (7) | 0.0159 (3) | |
N3 | 0.3187 (2) | 0.95345 (13) | 0.18278 (7) | 0.0200 (3) | |
C9 | 0.3513 (2) | 0.99941 (16) | 0.24432 (8) | 0.0203 (3) | |
H9 | 0.255896 | 0.983929 | 0.274966 | 0.024* | |
C10 | 0.5211 (2) | 1.06857 (16) | 0.26338 (8) | 0.0190 (3) | |
H10 | 0.544104 | 1.101156 | 0.306918 | 0.023* | |
C11 | 0.6586 (2) | 1.09001 (16) | 0.21778 (8) | 0.0184 (3) | |
C12 | 0.6214 (3) | 1.04238 (17) | 0.15422 (8) | 0.0227 (4) | |
H12 | 0.713483 | 1.057596 | 0.122442 | 0.027* | |
C13 | 0.4504 (3) | 0.97326 (17) | 0.13803 (8) | 0.0225 (4) | |
H13 | 0.424425 | 0.939030 | 0.094909 | 0.027* | |
C14 | 0.1377 (3) | 0.8760 (2) | 0.16333 (10) | 0.0329 (4) | |
H14A | 0.060470 | 0.921643 | 0.127433 | 0.049* | |
H14B | 0.057884 | 0.867673 | 0.200918 | 0.049* | |
H14C | 0.174935 | 0.787422 | 0.148766 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0274 (2) | 0.01124 (19) | 0.0201 (2) | 0.00040 (15) | 0.00313 (16) | 0.00030 (14) |
N4 | 0.0304 (9) | 0.0302 (8) | 0.0222 (8) | −0.0069 (7) | 0.0042 (6) | 0.0031 (6) |
Cl2 | 0.0262 (2) | 0.0191 (2) | 0.01427 (19) | −0.00147 (15) | 0.00402 (15) | 0.00307 (14) |
C15 | 0.0293 (10) | 0.0203 (9) | 0.0162 (8) | 0.0010 (7) | 0.0058 (7) | 0.0029 (6) |
O1 | 0.0232 (6) | 0.0183 (6) | 0.0153 (6) | 0.0001 (5) | 0.0041 (5) | −0.0041 (4) |
O2 | 0.0326 (7) | 0.0168 (6) | 0.0157 (6) | 0.0043 (5) | 0.0058 (5) | −0.0024 (4) |
N1 | 0.0253 (8) | 0.0175 (8) | 0.0269 (8) | −0.0020 (6) | 0.0016 (6) | −0.0018 (6) |
N2 | 0.0263 (8) | 0.0241 (8) | 0.0193 (7) | −0.0027 (6) | 0.0045 (6) | 0.0015 (6) |
C1 | 0.0140 (7) | 0.0150 (8) | 0.0137 (7) | 0.0005 (6) | 0.0006 (6) | −0.0006 (6) |
C2 | 0.0144 (7) | 0.0124 (7) | 0.0167 (8) | 0.0010 (6) | 0.0007 (6) | −0.0009 (6) |
C3 | 0.0137 (7) | 0.0160 (8) | 0.0141 (7) | 0.0002 (6) | 0.0015 (6) | 0.0015 (6) |
C4 | 0.0149 (7) | 0.0152 (8) | 0.0160 (8) | 0.0029 (6) | 0.0003 (6) | 0.0001 (6) |
C5 | 0.0170 (8) | 0.0101 (7) | 0.0165 (8) | −0.0004 (6) | 0.0003 (6) | 0.0017 (6) |
C6 | 0.0151 (7) | 0.0164 (8) | 0.0130 (7) | 0.0004 (6) | 0.0019 (6) | 0.0021 (6) |
C7 | 0.0164 (8) | 0.0188 (8) | 0.0135 (7) | 0.0003 (6) | 0.0023 (6) | −0.0004 (6) |
C8 | 0.0177 (8) | 0.0135 (8) | 0.0163 (8) | 0.0012 (6) | 0.0007 (6) | −0.0018 (6) |
N3 | 0.0228 (7) | 0.0143 (7) | 0.0219 (7) | 0.0021 (6) | −0.0039 (6) | −0.0001 (5) |
C9 | 0.0230 (9) | 0.0196 (8) | 0.0183 (8) | 0.0046 (7) | 0.0019 (7) | 0.0025 (6) |
C10 | 0.0228 (8) | 0.0192 (8) | 0.0148 (8) | 0.0028 (7) | 0.0009 (6) | −0.0005 (6) |
C11 | 0.0229 (8) | 0.0142 (8) | 0.0182 (8) | 0.0022 (6) | 0.0017 (6) | 0.0020 (6) |
C12 | 0.0291 (9) | 0.0233 (9) | 0.0164 (8) | 0.0030 (7) | 0.0055 (7) | 0.0019 (6) |
C13 | 0.0311 (9) | 0.0200 (8) | 0.0158 (8) | 0.0068 (7) | −0.0018 (7) | −0.0034 (6) |
C14 | 0.0305 (10) | 0.0291 (10) | 0.0374 (11) | −0.0056 (8) | −0.0067 (8) | −0.0038 (8) |
Cl1—C5 | 1.7174 (15) | C5—C6 | 1.356 (2) |
N4—C15 | 1.142 (2) | N3—C9 | 1.342 (2) |
Cl2—C6 | 1.7150 (15) | N3—C13 | 1.345 (2) |
C15—C11 | 1.444 (2) | N3—C14 | 1.479 (2) |
O1—C1 | 1.2432 (18) | C9—C10 | 1.373 (2) |
O2—C4 | 1.2420 (18) | C9—H9 | 0.9500 |
N1—C7 | 1.142 (2) | C10—C11 | 1.389 (2) |
N2—C8 | 1.145 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.450 (2) | C11—C12 | 1.389 (2) |
C1—C6 | 1.468 (2) | C12—C13 | 1.368 (2) |
C2—C3 | 1.383 (2) | C12—H12 | 0.9500 |
C2—C7 | 1.435 (2) | C13—H13 | 0.9500 |
C3—C8 | 1.437 (2) | C14—H14A | 0.9800 |
C3—C4 | 1.455 (2) | C14—H14B | 0.9800 |
C4—C5 | 1.461 (2) | C14—H14C | 0.9800 |
N4—C15—C11 | 176.59 (19) | C13—N3—C14 | 118.46 (14) |
O1—C1—C2 | 122.62 (14) | N3—C9—C10 | 120.63 (15) |
O1—C1—C6 | 122.88 (14) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.48 (13) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.58 (14) | C9—C10—C11 | 118.73 (15) |
C3—C2—C1 | 122.78 (14) | C9—C10—H10 | 120.6 |
C7—C2—C1 | 115.60 (13) | C11—C10—H10 | 120.6 |
C2—C3—C8 | 121.06 (14) | C10—C11—C12 | 119.72 (16) |
C2—C3—C4 | 122.09 (14) | C10—C11—C15 | 120.99 (15) |
C8—C3—C4 | 116.85 (13) | C12—C11—C15 | 119.25 (15) |
O2—C4—C3 | 122.68 (14) | C13—C12—C11 | 119.07 (15) |
O2—C4—C5 | 122.65 (14) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.64 (13) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.96 (14) | N3—C13—C12 | 120.43 (15) |
C6—C5—Cl1 | 121.44 (12) | N3—C13—H13 | 119.8 |
C4—C5—Cl1 | 115.60 (11) | C12—C13—H13 | 119.8 |
C5—C6—C1 | 122.60 (14) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.03 (12) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.36 (11) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.41 (17) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.19 (17) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.41 (15) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.10 (15) | ||
O1—C1—C2—C3 | −176.76 (14) | Cl1—C5—C6—C1 | 179.62 (12) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.49 (12) |
O1—C1—C2—C7 | 5.5 (2) | Cl1—C5—C6—Cl2 | 0.7 (2) |
C6—C1—C2—C7 | −173.44 (13) | O1—C1—C6—C5 | 176.46 (15) |
C7—C2—C3—C8 | −0.5 (2) | C2—C1—C6—C5 | −4.6 (2) |
C1—C2—C3—C8 | −178.07 (14) | O1—C1—C6—Cl2 | −4.5 (2) |
C7—C2—C3—C4 | 178.68 (14) | C2—C1—C6—Cl2 | 174.45 (11) |
C1—C2—C3—C4 | 1.1 (2) | C13—N3—C9—C10 | 0.1 (2) |
C2—C3—C4—O2 | 175.76 (15) | C14—N3—C9—C10 | 178.38 (15) |
C8—C3—C4—O2 | −5.0 (2) | N3—C9—C10—C11 | 0.0 (2) |
C2—C3—C4—C5 | −6.1 (2) | C9—C10—C11—C12 | 0.5 (2) |
C8—C3—C4—C5 | 173.13 (13) | C9—C10—C11—C15 | −177.06 (15) |
O2—C4—C5—C6 | −176.01 (15) | C10—C11—C12—C13 | −1.0 (2) |
C3—C4—C5—C6 | 5.8 (2) | C15—C11—C12—C13 | 176.64 (15) |
O2—C4—C5—Cl1 | 3.8 (2) | C9—N3—C13—C12 | −0.6 (2) |
C3—C4—C5—Cl1 | −174.31 (11) | C14—N3—C13—C12 | −178.89 (16) |
C4—C5—C6—C1 | −0.5 (2) | C11—C12—C13—N3 | 1.0 (2) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.649 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.78877 (15) Å | Cell parameters from 4533 reflections |
b = 10.07003 (19) Å | θ = 2.0–27.9° |
c = 20.4706 (4) Å | µ = 0.48 mm−1 |
β = 94.7503 (18)° | T = 180 K |
V = 1394.62 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3194 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −9→7 |
Tmin = 0.927, Tmax = 1.000 | k = −13→12 |
9309 measured reflections | l = −26→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0347P)2 + 0.5717P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3194 reflections | Δρmax = 0.30 e Å−3 |
209 parameters | Δρmin = −0.26 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 | ||
Cl1 | 0.20675 (6) | 0.11253 (4) | −0.00703 (2) | 0.02296 (11) | |
N4 | 0.9938 (2) | 1.20410 (17) | 0.24875 (7) | 0.0327 (4) | |
Cl2 | 0.11771 (6) | 0.28107 (4) | 0.11733 (2) | 0.02312 (11) | |
C15 | 0.8427 (3) | 1.15624 (17) | 0.23597 (8) | 0.0248 (4) | |
O1 | 0.13519 (17) | 0.56711 (11) | 0.09447 (5) | 0.0222 (3) | |
O2 | 0.29018 (18) | 0.27763 (11) | −0.11858 (5) | 0.0253 (3) | |
N1 | 0.2974 (2) | 0.81371 (14) | −0.00674 (7) | 0.0270 (3) | |
N2 | 0.4169 (2) | 0.59838 (15) | −0.16795 (7) | 0.0272 (3) | |
C1 | 0.1807 (2) | 0.50017 (15) | 0.04681 (7) | 0.0166 (3) | |
C2 | 0.2473 (2) | 0.56039 (15) | −0.01182 (7) | 0.0166 (3) | |
C3 | 0.2884 (2) | 0.48686 (16) | −0.06607 (7) | 0.0168 (3) | |
C4 | 0.2643 (2) | 0.34370 (16) | −0.06888 (7) | 0.0177 (3) | |
C5 | 0.2135 (2) | 0.28306 (15) | −0.00759 (7) | 0.0172 (3) | |
C6 | 0.1746 (2) | 0.35454 (16) | 0.04583 (7) | 0.0170 (3) | |
C7 | 0.2753 (2) | 0.70147 (16) | −0.00923 (7) | 0.0184 (3) | |
C8 | 0.3593 (2) | 0.54977 (16) | −0.12270 (7) | 0.0186 (3) | |
N3 | 0.3191 (2) | 0.95319 (13) | 0.18284 (7) | 0.0235 (3) | |
C9 | 0.3518 (3) | 0.99934 (17) | 0.24427 (8) | 0.0242 (4) | |
H9 | 0.256456 | 0.984227 | 0.274920 | 0.029* | |
C10 | 0.5213 (2) | 1.06812 (16) | 0.26331 (8) | 0.0222 (3) | |
H10 | 0.544796 | 1.100397 | 0.306869 | 0.027* | |
C11 | 0.6579 (2) | 1.08951 (16) | 0.21757 (8) | 0.0211 (3) | |
C12 | 0.6206 (3) | 1.04205 (18) | 0.15417 (8) | 0.0266 (4) | |
H12 | 0.712278 | 1.057347 | 0.122342 | 0.032* | |
C13 | 0.4504 (3) | 0.97304 (17) | 0.13815 (8) | 0.0269 (4) | |
H13 | 0.424574 | 0.938746 | 0.095056 | 0.032* | |
C14 | 0.1383 (3) | 0.8760 (2) | 0.16358 (11) | 0.0388 (5) | |
H14A | 0.060119 | 0.922339 | 0.128222 | 0.058* | |
H14B | 0.059943 | 0.866523 | 0.201414 | 0.058* | |
H14C | 0.175183 | 0.787835 | 0.148340 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0323 (2) | 0.01302 (19) | 0.0238 (2) | 0.00067 (15) | 0.00413 (16) | 0.00045 (14) |
N4 | 0.0349 (9) | 0.0355 (9) | 0.0282 (8) | −0.0081 (7) | 0.0057 (7) | 0.0045 (6) |
Cl2 | 0.0306 (2) | 0.0222 (2) | 0.01695 (19) | −0.00181 (16) | 0.00479 (15) | 0.00360 (14) |
C15 | 0.0333 (10) | 0.0225 (9) | 0.0195 (8) | 0.0005 (8) | 0.0071 (7) | 0.0030 (6) |
O1 | 0.0277 (6) | 0.0210 (6) | 0.0183 (6) | 0.0008 (5) | 0.0047 (5) | −0.0051 (4) |
O2 | 0.0387 (7) | 0.0185 (6) | 0.0194 (6) | 0.0045 (5) | 0.0068 (5) | −0.0028 (4) |
N1 | 0.0303 (8) | 0.0191 (8) | 0.0313 (8) | −0.0022 (6) | 0.0015 (6) | −0.0017 (6) |
N2 | 0.0324 (8) | 0.0270 (8) | 0.0228 (8) | −0.0035 (6) | 0.0060 (6) | 0.0030 (6) |
C1 | 0.0155 (7) | 0.0176 (8) | 0.0166 (7) | 0.0008 (6) | −0.0002 (6) | −0.0009 (6) |
C2 | 0.0163 (7) | 0.0148 (7) | 0.0188 (7) | 0.0014 (6) | 0.0006 (6) | 0.0002 (6) |
C3 | 0.0173 (7) | 0.0175 (8) | 0.0156 (7) | 0.0004 (6) | 0.0018 (6) | 0.0016 (6) |
C4 | 0.0180 (8) | 0.0170 (8) | 0.0182 (8) | 0.0038 (6) | 0.0014 (6) | 0.0001 (6) |
C5 | 0.0184 (8) | 0.0133 (7) | 0.0197 (8) | 0.0003 (6) | 0.0005 (6) | 0.0016 (6) |
C6 | 0.0174 (8) | 0.0185 (8) | 0.0151 (7) | −0.0002 (6) | 0.0016 (6) | 0.0025 (6) |
C7 | 0.0181 (8) | 0.0214 (9) | 0.0160 (7) | 0.0004 (6) | 0.0021 (6) | −0.0002 (6) |
C8 | 0.0205 (8) | 0.0161 (8) | 0.0191 (8) | 0.0017 (6) | 0.0014 (6) | −0.0029 (6) |
N3 | 0.0273 (8) | 0.0171 (7) | 0.0248 (7) | 0.0029 (6) | −0.0046 (6) | −0.0006 (5) |
C9 | 0.0270 (9) | 0.0240 (9) | 0.0217 (8) | 0.0030 (7) | 0.0027 (7) | 0.0028 (7) |
C10 | 0.0271 (9) | 0.0226 (8) | 0.0170 (8) | 0.0041 (7) | 0.0015 (6) | −0.0005 (6) |
C11 | 0.0267 (9) | 0.0162 (8) | 0.0204 (8) | 0.0032 (6) | 0.0025 (7) | 0.0023 (6) |
C12 | 0.0332 (10) | 0.0282 (9) | 0.0191 (8) | 0.0041 (8) | 0.0059 (7) | 0.0019 (7) |
C13 | 0.0379 (10) | 0.0240 (9) | 0.0182 (8) | 0.0063 (8) | −0.0014 (7) | −0.0027 (6) |
C14 | 0.0344 (11) | 0.0349 (11) | 0.0451 (12) | −0.0075 (9) | −0.0084 (9) | −0.0061 (9) |
Cl1—C5 | 1.7179 (15) | C5—C6 | 1.353 (2) |
N4—C15 | 1.144 (2) | N3—C13 | 1.344 (2) |
Cl2—C6 | 1.7124 (15) | N3—C9 | 1.342 (2) |
C15—C11 | 1.445 (2) | N3—C14 | 1.478 (2) |
O1—C1 | 1.2458 (18) | C9—C10 | 1.372 (2) |
O2—C4 | 1.2401 (18) | C9—H9 | 0.9500 |
N1—C7 | 1.141 (2) | C10—C11 | 1.388 (2) |
N2—C8 | 1.145 (2) | C10—H10 | 0.9500 |
C1—C2 | 1.450 (2) | C11—C12 | 1.386 (2) |
C1—C6 | 1.467 (2) | C12—C13 | 1.365 (3) |
C2—C3 | 1.382 (2) | C12—H12 | 0.9500 |
C2—C7 | 1.434 (2) | C13—H13 | 0.9500 |
C3—C8 | 1.438 (2) | C14—H14A | 0.9800 |
C3—C4 | 1.452 (2) | C14—H14B | 0.9800 |
C4—C5 | 1.462 (2) | C14—H14C | 0.9800 |
N4—C15—C11 | 176.43 (19) | C9—N3—C14 | 120.09 (15) |
O1—C1—C2 | 122.45 (14) | N3—C9—C10 | 120.72 (15) |
O1—C1—C6 | 122.89 (14) | N3—C9—H9 | 119.6 |
C2—C1—C6 | 114.66 (13) | C10—C9—H9 | 119.6 |
C3—C2—C7 | 121.70 (14) | C9—C10—C11 | 118.57 (15) |
C3—C2—C1 | 122.58 (14) | C9—C10—H10 | 120.7 |
C7—C2—C1 | 115.68 (13) | C11—C10—H10 | 120.7 |
C2—C3—C8 | 120.99 (14) | C12—C11—C10 | 119.86 (16) |
C2—C3—C4 | 122.30 (14) | C12—C11—C15 | 119.42 (15) |
C8—C3—C4 | 116.71 (13) | C10—C11—C15 | 120.67 (15) |
O2—C4—C3 | 122.84 (14) | C13—C12—C11 | 119.05 (16) |
O2—C4—C5 | 122.64 (14) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.49 (13) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 123.16 (14) | N3—C13—C12 | 120.54 (15) |
C6—C5—Cl1 | 121.28 (12) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.56 (11) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.38 (14) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.26 (13) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.36 (11) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.55 (17) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.14 (18) | H14A—C14—H14C | 109.5 |
C13—N3—C9 | 121.25 (15) | H14B—C14—H14C | 109.5 |
C13—N3—C14 | 118.64 (15) | ||
O1—C1—C2—C3 | −176.64 (14) | Cl1—C5—C6—C1 | 179.55 (12) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.35 (12) |
O1—C1—C2—C7 | 5.6 (2) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.44 (13) | O1—C1—C6—C5 | 176.13 (15) |
C7—C2—C3—C8 | −0.7 (2) | C2—C1—C6—C5 | −4.8 (2) |
C1—C2—C3—C8 | −178.29 (14) | O1—C1—C6—Cl2 | −4.6 (2) |
C7—C2—C3—C4 | 178.80 (14) | C2—C1—C6—Cl2 | 174.42 (11) |
C1—C2—C3—C4 | 1.2 (2) | C13—N3—C9—C10 | −0.2 (2) |
C2—C3—C4—O2 | 175.89 (15) | C14—N3—C9—C10 | 178.25 (16) |
C8—C3—C4—O2 | −4.6 (2) | N3—C9—C10—C11 | 0.3 (2) |
C2—C3—C4—C5 | −6.0 (2) | C9—C10—C11—C12 | 0.2 (2) |
C8—C3—C4—C5 | 173.45 (13) | C9—C10—C11—C15 | −177.25 (16) |
O2—C4—C5—C6 | −176.35 (15) | C10—C11—C12—C13 | −0.9 (2) |
C3—C4—C5—C6 | 5.6 (2) | C15—C11—C12—C13 | 176.58 (16) |
O2—C4—C5—Cl1 | 3.9 (2) | C9—N3—C13—C12 | −0.5 (2) |
C3—C4—C5—Cl1 | −174.16 (11) | C14—N3—C13—C12 | −179.00 (17) |
C4—C5—C6—C1 | −0.2 (2) | C11—C12—C13—N3 | 1.1 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.644 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.80352 (17) Å | Cell parameters from 4285 reflections |
b = 10.0725 (2) Å | θ = 2.0–27.9° |
c = 20.4774 (4) Å | µ = 0.48 mm−1 |
β = 94.754 (2)° | T = 210 K |
V = 1398.45 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3199 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2633 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −7→9 |
Tmin = 0.932, Tmax = 1.000 | k = −13→12 |
9343 measured reflections | l = −27→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0318P)2 + 0.4275P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3199 reflections | Δρmax = 0.29 e Å−3 |
209 parameters | Δρmin = −0.23 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 | ||
Cl1 | 0.20616 (7) | 0.11275 (4) | −0.00708 (2) | 0.02676 (12) | |
N4 | 0.9921 (3) | 1.20339 (18) | 0.24850 (8) | 0.0382 (4) | |
Cl2 | 0.11731 (6) | 0.28110 (4) | 0.11722 (2) | 0.02697 (12) | |
C15 | 0.8419 (3) | 1.15576 (19) | 0.23570 (9) | 0.0293 (4) | |
O1 | 0.13556 (18) | 0.56682 (12) | 0.09442 (5) | 0.0255 (3) | |
O2 | 0.29002 (19) | 0.27781 (12) | −0.11834 (6) | 0.0291 (3) | |
N1 | 0.2976 (2) | 0.81332 (15) | −0.00675 (8) | 0.0316 (4) | |
N2 | 0.4172 (2) | 0.59824 (16) | −0.16752 (7) | 0.0315 (4) | |
C1 | 0.1807 (2) | 0.50016 (16) | 0.04675 (8) | 0.0194 (3) | |
C2 | 0.2471 (2) | 0.56018 (16) | −0.01166 (8) | 0.0190 (3) | |
C3 | 0.2886 (2) | 0.48704 (16) | −0.06601 (8) | 0.0192 (3) | |
C4 | 0.2641 (2) | 0.34358 (16) | −0.06871 (8) | 0.0204 (3) | |
C5 | 0.2135 (2) | 0.28302 (16) | −0.00758 (8) | 0.0198 (3) | |
C6 | 0.1746 (2) | 0.35484 (16) | 0.04577 (8) | 0.0199 (3) | |
C7 | 0.2757 (2) | 0.70120 (17) | −0.00908 (8) | 0.0211 (3) | |
C8 | 0.3596 (2) | 0.54999 (17) | −0.12232 (8) | 0.0221 (4) | |
N3 | 0.3193 (2) | 0.95323 (14) | 0.18294 (7) | 0.0274 (3) | |
C9 | 0.3524 (3) | 0.99933 (18) | 0.24437 (8) | 0.0273 (4) | |
H9 | 0.258658 | 0.984356 | 0.274807 | 0.033* | |
C10 | 0.5213 (3) | 1.06792 (17) | 0.26309 (8) | 0.0258 (4) | |
H10 | 0.544463 | 1.100075 | 0.306137 | 0.031* | |
C11 | 0.6573 (3) | 1.08913 (17) | 0.21769 (8) | 0.0245 (4) | |
C12 | 0.6202 (3) | 1.04183 (19) | 0.15427 (8) | 0.0300 (4) | |
H12 | 0.710647 | 1.056924 | 0.122782 | 0.036* | |
C13 | 0.4507 (3) | 0.97321 (18) | 0.13836 (9) | 0.0316 (4) | |
H13 | 0.425144 | 0.939375 | 0.095723 | 0.038* | |
C14 | 0.1395 (3) | 0.8758 (2) | 0.16371 (12) | 0.0454 (5) | |
H14A | 0.062893 | 0.921026 | 0.128328 | 0.068* | |
H14B | 0.061203 | 0.867377 | 0.200993 | 0.068* | |
H14C | 0.176121 | 0.788281 | 0.149183 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0378 (3) | 0.0152 (2) | 0.0276 (2) | 0.00082 (17) | 0.00461 (18) | 0.00053 (15) |
N4 | 0.0420 (10) | 0.0416 (10) | 0.0316 (9) | −0.0103 (8) | 0.0064 (7) | 0.0051 (7) |
Cl2 | 0.0358 (3) | 0.0260 (2) | 0.0196 (2) | −0.00214 (18) | 0.00562 (17) | 0.00438 (16) |
C15 | 0.0387 (11) | 0.0275 (10) | 0.0224 (9) | 0.0000 (8) | 0.0071 (8) | 0.0034 (7) |
O1 | 0.0331 (7) | 0.0244 (6) | 0.0196 (6) | 0.0001 (5) | 0.0055 (5) | −0.0056 (5) |
O2 | 0.0450 (8) | 0.0217 (7) | 0.0215 (6) | 0.0048 (6) | 0.0084 (5) | −0.0035 (5) |
N1 | 0.0367 (9) | 0.0218 (9) | 0.0364 (9) | −0.0027 (7) | 0.0027 (7) | −0.0017 (6) |
N2 | 0.0374 (9) | 0.0316 (9) | 0.0261 (8) | −0.0039 (7) | 0.0067 (7) | 0.0036 (6) |
C1 | 0.0188 (8) | 0.0207 (8) | 0.0185 (8) | 0.0004 (6) | 0.0001 (6) | −0.0002 (6) |
C2 | 0.0188 (8) | 0.0170 (8) | 0.0210 (8) | 0.0008 (6) | 0.0004 (6) | 0.0005 (6) |
C3 | 0.0191 (8) | 0.0200 (8) | 0.0185 (8) | 0.0001 (6) | 0.0025 (6) | 0.0019 (6) |
C4 | 0.0216 (8) | 0.0192 (8) | 0.0206 (8) | 0.0033 (6) | 0.0018 (6) | −0.0004 (6) |
C5 | 0.0221 (8) | 0.0151 (8) | 0.0220 (8) | 0.0001 (6) | 0.0004 (6) | 0.0015 (6) |
C6 | 0.0207 (8) | 0.0209 (8) | 0.0182 (8) | 0.0003 (6) | 0.0027 (6) | 0.0023 (6) |
C7 | 0.0204 (8) | 0.0232 (9) | 0.0199 (8) | −0.0001 (7) | 0.0031 (6) | −0.0009 (6) |
C8 | 0.0237 (9) | 0.0199 (9) | 0.0226 (9) | 0.0014 (7) | 0.0018 (7) | −0.0025 (7) |
N3 | 0.0309 (8) | 0.0210 (8) | 0.0288 (8) | 0.0031 (6) | −0.0052 (6) | −0.0014 (6) |
C9 | 0.0307 (10) | 0.0276 (10) | 0.0236 (9) | 0.0032 (8) | 0.0021 (7) | 0.0022 (7) |
C10 | 0.0321 (10) | 0.0258 (9) | 0.0196 (8) | 0.0033 (7) | 0.0025 (7) | −0.0011 (7) |
C11 | 0.0318 (10) | 0.0195 (9) | 0.0223 (9) | 0.0026 (7) | 0.0017 (7) | 0.0021 (6) |
C12 | 0.0379 (10) | 0.0321 (10) | 0.0208 (9) | 0.0034 (8) | 0.0067 (8) | 0.0001 (7) |
C13 | 0.0454 (11) | 0.0270 (10) | 0.0216 (9) | 0.0088 (8) | −0.0023 (8) | −0.0047 (7) |
C14 | 0.0404 (12) | 0.0400 (12) | 0.0536 (14) | −0.0072 (10) | −0.0088 (10) | −0.0065 (10) |
Cl1—C5 | 1.7158 (16) | C5—C6 | 1.354 (2) |
N4—C15 | 1.139 (2) | N3—C9 | 1.342 (2) |
Cl2—C6 | 1.7142 (16) | N3—C13 | 1.345 (2) |
C15—C11 | 1.445 (3) | N3—C14 | 1.476 (2) |
O1—C1 | 1.2441 (19) | C9—C10 | 1.368 (3) |
O2—C4 | 1.2380 (19) | C9—H9 | 0.9400 |
N1—C7 | 1.140 (2) | C10—C11 | 1.382 (2) |
N2—C8 | 1.143 (2) | C10—H10 | 0.9400 |
C1—C2 | 1.446 (2) | C11—C12 | 1.387 (2) |
C1—C6 | 1.464 (2) | C12—C13 | 1.361 (3) |
C2—C3 | 1.383 (2) | C12—H12 | 0.9400 |
C2—C7 | 1.434 (2) | C13—H13 | 0.9400 |
C3—C8 | 1.434 (2) | C14—H14A | 0.9700 |
C3—C4 | 1.455 (2) | C14—H14B | 0.9700 |
C4—C5 | 1.459 (2) | C14—H14C | 0.9700 |
N4—C15—C11 | 176.7 (2) | C13—N3—C14 | 118.74 (16) |
O1—C1—C2 | 122.54 (15) | N3—C9—C10 | 120.59 (16) |
O1—C1—C6 | 122.79 (15) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.66 (14) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.40 (14) | C9—C10—C11 | 118.90 (16) |
C3—C2—C1 | 122.79 (15) | C9—C10—H10 | 120.5 |
C7—C2—C1 | 115.75 (14) | C11—C10—H10 | 120.5 |
C2—C3—C8 | 121.07 (15) | C10—C11—C12 | 119.81 (17) |
C2—C3—C4 | 121.94 (14) | C10—C11—C15 | 121.10 (16) |
C8—C3—C4 | 116.99 (14) | C12—C11—C15 | 119.05 (16) |
O2—C4—C3 | 122.60 (15) | C13—C12—C11 | 118.92 (17) |
O2—C4—C5 | 122.72 (15) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.65 (14) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.98 (15) | N3—C13—C12 | 120.76 (16) |
C6—C5—Cl1 | 121.43 (13) | N3—C13—H13 | 119.6 |
C4—C5—Cl1 | 115.59 (12) | C12—C13—H13 | 119.6 |
C5—C6—C1 | 122.52 (15) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.03 (13) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.45 (12) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.6 (2) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 178.90 (19) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.01 (16) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.22 (16) | ||
O1—C1—C2—C3 | −176.86 (15) | Cl1—C5—C6—C1 | 179.72 (12) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.50 (12) |
O1—C1—C2—C7 | 5.6 (2) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.24 (14) | O1—C1—C6—C5 | 176.28 (16) |
C7—C2—C3—C8 | −0.8 (2) | C2—C1—C6—C5 | −4.9 (2) |
C1—C2—C3—C8 | −178.20 (15) | O1—C1—C6—Cl2 | −4.4 (2) |
C7—C2—C3—C4 | 178.71 (15) | C2—C1—C6—Cl2 | 174.48 (11) |
C1—C2—C3—C4 | 1.3 (2) | C13—N3—C9—C10 | 0.0 (3) |
C2—C3—C4—O2 | 175.85 (16) | C14—N3—C9—C10 | 178.15 (17) |
C8—C3—C4—O2 | −4.6 (2) | N3—C9—C10—C11 | 0.1 (3) |
C2—C3—C4—C5 | −6.2 (2) | C9—C10—C11—C12 | 0.5 (3) |
C8—C3—C4—C5 | 173.30 (14) | C9—C10—C11—C15 | −177.22 (17) |
O2—C4—C5—C6 | −176.38 (16) | C10—C11—C12—C13 | −1.0 (3) |
C3—C4—C5—C6 | 5.7 (2) | C15—C11—C12—C13 | 176.69 (17) |
O2—C4—C5—Cl1 | 3.7 (2) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.19 (11) | C14—N3—C13—C12 | −178.78 (18) |
C4—C5—C6—C1 | −0.2 (3) | C11—C12—C13—N3 | 1.1 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.632 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.83004 (15) Å | Cell parameters from 4069 reflections |
b = 10.08887 (19) Å | θ = 2.0–27.8° |
c = 20.5119 (4) Å | µ = 0.48 mm−1 |
β = 94.7341 (18)° | T = 240 K |
V = 1408.60 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3218 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2597 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −7→9 |
Tmin = 0.953, Tmax = 1.000 | k = −13→12 |
9373 measured reflections | l = −26→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0355P)2 + 0.3774P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3218 reflections | Δρmax = 0.29 e Å−3 |
209 parameters | Δρmin = −0.21 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 | ||
Cl1 | 0.20550 (7) | 0.11296 (4) | −0.00711 (2) | 0.03081 (13) | |
N4 | 0.9903 (3) | 1.20316 (19) | 0.24822 (8) | 0.0438 (4) | |
Cl2 | 0.11695 (7) | 0.28108 (4) | 0.11712 (2) | 0.03079 (13) | |
C15 | 0.8405 (3) | 1.1551 (2) | 0.23559 (9) | 0.0335 (4) | |
O1 | 0.13561 (18) | 0.56679 (12) | 0.09447 (6) | 0.0291 (3) | |
O2 | 0.2899 (2) | 0.27785 (12) | −0.11820 (6) | 0.0334 (3) | |
N1 | 0.2980 (2) | 0.81298 (16) | −0.00668 (8) | 0.0362 (4) | |
N2 | 0.4169 (3) | 0.59838 (17) | −0.16717 (8) | 0.0369 (4) | |
C1 | 0.1806 (2) | 0.49992 (17) | 0.04684 (8) | 0.0220 (3) | |
C2 | 0.2474 (2) | 0.56018 (17) | −0.01156 (8) | 0.0219 (3) | |
C3 | 0.2882 (2) | 0.48681 (17) | −0.06584 (8) | 0.0219 (3) | |
C4 | 0.2642 (2) | 0.34373 (17) | −0.06852 (8) | 0.0229 (4) | |
C5 | 0.2129 (2) | 0.28316 (16) | −0.00745 (8) | 0.0217 (3) | |
C6 | 0.1743 (2) | 0.35483 (17) | 0.04572 (8) | 0.0221 (4) | |
C7 | 0.2756 (3) | 0.70122 (18) | −0.00907 (8) | 0.0243 (4) | |
C8 | 0.3592 (2) | 0.54964 (17) | −0.12210 (8) | 0.0252 (4) | |
N3 | 0.3200 (2) | 0.95327 (15) | 0.18300 (7) | 0.0313 (4) | |
C9 | 0.3528 (3) | 0.99914 (19) | 0.24424 (9) | 0.0312 (4) | |
H9 | 0.259450 | 0.983975 | 0.274609 | 0.037* | |
C10 | 0.5209 (3) | 1.06789 (18) | 0.26304 (8) | 0.0290 (4) | |
H10 | 0.543814 | 1.100090 | 0.305995 | 0.035* | |
C11 | 0.6569 (3) | 1.08911 (17) | 0.21748 (9) | 0.0280 (4) | |
C12 | 0.6198 (3) | 1.0414 (2) | 0.15439 (9) | 0.0346 (4) | |
H12 | 0.710095 | 1.055996 | 0.122962 | 0.042* | |
C13 | 0.4506 (3) | 0.97288 (19) | 0.13846 (9) | 0.0354 (5) | |
H13 | 0.425129 | 0.939041 | 0.095908 | 0.042* | |
C14 | 0.1403 (3) | 0.8762 (2) | 0.16393 (12) | 0.0510 (6) | |
H14A | 0.061427 | 0.869297 | 0.200996 | 0.077* | |
H14B | 0.176403 | 0.788179 | 0.150157 | 0.077* | |
H14C | 0.065219 | 0.920600 | 0.128127 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0438 (3) | 0.0170 (2) | 0.0321 (2) | 0.00105 (18) | 0.00549 (19) | 0.00061 (16) |
N4 | 0.0489 (11) | 0.0477 (11) | 0.0354 (10) | −0.0117 (9) | 0.0069 (8) | 0.0060 (8) |
Cl2 | 0.0413 (3) | 0.0298 (3) | 0.0219 (2) | −0.00272 (19) | 0.00638 (18) | 0.00484 (16) |
C15 | 0.0431 (12) | 0.0318 (11) | 0.0266 (10) | −0.0018 (9) | 0.0083 (8) | 0.0036 (8) |
O1 | 0.0375 (7) | 0.0276 (7) | 0.0228 (6) | 0.0009 (6) | 0.0066 (5) | −0.0070 (5) |
O2 | 0.0517 (9) | 0.0253 (7) | 0.0243 (7) | 0.0055 (6) | 0.0095 (6) | −0.0040 (5) |
N1 | 0.0420 (10) | 0.0236 (9) | 0.0429 (10) | −0.0031 (7) | 0.0033 (8) | −0.0014 (7) |
N2 | 0.0438 (10) | 0.0375 (10) | 0.0301 (9) | −0.0059 (8) | 0.0078 (7) | 0.0048 (7) |
C1 | 0.0223 (8) | 0.0224 (9) | 0.0210 (8) | 0.0006 (7) | 0.0002 (6) | −0.0003 (7) |
C2 | 0.0222 (8) | 0.0205 (9) | 0.0230 (8) | 0.0005 (7) | 0.0018 (7) | −0.0005 (6) |
C3 | 0.0234 (8) | 0.0215 (9) | 0.0210 (8) | 0.0010 (7) | 0.0029 (6) | 0.0014 (6) |
C4 | 0.0257 (9) | 0.0213 (9) | 0.0220 (8) | 0.0037 (7) | 0.0031 (7) | −0.0010 (6) |
C5 | 0.0245 (9) | 0.0161 (8) | 0.0243 (9) | 0.0009 (7) | 0.0017 (7) | 0.0011 (6) |
C6 | 0.0236 (9) | 0.0231 (9) | 0.0198 (8) | 0.0003 (7) | 0.0023 (7) | 0.0027 (6) |
C7 | 0.0246 (9) | 0.0260 (10) | 0.0223 (9) | 0.0000 (7) | 0.0023 (7) | −0.0004 (7) |
C8 | 0.0276 (9) | 0.0217 (9) | 0.0260 (9) | 0.0006 (7) | 0.0012 (7) | −0.0018 (7) |
N3 | 0.0363 (9) | 0.0236 (8) | 0.0328 (9) | 0.0038 (7) | −0.0045 (7) | −0.0013 (6) |
C9 | 0.0344 (10) | 0.0318 (10) | 0.0275 (10) | 0.0034 (8) | 0.0029 (8) | 0.0021 (8) |
C10 | 0.0347 (10) | 0.0323 (10) | 0.0200 (9) | 0.0048 (8) | 0.0023 (7) | −0.0009 (7) |
C11 | 0.0349 (10) | 0.0225 (9) | 0.0267 (9) | 0.0031 (7) | 0.0030 (8) | 0.0025 (7) |
C12 | 0.0444 (12) | 0.0361 (11) | 0.0242 (9) | 0.0035 (9) | 0.0085 (8) | 0.0001 (8) |
C13 | 0.0495 (12) | 0.0325 (11) | 0.0230 (9) | 0.0089 (9) | −0.0030 (8) | −0.0056 (8) |
C14 | 0.0454 (13) | 0.0476 (14) | 0.0574 (15) | −0.0089 (11) | −0.0113 (11) | −0.0065 (11) |
Cl1—C5 | 1.7178 (16) | C5—C6 | 1.352 (2) |
N4—C15 | 1.142 (3) | N3—C9 | 1.340 (2) |
Cl2—C6 | 1.7168 (17) | N3—C13 | 1.343 (2) |
C15—C11 | 1.442 (3) | N3—C14 | 1.478 (3) |
O1—C1 | 1.2466 (19) | C9—C10 | 1.369 (3) |
O2—C4 | 1.241 (2) | C9—H9 | 0.9400 |
N1—C7 | 1.138 (2) | C10—C11 | 1.387 (2) |
N2—C8 | 1.145 (2) | C10—H10 | 0.9400 |
C1—C2 | 1.450 (2) | C11—C12 | 1.385 (3) |
C1—C6 | 1.465 (2) | C12—C13 | 1.362 (3) |
C2—C3 | 1.384 (2) | C12—H12 | 0.9400 |
C2—C7 | 1.436 (2) | C13—H13 | 0.9400 |
C3—C8 | 1.436 (2) | C14—H14A | 0.9700 |
C3—C4 | 1.453 (2) | C14—H14B | 0.9700 |
C4—C5 | 1.462 (2) | C14—H14C | 0.9700 |
N4—C15—C11 | 176.8 (2) | C13—N3—C14 | 118.75 (17) |
O1—C1—C2 | 122.36 (16) | N3—C9—C10 | 120.68 (17) |
O1—C1—C6 | 122.99 (15) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.64 (14) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.55 (15) | C9—C10—C11 | 118.74 (17) |
C3—C2—C1 | 122.54 (16) | C9—C10—H10 | 120.6 |
C7—C2—C1 | 115.88 (15) | C11—C10—H10 | 120.6 |
C2—C3—C8 | 120.94 (15) | C12—C11—C10 | 119.67 (18) |
C2—C3—C4 | 122.16 (15) | C12—C11—C15 | 119.32 (17) |
C8—C3—C4 | 116.90 (14) | C10—C11—C15 | 120.95 (16) |
O2—C4—C3 | 122.68 (15) | C13—C12—C11 | 119.12 (18) |
O2—C4—C5 | 122.66 (16) | C13—C12—H12 | 120.4 |
C3—C4—C5 | 114.64 (14) | C11—C12—H12 | 120.4 |
C6—C5—C4 | 122.94 (15) | N3—C13—C12 | 120.60 (17) |
C6—C5—Cl1 | 121.55 (13) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.50 (12) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.66 (15) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 121.98 (13) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.36 (12) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.57 (19) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.2 (2) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.18 (17) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.04 (17) | ||
O1—C1—C2—C3 | −176.67 (16) | Cl1—C5—C6—C1 | 179.68 (13) |
C6—C1—C2—C3 | 4.5 (2) | C4—C5—C6—Cl2 | −179.30 (13) |
O1—C1—C2—C7 | 5.4 (2) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.47 (14) | O1—C1—C6—C5 | 176.25 (16) |
C7—C2—C3—C8 | −0.4 (2) | C2—C1—C6—C5 | −4.9 (2) |
C1—C2—C3—C8 | −178.26 (15) | O1—C1—C6—Cl2 | −4.4 (2) |
C7—C2—C3—C4 | 178.70 (16) | C2—C1—C6—Cl2 | 174.40 (12) |
C1—C2—C3—C4 | 0.9 (3) | C13—N3—C9—C10 | 0.2 (3) |
C2—C3—C4—O2 | 175.92 (17) | C14—N3—C9—C10 | 178.40 (18) |
C8—C3—C4—O2 | −4.9 (3) | N3—C9—C10—C11 | 0.0 (3) |
C2—C3—C4—C5 | −5.7 (2) | C9—C10—C11—C12 | 0.3 (3) |
C8—C3—C4—C5 | 173.44 (15) | C9—C10—C11—C15 | −176.89 (18) |
O2—C4—C5—C6 | −176.29 (17) | C10—C11—C12—C13 | −0.7 (3) |
C3—C4—C5—C6 | 5.3 (2) | C15—C11—C12—C13 | 176.52 (18) |
O2—C4—C5—Cl1 | 4.0 (2) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.39 (12) | C14—N3—C13—C12 | −178.85 (19) |
C4—C5—C6—C1 | 0.0 (3) | C11—C12—C13—N3 | 0.9 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.626 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.84899 (17) Å | Cell parameters from 3845 reflections |
b = 10.0928 (2) Å | θ = 2.0–27.8° |
c = 20.5226 (4) Å | µ = 0.47 mm−1 |
β = 94.715 (2)° | T = 270 K |
V = 1413.83 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3225 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2539 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −7→9 |
Tmin = 0.926, Tmax = 1.000 | k = −13→12 |
9414 measured reflections | l = −26→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0318P)2 + 0.3721P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3225 reflections | Δρmax = 0.28 e Å−3 |
209 parameters | Δρmin = −0.25 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 | ||
Cl1 | 0.20489 (7) | 0.11321 (4) | −0.00712 (2) | 0.03500 (13) | |
N4 | 0.9890 (3) | 1.20268 (19) | 0.24804 (8) | 0.0493 (5) | |
Cl2 | 0.11661 (7) | 0.28116 (5) | 0.11697 (2) | 0.03491 (13) | |
C15 | 0.8397 (3) | 1.1552 (2) | 0.23537 (9) | 0.0377 (4) | |
O1 | 0.13567 (18) | 0.56664 (12) | 0.09449 (6) | 0.0326 (3) | |
O2 | 0.2899 (2) | 0.27787 (12) | −0.11795 (6) | 0.0378 (3) | |
N1 | 0.2984 (2) | 0.81252 (16) | −0.00660 (8) | 0.0407 (4) | |
N2 | 0.4170 (3) | 0.59821 (16) | −0.16682 (8) | 0.0407 (4) | |
C1 | 0.1803 (2) | 0.49997 (17) | 0.04689 (8) | 0.0248 (4) | |
C2 | 0.2470 (2) | 0.55998 (16) | −0.01139 (8) | 0.0238 (3) | |
C3 | 0.2884 (2) | 0.48669 (16) | −0.06561 (8) | 0.0238 (3) | |
C4 | 0.2641 (2) | 0.34373 (17) | −0.06845 (8) | 0.0261 (4) | |
C5 | 0.2126 (2) | 0.28310 (16) | −0.00744 (8) | 0.0247 (4) | |
C6 | 0.1742 (2) | 0.35464 (17) | 0.04563 (8) | 0.0249 (4) | |
C7 | 0.2759 (2) | 0.70081 (18) | −0.00900 (8) | 0.0273 (4) | |
C8 | 0.3591 (3) | 0.54982 (17) | −0.12183 (8) | 0.0279 (4) | |
N3 | 0.3205 (2) | 0.95322 (15) | 0.18318 (7) | 0.0352 (4) | |
C9 | 0.3536 (3) | 0.99919 (19) | 0.24421 (9) | 0.0351 (4) | |
H9 | 0.261562 | 0.984432 | 0.274301 | 0.042* | |
C10 | 0.5209 (3) | 1.06753 (18) | 0.26280 (9) | 0.0327 (4) | |
H10 | 0.543473 | 1.099447 | 0.305262 | 0.039* | |
C11 | 0.6561 (3) | 1.08850 (17) | 0.21750 (8) | 0.0309 (4) | |
C12 | 0.6191 (3) | 1.0410 (2) | 0.15442 (9) | 0.0391 (5) | |
H12 | 0.708190 | 1.055481 | 0.123313 | 0.047* | |
C13 | 0.4507 (3) | 0.97289 (19) | 0.13863 (9) | 0.0397 (5) | |
H13 | 0.425299 | 0.939553 | 0.096540 | 0.048* | |
C14 | 0.1411 (3) | 0.8761 (2) | 0.16426 (13) | 0.0585 (6) | |
H14A | 0.064578 | 0.867998 | 0.201195 | 0.088* | |
H14B | 0.176709 | 0.789502 | 0.149921 | 0.088* | |
H14C | 0.065686 | 0.920736 | 0.129377 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0497 (3) | 0.0194 (2) | 0.0364 (3) | 0.00091 (19) | 0.0064 (2) | 0.00062 (17) |
N4 | 0.0518 (11) | 0.0567 (12) | 0.0399 (10) | −0.0136 (10) | 0.0079 (8) | 0.0071 (8) |
Cl2 | 0.0465 (3) | 0.0337 (3) | 0.0252 (2) | −0.0030 (2) | 0.00737 (19) | 0.00588 (17) |
C15 | 0.0476 (12) | 0.0376 (11) | 0.0291 (10) | −0.0006 (10) | 0.0094 (9) | 0.0040 (8) |
O1 | 0.0422 (7) | 0.0307 (7) | 0.0257 (6) | 0.0006 (6) | 0.0075 (5) | −0.0074 (5) |
O2 | 0.0588 (9) | 0.0285 (7) | 0.0273 (7) | 0.0058 (6) | 0.0105 (6) | −0.0056 (5) |
N1 | 0.0480 (10) | 0.0268 (9) | 0.0472 (10) | −0.0041 (8) | 0.0033 (8) | −0.0024 (7) |
N2 | 0.0493 (10) | 0.0403 (10) | 0.0334 (9) | −0.0054 (8) | 0.0094 (8) | 0.0045 (7) |
C1 | 0.0250 (9) | 0.0261 (9) | 0.0233 (8) | 0.0014 (7) | 0.0013 (7) | −0.0012 (7) |
C2 | 0.0250 (9) | 0.0216 (8) | 0.0246 (8) | 0.0016 (7) | 0.0005 (7) | −0.0013 (6) |
C3 | 0.0250 (8) | 0.0239 (9) | 0.0227 (8) | 0.0005 (7) | 0.0030 (6) | 0.0012 (6) |
C4 | 0.0280 (9) | 0.0242 (9) | 0.0262 (9) | 0.0049 (7) | 0.0026 (7) | −0.0006 (7) |
C5 | 0.0285 (9) | 0.0195 (8) | 0.0258 (9) | 0.0018 (7) | 0.0008 (7) | 0.0013 (6) |
C6 | 0.0270 (9) | 0.0265 (9) | 0.0213 (8) | 0.0008 (7) | 0.0033 (7) | 0.0025 (6) |
C7 | 0.0275 (9) | 0.0286 (10) | 0.0261 (9) | 0.0003 (7) | 0.0028 (7) | −0.0004 (7) |
C8 | 0.0317 (9) | 0.0246 (9) | 0.0273 (9) | 0.0014 (7) | 0.0020 (7) | −0.0016 (7) |
N3 | 0.0396 (9) | 0.0269 (8) | 0.0375 (9) | 0.0037 (7) | −0.0056 (7) | −0.0015 (7) |
C9 | 0.0393 (11) | 0.0368 (11) | 0.0292 (10) | 0.0039 (9) | 0.0026 (8) | 0.0028 (8) |
C10 | 0.0395 (11) | 0.0350 (10) | 0.0236 (9) | 0.0042 (8) | 0.0023 (8) | −0.0018 (7) |
C11 | 0.0396 (11) | 0.0255 (9) | 0.0277 (9) | 0.0040 (8) | 0.0030 (8) | 0.0020 (7) |
C12 | 0.0502 (12) | 0.0415 (12) | 0.0266 (9) | 0.0036 (10) | 0.0093 (9) | 0.0004 (8) |
C13 | 0.0547 (13) | 0.0369 (11) | 0.0265 (9) | 0.0112 (10) | −0.0022 (9) | −0.0058 (8) |
C14 | 0.0520 (14) | 0.0526 (15) | 0.0683 (17) | −0.0093 (12) | −0.0112 (12) | −0.0067 (12) |
Cl1—C5 | 1.7155 (17) | C5—C6 | 1.350 (2) |
N4—C15 | 1.140 (3) | N3—C9 | 1.337 (2) |
Cl2—C6 | 1.7160 (16) | N3—C13 | 1.343 (2) |
C15—C11 | 1.447 (3) | N3—C14 | 1.479 (3) |
O1—C1 | 1.2450 (19) | C9—C10 | 1.365 (3) |
O2—C4 | 1.2388 (19) | C9—H9 | 0.9300 |
N1—C7 | 1.138 (2) | C10—C11 | 1.381 (2) |
N2—C8 | 1.144 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.448 (2) | C11—C12 | 1.384 (2) |
C1—C6 | 1.468 (2) | C12—C13 | 1.359 (3) |
C2—C3 | 1.385 (2) | C12—H12 | 0.9300 |
C2—C7 | 1.435 (2) | C13—H13 | 0.9300 |
C3—C8 | 1.437 (2) | C14—H14A | 0.9600 |
C3—C4 | 1.453 (2) | C14—H14B | 0.9600 |
C4—C5 | 1.463 (2) | C14—H14C | 0.9600 |
N4—C15—C11 | 176.6 (2) | C13—N3—C14 | 118.86 (17) |
O1—C1—C2 | 122.46 (16) | N3—C9—C10 | 120.73 (17) |
O1—C1—C6 | 123.06 (15) | N3—C9—H9 | 119.6 |
C2—C1—C6 | 114.46 (14) | C10—C9—H9 | 119.6 |
C3—C2—C7 | 121.32 (15) | C9—C10—C11 | 118.89 (17) |
C3—C2—C1 | 122.66 (15) | C9—C10—H10 | 120.6 |
C7—C2—C1 | 115.97 (14) | C11—C10—H10 | 120.6 |
C2—C3—C8 | 120.88 (15) | C10—C11—C12 | 119.68 (18) |
C2—C3—C4 | 122.17 (15) | C10—C11—C15 | 121.17 (16) |
C8—C3—C4 | 116.95 (14) | C12—C11—C15 | 119.11 (17) |
O2—C4—C3 | 122.83 (15) | C13—C12—C11 | 118.98 (18) |
O2—C4—C5 | 122.57 (16) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.57 (14) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.91 (15) | N3—C13—C12 | 120.70 (17) |
C6—C5—Cl1 | 121.56 (13) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.53 (12) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.79 (15) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.05 (13) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.16 (12) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.5 (2) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 178.87 (19) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.01 (17) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.10 (17) | ||
O1—C1—C2—C3 | −176.99 (16) | Cl1—C5—C6—C1 | 179.78 (13) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.31 (13) |
O1—C1—C2—C7 | 5.4 (2) | Cl1—C5—C6—Cl2 | 0.3 (2) |
C6—C1—C2—C7 | −173.26 (14) | O1—C1—C6—C5 | 176.30 (16) |
C7—C2—C3—C8 | −0.9 (2) | C2—C1—C6—C5 | −5.0 (2) |
C1—C2—C3—C8 | −178.38 (15) | O1—C1—C6—Cl2 | −4.2 (2) |
C7—C2—C3—C4 | 178.69 (15) | C2—C1—C6—Cl2 | 174.46 (11) |
C1—C2—C3—C4 | 1.2 (3) | C13—N3—C9—C10 | 0.0 (3) |
C2—C3—C4—O2 | 175.81 (16) | C14—N3—C9—C10 | 178.28 (18) |
C8—C3—C4—O2 | −4.6 (2) | N3—C9—C10—C11 | 0.0 (3) |
C2—C3—C4—C5 | −6.0 (2) | C9—C10—C11—C12 | 0.5 (3) |
C8—C3—C4—C5 | 173.60 (14) | C9—C10—C11—C15 | −177.26 (18) |
O2—C4—C5—C6 | −176.45 (17) | C10—C11—C12—C13 | −0.9 (3) |
C3—C4—C5—C6 | 5.4 (2) | C15—C11—C12—C13 | 176.91 (18) |
O2—C4—C5—Cl1 | 3.9 (2) | C9—N3—C13—C12 | −0.5 (3) |
C3—C4—C5—Cl1 | −174.29 (12) | C14—N3—C13—C12 | −178.72 (19) |
C4—C5—C6—C1 | 0.1 (3) | C11—C12—C13—N3 | 0.9 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.622 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.86364 (18) Å | Cell parameters from 3676 reflections |
b = 10.0969 (2) Å | θ = 2.0–27.3° |
c = 20.5284 (4) Å | µ = 0.47 mm−1 |
β = 94.703 (2)° | T = 293 K |
V = 1417.86 (5) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3235 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2494 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −9→7 |
Tmin = 0.956, Tmax = 1.000 | k = −13→12 |
9438 measured reflections | l = −26→27 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0329P)2 + 0.3465P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3235 reflections | Δρmax = 0.26 e Å−3 |
209 parameters | Δρmin = −0.22 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 | ||
Cl1 | 0.20442 (8) | 0.11340 (4) | −0.00715 (2) | 0.03848 (14) | |
N4 | 0.9875 (3) | 1.2023 (2) | 0.24795 (9) | 0.0539 (5) | |
Cl2 | 0.11641 (7) | 0.28119 (5) | 0.11692 (2) | 0.03839 (14) | |
C15 | 0.8391 (3) | 1.1547 (2) | 0.23541 (9) | 0.0413 (5) | |
O1 | 0.13604 (19) | 0.56657 (13) | 0.09443 (6) | 0.0354 (3) | |
O2 | 0.2898 (2) | 0.27812 (13) | −0.11782 (6) | 0.0413 (3) | |
N1 | 0.2985 (3) | 0.81196 (17) | −0.00661 (9) | 0.0440 (4) | |
N2 | 0.4168 (3) | 0.59814 (17) | −0.16661 (8) | 0.0440 (4) | |
C1 | 0.1810 (2) | 0.49968 (18) | 0.04692 (8) | 0.0271 (4) | |
C2 | 0.2470 (2) | 0.56022 (17) | −0.01128 (8) | 0.0264 (4) | |
C3 | 0.2880 (2) | 0.48656 (17) | −0.06545 (8) | 0.0261 (4) | |
C4 | 0.2638 (3) | 0.34397 (18) | −0.06828 (8) | 0.0285 (4) | |
C5 | 0.2125 (3) | 0.28326 (17) | −0.00744 (8) | 0.0270 (4) | |
C6 | 0.1734 (2) | 0.35462 (18) | 0.04562 (8) | 0.0271 (4) | |
C7 | 0.2760 (3) | 0.70050 (19) | −0.00887 (8) | 0.0296 (4) | |
C8 | 0.3594 (3) | 0.54937 (18) | −0.12160 (9) | 0.0305 (4) | |
N3 | 0.3207 (2) | 0.95306 (16) | 0.18317 (8) | 0.0382 (4) | |
C9 | 0.3538 (3) | 0.9991 (2) | 0.24416 (9) | 0.0383 (5) | |
H9 | 0.261957 | 0.984447 | 0.274251 | 0.046* | |
C10 | 0.5209 (3) | 1.06728 (19) | 0.26276 (9) | 0.0351 (4) | |
H10 | 0.543329 | 1.099087 | 0.305224 | 0.042* | |
C11 | 0.6563 (3) | 1.08840 (18) | 0.21747 (9) | 0.0341 (4) | |
C12 | 0.6191 (3) | 1.0409 (2) | 0.15453 (9) | 0.0423 (5) | |
H12 | 0.707679 | 1.055431 | 0.123347 | 0.051* | |
C13 | 0.4503 (3) | 0.9725 (2) | 0.13885 (10) | 0.0446 (5) | |
H13 | 0.425056 | 0.938885 | 0.096822 | 0.054* | |
C14 | 0.1423 (4) | 0.8759 (3) | 0.16434 (14) | 0.0641 (7) | |
H14A | 0.068444 | 0.919321 | 0.128762 | 0.096* | |
H14B | 0.064398 | 0.869573 | 0.200978 | 0.096* | |
H14C | 0.177975 | 0.788680 | 0.151022 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0549 (3) | 0.0215 (2) | 0.0396 (3) | 0.0013 (2) | 0.0070 (2) | 0.00094 (18) |
N4 | 0.0570 (12) | 0.0604 (13) | 0.0450 (11) | −0.0147 (10) | 0.0090 (9) | 0.0068 (9) |
Cl2 | 0.0519 (3) | 0.0367 (3) | 0.0274 (2) | −0.0031 (2) | 0.0082 (2) | 0.00623 (18) |
C15 | 0.0518 (13) | 0.0411 (12) | 0.0320 (11) | −0.0026 (10) | 0.0106 (10) | 0.0050 (9) |
O1 | 0.0461 (8) | 0.0342 (7) | 0.0266 (7) | 0.0006 (6) | 0.0080 (6) | −0.0075 (5) |
O2 | 0.0640 (10) | 0.0296 (7) | 0.0316 (7) | 0.0062 (7) | 0.0114 (7) | −0.0052 (6) |
N1 | 0.0509 (11) | 0.0283 (10) | 0.0527 (11) | −0.0048 (8) | 0.0031 (8) | −0.0020 (8) |
N2 | 0.0535 (11) | 0.0438 (11) | 0.0358 (10) | −0.0065 (8) | 0.0100 (8) | 0.0050 (8) |
C1 | 0.0281 (9) | 0.0279 (10) | 0.0252 (9) | 0.0011 (7) | 0.0021 (7) | −0.0016 (7) |
C2 | 0.0282 (9) | 0.0230 (9) | 0.0279 (9) | 0.0016 (7) | 0.0017 (7) | −0.0021 (7) |
C3 | 0.0267 (9) | 0.0263 (9) | 0.0255 (9) | 0.0022 (7) | 0.0026 (7) | 0.0020 (7) |
C4 | 0.0321 (10) | 0.0259 (9) | 0.0275 (9) | 0.0044 (8) | 0.0031 (7) | −0.0008 (7) |
C5 | 0.0302 (9) | 0.0205 (9) | 0.0302 (9) | 0.0018 (7) | 0.0013 (7) | 0.0015 (7) |
C6 | 0.0302 (9) | 0.0277 (9) | 0.0238 (9) | 0.0005 (7) | 0.0041 (7) | 0.0024 (7) |
C7 | 0.0309 (10) | 0.0293 (10) | 0.0287 (9) | 0.0005 (8) | 0.0028 (7) | −0.0007 (7) |
C8 | 0.0334 (10) | 0.0277 (10) | 0.0302 (10) | 0.0012 (8) | 0.0021 (8) | −0.0016 (8) |
N3 | 0.0441 (10) | 0.0293 (9) | 0.0395 (9) | 0.0033 (7) | −0.0061 (8) | −0.0018 (7) |
C9 | 0.0420 (11) | 0.0400 (12) | 0.0330 (10) | 0.0033 (9) | 0.0037 (9) | 0.0025 (8) |
C10 | 0.0422 (11) | 0.0369 (11) | 0.0264 (10) | 0.0040 (9) | 0.0037 (8) | −0.0025 (8) |
C11 | 0.0438 (11) | 0.0274 (10) | 0.0310 (10) | 0.0040 (8) | 0.0036 (8) | 0.0029 (7) |
C12 | 0.0545 (13) | 0.0442 (13) | 0.0293 (10) | 0.0052 (10) | 0.0090 (9) | 0.0004 (9) |
C13 | 0.0620 (14) | 0.0400 (12) | 0.0308 (10) | 0.0108 (11) | −0.0025 (10) | −0.0072 (9) |
C14 | 0.0557 (15) | 0.0596 (16) | 0.0740 (18) | −0.0116 (13) | −0.0135 (13) | −0.0091 (13) |
Cl1—C5 | 1.7160 (17) | C5—C6 | 1.351 (2) |
N4—C15 | 1.136 (3) | N3—C9 | 1.337 (2) |
Cl2—C6 | 1.7144 (17) | N3—C13 | 1.338 (3) |
C15—C11 | 1.443 (3) | N3—C14 | 1.476 (3) |
O1—C1 | 1.246 (2) | C9—C10 | 1.365 (3) |
O2—C4 | 1.240 (2) | C9—H9 | 0.9300 |
N1—C7 | 1.136 (2) | C10—C11 | 1.384 (3) |
N2—C8 | 1.145 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.448 (2) | C11—C12 | 1.382 (3) |
C1—C6 | 1.466 (2) | C12—C13 | 1.365 (3) |
C2—C3 | 1.386 (2) | C12—H12 | 0.9300 |
C2—C7 | 1.431 (2) | C13—H13 | 0.9300 |
C3—C8 | 1.436 (2) | C14—H14A | 0.9600 |
C3—C4 | 1.450 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.460 (2) | C14—H14C | 0.9600 |
N4—C15—C11 | 176.7 (2) | C13—N3—C14 | 118.87 (18) |
O1—C1—C2 | 122.12 (16) | N3—C9—C10 | 120.79 (18) |
O1—C1—C6 | 123.05 (16) | N3—C9—H9 | 119.6 |
C2—C1—C6 | 114.83 (15) | C10—C9—H9 | 119.6 |
C3—C2—C7 | 121.49 (16) | C9—C10—C11 | 119.01 (18) |
C3—C2—C1 | 122.25 (16) | C9—C10—H10 | 120.5 |
C7—C2—C1 | 116.21 (15) | C11—C10—H10 | 120.5 |
C2—C3—C8 | 120.79 (16) | C12—C11—C10 | 119.43 (19) |
C2—C3—C4 | 122.35 (15) | C12—C11—C15 | 119.32 (18) |
C8—C3—C4 | 116.85 (15) | C10—C11—C15 | 121.20 (17) |
O2—C4—C3 | 122.79 (16) | C13—C12—C11 | 118.98 (19) |
O2—C4—C5 | 122.51 (17) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.67 (15) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.92 (16) | N3—C13—C12 | 120.85 (18) |
C6—C5—Cl1 | 121.44 (14) | N3—C13—H13 | 119.6 |
C4—C5—Cl1 | 115.64 (13) | C12—C13—H13 | 119.6 |
C5—C6—C1 | 122.59 (16) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.14 (14) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.26 (13) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.6 (2) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.3 (2) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 120.93 (18) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.17 (19) | ||
O1—C1—C2—C3 | −176.79 (16) | Cl1—C5—C6—C1 | 179.41 (13) |
C6—C1—C2—C3 | 3.8 (2) | C4—C5—C6—Cl2 | −179.16 (13) |
O1—C1—C2—C7 | 5.8 (3) | Cl1—C5—C6—Cl2 | 0.9 (2) |
C6—C1—C2—C7 | −173.58 (15) | O1—C1—C6—C5 | 176.41 (17) |
C7—C2—C3—C8 | −0.7 (3) | C2—C1—C6—C5 | −4.2 (2) |
C1—C2—C3—C8 | −177.95 (16) | O1—C1—C6—Cl2 | −5.0 (2) |
C7—C2—C3—C4 | 178.58 (16) | C2—C1—C6—Cl2 | 174.46 (12) |
C1—C2—C3—C4 | 1.4 (3) | C13—N3—C9—C10 | 0.1 (3) |
C2—C3—C4—O2 | 175.91 (17) | C14—N3—C9—C10 | 178.10 (19) |
C8—C3—C4—O2 | −4.8 (3) | N3—C9—C10—C11 | 0.0 (3) |
C2—C3—C4—C5 | −6.0 (2) | C9—C10—C11—C12 | 0.4 (3) |
C8—C3—C4—C5 | 173.36 (15) | C9—C10—C11—C15 | −177.20 (19) |
O2—C4—C5—C6 | −176.24 (17) | C10—C11—C12—C13 | −1.0 (3) |
C3—C4—C5—C6 | 5.6 (3) | C15—C11—C12—C13 | 176.71 (19) |
O2—C4—C5—Cl1 | 3.7 (2) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.40 (12) | C14—N3—C13—C12 | −178.7 (2) |
C4—C5—C6—C1 | −0.6 (3) | C11—C12—C13—N3 | 1.1 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.87524 (18) Å | Cell parameters from 3535 reflections |
b = 10.1004 (2) Å | θ = 2.0–27.3° |
c = 20.5391 (4) Å | µ = 0.47 mm−1 |
β = 94.709 (2)° | T = 310 K |
V = 1421.47 (6) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3240 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −9→7 |
Tmin = 0.935, Tmax = 1.000 | k = −13→12 |
9454 measured reflections | l = −26→27 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0329P)2 + 0.2983P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3240 reflections | Δρmax = 0.29 e Å−3 |
209 parameters | Δρmin = −0.21 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 | ||
Cl1 | 0.20418 (8) | 0.11356 (4) | −0.00714 (2) | 0.04083 (14) | |
N4 | 0.9864 (3) | 1.2019 (2) | 0.24776 (9) | 0.0586 (5) | |
Cl2 | 0.11636 (7) | 0.28123 (5) | 0.11686 (2) | 0.04084 (14) | |
C15 | 0.8386 (3) | 1.1540 (2) | 0.23528 (10) | 0.0440 (5) | |
O1 | 0.13615 (19) | 0.56638 (12) | 0.09440 (6) | 0.0379 (3) | |
O2 | 0.2894 (2) | 0.27842 (13) | −0.11771 (6) | 0.0435 (3) | |
N1 | 0.2991 (3) | 0.81168 (17) | −0.00660 (9) | 0.0475 (4) | |
N2 | 0.4169 (3) | 0.59787 (18) | −0.16625 (8) | 0.0475 (4) | |
C1 | 0.1807 (2) | 0.49981 (17) | 0.04688 (8) | 0.0291 (4) | |
C2 | 0.2473 (2) | 0.55983 (17) | −0.01123 (8) | 0.0283 (4) | |
C3 | 0.2884 (2) | 0.48655 (17) | −0.06549 (8) | 0.0282 (4) | |
C4 | 0.2641 (3) | 0.34420 (17) | −0.06819 (8) | 0.0301 (4) | |
C5 | 0.2121 (3) | 0.28340 (16) | −0.00733 (8) | 0.0287 (4) | |
C6 | 0.1738 (2) | 0.35467 (17) | 0.04569 (8) | 0.0287 (4) | |
C7 | 0.2762 (3) | 0.70045 (19) | −0.00863 (8) | 0.0321 (4) | |
C8 | 0.3590 (3) | 0.54931 (18) | −0.12146 (9) | 0.0320 (4) | |
N3 | 0.3212 (2) | 0.95320 (15) | 0.18324 (8) | 0.0403 (4) | |
C9 | 0.3538 (3) | 0.9990 (2) | 0.24407 (9) | 0.0406 (5) | |
H9 | 0.261958 | 0.984404 | 0.274118 | 0.049* | |
C10 | 0.5209 (3) | 1.06724 (19) | 0.26265 (9) | 0.0379 (4) | |
H10 | 0.543398 | 1.099030 | 0.305092 | 0.046* | |
C11 | 0.6558 (3) | 1.08828 (18) | 0.21744 (9) | 0.0366 (4) | |
C12 | 0.6181 (3) | 1.0407 (2) | 0.15444 (9) | 0.0459 (5) | |
H12 | 0.706405 | 1.055207 | 0.123228 | 0.055* | |
C13 | 0.4501 (3) | 0.9724 (2) | 0.13883 (9) | 0.0459 (5) | |
H13 | 0.424712 | 0.938802 | 0.096846 | 0.055* | |
C14 | 0.1424 (4) | 0.8763 (3) | 0.16438 (14) | 0.0679 (7) | |
H14A | 0.069168 | 0.919599 | 0.128695 | 0.102* | |
H14B | 0.064365 | 0.870472 | 0.200947 | 0.102* | |
H14C | 0.177645 | 0.788878 | 0.151263 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0580 (3) | 0.0227 (2) | 0.0423 (3) | 0.0014 (2) | 0.0074 (2) | 0.00052 (18) |
N4 | 0.0637 (13) | 0.0657 (13) | 0.0473 (11) | −0.0182 (11) | 0.0092 (10) | 0.0072 (9) |
Cl2 | 0.0547 (3) | 0.0395 (3) | 0.0292 (2) | −0.0034 (2) | 0.0089 (2) | 0.00669 (18) |
C15 | 0.0560 (14) | 0.0425 (12) | 0.0347 (11) | −0.0035 (11) | 0.0108 (10) | 0.0056 (9) |
O1 | 0.0501 (8) | 0.0358 (7) | 0.0289 (7) | 0.0006 (6) | 0.0087 (6) | −0.0085 (5) |
O2 | 0.0676 (10) | 0.0328 (7) | 0.0317 (7) | 0.0077 (7) | 0.0126 (6) | −0.0050 (6) |
N1 | 0.0556 (11) | 0.0296 (10) | 0.0570 (11) | −0.0049 (8) | 0.0038 (9) | −0.0028 (8) |
N2 | 0.0558 (11) | 0.0484 (11) | 0.0391 (10) | −0.0079 (9) | 0.0098 (8) | 0.0062 (8) |
C1 | 0.0311 (9) | 0.0288 (9) | 0.0271 (9) | 0.0009 (7) | 0.0020 (7) | −0.0019 (7) |
C2 | 0.0305 (9) | 0.0249 (9) | 0.0295 (9) | 0.0009 (7) | 0.0029 (7) | −0.0006 (7) |
C3 | 0.0303 (9) | 0.0279 (9) | 0.0266 (9) | 0.0017 (7) | 0.0033 (7) | 0.0019 (7) |
C4 | 0.0348 (10) | 0.0284 (9) | 0.0274 (9) | 0.0053 (8) | 0.0042 (7) | −0.0003 (7) |
C5 | 0.0330 (9) | 0.0223 (9) | 0.0306 (9) | 0.0017 (7) | 0.0011 (7) | 0.0013 (7) |
C6 | 0.0322 (9) | 0.0302 (9) | 0.0239 (8) | 0.0012 (7) | 0.0040 (7) | 0.0032 (7) |
C7 | 0.0331 (10) | 0.0321 (11) | 0.0312 (10) | 0.0009 (8) | 0.0029 (7) | −0.0006 (7) |
C8 | 0.0352 (10) | 0.0294 (10) | 0.0315 (9) | 0.0010 (8) | 0.0036 (8) | −0.0005 (8) |
N3 | 0.0468 (10) | 0.0312 (9) | 0.0413 (10) | 0.0035 (7) | −0.0065 (8) | −0.0009 (7) |
C9 | 0.0448 (12) | 0.0425 (12) | 0.0348 (10) | 0.0038 (9) | 0.0042 (9) | 0.0029 (8) |
C10 | 0.0451 (11) | 0.0423 (11) | 0.0262 (9) | 0.0056 (9) | 0.0024 (8) | −0.0028 (8) |
C11 | 0.0475 (12) | 0.0303 (10) | 0.0322 (10) | 0.0040 (8) | 0.0051 (8) | 0.0018 (7) |
C12 | 0.0570 (13) | 0.0502 (13) | 0.0316 (10) | 0.0049 (11) | 0.0108 (9) | −0.0004 (9) |
C13 | 0.0642 (14) | 0.0429 (12) | 0.0295 (10) | 0.0096 (11) | −0.0031 (10) | −0.0070 (9) |
C14 | 0.0629 (16) | 0.0578 (16) | 0.0795 (18) | −0.0114 (13) | −0.0155 (13) | −0.0086 (13) |
Cl1—C5 | 1.7163 (17) | C5—C6 | 1.349 (2) |
N4—C15 | 1.135 (3) | N3—C9 | 1.334 (2) |
Cl2—C6 | 1.7141 (17) | N3—C13 | 1.337 (3) |
C15—C11 | 1.442 (3) | N3—C14 | 1.478 (3) |
O1—C1 | 1.2440 (19) | C9—C10 | 1.367 (3) |
O2—C4 | 1.239 (2) | C9—H9 | 0.9300 |
N1—C7 | 1.135 (2) | C10—C11 | 1.382 (3) |
N2—C8 | 1.142 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.446 (2) | C11—C12 | 1.385 (3) |
C1—C6 | 1.467 (2) | C12—C13 | 1.361 (3) |
C2—C3 | 1.386 (2) | C12—H12 | 0.9300 |
C2—C7 | 1.434 (2) | C13—H13 | 0.9300 |
C3—C8 | 1.432 (2) | C14—H14A | 0.9600 |
C3—C4 | 1.448 (2) | C14—H14B | 0.9600 |
C4—C5 | 1.463 (2) | C14—H14C | 0.9600 |
N4—C15—C11 | 177.1 (2) | C13—N3—C14 | 118.76 (18) |
O1—C1—C2 | 122.41 (16) | N3—C9—C10 | 120.60 (18) |
O1—C1—C6 | 122.93 (16) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.65 (15) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.47 (15) | C9—C10—C11 | 119.04 (18) |
C3—C2—C1 | 122.61 (16) | C9—C10—H10 | 120.5 |
C7—C2—C1 | 115.87 (15) | C11—C10—H10 | 120.5 |
C2—C3—C8 | 120.93 (16) | C10—C11—C12 | 119.33 (19) |
C2—C3—C4 | 122.04 (15) | C10—C11—C15 | 121.30 (17) |
C8—C3—C4 | 117.03 (15) | C12—C11—C15 | 119.32 (18) |
O2—C4—C3 | 122.71 (16) | C13—C12—C11 | 119.10 (19) |
O2—C4—C5 | 122.47 (16) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.81 (14) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.89 (16) | N3—C13—C12 | 120.69 (18) |
C6—C5—Cl1 | 121.54 (14) | N3—C13—H13 | 119.7 |
C4—C5—Cl1 | 115.56 (12) | C12—C13—H13 | 119.7 |
C5—C6—C1 | 122.59 (15) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 122.09 (14) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.31 (12) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.9 (3) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.1 (2) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 121.24 (18) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 119.98 (18) | ||
O1—C1—C2—C3 | −176.91 (16) | Cl1—C5—C6—C1 | 179.64 (13) |
C6—C1—C2—C3 | 4.3 (2) | C4—C5—C6—Cl2 | −179.11 (13) |
O1—C1—C2—C7 | 5.5 (2) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.37 (15) | O1—C1—C6—C5 | 176.28 (17) |
C7—C2—C3—C8 | −0.8 (3) | C2—C1—C6—C5 | −4.9 (2) |
C1—C2—C3—C8 | −178.33 (16) | O1—C1—C6—Cl2 | −4.4 (2) |
C7—C2—C3—C4 | 178.60 (16) | C2—C1—C6—Cl2 | 174.41 (12) |
C1—C2—C3—C4 | 1.1 (3) | C13—N3—C9—C10 | 0.0 (3) |
C2—C3—C4—O2 | 175.73 (17) | C14—N3—C9—C10 | 178.26 (19) |
C8—C3—C4—O2 | −4.8 (3) | N3—C9—C10—C11 | 0.1 (3) |
C2—C3—C4—C5 | −5.8 (2) | C9—C10—C11—C12 | 0.4 (3) |
C8—C3—C4—C5 | 173.68 (15) | C9—C10—C11—C15 | −176.99 (19) |
O2—C4—C5—C6 | −176.31 (17) | C10—C11—C12—C13 | −1.0 (3) |
C3—C4—C5—C6 | 5.2 (3) | C15—C11—C12—C13 | 176.47 (19) |
O2—C4—C5—Cl1 | 4.2 (2) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.33 (12) | C14—N3—C13—C12 | −178.9 (2) |
C4—C5—C6—C1 | 0.1 (3) | C11—C12—C13—N3 | 1.1 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.610 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8983 (2) Å | Cell parameters from 3314 reflections |
b = 10.1074 (2) Å | θ = 2.0–26.7° |
c = 20.5530 (4) Å | µ = 0.47 mm−1 |
β = 94.690 (2)° | T = 340 K |
V = 1428.23 (6) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 3257 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −7→9 |
Tmin = 0.944, Tmax = 1.000 | k = −13→12 |
9495 measured reflections | l = −27→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0319P)2 + 0.2909P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3257 reflections | Δρmax = 0.24 e Å−3 |
209 parameters | Δρmin = −0.21 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 | ||
Cl1 | 0.20362 (8) | 0.11394 (5) | −0.00713 (2) | 0.04606 (15) | |
N4 | 0.9854 (3) | 1.2014 (2) | 0.24749 (9) | 0.0645 (6) | |
Cl2 | 0.11624 (8) | 0.28136 (5) | 0.11675 (2) | 0.04566 (15) | |
C15 | 0.8373 (4) | 1.1540 (2) | 0.23510 (10) | 0.0487 (5) | |
O1 | 0.1365 (2) | 0.56633 (13) | 0.09451 (6) | 0.0430 (3) | |
O2 | 0.2895 (2) | 0.27844 (13) | −0.11746 (6) | 0.0487 (4) | |
N1 | 0.2993 (3) | 0.81123 (18) | −0.00653 (9) | 0.0530 (5) | |
N2 | 0.4163 (3) | 0.59816 (18) | −0.16611 (9) | 0.0525 (5) | |
C1 | 0.1812 (3) | 0.49967 (18) | 0.04711 (8) | 0.0321 (4) | |
C2 | 0.2473 (2) | 0.55989 (17) | −0.01105 (8) | 0.0305 (4) | |
C3 | 0.2882 (2) | 0.48642 (18) | −0.06520 (8) | 0.0309 (4) | |
C4 | 0.2636 (3) | 0.34431 (18) | −0.06801 (9) | 0.0329 (4) | |
C5 | 0.2123 (3) | 0.28353 (17) | −0.00716 (8) | 0.0320 (4) | |
C6 | 0.1739 (3) | 0.35503 (18) | 0.04580 (8) | 0.0320 (4) | |
C7 | 0.2762 (3) | 0.7002 (2) | −0.00866 (9) | 0.0357 (4) | |
C8 | 0.3589 (3) | 0.54916 (19) | −0.12116 (9) | 0.0357 (4) | |
N3 | 0.3216 (2) | 0.95297 (16) | 0.18331 (8) | 0.0451 (4) | |
C9 | 0.3548 (3) | 0.9990 (2) | 0.24414 (10) | 0.0454 (5) | |
H9 | 0.263497 | 0.984593 | 0.274251 | 0.054* | |
C10 | 0.5212 (3) | 1.0671 (2) | 0.26262 (9) | 0.0422 (5) | |
H10 | 0.543989 | 1.098896 | 0.305012 | 0.051* | |
C11 | 0.6551 (3) | 1.08784 (19) | 0.21737 (9) | 0.0402 (5) | |
C12 | 0.6176 (3) | 1.0400 (2) | 0.15450 (10) | 0.0502 (5) | |
H12 | 0.705663 | 1.054132 | 0.123293 | 0.060* | |
C13 | 0.4505 (3) | 0.9723 (2) | 0.13911 (10) | 0.0520 (6) | |
H13 | 0.425136 | 0.938709 | 0.097147 | 0.062* | |
C14 | 0.1434 (4) | 0.8761 (3) | 0.16463 (14) | 0.0754 (8) | |
H14A | 0.071488 | 0.918310 | 0.128436 | 0.113* | |
H14B | 0.064609 | 0.871786 | 0.200974 | 0.113* | |
H14C | 0.178418 | 0.788140 | 0.152363 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0656 (4) | 0.0258 (2) | 0.0475 (3) | 0.0013 (2) | 0.0089 (2) | 0.0007 (2) |
N4 | 0.0687 (14) | 0.0738 (15) | 0.0517 (12) | −0.0195 (12) | 0.0096 (10) | 0.0101 (10) |
Cl2 | 0.0613 (3) | 0.0441 (3) | 0.0327 (3) | −0.0034 (2) | 0.0099 (2) | 0.0071 (2) |
C15 | 0.0613 (15) | 0.0480 (13) | 0.0381 (12) | −0.0030 (12) | 0.0120 (11) | 0.0058 (9) |
O1 | 0.0570 (9) | 0.0404 (8) | 0.0326 (7) | 0.0015 (7) | 0.0097 (6) | −0.0092 (6) |
O2 | 0.0755 (10) | 0.0361 (8) | 0.0359 (8) | 0.0069 (7) | 0.0140 (7) | −0.0060 (6) |
N1 | 0.0630 (12) | 0.0330 (11) | 0.0628 (12) | −0.0057 (9) | 0.0047 (9) | −0.0035 (8) |
N2 | 0.0632 (12) | 0.0526 (12) | 0.0428 (10) | −0.0080 (9) | 0.0116 (9) | 0.0067 (8) |
C1 | 0.0355 (10) | 0.0318 (10) | 0.0288 (9) | 0.0020 (8) | 0.0022 (8) | −0.0011 (7) |
C2 | 0.0327 (10) | 0.0272 (9) | 0.0315 (9) | 0.0020 (8) | 0.0029 (7) | −0.0004 (7) |
C3 | 0.0332 (10) | 0.0300 (10) | 0.0297 (9) | 0.0022 (8) | 0.0035 (7) | 0.0025 (7) |
C4 | 0.0374 (10) | 0.0304 (10) | 0.0312 (10) | 0.0057 (8) | 0.0038 (8) | −0.0012 (7) |
C5 | 0.0362 (10) | 0.0246 (9) | 0.0351 (10) | 0.0023 (8) | 0.0027 (8) | 0.0027 (7) |
C6 | 0.0362 (10) | 0.0317 (10) | 0.0284 (9) | 0.0008 (8) | 0.0043 (8) | 0.0033 (7) |
C7 | 0.0382 (11) | 0.0350 (11) | 0.0338 (10) | −0.0009 (8) | 0.0026 (8) | 0.0001 (8) |
C8 | 0.0395 (11) | 0.0327 (10) | 0.0348 (10) | 0.0006 (8) | 0.0019 (8) | −0.0014 (8) |
N3 | 0.0518 (11) | 0.0353 (10) | 0.0464 (10) | 0.0050 (8) | −0.0065 (8) | −0.0024 (8) |
C9 | 0.0499 (13) | 0.0475 (13) | 0.0389 (11) | 0.0037 (10) | 0.0051 (9) | 0.0029 (9) |
C10 | 0.0520 (13) | 0.0448 (12) | 0.0298 (10) | 0.0046 (10) | 0.0044 (9) | −0.0020 (8) |
C11 | 0.0522 (13) | 0.0335 (11) | 0.0349 (11) | 0.0036 (9) | 0.0042 (9) | 0.0028 (8) |
C12 | 0.0634 (15) | 0.0543 (14) | 0.0343 (11) | 0.0029 (12) | 0.0115 (10) | 0.0002 (10) |
C13 | 0.0714 (16) | 0.0482 (14) | 0.0351 (11) | 0.0115 (12) | −0.0032 (11) | −0.0082 (10) |
C14 | 0.0694 (18) | 0.0661 (18) | 0.087 (2) | −0.0152 (14) | −0.0142 (15) | −0.0113 (14) |
Cl1—C5 | 1.7152 (18) | C5—C6 | 1.351 (2) |
N4—C15 | 1.138 (3) | N3—C13 | 1.336 (3) |
Cl2—C6 | 1.7129 (17) | N3—C9 | 1.336 (2) |
C15—C11 | 1.445 (3) | N3—C14 | 1.478 (3) |
O1—C1 | 1.244 (2) | C9—C10 | 1.365 (3) |
O2—C4 | 1.240 (2) | C9—H9 | 0.9300 |
N1—C7 | 1.134 (2) | C10—C11 | 1.379 (3) |
N2—C8 | 1.147 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.448 (2) | C11—C12 | 1.384 (3) |
C1—C6 | 1.463 (3) | C12—C13 | 1.356 (3) |
C2—C3 | 1.386 (2) | C12—H12 | 0.9300 |
C2—C7 | 1.433 (3) | C13—H13 | 0.9300 |
C3—C8 | 1.434 (2) | C14—H14A | 0.9600 |
C3—C4 | 1.447 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.462 (2) | C14—H14C | 0.9600 |
N4—C15—C11 | 176.6 (2) | C9—N3—C14 | 120.1 (2) |
O1—C1—C2 | 122.26 (17) | N3—C9—C10 | 120.79 (19) |
O1—C1—C6 | 123.05 (16) | N3—C9—H9 | 119.6 |
C2—C1—C6 | 114.68 (15) | C10—C9—H9 | 119.6 |
C3—C2—C7 | 121.41 (16) | C9—C10—C11 | 118.89 (19) |
C3—C2—C1 | 122.43 (16) | C9—C10—H10 | 120.6 |
C7—C2—C1 | 116.11 (16) | C11—C10—H10 | 120.6 |
C2—C3—C8 | 120.82 (16) | C10—C11—C12 | 119.5 (2) |
C2—C3—C4 | 122.20 (16) | C10—C11—C15 | 121.15 (18) |
C8—C3—C4 | 116.98 (16) | C12—C11—C15 | 119.32 (19) |
O2—C4—C3 | 122.78 (17) | C13—C12—C11 | 119.0 (2) |
O2—C4—C5 | 122.44 (17) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 114.75 (15) | C11—C12—H12 | 120.5 |
C6—C5—C4 | 122.79 (17) | N3—C13—C12 | 121.02 (19) |
C6—C5—Cl1 | 121.68 (14) | N3—C13—H13 | 119.5 |
C4—C5—Cl1 | 115.54 (13) | C12—C13—H13 | 119.5 |
C5—C6—C1 | 122.73 (16) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 121.87 (15) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.39 (13) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.7 (2) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.3 (2) | H14A—C14—H14C | 109.5 |
C13—N3—C9 | 120.82 (19) | H14B—C14—H14C | 109.5 |
C13—N3—C14 | 119.05 (19) | ||
O1—C1—C2—C3 | −176.80 (17) | Cl1—C5—C6—C1 | 179.71 (14) |
C6—C1—C2—C3 | 3.9 (3) | C4—C5—C6—Cl2 | −179.43 (14) |
O1—C1—C2—C7 | 5.7 (3) | Cl1—C5—C6—Cl2 | 0.6 (2) |
C6—C1—C2—C7 | −173.53 (16) | O1—C1—C6—C5 | 176.25 (18) |
C7—C2—C3—C8 | −0.8 (3) | C2—C1—C6—C5 | −4.5 (3) |
C1—C2—C3—C8 | −178.09 (16) | O1—C1—C6—Cl2 | −4.6 (2) |
C7—C2—C3—C4 | 178.76 (17) | C2—C1—C6—Cl2 | 174.66 (12) |
C1—C2—C3—C4 | 1.4 (3) | C13—N3—C9—C10 | 0.1 (3) |
C2—C3—C4—O2 | 175.93 (18) | C14—N3—C9—C10 | 178.2 (2) |
C8—C3—C4—O2 | −4.5 (3) | N3—C9—C10—C11 | 0.1 (3) |
C2—C3—C4—C5 | −6.1 (3) | C9—C10—C11—C12 | 0.3 (3) |
C8—C3—C4—C5 | 173.43 (16) | C9—C10—C11—C15 | −177.2 (2) |
O2—C4—C5—C6 | −176.43 (18) | C10—C11—C12—C13 | −0.8 (3) |
C3—C4—C5—C6 | 5.6 (3) | C15—C11—C12—C13 | 176.8 (2) |
O2—C4—C5—Cl1 | 3.5 (2) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.44 (13) | C14—N3—C13—C12 | −178.7 (2) |
C4—C5—C6—C1 | −0.3 (3) | C11—C12—C13—N3 | 0.9 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.601 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9227 (2) Å | Cell parameters from 3098 reflections |
b = 10.1152 (2) Å | θ = 2.0–26.7° |
c = 20.5732 (5) Å | µ = 0.47 mm−1 |
β = 94.691 (3)° | T = 370 K |
V = 1435.81 (7) Å3 | Block, black |
Z = 4 | 0.40 × 0.15 × 0.07 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 2318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −9→7 |
Tmin = 0.939, Tmax = 1.000 | k = −13→12 |
9538 measured reflections | l = −26→27 |
3278 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0336P)2 + 0.2488P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3278 reflections | Δρmax = 0.21 e Å−3 |
209 parameters | Δρmin = −0.21 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 | ||
Cl1 | 0.20329 (8) | 0.11434 (5) | −0.00714 (3) | 0.05121 (17) | |
N4 | 0.9835 (3) | 1.2008 (2) | 0.24711 (10) | 0.0718 (6) | |
Cl2 | 0.11629 (8) | 0.28167 (5) | 0.11673 (2) | 0.05103 (16) | |
C15 | 0.8364 (4) | 1.1537 (2) | 0.23493 (11) | 0.0546 (6) | |
O1 | 0.1370 (2) | 0.56620 (14) | 0.09453 (6) | 0.0482 (4) | |
O2 | 0.2896 (2) | 0.27898 (14) | −0.11726 (6) | 0.0540 (4) | |
N1 | 0.2995 (3) | 0.81096 (19) | −0.00651 (9) | 0.0587 (5) | |
N2 | 0.4158 (3) | 0.59791 (19) | −0.16570 (9) | 0.0585 (5) | |
C1 | 0.1814 (3) | 0.50002 (19) | 0.04716 (9) | 0.0358 (4) | |
C2 | 0.2479 (3) | 0.55989 (18) | −0.01088 (9) | 0.0345 (4) | |
C3 | 0.2888 (3) | 0.48661 (18) | −0.06500 (8) | 0.0341 (4) | |
C4 | 0.2641 (3) | 0.34441 (19) | −0.06768 (9) | 0.0370 (4) | |
C5 | 0.2119 (3) | 0.28391 (18) | −0.00713 (9) | 0.0356 (4) | |
C6 | 0.1740 (3) | 0.35534 (18) | 0.04582 (9) | 0.0353 (4) | |
C7 | 0.2762 (3) | 0.7001 (2) | −0.00859 (9) | 0.0395 (5) | |
C8 | 0.3589 (3) | 0.54945 (19) | −0.12087 (9) | 0.0400 (5) | |
N3 | 0.3222 (3) | 0.95302 (17) | 0.18346 (9) | 0.0502 (5) | |
C9 | 0.3554 (3) | 0.9990 (2) | 0.24421 (10) | 0.0497 (5) | |
H9 | 0.264658 | 0.984599 | 0.274368 | 0.060* | |
C10 | 0.5211 (3) | 1.0669 (2) | 0.26237 (10) | 0.0463 (5) | |
H10 | 0.543669 | 1.099022 | 0.304670 | 0.056* | |
C11 | 0.6548 (3) | 1.08754 (19) | 0.21738 (10) | 0.0445 (5) | |
C12 | 0.6171 (4) | 1.0396 (2) | 0.15467 (10) | 0.0548 (6) | |
H12 | 0.704989 | 1.053577 | 0.123500 | 0.066* | |
C13 | 0.4509 (4) | 0.9721 (2) | 0.13920 (11) | 0.0566 (6) | |
H13 | 0.425770 | 0.938613 | 0.097271 | 0.068* | |
C14 | 0.1442 (4) | 0.8762 (3) | 0.16488 (15) | 0.0835 (9) | |
H14A | 0.074415 | 0.916950 | 0.127911 | 0.125* | |
H14B | 0.063986 | 0.874317 | 0.200800 | 0.125* | |
H14C | 0.178659 | 0.787515 | 0.153895 | 0.125* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0736 (4) | 0.0280 (3) | 0.0528 (3) | 0.0014 (2) | 0.0099 (3) | 0.0010 (2) |
N4 | 0.0777 (15) | 0.0817 (16) | 0.0569 (13) | −0.0218 (13) | 0.0119 (11) | 0.0108 (11) |
Cl2 | 0.0689 (4) | 0.0492 (3) | 0.0361 (3) | −0.0039 (3) | 0.0110 (2) | 0.0080 (2) |
C15 | 0.0680 (16) | 0.0545 (14) | 0.0426 (13) | −0.0060 (13) | 0.0133 (12) | 0.0068 (10) |
O1 | 0.0657 (9) | 0.0456 (8) | 0.0344 (7) | 0.0013 (7) | 0.0114 (7) | −0.0095 (6) |
O2 | 0.0859 (11) | 0.0394 (8) | 0.0386 (8) | 0.0087 (8) | 0.0157 (7) | −0.0052 (6) |
N1 | 0.0703 (13) | 0.0360 (11) | 0.0695 (13) | −0.0061 (9) | 0.0037 (10) | −0.0035 (9) |
N2 | 0.0716 (13) | 0.0603 (13) | 0.0450 (11) | −0.0094 (10) | 0.0131 (10) | 0.0065 (9) |
C1 | 0.0400 (11) | 0.0353 (11) | 0.0321 (10) | 0.0026 (8) | 0.0031 (8) | −0.0008 (8) |
C2 | 0.0372 (11) | 0.0293 (10) | 0.0368 (10) | 0.0017 (8) | 0.0027 (8) | −0.0004 (8) |
C3 | 0.0379 (10) | 0.0329 (10) | 0.0318 (9) | 0.0032 (8) | 0.0035 (8) | 0.0026 (7) |
C4 | 0.0435 (11) | 0.0339 (10) | 0.0339 (10) | 0.0072 (9) | 0.0050 (8) | −0.0010 (8) |
C5 | 0.0428 (11) | 0.0273 (10) | 0.0368 (10) | 0.0023 (8) | 0.0034 (8) | 0.0021 (8) |
C6 | 0.0410 (11) | 0.0345 (10) | 0.0305 (10) | 0.0008 (8) | 0.0044 (8) | 0.0041 (7) |
C7 | 0.0434 (11) | 0.0367 (12) | 0.0386 (11) | 0.0010 (9) | 0.0042 (9) | −0.0008 (8) |
C8 | 0.0451 (12) | 0.0367 (11) | 0.0383 (11) | 0.0030 (9) | 0.0040 (9) | −0.0015 (9) |
N3 | 0.0581 (12) | 0.0391 (10) | 0.0515 (11) | 0.0047 (9) | −0.0069 (9) | −0.0016 (8) |
C9 | 0.0558 (14) | 0.0520 (13) | 0.0415 (12) | 0.0047 (11) | 0.0058 (10) | 0.0030 (10) |
C10 | 0.0563 (13) | 0.0505 (13) | 0.0323 (11) | 0.0049 (11) | 0.0050 (10) | −0.0034 (9) |
C11 | 0.0571 (14) | 0.0369 (11) | 0.0399 (11) | 0.0054 (10) | 0.0063 (10) | 0.0031 (8) |
C12 | 0.0672 (15) | 0.0619 (15) | 0.0365 (12) | 0.0043 (13) | 0.0122 (11) | −0.0011 (10) |
C13 | 0.0762 (17) | 0.0543 (15) | 0.0378 (12) | 0.0129 (13) | −0.0043 (12) | −0.0101 (10) |
C14 | 0.0752 (19) | 0.075 (2) | 0.096 (2) | −0.0159 (15) | −0.0167 (16) | −0.0124 (16) |
Cl1—C5 | 1.7162 (19) | C5—C6 | 1.351 (2) |
N4—C15 | 1.134 (3) | N3—C9 | 1.336 (3) |
Cl2—C6 | 1.7143 (18) | N3—C13 | 1.339 (3) |
C15—C11 | 1.444 (3) | N3—C14 | 1.481 (3) |
O1—C1 | 1.242 (2) | C9—C10 | 1.363 (3) |
O2—C4 | 1.241 (2) | C9—H9 | 0.9300 |
N1—C7 | 1.133 (2) | C10—C11 | 1.377 (3) |
N2—C8 | 1.143 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.447 (2) | C11—C12 | 1.383 (3) |
C1—C6 | 1.465 (3) | C12—C13 | 1.353 (3) |
C2—C3 | 1.386 (2) | C12—H12 | 0.9300 |
C2—C7 | 1.432 (3) | C13—H13 | 0.9300 |
C3—C8 | 1.433 (3) | C14—H14A | 0.9600 |
C3—C4 | 1.449 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.460 (2) | C14—H14C | 0.9600 |
N4—C15—C11 | 176.6 (3) | C13—N3—C14 | 119.1 (2) |
O1—C1—C2 | 122.55 (17) | N3—C9—C10 | 120.6 (2) |
O1—C1—C6 | 122.88 (17) | N3—C9—H9 | 119.7 |
C2—C1—C6 | 114.56 (16) | C10—C9—H9 | 119.7 |
C3—C2—C7 | 121.31 (17) | C9—C10—C11 | 119.26 (19) |
C3—C2—C1 | 122.60 (17) | C9—C10—H10 | 120.4 |
C7—C2—C1 | 116.06 (16) | C11—C10—H10 | 120.4 |
C2—C3—C8 | 120.81 (17) | C10—C11—C12 | 119.2 (2) |
C2—C3—C4 | 122.03 (16) | C10—C11—C15 | 121.42 (19) |
C8—C3—C4 | 117.16 (16) | C12—C11—C15 | 119.31 (19) |
O2—C4—C3 | 122.46 (17) | C13—C12—C11 | 119.2 (2) |
O2—C4—C5 | 122.66 (18) | C13—C12—H12 | 120.4 |
C3—C4—C5 | 114.86 (16) | C11—C12—H12 | 120.4 |
C6—C5—C4 | 122.82 (17) | N3—C13—C12 | 120.9 (2) |
C6—C5—Cl1 | 121.72 (14) | N3—C13—H13 | 119.6 |
C4—C5—Cl1 | 115.46 (13) | C12—C13—H13 | 119.6 |
C5—C6—C1 | 122.75 (17) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 121.87 (15) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.38 (13) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.6 (2) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 179.0 (2) | H14A—C14—H14C | 109.5 |
C9—N3—C13 | 120.8 (2) | H14B—C14—H14C | 109.5 |
C9—N3—C14 | 120.0 (2) | ||
O1—C1—C2—C3 | −176.90 (18) | Cl1—C5—C6—C1 | 179.65 (14) |
C6—C1—C2—C3 | 4.1 (3) | C4—C5—C6—Cl2 | −179.06 (14) |
O1—C1—C2—C7 | 5.3 (3) | Cl1—C5—C6—Cl2 | 0.4 (2) |
C6—C1—C2—C7 | −173.73 (16) | O1—C1—C6—C5 | 176.16 (19) |
C7—C2—C3—C8 | −0.8 (3) | C2—C1—C6—C5 | −4.8 (3) |
C1—C2—C3—C8 | −178.44 (17) | O1—C1—C6—Cl2 | −4.5 (3) |
C7—C2—C3—C4 | 178.90 (17) | C2—C1—C6—Cl2 | 174.51 (13) |
C1—C2—C3—C4 | 1.2 (3) | C13—N3—C9—C10 | 0.2 (3) |
C2—C3—C4—O2 | 175.71 (18) | C14—N3—C9—C10 | 178.3 (2) |
C8—C3—C4—O2 | −4.6 (3) | N3—C9—C10—C11 | −0.1 (3) |
C2—C3—C4—C5 | −5.7 (3) | C9—C10—C11—C12 | 0.4 (3) |
C8—C3—C4—C5 | 173.93 (16) | C9—C10—C11—C15 | −177.2 (2) |
O2—C4—C5—C6 | −176.39 (19) | C10—C11—C12—C13 | −0.8 (3) |
C3—C4—C5—C6 | 5.1 (3) | C15—C11—C12—C13 | 176.9 (2) |
O2—C4—C5—Cl1 | 4.1 (3) | C9—N3—C13—C12 | −0.6 (3) |
C3—C4—C5—Cl1 | −174.41 (13) | C14—N3—C13—C12 | −178.7 (2) |
C4—C5—C6—C1 | 0.2 (3) | C11—C12—C13—N3 | 0.9 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.618 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8687 (6) Å | Cell parameters from 1546 reflections |
b = 10.105 (2) Å | θ = 2.0–23.5° |
c = 20.5426 (19) Å | µ = 0.47 mm−1 |
β = 94.681 (7)° | T = 293 K |
V = 1421.1 (4) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1558 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.364 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −8→8 |
Tmin = 0.360, Tmax = 0.450 | k = −8→8 |
7420 measured reflections | l = −23→23 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1558 reflections | Δρmax = 0.28 e Å−3 |
209 parameters | Δρmin = −0.25 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 | ||
Cl1 | 0.20423 (15) | 0.11377 (18) | −0.00716 (5) | 0.0440 (6) | |
N4 | 0.9885 (5) | 1.2027 (5) | 0.24780 (16) | 0.0539 (18) | |
Cl2 | 0.11620 (14) | 0.28082 (16) | 0.11688 (5) | 0.0418 (5) | |
C15 | 0.8390 (7) | 1.1550 (6) | 0.23521 (19) | 0.0423 (19) | |
O1 | 0.1359 (4) | 0.5662 (4) | 0.09452 (13) | 0.0407 (13) | |
O2 | 0.2899 (4) | 0.2777 (4) | −0.11775 (13) | 0.0453 (14) | |
N1 | 0.2994 (7) | 0.8128 (7) | −0.00668 (18) | 0.049 (2) | |
N2 | 0.4167 (5) | 0.5980 (5) | −0.16687 (18) | 0.0484 (19) | |
C1 | 0.1801 (6) | 0.4993 (7) | 0.04724 (18) | 0.0309 (16) | |
C2 | 0.2475 (6) | 0.5612 (7) | −0.01107 (18) | 0.0315 (17) | |
C3 | 0.2877 (6) | 0.4856 (7) | −0.06535 (18) | 0.0307 (16) | |
C4 | 0.2638 (6) | 0.3461 (7) | −0.0688 (2) | 0.0332 (16) | |
C5 | 0.2125 (5) | 0.2846 (7) | −0.00726 (18) | 0.0284 (15) | |
C6 | 0.1743 (6) | 0.3566 (7) | 0.04548 (18) | 0.0310 (16) | |
C7 | 0.2762 (7) | 0.6997 (9) | −0.00885 (18) | 0.031 (2) | |
C8 | 0.3590 (5) | 0.5495 (6) | −0.1216 (2) | 0.0329 (19) | |
N3 | 0.3207 (4) | 0.9538 (5) | 0.18291 (17) | 0.0438 (17) | |
C9 | 0.3545 (6) | 1.0012 (7) | 0.2442 (2) | 0.042 (2) | |
H9 | 0.261838 | 0.988349 | 0.274115 | 0.051* | |
C10 | 0.5202 (5) | 1.0669 (6) | 0.26252 (18) | 0.0365 (18) | |
H10 | 0.543702 | 1.097098 | 0.305199 | 0.044* | |
C11 | 0.6557 (5) | 1.0892 (6) | 0.21732 (19) | 0.038 (2) | |
C12 | 0.6175 (6) | 1.0409 (7) | 0.1545 (2) | 0.044 (2) | |
H12 | 0.705698 | 1.055548 | 0.123244 | 0.053* | |
C13 | 0.4501 (6) | 0.9718 (6) | 0.1387 (2) | 0.048 (2) | |
H13 | 0.425909 | 0.937043 | 0.096883 | 0.058* | |
C14 | 0.1423 (6) | 0.8783 (8) | 0.1642 (2) | 0.069 (3) | |
H14A | 0.064144 | 0.872863 | 0.200797 | 0.103* | |
H14B | 0.176730 | 0.790699 | 0.151119 | 0.103* | |
H14C | 0.069459 | 0.921818 | 0.128550 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0577 (7) | 0.033 (2) | 0.0426 (8) | 0.0008 (8) | 0.0091 (5) | 0.0010 (6) |
N4 | 0.060 (2) | 0.057 (7) | 0.046 (3) | −0.020 (3) | 0.0120 (19) | 0.004 (2) |
Cl2 | 0.0536 (7) | 0.0411 (18) | 0.0315 (7) | −0.0026 (7) | 0.0089 (5) | 0.0066 (6) |
C15 | 0.055 (3) | 0.045 (7) | 0.028 (3) | −0.003 (3) | 0.010 (2) | 0.004 (2) |
O1 | 0.0512 (16) | 0.042 (5) | 0.0302 (19) | 0.004 (2) | 0.0090 (13) | −0.0083 (16) |
O2 | 0.0666 (19) | 0.037 (5) | 0.034 (2) | 0.006 (2) | 0.0132 (14) | −0.0069 (16) |
N1 | 0.061 (3) | 0.036 (7) | 0.051 (3) | −0.004 (4) | 0.0042 (18) | 0.000 (3) |
N2 | 0.055 (2) | 0.047 (7) | 0.044 (3) | −0.012 (3) | 0.0123 (18) | 0.003 (2) |
C1 | 0.030 (2) | 0.036 (6) | 0.026 (3) | 0.001 (3) | 0.0032 (17) | −0.003 (2) |
C2 | 0.027 (2) | 0.036 (6) | 0.031 (3) | 0.001 (3) | 0.0008 (18) | −0.002 (2) |
C3 | 0.031 (2) | 0.033 (6) | 0.030 (3) | 0.005 (3) | 0.0066 (17) | 0.002 (2) |
C4 | 0.034 (2) | 0.036 (6) | 0.030 (3) | 0.014 (3) | 0.0046 (18) | 0.001 (2) |
C5 | 0.031 (2) | 0.017 (5) | 0.037 (3) | −0.001 (3) | 0.0029 (18) | 0.001 (2) |
C6 | 0.032 (2) | 0.039 (5) | 0.022 (2) | 0.004 (3) | 0.0045 (17) | 0.002 (2) |
C7 | 0.031 (2) | 0.037 (7) | 0.027 (3) | 0.003 (5) | 0.0051 (17) | 0.002 (3) |
C8 | 0.034 (2) | 0.030 (7) | 0.035 (3) | −0.005 (3) | 0.0018 (19) | −0.005 (2) |
N3 | 0.043 (2) | 0.046 (6) | 0.040 (2) | 0.002 (2) | −0.0066 (17) | −0.004 (2) |
C9 | 0.044 (2) | 0.046 (7) | 0.037 (3) | 0.007 (3) | 0.0051 (19) | 0.000 (2) |
C10 | 0.040 (2) | 0.044 (7) | 0.025 (3) | 0.006 (3) | 0.0011 (18) | 0.000 (2) |
C11 | 0.042 (2) | 0.037 (7) | 0.034 (3) | 0.001 (3) | 0.0047 (19) | 0.007 (2) |
C12 | 0.052 (2) | 0.049 (7) | 0.032 (3) | −0.003 (3) | 0.009 (2) | −0.002 (2) |
C13 | 0.062 (3) | 0.050 (7) | 0.033 (3) | 0.009 (3) | 0.002 (2) | −0.002 (2) |
C14 | 0.071 (3) | 0.049 (10) | 0.084 (4) | −0.016 (4) | −0.008 (3) | −0.012 (3) |
Cl1—C5 | 1.727 (7) | C5—C6 | 1.349 (6) |
N4—C15 | 1.145 (5) | N3—C13 | 1.334 (5) |
Cl2—C6 | 1.730 (5) | N3—C9 | 1.349 (5) |
C15—C11 | 1.444 (6) | N3—C14 | 1.468 (6) |
O1—C1 | 1.241 (5) | C9—C10 | 1.345 (6) |
O2—C4 | 1.246 (6) | C9—H9 | 0.9300 |
N1—C7 | 1.155 (8) | C10—C11 | 1.386 (5) |
N2—C8 | 1.150 (5) | C10—H10 | 0.9300 |
C1—C6 | 1.443 (8) | C11—C12 | 1.385 (6) |
C1—C2 | 1.460 (6) | C12—C13 | 1.361 (6) |
C2—C3 | 1.398 (7) | C12—H12 | 0.9300 |
C2—C7 | 1.413 (8) | C13—H13 | 0.9300 |
C3—C4 | 1.420 (8) | C14—H14A | 0.9600 |
C3—C8 | 1.444 (6) | C14—H14B | 0.9600 |
C4—C5 | 1.476 (6) | C14—H14C | 0.9600 |
N4—C15—C11 | 176.8 (6) | C9—N3—C14 | 120.3 (4) |
O1—C1—C6 | 123.8 (4) | C10—C9—N3 | 121.0 (4) |
O1—C1—C2 | 121.5 (6) | C10—C9—H9 | 119.5 |
C6—C1—C2 | 114.7 (4) | N3—C9—H9 | 119.5 |
C3—C2—C7 | 122.0 (5) | C9—C10—C11 | 119.5 (4) |
C3—C2—C1 | 121.1 (6) | C9—C10—H10 | 120.3 |
C7—C2—C1 | 116.8 (4) | C11—C10—H10 | 120.3 |
C2—C3—C4 | 123.5 (5) | C12—C11—C10 | 118.7 (4) |
C2—C3—C8 | 119.7 (6) | C12—C11—C15 | 119.7 (4) |
C4—C3—C8 | 116.7 (4) | C10—C11—C15 | 121.6 (4) |
O2—C4—C3 | 124.5 (5) | C13—C12—C11 | 119.7 (4) |
O2—C4—C5 | 121.2 (6) | C13—C12—H12 | 120.1 |
C3—C4—C5 | 114.2 (4) | C11—C12—H12 | 120.1 |
C6—C5—C4 | 122.4 (6) | N3—C13—C12 | 120.3 (4) |
C6—C5—Cl1 | 122.0 (4) | N3—C13—H13 | 119.9 |
C4—C5—Cl1 | 115.6 (4) | C12—C13—H13 | 119.9 |
C5—C6—C1 | 123.6 (5) | N3—C14—H14A | 109.5 |
C5—C6—Cl2 | 121.0 (5) | N3—C14—H14B | 109.5 |
C1—C6—Cl2 | 115.4 (3) | H14A—C14—H14B | 109.5 |
N1—C7—C2 | 179.6 (5) | N3—C14—H14C | 109.5 |
N2—C8—C3 | 178.6 (6) | H14A—C14—H14C | 109.5 |
C13—N3—C9 | 120.9 (4) | H14B—C14—H14C | 109.5 |
C13—N3—C14 | 118.8 (4) | ||
O1—C1—C2—C3 | −176.8 (4) | Cl1—C5—C6—C1 | 179.9 (3) |
C6—C1—C2—C3 | 4.6 (6) | C4—C5—C6—Cl2 | −179.6 (3) |
O1—C1—C2—C7 | 5.4 (6) | Cl1—C5—C6—Cl2 | 0.5 (5) |
C6—C1—C2—C7 | −173.3 (4) | O1—C1—C6—C5 | 176.4 (3) |
C7—C2—C3—C4 | 178.9 (4) | C2—C1—C6—C5 | −5.0 (6) |
C1—C2—C3—C4 | 1.2 (7) | O1—C1—C6—Cl2 | −4.2 (6) |
C7—C2—C3—C8 | −0.7 (6) | C2—C1—C6—Cl2 | 174.4 (2) |
C1—C2—C3—C8 | −178.4 (3) | C13—N3—C9—C10 | −0.6 (8) |
C2—C3—C4—O2 | 176.4 (4) | C14—N3—C9—C10 | 177.8 (6) |
C8—C3—C4—O2 | −4.0 (7) | N3—C9—C10—C11 | 1.8 (8) |
C2—C3—C4—C5 | −6.2 (6) | C9—C10—C11—C12 | −1.1 (8) |
C8—C3—C4—C5 | 173.3 (3) | C9—C10—C11—C15 | −177.7 (6) |
O2—C4—C5—C6 | −176.8 (4) | C10—C11—C12—C13 | −0.7 (8) |
C3—C4—C5—C6 | 5.8 (6) | C15—C11—C12—C13 | 176.0 (6) |
O2—C4—C5—Cl1 | 3.2 (5) | C9—N3—C13—C12 | −1.2 (8) |
C3—C4—C5—Cl1 | −174.3 (3) | C14—N3—C13—C12 | −179.7 (6) |
C4—C5—C6—C1 | −0.2 (6) | C11—C12—C13—N3 | 1.9 (8) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.632 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8312 (4) Å | Cell parameters from 1555 reflections |
b = 10.0839 (16) Å | θ = 2.0–22.5° |
c = 20.5232 (15) Å | µ = 0.48 mm−1 |
β = 94.635 (6)° | T = 293 K |
V = 1409.1 (3) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1542 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 922 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.365 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −8→8 |
Tmin = 0.361, Tmax = 0.450 | k = −8→8 |
7278 measured reflections | l = −23→23 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1542 reflections | Δρmax = 0.21 e Å−3 |
208 parameters | Δρmin = −0.24 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 | ||
Cl1 | 0.20496 (16) | 0.11322 (18) | −0.00723 (5) | 0.0405 (5) | |
Cl2 | 0.11722 (15) | 0.28077 (17) | 0.11705 (5) | 0.0392 (5) | |
O1 | 0.1366 (4) | 0.5671 (4) | 0.09439 (13) | 0.0362 (13) | |
O2 | 0.2907 (4) | 0.2775 (4) | −0.11802 (13) | 0.0425 (15) | |
N1 | 0.2986 (7) | 0.8138 (7) | −0.00673 (19) | 0.047 (2) | |
N2 | 0.4175 (5) | 0.5977 (6) | −0.16718 (19) | 0.0455 (19) | |
N3 | 0.3199 (5) | 0.9541 (5) | 0.18265 (18) | 0.0376 (16) | |
N4 | 0.9898 (6) | 1.2036 (6) | 0.24820 (17) | 0.058 (2) | |
C1 | 0.1809 (6) | 0.4994 (7) | 0.0471 (2) | 0.0287 (16) | |
C2 | 0.2483 (6) | 0.5615 (7) | −0.01178 (19) | 0.0258 (16) | |
C3 | 0.2895 (6) | 0.4861 (7) | −0.0655 (2) | 0.0268 (16) | |
C4 | 0.2639 (6) | 0.3450 (7) | −0.0686 (2) | 0.0311 (16) | |
C5 | 0.2130 (6) | 0.2834 (7) | −0.00737 (19) | 0.0259 (15) | |
C6 | 0.1743 (6) | 0.3548 (7) | 0.04544 (19) | 0.0281 (15) | |
C7 | 0.2761 (7) | 0.7011 (9) | −0.0093 (2) | 0.0282 (19) | |
C8 | 0.3596 (5) | 0.5494 (6) | −0.1218 (2) | 0.0277 (18) | |
C9 | 0.3539 (6) | 1.0006 (6) | 0.2441 (2) | 0.036 (2) | |
H9 | 0.261183 | 0.986666 | 0.274177 | 0.043* | |
C10 | 0.5202 (6) | 1.0669 (6) | 0.2625 (2) | 0.0365 (19) | |
H10 | 0.543428 | 1.096976 | 0.305312 | 0.044* | |
C11 | 0.6562 (6) | 1.0901 (6) | 0.2176 (2) | 0.037 (2) | |
C12 | 0.6193 (7) | 1.0417 (7) | 0.1546 (2) | 0.043 (2) | |
H12 | 0.708829 | 1.055997 | 0.123484 | 0.052* | |
C13 | 0.4504 (6) | 0.9729 (7) | 0.1387 (2) | 0.046 (2) | |
H13 | 0.426007 | 0.938711 | 0.096706 | 0.055* | |
C14 | 0.1404 (7) | 0.8770 (7) | 0.1641 (3) | 0.066 (3) | |
H14A | 0.061370 | 0.871993 | 0.200605 | 0.099* | |
H14B | 0.067107 | 0.919641 | 0.128075 | 0.099* | |
H14C | 0.175891 | 0.789080 | 0.151421 | 0.099* | |
C15 | 0.8396 (7) | 1.1542 (7) | 0.2353 (2) | 0.040 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0550 (7) | 0.026 (2) | 0.0412 (9) | 0.0006 (9) | 0.0087 (5) | 0.0010 (6) |
Cl2 | 0.0526 (7) | 0.0359 (19) | 0.0301 (8) | −0.0039 (8) | 0.0104 (5) | 0.0073 (6) |
O1 | 0.0502 (17) | 0.031 (5) | 0.028 (2) | 0.002 (2) | 0.0078 (14) | −0.0083 (16) |
O2 | 0.063 (2) | 0.037 (5) | 0.028 (2) | 0.009 (2) | 0.0111 (15) | −0.0071 (17) |
N1 | 0.058 (3) | 0.036 (7) | 0.048 (3) | −0.002 (4) | 0.0051 (19) | −0.006 (3) |
N2 | 0.051 (2) | 0.047 (7) | 0.041 (3) | −0.004 (3) | 0.0134 (19) | 0.001 (2) |
N3 | 0.046 (2) | 0.029 (6) | 0.037 (3) | 0.004 (2) | −0.0024 (18) | 0.000 (2) |
N4 | 0.059 (3) | 0.075 (7) | 0.040 (3) | −0.018 (3) | 0.009 (2) | 0.006 (2) |
C1 | 0.029 (2) | 0.033 (6) | 0.023 (3) | 0.005 (3) | −0.0018 (19) | 0.001 (2) |
C2 | 0.024 (2) | 0.024 (6) | 0.029 (3) | 0.004 (3) | 0.0039 (19) | 0.002 (2) |
C3 | 0.027 (2) | 0.027 (6) | 0.028 (3) | 0.004 (3) | 0.0095 (19) | 0.000 (2) |
C4 | 0.032 (2) | 0.032 (6) | 0.029 (3) | 0.009 (3) | 0.004 (2) | 0.004 (2) |
C5 | 0.035 (2) | 0.012 (6) | 0.031 (3) | −0.002 (3) | 0.0043 (19) | 0.002 (2) |
C6 | 0.028 (2) | 0.031 (5) | 0.026 (3) | 0.000 (3) | 0.0042 (19) | 0.003 (2) |
C7 | 0.029 (3) | 0.027 (7) | 0.029 (3) | 0.006 (5) | 0.0052 (19) | −0.001 (3) |
C8 | 0.031 (2) | 0.018 (7) | 0.035 (3) | −0.002 (3) | 0.006 (2) | −0.004 (2) |
C9 | 0.045 (3) | 0.029 (7) | 0.035 (3) | 0.009 (3) | 0.012 (2) | 0.000 (2) |
C10 | 0.038 (2) | 0.046 (7) | 0.025 (3) | 0.003 (3) | 0.002 (2) | 0.002 (2) |
C11 | 0.044 (2) | 0.039 (7) | 0.029 (3) | 0.007 (3) | 0.006 (2) | 0.006 (2) |
C12 | 0.052 (3) | 0.045 (8) | 0.034 (3) | −0.003 (3) | 0.012 (2) | −0.002 (3) |
C13 | 0.060 (3) | 0.048 (7) | 0.028 (3) | 0.011 (3) | 0.003 (2) | −0.005 (2) |
C14 | 0.071 (3) | 0.043 (10) | 0.083 (5) | −0.014 (4) | −0.005 (3) | −0.010 (3) |
C15 | 0.054 (3) | 0.041 (7) | 0.027 (3) | −0.002 (3) | 0.009 (2) | 0.005 (2) |
Cl1—C5 | 1.717 (7) | C3—C8 | 1.437 (6) |
Cl2—C6 | 1.721 (5) | C4—C5 | 1.468 (7) |
O1—C1 | 1.244 (6) | C5—C6 | 1.345 (7) |
O2—C4 | 1.248 (6) | C9—C10 | 1.346 (6) |
N1—C7 | 1.147 (8) | C9—H9 | 0.9300 |
N2—C8 | 1.149 (5) | C10—C11 | 1.381 (5) |
N3—C13 | 1.333 (5) | C10—H10 | 0.9300 |
N3—C9 | 1.348 (5) | C11—C12 | 1.386 (6) |
N3—C14 | 1.476 (6) | C11—C15 | 1.430 (7) |
N4—C15 | 1.152 (6) | C12—C13 | 1.364 (7) |
C1—C6 | 1.460 (8) | C12—H12 | 0.9300 |
C1—C2 | 1.467 (7) | C13—H13 | 0.9300 |
C2—C3 | 1.386 (7) | C14—H14A | 0.9600 |
C2—C7 | 1.421 (8) | C14—H14B | 0.9600 |
C3—C4 | 1.434 (8) | C14—H14C | 0.9600 |
C13—N3—C9 | 120.7 (4) | C10—C9—N3 | 120.9 (4) |
C13—N3—C14 | 119.2 (4) | C10—C9—H9 | 119.5 |
C9—N3—C14 | 120.1 (4) | N3—C9—H9 | 119.5 |
O1—C1—C6 | 123.9 (5) | C9—C10—C11 | 119.6 (4) |
O1—C1—C2 | 121.4 (6) | C9—C10—H10 | 120.2 |
C6—C1—C2 | 114.7 (4) | C11—C10—H10 | 120.2 |
C3—C2—C7 | 122.5 (5) | C10—C11—C12 | 118.8 (5) |
C3—C2—C1 | 121.2 (6) | C10—C11—C15 | 122.0 (4) |
C7—C2—C1 | 116.3 (4) | C12—C11—C15 | 119.0 (4) |
C2—C3—C4 | 123.2 (5) | C13—C12—C11 | 119.3 (4) |
C2—C3—C8 | 119.9 (6) | C13—C12—H12 | 120.4 |
C4—C3—C8 | 116.9 (4) | C11—C12—H12 | 120.4 |
O2—C4—C3 | 123.5 (5) | N3—C13—C12 | 120.7 (4) |
O2—C4—C5 | 121.7 (6) | N3—C13—H13 | 119.7 |
C3—C4—C5 | 114.7 (4) | C12—C13—H13 | 119.7 |
C6—C5—C4 | 122.6 (6) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.7 (4) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 115.8 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.1 (5) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 121.9 (5) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 115.0 (3) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 179.5 (5) | N4—C15—C11 | 178.1 (6) |
N2—C8—C3 | 178.6 (6) | ||
O1—C1—C2—C3 | −177.2 (4) | Cl1—C5—C6—C1 | 179.7 (3) |
C6—C1—C2—C3 | 3.8 (6) | C4—C5—C6—Cl2 | −179.4 (3) |
O1—C1—C2—C7 | 5.3 (6) | Cl1—C5—C6—Cl2 | 0.9 (5) |
C6—C1—C2—C7 | −173.7 (4) | O1—C1—C6—C5 | 176.5 (4) |
C7—C2—C3—C4 | 179.5 (4) | C2—C1—C6—C5 | −4.6 (6) |
C1—C2—C3—C4 | 2.1 (7) | O1—C1—C6—Cl2 | −4.6 (6) |
C7—C2—C3—C8 | −1.2 (7) | C2—C1—C6—Cl2 | 174.3 (3) |
C1—C2—C3—C8 | −178.5 (4) | C13—N3—C9—C10 | −0.1 (8) |
C2—C3—C4—O2 | 176.1 (4) | C14—N3—C9—C10 | 177.6 (6) |
C8—C3—C4—O2 | −3.3 (7) | N3—C9—C10—C11 | 1.3 (8) |
C2—C3—C4—C5 | −7.1 (7) | C9—C10—C11—C12 | −1.3 (8) |
C8—C3—C4—C5 | 173.6 (3) | C9—C10—C11—C15 | −176.8 (6) |
O2—C4—C5—C6 | −176.7 (4) | C10—C11—C12—C13 | 0.1 (8) |
C3—C4—C5—C6 | 6.3 (6) | C15—C11—C12—C13 | 175.7 (6) |
O2—C4—C5—Cl1 | 3.1 (6) | C9—N3—C13—C12 | −1.2 (8) |
C3—C4—C5—Cl1 | −173.9 (3) | C14—N3—C13—C12 | −178.9 (6) |
C4—C5—C6—C1 | −0.6 (7) | C11—C12—C13—N3 | 1.2 (9) |
C15H7Cl2N4O2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.664 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7445 (3) Å | Cell parameters from 1864 reflections |
b = 10.0486 (12) Å | θ = 2.0–25.4° |
c = 20.4539 (11) Å | µ = 0.49 mm−1 |
β = 94.589 (4)° | T = 293 K |
V = 1381.77 (19) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1500 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.368 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −8→8 |
Tmin = 0.364, Tmax = 0.450 | k = −8→8 |
7093 measured reflections | l = −23→23 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2564P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1500 reflections | Δρmax = 0.29 e Å−3 |
209 parameters | Δρmin = −0.22 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 | ||
Cl1 | 0.20679 (15) | 0.11222 (17) | −0.00714 (5) | 0.0355 (5) | |
Cl2 | 0.11879 (15) | 0.28046 (16) | 0.11746 (5) | 0.0345 (5) | |
O1 | 0.1374 (4) | 0.5672 (4) | 0.09451 (13) | 0.0308 (12) | |
O2 | 0.2924 (4) | 0.2769 (4) | −0.11835 (13) | 0.0350 (13) | |
N1 | 0.2986 (7) | 0.8156 (7) | −0.00721 (18) | 0.0415 (18) | |
N2 | 0.4176 (5) | 0.5979 (5) | −0.16858 (18) | 0.0379 (17) | |
N3 | 0.3175 (5) | 0.9551 (5) | 0.18243 (17) | 0.0329 (15) | |
N4 | 0.9944 (6) | 1.2060 (6) | 0.24859 (17) | 0.0495 (18) | |
C1 | 0.1831 (5) | 0.4984 (7) | 0.04660 (19) | 0.0234 (15) | |
C2 | 0.2485 (5) | 0.5624 (7) | −0.01190 (19) | 0.0246 (15) | |
C3 | 0.2900 (5) | 0.4855 (7) | −0.06599 (18) | 0.0226 (15) | |
C4 | 0.2666 (6) | 0.3443 (7) | −0.0684 (2) | 0.0274 (16) | |
C5 | 0.2150 (5) | 0.2822 (7) | −0.00754 (18) | 0.0216 (14) | |
C6 | 0.1751 (6) | 0.3538 (6) | 0.04551 (19) | 0.0231 (14) | |
C7 | 0.2761 (7) | 0.7021 (9) | −0.00957 (18) | 0.0231 (17) | |
C8 | 0.3599 (5) | 0.5504 (6) | −0.1228 (2) | 0.0241 (17) | |
C9 | 0.3509 (6) | 1.0004 (6) | 0.2437 (2) | 0.0332 (19) | |
H9 | 0.256993 | 0.985238 | 0.273762 | 0.040* | |
C10 | 0.5195 (5) | 1.0682 (6) | 0.26280 (19) | 0.0315 (18) | |
H10 | 0.541921 | 1.098961 | 0.305634 | 0.038* | |
C11 | 0.6574 (6) | 1.0908 (6) | 0.2177 (2) | 0.0327 (18) | |
C12 | 0.6206 (6) | 1.0421 (7) | 0.1544 (2) | 0.0383 (19) | |
H12 | 0.712226 | 1.055871 | 0.123472 | 0.046* | |
C13 | 0.4507 (6) | 0.9746 (6) | 0.1381 (2) | 0.0390 (18) | |
H13 | 0.425903 | 0.941340 | 0.095820 | 0.047* | |
C14 | 0.1374 (6) | 0.8761 (8) | 0.1629 (2) | 0.057 (2) | |
H14A | 0.175765 | 0.789216 | 0.148995 | 0.086* | |
H14B | 0.061790 | 0.919936 | 0.127369 | 0.086* | |
H14C | 0.057754 | 0.867902 | 0.199505 | 0.086* | |
C15 | 0.8418 (7) | 1.1565 (6) | 0.23604 (19) | 0.0362 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0473 (6) | 0.0218 (18) | 0.0378 (9) | 0.0000 (8) | 0.0068 (5) | 0.0008 (5) |
Cl2 | 0.0470 (6) | 0.0314 (17) | 0.0262 (7) | −0.0020 (7) | 0.0090 (5) | 0.0065 (5) |
O1 | 0.0421 (15) | 0.023 (4) | 0.0280 (19) | 0.0008 (19) | 0.0081 (13) | −0.0067 (15) |
O2 | 0.0546 (18) | 0.023 (5) | 0.029 (2) | 0.006 (2) | 0.0084 (13) | −0.0054 (15) |
N1 | 0.047 (2) | 0.028 (6) | 0.049 (3) | −0.008 (4) | 0.0061 (17) | −0.002 (3) |
N2 | 0.046 (2) | 0.031 (6) | 0.038 (3) | −0.003 (3) | 0.0111 (17) | 0.000 (2) |
N3 | 0.0379 (19) | 0.025 (5) | 0.034 (2) | 0.003 (2) | −0.0045 (16) | −0.0011 (18) |
N4 | 0.053 (2) | 0.057 (7) | 0.039 (3) | −0.013 (3) | 0.0094 (19) | 0.004 (2) |
C1 | 0.022 (2) | 0.025 (5) | 0.024 (3) | 0.000 (3) | −0.0014 (17) | 0.0014 (19) |
C2 | 0.022 (2) | 0.024 (5) | 0.028 (3) | 0.004 (3) | 0.0035 (17) | 0.002 (2) |
C3 | 0.022 (2) | 0.021 (5) | 0.025 (3) | 0.006 (3) | 0.0035 (16) | 0.000 (2) |
C4 | 0.027 (2) | 0.027 (5) | 0.029 (3) | 0.004 (3) | 0.0053 (18) | 0.001 (2) |
C5 | 0.0246 (19) | 0.007 (5) | 0.033 (3) | −0.003 (3) | 0.0038 (17) | 0.002 (2) |
C6 | 0.025 (2) | 0.020 (5) | 0.024 (3) | 0.003 (3) | 0.0048 (17) | 0.0024 (19) |
C7 | 0.024 (2) | 0.020 (6) | 0.025 (3) | 0.001 (4) | 0.0018 (16) | 0.001 (2) |
C8 | 0.029 (2) | 0.016 (6) | 0.028 (3) | 0.000 (3) | 0.0043 (18) | −0.002 (2) |
C9 | 0.040 (2) | 0.030 (7) | 0.031 (3) | 0.009 (3) | 0.0056 (19) | 0.002 (2) |
C10 | 0.034 (2) | 0.039 (7) | 0.021 (3) | 0.002 (3) | 0.0014 (17) | 0.000 (2) |
C11 | 0.035 (2) | 0.035 (7) | 0.027 (3) | 0.003 (3) | 0.0032 (18) | 0.005 (2) |
C12 | 0.042 (2) | 0.044 (7) | 0.030 (3) | 0.003 (3) | 0.009 (2) | −0.002 (2) |
C13 | 0.051 (3) | 0.039 (7) | 0.026 (3) | 0.009 (3) | −0.002 (2) | −0.002 (2) |
C14 | 0.052 (3) | 0.044 (9) | 0.073 (4) | −0.008 (3) | −0.013 (2) | −0.005 (3) |
C15 | 0.051 (3) | 0.032 (7) | 0.027 (3) | −0.007 (3) | 0.011 (2) | 0.006 (2) |
Cl1—C5 | 1.709 (6) | C3—C8 | 1.444 (6) |
Cl2—C6 | 1.716 (5) | C4—C5 | 1.459 (6) |
O1—C1 | 1.257 (5) | C5—C6 | 1.347 (7) |
O2—C4 | 1.250 (6) | C9—C10 | 1.356 (6) |
N1—C7 | 1.151 (8) | C9—H9 | 0.9300 |
N2—C8 | 1.147 (5) | C10—C11 | 1.379 (5) |
N3—C9 | 1.335 (5) | C10—H10 | 0.9300 |
N3—C13 | 1.341 (5) | C11—C12 | 1.388 (6) |
N3—C14 | 1.479 (6) | C11—C15 | 1.431 (7) |
N4—C15 | 1.153 (5) | C12—C13 | 1.350 (6) |
C1—C6 | 1.454 (8) | C12—H12 | 0.9300 |
C1—C2 | 1.458 (6) | C13—H13 | 0.9300 |
C2—C3 | 1.396 (7) | C14—H14A | 0.9600 |
C2—C7 | 1.417 (8) | C14—H14B | 0.9600 |
C3—C4 | 1.428 (8) | C14—H14C | 0.9600 |
C9—N3—C13 | 120.8 (4) | N3—C9—C10 | 121.1 (4) |
C9—N3—C14 | 120.7 (4) | N3—C9—H9 | 119.5 |
C13—N3—C14 | 118.4 (4) | C10—C9—H9 | 119.5 |
O1—C1—C6 | 123.4 (4) | C9—C10—C11 | 119.0 (4) |
O1—C1—C2 | 120.4 (6) | C9—C10—H10 | 120.5 |
C6—C1—C2 | 116.2 (4) | C11—C10—H10 | 120.5 |
C3—C2—C7 | 122.8 (4) | C10—C11—C12 | 119.1 (4) |
C3—C2—C1 | 120.0 (6) | C10—C11—C15 | 121.3 (4) |
C7—C2—C1 | 117.2 (4) | C12—C11—C15 | 119.6 (4) |
C2—C3—C4 | 123.3 (4) | C13—C12—C11 | 119.5 (4) |
C2—C3—C8 | 119.1 (6) | C13—C12—H12 | 120.2 |
C4—C3—C8 | 117.6 (4) | C11—C12—H12 | 120.2 |
O2—C4—C3 | 123.0 (4) | N3—C13—C12 | 120.5 (4) |
O2—C4—C5 | 121.5 (6) | N3—C13—H13 | 119.7 |
C3—C4—C5 | 115.4 (4) | C12—C13—H13 | 119.7 |
C6—C5—C4 | 122.3 (6) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.4 (4) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 116.2 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 122.5 (4) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 122.2 (5) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 115.3 (3) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 179.5 (4) | N4—C15—C11 | 176.8 (5) |
N2—C8—C3 | 177.7 (6) | ||
O1—C1—C2—C3 | −177.0 (4) | Cl1—C5—C6—C1 | 179.4 (3) |
C6—C1—C2—C3 | 3.1 (5) | C4—C5—C6—Cl2 | −178.8 (3) |
O1—C1—C2—C7 | 5.9 (5) | Cl1—C5—C6—Cl2 | 1.4 (5) |
C6—C1—C2—C7 | −174.0 (4) | O1—C1—C6—C5 | 176.6 (3) |
C7—C2—C3—C4 | 178.7 (4) | C2—C1—C6—C5 | −3.5 (6) |
C1—C2—C3—C4 | 1.8 (6) | O1—C1—C6—Cl2 | −5.3 (5) |
C7—C2—C3—C8 | −1.3 (6) | C2—C1—C6—Cl2 | 174.5 (3) |
C1—C2—C3—C8 | −178.3 (3) | C13—N3—C9—C10 | 0.5 (8) |
C2—C3—C4—O2 | 175.6 (4) | C14—N3—C9—C10 | 177.2 (6) |
C8—C3—C4—O2 | −4.4 (6) | N3—C9—C10—C11 | 0.3 (8) |
C2—C3—C4—C5 | −6.0 (6) | C9—C10—C11—C12 | −0.8 (8) |
C8—C3—C4—C5 | 174.1 (3) | C9—C10—C11—C15 | −177.2 (6) |
O2—C4—C5—C6 | −176.0 (4) | C10—C11—C12—C13 | 0.4 (8) |
C3—C4—C5—C6 | 5.5 (6) | C15—C11—C12—C13 | 176.9 (6) |
O2—C4—C5—Cl1 | 3.8 (5) | C9—N3—C13—C12 | −0.9 (8) |
C3—C4—C5—Cl1 | −174.7 (3) | C14—N3—C13—C12 | −177.7 (6) |
C4—C5—C6—C1 | −0.9 (6) | C11—C12—C13—N3 | 0.4 (8) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.710 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6277 (4) Å | Cell parameters from 1833 reflections |
b = 10.0050 (17) Å | θ = 2.0–26.4° |
c = 20.3418 (16) Å | µ = 0.50 mm−1 |
β = 94.609 (5)° | T = 293 K |
V = 1344.5 (3) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1457 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 980 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.369 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.364, Tmax = 0.450 | k = −8→8 |
6881 measured reflections | l = −23→23 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0578P)2 + 1.4732P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.002 |
1457 reflections | Δρmax = 0.27 e Å−3 |
209 parameters | Δρmin = −0.31 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 | ||
Cl1 | 0.20949 (18) | 0.11052 (19) | −0.00704 (6) | 0.0330 (6) | |
Cl2 | 0.12077 (17) | 0.28017 (18) | 0.11832 (5) | 0.0326 (6) | |
O1 | 0.1399 (4) | 0.5688 (4) | 0.09474 (15) | 0.0304 (14) | |
O2 | 0.2954 (5) | 0.2756 (5) | −0.11898 (15) | 0.0346 (15) | |
N1 | 0.2959 (7) | 0.8166 (8) | −0.0078 (2) | 0.0377 (19) | |
N2 | 0.4178 (6) | 0.5986 (6) | −0.1704 (2) | 0.0375 (19) | |
N3 | 0.3154 (5) | 0.9561 (6) | 0.18186 (19) | 0.0324 (16) | |
N4 | 1.0016 (7) | 1.2095 (7) | 0.2502 (2) | 0.048 (2) | |
C1 | 0.1855 (6) | 0.4984 (8) | 0.0472 (2) | 0.0236 (16) | |
C2 | 0.2496 (6) | 0.5617 (8) | −0.0127 (2) | 0.0248 (16) | |
C3 | 0.2922 (7) | 0.4862 (8) | −0.0670 (2) | 0.0226 (16) | |
C4 | 0.2693 (7) | 0.3445 (8) | −0.0692 (2) | 0.0252 (16) | |
C5 | 0.2185 (6) | 0.2808 (7) | −0.0074 (2) | 0.0209 (15) | |
C6 | 0.1773 (6) | 0.3535 (7) | 0.0459 (2) | 0.0229 (15) | |
C7 | 0.2769 (8) | 0.7020 (10) | −0.0106 (2) | 0.0229 (18) | |
C8 | 0.3600 (6) | 0.5507 (7) | −0.1244 (2) | 0.0262 (19) | |
C9 | 0.3471 (7) | 0.9996 (7) | 0.2437 (2) | 0.032 (2) | |
H9 | 0.252251 | 0.982063 | 0.273831 | 0.038* | |
C10 | 0.5175 (7) | 1.0697 (7) | 0.2629 (2) | 0.033 (2) | |
H10 | 0.538829 | 1.101048 | 0.305912 | 0.040* | |
C11 | 0.6592 (7) | 1.0939 (7) | 0.2178 (2) | 0.031 (2) | |
C12 | 0.6233 (7) | 1.0460 (8) | 0.1542 (2) | 0.037 (2) | |
H12 | 0.716994 | 1.060206 | 0.123307 | 0.045* | |
C13 | 0.4506 (7) | 0.9781 (8) | 0.1376 (2) | 0.039 (2) | |
H13 | 0.425231 | 0.946261 | 0.094757 | 0.047* | |
C14 | 0.1322 (8) | 0.8774 (9) | 0.1614 (3) | 0.045 (2) | |
H14A | 0.171221 | 0.790284 | 0.147202 | 0.068* | |
H14B | 0.056244 | 0.922097 | 0.125705 | 0.068* | |
H14C | 0.050192 | 0.868652 | 0.197965 | 0.068* | |
C15 | 0.8476 (8) | 1.1602 (7) | 0.2372 (2) | 0.0295 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0443 (7) | 0.022 (2) | 0.0335 (9) | 0.0000 (8) | 0.0078 (5) | 0.0005 (6) |
Cl2 | 0.0444 (7) | 0.0300 (19) | 0.0246 (8) | −0.0025 (8) | 0.0091 (5) | 0.0059 (6) |
O1 | 0.0391 (18) | 0.027 (5) | 0.026 (2) | 0.002 (2) | 0.0086 (14) | −0.0090 (17) |
O2 | 0.053 (2) | 0.028 (5) | 0.024 (2) | 0.006 (2) | 0.0088 (15) | −0.0037 (16) |
N1 | 0.044 (3) | 0.030 (6) | 0.040 (3) | 0.004 (4) | 0.0087 (19) | −0.002 (3) |
N2 | 0.044 (2) | 0.038 (7) | 0.031 (3) | −0.004 (3) | 0.0095 (19) | 0.001 (2) |
N3 | 0.034 (2) | 0.030 (6) | 0.032 (3) | 0.005 (2) | −0.0023 (17) | −0.002 (2) |
N4 | 0.052 (3) | 0.057 (7) | 0.036 (3) | −0.012 (3) | 0.007 (2) | 0.004 (2) |
C1 | 0.020 (2) | 0.027 (6) | 0.024 (3) | 0.001 (3) | 0.0042 (19) | 0.000 (2) |
C2 | 0.025 (2) | 0.028 (6) | 0.023 (3) | 0.007 (3) | 0.0049 (19) | 0.002 (2) |
C3 | 0.024 (2) | 0.021 (6) | 0.023 (3) | 0.000 (3) | 0.0048 (19) | 0.002 (2) |
C4 | 0.027 (2) | 0.028 (6) | 0.021 (3) | 0.003 (3) | 0.0055 (19) | 0.000 (2) |
C5 | 0.020 (2) | 0.016 (6) | 0.026 (3) | −0.001 (3) | −0.0004 (18) | 0.004 (2) |
C6 | 0.023 (2) | 0.024 (5) | 0.022 (3) | 0.000 (3) | 0.0024 (18) | 0.000 (2) |
C7 | 0.025 (3) | 0.022 (6) | 0.023 (3) | 0.013 (4) | 0.0050 (18) | 0.003 (3) |
C8 | 0.030 (2) | 0.023 (7) | 0.026 (3) | −0.001 (3) | 0.006 (2) | −0.003 (2) |
C9 | 0.038 (3) | 0.032 (8) | 0.026 (3) | 0.004 (3) | 0.006 (2) | −0.001 (2) |
C10 | 0.032 (2) | 0.044 (7) | 0.023 (3) | 0.003 (3) | 0.004 (2) | 0.001 (2) |
C11 | 0.036 (2) | 0.029 (7) | 0.027 (3) | 0.005 (3) | 0.006 (2) | 0.001 (2) |
C12 | 0.040 (3) | 0.047 (8) | 0.025 (3) | 0.006 (3) | 0.008 (2) | 0.003 (3) |
C13 | 0.047 (3) | 0.046 (8) | 0.025 (3) | 0.008 (3) | 0.001 (2) | −0.002 (2) |
C14 | 0.051 (3) | 0.017 (9) | 0.065 (5) | −0.006 (3) | −0.010 (3) | −0.005 (3) |
C15 | 0.044 (3) | 0.021 (7) | 0.025 (3) | −0.001 (3) | 0.010 (2) | 0.008 (2) |
Cl1—C5 | 1.705 (7) | C3—C8 | 1.437 (7) |
Cl2—C6 | 1.714 (5) | C4—C5 | 1.473 (7) |
O1—C1 | 1.252 (6) | C5—C6 | 1.351 (8) |
O2—C4 | 1.249 (6) | C9—C10 | 1.360 (7) |
N1—C7 | 1.155 (8) | C9—H9 | 0.9300 |
N2—C8 | 1.145 (6) | C10—C11 | 1.385 (6) |
N3—C9 | 1.331 (6) | C10—H10 | 0.9300 |
N3—C13 | 1.339 (6) | C11—C12 | 1.382 (7) |
N3—C14 | 1.479 (7) | C11—C15 | 1.441 (8) |
N4—C15 | 1.145 (6) | C12—C13 | 1.350 (8) |
C1—C6 | 1.451 (9) | C12—H12 | 0.9300 |
C1—C2 | 1.467 (7) | C13—H13 | 0.9300 |
C2—C3 | 1.386 (8) | C14—H14A | 0.9600 |
C2—C7 | 1.415 (10) | C14—H14B | 0.9600 |
C3—C4 | 1.426 (9) | C14—H14C | 0.9600 |
C9—N3—C13 | 121.2 (5) | N3—C9—C10 | 120.3 (4) |
C9—N3—C14 | 120.3 (4) | N3—C9—H9 | 119.8 |
C13—N3—C14 | 118.5 (4) | C10—C9—H9 | 119.8 |
O1—C1—C6 | 124.5 (5) | C9—C10—C11 | 119.4 (5) |
O1—C1—C2 | 120.2 (7) | C9—C10—H10 | 120.3 |
C6—C1—C2 | 115.4 (5) | C11—C10—H10 | 120.3 |
C3—C2—C7 | 122.1 (5) | C12—C11—C10 | 118.9 (5) |
C3—C2—C1 | 121.2 (7) | C12—C11—C15 | 119.8 (4) |
C7—C2—C1 | 116.6 (5) | C10—C11—C15 | 121.2 (4) |
C2—C3—C4 | 122.6 (5) | C13—C12—C11 | 119.2 (4) |
C2—C3—C8 | 119.9 (7) | C13—C12—H12 | 120.4 |
C4—C3—C8 | 117.5 (5) | C11—C12—H12 | 120.4 |
O2—C4—C3 | 123.5 (5) | N3—C13—C12 | 120.9 (5) |
O2—C4—C5 | 120.6 (7) | N3—C13—H13 | 119.6 |
C3—C4—C5 | 115.8 (5) | C12—C13—H13 | 119.6 |
C6—C5—C4 | 121.8 (7) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.7 (4) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 116.5 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 122.9 (5) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 122.1 (6) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 115.0 (4) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 178.4 (5) | N4—C15—C11 | 176.6 (6) |
N2—C8—C3 | 177.8 (7) | ||
O1—C1—C2—C3 | −177.1 (4) | Cl1—C5—C6—C1 | 179.4 (3) |
C6—C1—C2—C3 | 2.0 (6) | C4—C5—C6—Cl2 | −179.3 (3) |
O1—C1—C2—C7 | 6.5 (6) | Cl1—C5—C6—Cl2 | 2.0 (6) |
C6—C1—C2—C7 | −174.4 (4) | O1—C1—C6—C5 | 176.8 (4) |
C7—C2—C3—C4 | 178.6 (4) | C2—C1—C6—C5 | −2.3 (7) |
C1—C2—C3—C4 | 2.5 (7) | O1—C1—C6—Cl2 | −5.6 (6) |
C7—C2—C3—C8 | −2.1 (7) | C2—C1—C6—Cl2 | 175.3 (3) |
C1—C2—C3—C8 | −178.3 (4) | C13—N3—C9—C10 | 1.0 (9) |
C2—C3—C4—O2 | 175.6 (4) | C14—N3—C9—C10 | 178.6 (6) |
C8—C3—C4—O2 | −3.6 (7) | N3—C9—C10—C11 | −0.8 (10) |
C2—C3—C4—C5 | −6.4 (7) | C9—C10—C11—C12 | 0.0 (9) |
C8—C3—C4—C5 | 174.4 (4) | C9—C10—C11—C15 | −176.0 (6) |
O2—C4—C5—C6 | −175.9 (4) | C10—C11—C12—C13 | 0.7 (9) |
C3—C4—C5—C6 | 6.1 (6) | C15—C11—C12—C13 | 176.7 (7) |
O2—C4—C5—Cl1 | 2.9 (6) | C9—N3—C13—C12 | −0.4 (10) |
C3—C4—C5—Cl1 | −175.1 (3) | C14—N3—C13—C12 | −178.0 (7) |
C4—C5—C6—C1 | −1.8 (7) | C11—C12—C13—N3 | −0.5 (10) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.760 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5155 (3) Å | Cell parameters from 1909 reflections |
b = 9.9444 (12) Å | θ = 2.0–26.6° |
c = 20.2293 (11) Å | µ = 0.51 mm−1 |
β = 94.662 (4)° | T = 293 K |
V = 1306.37 (18) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1418 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 973 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.362 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.357, Tmax = 0.450 | k = −8→8 |
6645 measured reflections | l = −22→23 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1418 reflections | Δρmax = 0.22 e Å−3 |
209 parameters | Δρmin = −0.25 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 | ||
Cl1 | 0.21184 (14) | 0.10945 (16) | −0.00673 (5) | 0.0289 (5) | |
Cl2 | 0.12333 (14) | 0.27986 (15) | 0.11911 (4) | 0.0289 (5) | |
O1 | 0.1412 (4) | 0.5700 (4) | 0.09518 (12) | 0.0277 (12) | |
O2 | 0.2992 (4) | 0.2740 (4) | −0.11938 (12) | 0.0308 (13) | |
N1 | 0.2944 (6) | 0.8189 (7) | −0.00801 (16) | 0.0341 (17) | |
N2 | 0.4162 (5) | 0.6004 (5) | −0.17266 (17) | 0.0304 (16) | |
N3 | 0.3138 (4) | 0.9577 (5) | 0.18052 (15) | 0.0276 (14) | |
N4 | 1.0101 (5) | 1.2122 (5) | 0.25165 (15) | 0.0387 (16) | |
C1 | 0.1869 (5) | 0.4986 (7) | 0.04709 (18) | 0.0204 (15) | |
C2 | 0.2515 (5) | 0.5635 (7) | −0.01293 (18) | 0.0217 (15) | |
C3 | 0.2942 (5) | 0.4866 (6) | −0.06753 (18) | 0.0189 (14) | |
C4 | 0.2722 (5) | 0.3437 (7) | −0.06975 (19) | 0.0216 (15) | |
C5 | 0.2196 (5) | 0.2812 (7) | −0.00702 (17) | 0.0190 (14) | |
C6 | 0.1812 (6) | 0.3539 (6) | 0.04593 (18) | 0.0218 (14) | |
C7 | 0.2756 (6) | 0.7041 (9) | −0.01089 (18) | 0.0214 (17) | |
C8 | 0.3610 (5) | 0.5514 (6) | −0.1256 (2) | 0.0227 (17) | |
C9 | 0.3451 (6) | 1.0022 (6) | 0.24310 (19) | 0.0269 (17) | |
H9 | 0.247038 | 0.985079 | 0.272963 | 0.032* | |
C10 | 0.5176 (5) | 1.0715 (5) | 0.26343 (18) | 0.0249 (16) | |
H10 | 0.538978 | 1.102101 | 0.306892 | 0.030* | |
C11 | 0.6614 (5) | 1.0960 (6) | 0.21826 (19) | 0.0238 (17) | |
C12 | 0.6281 (6) | 1.0489 (6) | 0.15377 (19) | 0.0327 (18) | |
H12 | 0.724054 | 1.064546 | 0.123032 | 0.039* | |
C13 | 0.4526 (6) | 0.9797 (6) | 0.13644 (19) | 0.0328 (17) | |
H13 | 0.428441 | 0.947115 | 0.093421 | 0.039* | |
C14 | 0.1280 (6) | 0.8776 (7) | 0.1596 (2) | 0.046 (2) | |
H14A | 0.045250 | 0.867195 | 0.196401 | 0.069* | |
H14B | 0.168823 | 0.790662 | 0.144714 | 0.069* | |
H14C | 0.049632 | 0.923028 | 0.124058 | 0.069* | |
C15 | 0.8530 (7) | 1.1629 (6) | 0.23809 (18) | 0.0259 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0373 (6) | 0.0203 (18) | 0.0297 (8) | 0.0005 (7) | 0.0059 (4) | 0.0003 (5) |
Cl2 | 0.0367 (6) | 0.0283 (17) | 0.0224 (7) | −0.0033 (6) | 0.0067 (4) | 0.0057 (5) |
O1 | 0.0388 (15) | 0.022 (4) | 0.0235 (18) | 0.0025 (18) | 0.0072 (12) | −0.0095 (14) |
O2 | 0.0478 (17) | 0.023 (5) | 0.0231 (19) | 0.0055 (18) | 0.0089 (13) | −0.0049 (14) |
N1 | 0.035 (2) | 0.030 (6) | 0.037 (3) | −0.005 (3) | 0.0024 (15) | −0.001 (2) |
N2 | 0.0363 (19) | 0.028 (6) | 0.028 (2) | −0.003 (2) | 0.0062 (15) | 0.0023 (18) |
N3 | 0.0322 (18) | 0.022 (5) | 0.027 (2) | 0.003 (2) | −0.0052 (14) | −0.0026 (17) |
N4 | 0.044 (2) | 0.039 (6) | 0.034 (3) | −0.010 (3) | 0.0073 (18) | 0.0003 (19) |
C1 | 0.0181 (18) | 0.024 (5) | 0.020 (2) | 0.003 (3) | 0.0054 (16) | 0.0023 (19) |
C2 | 0.018 (2) | 0.025 (5) | 0.022 (2) | 0.003 (3) | 0.0024 (16) | 0.001 (2) |
C3 | 0.0197 (19) | 0.015 (5) | 0.022 (3) | −0.001 (3) | 0.0025 (16) | 0.0019 (19) |
C4 | 0.0182 (19) | 0.023 (5) | 0.024 (3) | 0.004 (3) | 0.0014 (16) | −0.001 (2) |
C5 | 0.0216 (19) | 0.011 (5) | 0.024 (3) | 0.000 (2) | 0.0012 (16) | 0.0017 (18) |
C6 | 0.022 (2) | 0.025 (5) | 0.019 (2) | 0.003 (3) | 0.0039 (16) | 0.0048 (18) |
C7 | 0.020 (2) | 0.022 (6) | 0.023 (3) | −0.003 (4) | 0.0027 (16) | 0.002 (2) |
C8 | 0.0207 (19) | 0.020 (6) | 0.027 (3) | −0.003 (2) | 0.0023 (17) | −0.003 (2) |
C9 | 0.030 (2) | 0.025 (7) | 0.026 (3) | 0.003 (2) | 0.0080 (17) | −0.001 (2) |
C10 | 0.029 (2) | 0.025 (6) | 0.020 (3) | 0.001 (2) | 0.0014 (16) | −0.0005 (18) |
C11 | 0.028 (2) | 0.015 (6) | 0.028 (3) | 0.003 (2) | 0.0046 (17) | 0.0038 (19) |
C12 | 0.039 (2) | 0.041 (7) | 0.019 (3) | 0.001 (3) | 0.0105 (18) | 0.000 (2) |
C13 | 0.043 (2) | 0.033 (6) | 0.022 (3) | 0.010 (3) | 0.0022 (18) | 0.000 (2) |
C14 | 0.042 (3) | 0.043 (8) | 0.051 (4) | −0.015 (3) | −0.014 (2) | −0.002 (3) |
C15 | 0.040 (2) | 0.015 (6) | 0.024 (3) | 0.001 (3) | 0.0093 (19) | 0.0049 (19) |
Cl1—C5 | 1.709 (6) | C3—C8 | 1.438 (6) |
Cl2—C6 | 1.722 (4) | C4—C5 | 1.478 (6) |
O1—C1 | 1.259 (5) | C5—C6 | 1.333 (6) |
O2—C4 | 1.244 (5) | C9—C10 | 1.354 (6) |
N1—C7 | 1.149 (7) | C9—H9 | 0.9300 |
N2—C8 | 1.152 (5) | C10—C11 | 1.382 (5) |
N3—C13 | 1.339 (5) | C10—H10 | 0.9300 |
N3—C9 | 1.341 (5) | C11—C12 | 1.386 (6) |
N3—C14 | 1.482 (6) | C11—C15 | 1.442 (6) |
N4—C15 | 1.148 (5) | C12—C13 | 1.356 (6) |
C1—C6 | 1.439 (8) | C12—H12 | 0.9300 |
C1—C2 | 1.467 (6) | C13—H13 | 0.9300 |
C2—C3 | 1.390 (7) | C14—H14A | 0.9600 |
C2—C7 | 1.407 (8) | C14—H14B | 0.9600 |
C3—C4 | 1.429 (8) | C14—H14C | 0.9600 |
C13—N3—C9 | 121.0 (4) | N3—C9—C10 | 120.9 (3) |
C13—N3—C14 | 118.5 (3) | N3—C9—H9 | 119.5 |
C9—N3—C14 | 120.4 (3) | C10—C9—H9 | 119.5 |
O1—C1—C6 | 124.6 (4) | C9—C10—C11 | 118.6 (4) |
O1—C1—C2 | 119.6 (6) | C9—C10—H10 | 120.7 |
C6—C1—C2 | 115.8 (4) | C11—C10—H10 | 120.7 |
C3—C2—C7 | 122.7 (4) | C10—C11—C12 | 120.0 (4) |
C3—C2—C1 | 120.4 (6) | C10—C11—C15 | 121.0 (4) |
C7—C2—C1 | 116.9 (4) | C12—C11—C15 | 118.9 (3) |
C2—C3—C4 | 123.1 (4) | C13—C12—C11 | 118.6 (4) |
C2—C3—C8 | 119.8 (6) | C13—C12—H12 | 120.7 |
C4—C3—C8 | 117.1 (4) | C11—C12—H12 | 120.7 |
O2—C4—C3 | 124.0 (4) | N3—C13—C12 | 120.8 (4) |
O2—C4—C5 | 121.1 (6) | N3—C13—H13 | 119.6 |
C3—C4—C5 | 114.9 (4) | C12—C13—H13 | 119.6 |
C6—C5—C4 | 122.2 (6) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 122.1 (4) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 115.6 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.3 (4) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 121.8 (5) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 114.9 (3) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 178.7 (4) | N4—C15—C11 | 176.6 (5) |
N2—C8—C3 | 178.4 (6) | ||
O1—C1—C2—C3 | −177.3 (4) | Cl1—C5—C6—C1 | 179.9 (3) |
C6—C1—C2—C3 | 2.8 (5) | C4—C5—C6—Cl2 | −179.1 (3) |
O1—C1—C2—C7 | 5.3 (5) | Cl1—C5—C6—Cl2 | 0.7 (5) |
C6—C1—C2—C7 | −174.6 (4) | O1—C1—C6—C5 | 176.2 (3) |
C7—C2—C3—C4 | 179.3 (4) | C2—C1—C6—C5 | −3.8 (6) |
C1—C2—C3—C4 | 2.1 (6) | O1—C1—C6—Cl2 | −4.5 (5) |
C7—C2—C3—C8 | −1.6 (6) | C2—C1—C6—Cl2 | 175.4 (2) |
C1—C2—C3—C8 | −178.9 (3) | C13—N3—C9—C10 | 0.5 (7) |
C2—C3—C4—O2 | 176.0 (3) | C14—N3—C9—C10 | 177.7 (5) |
C8—C3—C4—O2 | −3.0 (6) | N3—C9—C10—C11 | 0.1 (8) |
C2—C3—C4—C5 | −5.6 (5) | C9—C10—C11—C12 | −0.4 (7) |
C8—C3—C4—C5 | 175.3 (3) | C9—C10—C11—C15 | −176.6 (5) |
O2—C4—C5—C6 | −177.0 (4) | C10—C11—C12—C13 | 0.2 (7) |
C3—C4—C5—C6 | 4.6 (5) | C15—C11—C12—C13 | 176.5 (5) |
O2—C4—C5—Cl1 | 3.1 (5) | C9—N3—C13—C12 | −0.7 (8) |
C3—C4—C5—Cl1 | −175.2 (3) | C14—N3—C13—C12 | −178.0 (5) |
C4—C5—C6—C1 | 0.1 (6) | C11—C12—C13—N3 | 0.3 (8) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.795 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4387 (2) Å | Cell parameters from 1960 reflections |
b = 9.9135 (11) Å | θ = 2.0–26.7° |
c = 20.1349 (10) Å | µ = 0.52 mm−1 |
β = 94.729 (3)° | T = 293 K |
V = 1280.83 (16) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1390 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.372 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.368, Tmax = 0.449 | k = −8→8 |
6531 measured reflections | l = −23→22 |
Refinement on F2 | 192 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.2085P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1390 reflections | Δρmax = 0.25 e Å−3 |
209 parameters | Δρmin = −0.26 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 | ||
Cl1 | 0.21350 (15) | 0.10860 (16) | −0.00654 (5) | 0.0268 (5) | |
Cl2 | 0.12508 (14) | 0.27982 (16) | 0.11979 (5) | 0.0273 (5) | |
O1 | 0.1434 (4) | 0.5710 (4) | 0.09558 (13) | 0.0260 (12) | |
O2 | 0.3017 (4) | 0.2726 (4) | −0.11992 (13) | 0.0273 (13) | |
N1 | 0.2928 (6) | 0.8197 (7) | −0.00807 (17) | 0.0312 (17) | |
N2 | 0.4153 (5) | 0.5997 (5) | −0.17377 (18) | 0.0283 (16) | |
N3 | 0.3128 (5) | 0.9582 (5) | 0.18015 (16) | 0.0249 (14) | |
N4 | 1.0157 (5) | 1.2133 (6) | 0.25263 (16) | 0.0387 (17) | |
C1 | 0.1889 (6) | 0.4985 (7) | 0.04704 (19) | 0.0181 (15) | |
C2 | 0.2522 (6) | 0.5641 (7) | −0.01311 (19) | 0.0197 (15) | |
C3 | 0.2950 (6) | 0.4863 (7) | −0.06818 (19) | 0.0200 (15) | |
C4 | 0.2730 (6) | 0.3437 (7) | −0.0702 (2) | 0.0206 (15) | |
C5 | 0.2210 (5) | 0.2807 (7) | −0.00712 (18) | 0.0167 (14) | |
C6 | 0.1830 (5) | 0.3534 (7) | 0.04636 (19) | 0.0157 (14) | |
C7 | 0.2752 (7) | 0.7045 (9) | −0.01127 (19) | 0.0194 (18) | |
C8 | 0.3606 (6) | 0.5516 (6) | −0.1268 (2) | 0.0191 (17) | |
C9 | 0.3434 (6) | 1.0026 (6) | 0.24299 (19) | 0.0241 (18) | |
H9 | 0.244183 | 0.984948 | 0.272884 | 0.029* | |
C10 | 0.5165 (6) | 1.0727 (6) | 0.26342 (19) | 0.0265 (17) | |
H10 | 0.537111 | 1.103132 | 0.307159 | 0.032* | |
C11 | 0.6642 (6) | 1.0990 (6) | 0.2183 (2) | 0.0251 (18) | |
C12 | 0.6307 (6) | 1.0506 (6) | 0.1540 (2) | 0.0295 (18) | |
H12 | 0.728433 | 1.065702 | 0.123247 | 0.035* | |
C13 | 0.4534 (6) | 0.9805 (6) | 0.1360 (2) | 0.0284 (17) | |
H13 | 0.429587 | 0.947894 | 0.092744 | 0.034* | |
C14 | 0.1251 (6) | 0.8773 (8) | 0.1588 (2) | 0.044 (2) | |
H14A | 0.047405 | 0.921901 | 0.122382 | 0.066* | |
H14B | 0.039536 | 0.868205 | 0.195365 | 0.066* | |
H14C | 0.166895 | 0.789589 | 0.144719 | 0.066* | |
C15 | 0.8550 (7) | 1.1657 (6) | 0.23876 (19) | 0.0270 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0345 (6) | 0.0173 (18) | 0.0288 (8) | 0.0011 (7) | 0.0047 (4) | 0.0005 (5) |
Cl2 | 0.0342 (6) | 0.0273 (17) | 0.0209 (7) | −0.0026 (6) | 0.0060 (4) | 0.0050 (5) |
O1 | 0.0323 (15) | 0.022 (4) | 0.0243 (19) | 0.0028 (18) | 0.0060 (12) | −0.0070 (15) |
O2 | 0.0435 (17) | 0.016 (5) | 0.023 (2) | 0.0046 (18) | 0.0079 (13) | −0.0025 (14) |
N1 | 0.033 (2) | 0.025 (6) | 0.035 (3) | 0.001 (3) | 0.0023 (15) | −0.001 (2) |
N2 | 0.036 (2) | 0.022 (6) | 0.028 (3) | 0.001 (2) | 0.0056 (16) | 0.0017 (19) |
N3 | 0.0284 (18) | 0.019 (5) | 0.026 (2) | 0.005 (2) | −0.0046 (15) | −0.0015 (17) |
N4 | 0.039 (2) | 0.045 (6) | 0.032 (3) | −0.010 (3) | 0.0052 (18) | 0.000 (2) |
C1 | 0.0162 (19) | 0.019 (5) | 0.019 (3) | 0.004 (3) | 0.0002 (16) | −0.0003 (19) |
C2 | 0.018 (2) | 0.016 (5) | 0.026 (3) | 0.003 (3) | 0.0017 (17) | 0.003 (2) |
C3 | 0.0181 (19) | 0.019 (5) | 0.023 (3) | −0.001 (3) | 0.0011 (16) | 0.002 (2) |
C4 | 0.017 (2) | 0.022 (5) | 0.023 (3) | 0.002 (3) | 0.0011 (17) | 0.003 (2) |
C5 | 0.0202 (19) | 0.007 (5) | 0.023 (3) | 0.000 (2) | 0.0023 (17) | −0.0002 (19) |
C6 | 0.0169 (19) | 0.009 (5) | 0.021 (3) | 0.002 (3) | 0.0008 (16) | 0.0026 (19) |
C7 | 0.020 (2) | 0.017 (6) | 0.022 (3) | −0.001 (4) | 0.0059 (16) | 0.004 (3) |
C8 | 0.021 (2) | 0.012 (6) | 0.025 (3) | 0.001 (2) | 0.0023 (17) | −0.002 (2) |
C9 | 0.027 (2) | 0.022 (7) | 0.024 (3) | 0.002 (2) | 0.0022 (17) | 0.001 (2) |
C10 | 0.028 (2) | 0.035 (6) | 0.016 (3) | 0.003 (3) | 0.0011 (17) | 0.000 (2) |
C11 | 0.027 (2) | 0.024 (7) | 0.024 (3) | 0.000 (2) | 0.0033 (17) | 0.003 (2) |
C12 | 0.032 (2) | 0.039 (7) | 0.017 (3) | 0.003 (3) | 0.0055 (17) | 0.002 (2) |
C13 | 0.038 (2) | 0.028 (6) | 0.020 (3) | 0.013 (3) | 0.0006 (18) | 0.000 (2) |
C14 | 0.039 (3) | 0.044 (9) | 0.046 (4) | −0.011 (3) | −0.012 (2) | −0.002 (3) |
C15 | 0.036 (2) | 0.021 (7) | 0.024 (3) | −0.002 (3) | 0.0066 (19) | 0.006 (2) |
Cl1—C5 | 1.707 (6) | C3—C8 | 1.440 (6) |
Cl2—C6 | 1.717 (5) | C4—C5 | 1.478 (6) |
O1—C1 | 1.266 (6) | C5—C6 | 1.335 (7) |
O2—C4 | 1.251 (6) | C9—C10 | 1.349 (6) |
N1—C7 | 1.149 (7) | C9—H9 | 0.9300 |
N2—C8 | 1.141 (5) | C10—C11 | 1.393 (5) |
N3—C13 | 1.338 (5) | C10—H10 | 0.9300 |
N3—C9 | 1.339 (5) | C11—C12 | 1.382 (6) |
N3—C14 | 1.484 (6) | C11—C15 | 1.426 (6) |
N4—C15 | 1.150 (5) | C12—C13 | 1.359 (7) |
C1—C6 | 1.439 (8) | C12—H12 | 0.9300 |
C1—C2 | 1.462 (6) | C13—H13 | 0.9300 |
C2—C3 | 1.397 (7) | C14—H14A | 0.9600 |
C2—C7 | 1.400 (8) | C14—H14B | 0.9600 |
C3—C4 | 1.421 (8) | C14—H14C | 0.9600 |
C13—N3—C9 | 121.2 (4) | N3—C9—C10 | 120.7 (4) |
C13—N3—C14 | 118.4 (4) | N3—C9—H9 | 119.6 |
C9—N3—C14 | 120.3 (3) | C10—C9—H9 | 119.6 |
O1—C1—C6 | 124.5 (4) | C9—C10—C11 | 119.3 (4) |
O1—C1—C2 | 119.0 (6) | C9—C10—H10 | 120.4 |
C6—C1—C2 | 116.5 (4) | C11—C10—H10 | 120.4 |
C3—C2—C7 | 122.9 (4) | C12—C11—C10 | 119.0 (4) |
C3—C2—C1 | 119.9 (6) | C12—C11—C15 | 119.7 (3) |
C7—C2—C1 | 117.1 (4) | C10—C11—C15 | 121.1 (4) |
C2—C3—C4 | 123.1 (4) | C13—C12—C11 | 119.3 (4) |
C2—C3—C8 | 119.5 (6) | C13—C12—H12 | 120.3 |
C4—C3—C8 | 117.4 (4) | C11—C12—H12 | 120.3 |
O2—C4—C3 | 124.2 (4) | N3—C13—C12 | 120.5 (4) |
O2—C4—C5 | 120.6 (6) | N3—C13—H13 | 119.8 |
C3—C4—C5 | 115.2 (4) | C12—C13—H13 | 119.8 |
C6—C5—C4 | 122.3 (6) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.8 (4) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 115.9 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 122.7 (4) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 122.2 (5) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 115.1 (3) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 178.2 (4) | N4—C15—C11 | 175.3 (6) |
N2—C8—C3 | 177.9 (6) | ||
O1—C1—C2—C3 | −177.4 (4) | Cl1—C5—C6—C1 | 179.9 (3) |
C6—C1—C2—C3 | 2.5 (5) | C4—C5—C6—Cl2 | −179.4 (3) |
O1—C1—C2—C7 | 5.1 (5) | Cl1—C5—C6—Cl2 | 0.4 (5) |
C6—C1—C2—C7 | −174.9 (4) | O1—C1—C6—C5 | 176.2 (3) |
C7—C2—C3—C4 | 179.7 (4) | C2—C1—C6—C5 | −3.7 (6) |
C1—C2—C3—C4 | 2.4 (6) | O1—C1—C6—Cl2 | −4.3 (5) |
C7—C2—C3—C8 | −1.7 (6) | C2—C1—C6—Cl2 | 175.8 (2) |
C1—C2—C3—C8 | −178.9 (3) | C13—N3—C9—C10 | 0.7 (8) |
C2—C3—C4—O2 | 176.8 (4) | C14—N3—C9—C10 | 178.0 (5) |
C8—C3—C4—O2 | −1.9 (6) | N3—C9—C10—C11 | 0.2 (8) |
C2—C3—C4—C5 | −5.8 (6) | C9—C10—C11—C12 | −1.0 (8) |
C8—C3—C4—C5 | 175.5 (3) | C9—C10—C11—C15 | −176.2 (5) |
O2—C4—C5—C6 | −177.9 (4) | C10—C11—C12—C13 | 1.1 (7) |
C3—C4—C5—C6 | 4.6 (5) | C15—C11—C12—C13 | 176.3 (6) |
O2—C4—C5—Cl1 | 2.4 (5) | C9—N3—C13—C12 | −0.7 (8) |
C3—C4—C5—Cl1 | −175.2 (3) | C14—N3—C13—C12 | −178.0 (5) |
C4—C5—C6—C1 | 0.1 (6) | C11—C12—C13—N3 | −0.2 (8) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.834 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3580 (4) Å | Cell parameters from 1653 reflections |
b = 9.895 (2) Å | θ = 2.0–26.9° |
c = 20.0093 (18) Å | µ = 0.54 mm−1 |
β = 95.314 (7)° | T = 293 K |
V = 1253.5 (3) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1374 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.0° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.365 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.361, Tmax = 0.449 | k = −8→8 |
6405 measured reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.140 | H-atom parameters constrained |
wR(F2) = 0.377 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.36 | (Δ/σ)max < 0.001 |
1374 reflections | Δρmax = 1.50 e Å−3 |
94 parameters | Δρmin = −1.60 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 | ||
Cl1 | 0.2234 (4) | 0.1128 (4) | −0.00453 (13) | 0.0313 (10)* | |
Cl2 | 0.1324 (4) | 0.2836 (4) | 0.12234 (13) | 0.0295 (10)* | |
O1 | 0.1562 (11) | 0.5751 (11) | 0.0988 (4) | 0.034 (2)* | |
O2 | 0.3144 (11) | 0.2808 (11) | −0.1175 (4) | 0.035 (2)* | |
N1 | 0.2818 (12) | 0.8227 (19) | −0.0080 (4) | 0.032 (2)* | |
N2 | 0.4095 (12) | 0.6029 (13) | −0.1749 (5) | 0.032 (2)* | |
N3 | 0.3067 (12) | 0.9592 (13) | 0.1800 (4) | 0.030 (2)* | |
N4 | 1.0214 (12) | 1.2149 (13) | 0.2538 (4) | 0.032 (2)* | |
C1 | 0.2043 (14) | 0.5101 (18) | 0.0484 (5) | 0.028 (3)* | |
C2 | 0.2658 (13) | 0.5671 (17) | −0.0100 (5) | 0.025 (3)* | |
C3 | 0.3098 (14) | 0.4941 (17) | −0.0667 (5) | 0.026 (3)* | |
C4 | 0.2870 (13) | 0.3532 (17) | −0.0679 (5) | 0.024 (2)* | |
C5 | 0.2354 (13) | 0.2894 (17) | −0.0058 (5) | 0.024 (3)* | |
C6 | 0.1956 (14) | 0.3635 (17) | 0.0476 (5) | 0.025 (2)* | |
C7 | 0.2754 (14) | 0.706 (2) | −0.0105 (5) | 0.026 (3)* | |
C8 | 0.3631 (13) | 0.5566 (15) | −0.1261 (5) | 0.018 (2)* | |
C9 | 0.3403 (14) | 1.0026 (16) | 0.2426 (5) | 0.026 (3)* | |
H9 | 0.241867 | 0.982676 | 0.272777 | 0.031* | |
C10 | 0.5148 (15) | 1.0756 (15) | 0.2641 (6) | 0.031 (3)* | |
H10 | 0.534528 | 1.108034 | 0.307890 | 0.038* | |
C11 | 0.6646 (13) | 1.1006 (14) | 0.2180 (5) | 0.023 (2)* | |
C12 | 0.6309 (15) | 1.0473 (16) | 0.1538 (5) | 0.028 (3)* | |
H12 | 0.731694 | 1.058484 | 0.123450 | 0.034* | |
C13 | 0.4518 (14) | 0.9796 (16) | 0.1359 (5) | 0.029 (3)* | |
H13 | 0.427298 | 0.946223 | 0.092486 | 0.035* | |
C14 | 0.1202 (17) | 0.884 (2) | 0.1583 (7) | 0.052 (4)* | |
H14A | 0.159956 | 0.799005 | 0.139560 | 0.077* | |
H14B | 0.035580 | 0.934151 | 0.124818 | 0.077* | |
H14C | 0.040453 | 0.866910 | 0.195885 | 0.077* | |
C15 | 0.8584 (15) | 1.1687 (17) | 0.2391 (5) | 0.031 (3)* |
Cl1—C5 | 1.749 (17) | C3—C8 | 1.407 (16) |
Cl2—C6 | 1.770 (12) | C4—C5 | 1.458 (16) |
O1—C1 | 1.257 (15) | C5—C6 | 1.339 (17) |
O2—C4 | 1.249 (15) | C9—C10 | 1.360 (16) |
N1—C7 | 1.156 (18) | C9—H9 | 0.9300 |
N2—C8 | 1.142 (13) | C10—C11 | 1.408 (14) |
N3—C9 | 1.323 (13) | C10—H10 | 0.9300 |
N3—C13 | 1.350 (12) | C11—C12 | 1.385 (15) |
N3—C14 | 1.435 (16) | C11—C15 | 1.433 (15) |
N4—C15 | 1.146 (13) | C12—C13 | 1.341 (16) |
C1—C2 | 1.386 (16) | C12—H12 | 0.9300 |
C1—C6 | 1.45 (2) | C13—H13 | 0.9300 |
C2—C7 | 1.38 (2) | C14—H14A | 0.9600 |
C2—C3 | 1.395 (17) | C14—H14B | 0.9600 |
C3—C4 | 1.40 (2) | C14—H14C | 0.9600 |
C9—N3—C13 | 120.6 (9) | N3—C9—C10 | 121.9 (9) |
C9—N3—C14 | 120.9 (9) | N3—C9—H9 | 119.1 |
C13—N3—C14 | 118.4 (10) | C10—C9—H9 | 119.1 |
O1—C1—C2 | 125.2 (15) | C9—C10—C11 | 117.8 (10) |
O1—C1—C6 | 120.5 (11) | C9—C10—H10 | 121.1 |
C2—C1—C6 | 114.3 (11) | C11—C10—H10 | 121.1 |
C7—C2—C1 | 115.4 (11) | C12—C11—C10 | 119.0 (10) |
C7—C2—C3 | 119.9 (10) | C12—C11—C15 | 120.4 (8) |
C1—C2—C3 | 124.7 (15) | C10—C11—C15 | 120.3 (9) |
C2—C3—C4 | 120.0 (11) | C13—C12—C11 | 119.5 (9) |
C2—C3—C8 | 122.8 (14) | C13—C12—H12 | 120.3 |
C4—C3—C8 | 117.1 (10) | C11—C12—H12 | 120.3 |
O2—C4—C3 | 124.1 (11) | C12—C13—N3 | 121.0 (10) |
O2—C4—C5 | 119.2 (14) | C12—C13—H13 | 119.5 |
C3—C4—C5 | 116.6 (10) | N3—C13—H13 | 119.5 |
C6—C5—C4 | 121.1 (14) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.6 (10) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 117.3 (9) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.1 (11) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 120.2 (12) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 116.7 (8) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 177.0 (10) | N4—C15—C11 | 174.6 (15) |
N2—C8—C3 | 177.5 (14) | ||
O1—C1—C2—C7 | 0.8 (14) | Cl1—C5—C6—C1 | 179.9 (7) |
C6—C1—C2—C7 | −180.0 (8) | C4—C5—C6—Cl2 | 179.8 (6) |
O1—C1—C2—C3 | −177.0 (9) | Cl1—C5—C6—Cl2 | 0.9 (12) |
C6—C1—C2—C3 | 2.2 (14) | O1—C1—C6—C5 | 176.8 (9) |
C7—C2—C3—C4 | −175.9 (8) | C2—C1—C6—C5 | −2.5 (14) |
C1—C2—C3—C4 | 1.8 (15) | O1—C1—C6—Cl2 | −4.2 (12) |
C7—C2—C3—C8 | −0.5 (14) | C2—C1—C6—Cl2 | 176.6 (7) |
C1—C2—C3—C8 | 177.2 (8) | C13—N3—C9—C10 | 4 (2) |
C2—C3—C4—O2 | 176.9 (9) | C14—N3—C9—C10 | −179.3 (15) |
C8—C3—C4—O2 | 1.3 (14) | N3—C9—C10—C11 | −2 (2) |
C2—C3—C4—C5 | −5.4 (13) | C9—C10—C11—C12 | −1.6 (19) |
C8—C3—C4—C5 | 179.0 (8) | C9—C10—C11—C15 | −175.6 (13) |
O2—C4—C5—C6 | −177.0 (9) | C10—C11—C12—C13 | 4 (2) |
C3—C4—C5—C6 | 5.1 (13) | C15—C11—C12—C13 | 177.5 (14) |
O2—C4—C5—Cl1 | 2.0 (12) | C11—C12—C13—N3 | −2 (2) |
C3—C4—C5—Cl1 | −175.9 (7) | C9—N3—C13—C12 | −2 (2) |
C4—C5—C6—C1 | −1.2 (14) | C14—N3—C13—C12 | −178.7 (15) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.887 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2590 (2) Å | Cell parameters from 1965 reflections |
b = 9.8519 (12) Å | θ = 2.1–27.2° |
c = 19.8571 (11) Å | µ = 0.55 mm−1 |
β = 95.624 (4)° | T = 293 K |
V = 1218.56 (17) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1312 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.1° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.373 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.368, Tmax = 0.449 | k = −8→7 |
6137 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0596P)2 + 4.2141P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1312 reflections | Δρmax = 0.56 e Å−3 |
94 parameters | Δρmin = −0.72 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 | ||
Cl1 | 0.2320 (2) | 0.1163 (2) | −0.00400 (7) | 0.0230 (4)* | |
Cl2 | 0.1388 (2) | 0.2862 (2) | 0.12396 (7) | 0.0223 (4)* | |
O1 | 0.1674 (6) | 0.5777 (6) | 0.1016 (2) | 0.0236 (10)* | |
O2 | 0.3254 (6) | 0.2821 (6) | −0.1171 (2) | 0.0260 (11)* | |
N1 | 0.2653 (7) | 0.8311 (9) | −0.0089 (2) | 0.0241 (13)* | |
N2 | 0.4009 (7) | 0.6046 (8) | −0.1773 (3) | 0.0249 (13)* | |
N3 | 0.3035 (7) | 0.9609 (7) | 0.1792 (2) | 0.0241 (12)* | |
N4 | 1.0260 (8) | 1.2187 (8) | 0.2553 (3) | 0.0327 (14)* | |
C1 | 0.2132 (8) | 0.5102 (9) | 0.0517 (3) | 0.0169 (13)* | |
C2 | 0.2712 (8) | 0.5741 (9) | −0.0092 (3) | 0.0156 (13)* | |
C3 | 0.3157 (8) | 0.4961 (9) | −0.0652 (3) | 0.0161 (13)* | |
C4 | 0.2979 (8) | 0.3527 (9) | −0.0666 (3) | 0.0176 (14)* | |
C5 | 0.2441 (8) | 0.2892 (9) | −0.0034 (3) | 0.0158 (13)* | |
C6 | 0.2070 (8) | 0.3635 (9) | 0.0509 (3) | 0.0147 (13)* | |
C7 | 0.2702 (8) | 0.7140 (11) | −0.0094 (3) | 0.0140 (13)* | |
C8 | 0.3618 (8) | 0.5620 (8) | −0.1269 (3) | 0.0148 (13)* | |
C9 | 0.3369 (8) | 1.0069 (9) | 0.2431 (3) | 0.0220 (14)* | |
H9 | 0.235065 | 0.989696 | 0.273149 | 0.026* | |
C10 | 0.5156 (8) | 1.0778 (9) | 0.2646 (3) | 0.0231 (15)* | |
H10 | 0.537444 | 1.109611 | 0.308814 | 0.028* | |
C11 | 0.6658 (9) | 1.1019 (9) | 0.2190 (3) | 0.0225 (14)* | |
C12 | 0.6321 (9) | 1.0526 (9) | 0.1540 (3) | 0.0253 (15)* | |
H12 | 0.732286 | 1.068513 | 0.123320 | 0.030* | |
C13 | 0.4514 (9) | 0.9803 (9) | 0.1352 (3) | 0.0269 (15)* | |
H13 | 0.429594 | 0.944119 | 0.091765 | 0.032* | |
C14 | 0.1129 (9) | 0.8804 (11) | 0.1572 (3) | 0.0345 (17)* | |
H14A | 0.025467 | 0.871021 | 0.194013 | 0.052* | |
H14B | 0.156041 | 0.792192 | 0.143042 | 0.052* | |
H14C | 0.032127 | 0.925177 | 0.120014 | 0.052* | |
C15 | 0.8638 (9) | 1.1706 (9) | 0.2398 (3) | 0.0225 (15)* |
Cl1—C5 | 1.705 (9) | C3—C8 | 1.440 (8) |
Cl2—C6 | 1.728 (6) | C4—C5 | 1.471 (8) |
O1—C1 | 1.249 (8) | C5—C6 | 1.342 (9) |
O2—C4 | 1.246 (8) | C9—C10 | 1.351 (9) |
N1—C7 | 1.154 (9) | C9—H9 | 0.9300 |
N2—C8 | 1.134 (7) | C10—C11 | 1.388 (8) |
N3—C9 | 1.345 (8) | C10—H10 | 0.9300 |
N3—C13 | 1.348 (7) | C11—C12 | 1.374 (9) |
N3—C14 | 1.463 (9) | C11—C15 | 1.437 (9) |
N4—C15 | 1.135 (8) | C12—C13 | 1.358 (9) |
C1—C2 | 1.441 (9) | C12—H12 | 0.9300 |
C1—C6 | 1.446 (10) | C13—H13 | 0.9300 |
C2—C7 | 1.378 (10) | C14—H14A | 0.9600 |
C2—C3 | 1.403 (9) | C14—H14B | 0.9600 |
C3—C4 | 1.417 (10) | C14—H14C | 0.9600 |
C9—N3—C13 | 120.8 (6) | N3—C9—C10 | 121.3 (5) |
C9—N3—C14 | 120.8 (5) | N3—C9—H9 | 119.4 |
C13—N3—C14 | 118.3 (5) | C10—C9—H9 | 119.4 |
O1—C1—C2 | 121.9 (7) | C9—C10—C11 | 118.4 (6) |
O1—C1—C6 | 122.2 (6) | C9—C10—H10 | 120.8 |
C2—C1—C6 | 115.9 (5) | C11—C10—H10 | 120.8 |
C7—C2—C3 | 123.2 (6) | C12—C11—C10 | 120.0 (6) |
C7—C2—C1 | 116.0 (5) | C12—C11—C15 | 119.0 (5) |
C3—C2—C1 | 120.8 (7) | C10—C11—C15 | 120.8 (5) |
C2—C3—C4 | 122.7 (5) | C13—C12—C11 | 119.4 (5) |
C2—C3—C8 | 119.9 (7) | C13—C12—H12 | 120.3 |
C4—C3—C8 | 117.1 (5) | C11—C12—H12 | 120.3 |
O2—C4—C3 | 123.7 (6) | N3—C13—C12 | 120.1 (6) |
O2—C4—C5 | 120.7 (7) | N3—C13—H13 | 119.9 |
C3—C4—C5 | 115.6 (5) | C12—C13—H13 | 119.9 |
C6—C5—C4 | 121.7 (7) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 122.7 (5) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 115.6 (5) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.2 (6) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 120.6 (6) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 116.1 (4) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 178.5 (6) | N4—C15—C11 | 176.2 (8) |
N2—C8—C3 | 174.9 (8) | ||
O1—C1—C2—C7 | −0.8 (7) | Cl1—C5—C6—C1 | −178.9 (4) |
C6—C1—C2—C7 | 177.9 (5) | C4—C5—C6—Cl2 | 178.7 (4) |
O1—C1—C2—C3 | −178.1 (5) | Cl1—C5—C6—Cl2 | −1.3 (6) |
C6—C1—C2—C3 | 0.7 (7) | O1—C1—C6—C5 | 176.2 (5) |
C7—C2—C3—C4 | −174.3 (5) | C2—C1—C6—C5 | −2.5 (7) |
C1—C2—C3—C4 | 2.8 (8) | O1—C1—C6—Cl2 | −1.5 (7) |
C7—C2—C3—C8 | −0.4 (7) | C2—C1—C6—Cl2 | 179.7 (4) |
C1—C2—C3—C8 | 176.6 (4) | C13—N3—C9—C10 | 2.2 (11) |
C2—C3—C4—O2 | 176.0 (5) | C14—N3—C9—C10 | 178.0 (8) |
C8—C3—C4—O2 | 2.0 (8) | N3—C9—C10—C11 | −0.2 (12) |
C2—C3—C4—C5 | −4.2 (7) | C9—C10—C11—C12 | −0.9 (11) |
C8—C3—C4—C5 | −178.2 (4) | C9—C10—C11—C15 | −176.8 (8) |
O2—C4—C5—C6 | −177.9 (5) | C10—C11—C12—C13 | 0.0 (12) |
C3—C4—C5—C6 | 2.3 (7) | C15—C11—C12—C13 | 176.0 (8) |
O2—C4—C5—Cl1 | 2.1 (7) | C9—N3—C13—C12 | −3.1 (11) |
C3—C4—C5—Cl1 | −177.7 (4) | C14—N3—C13—C12 | −179.0 (8) |
C4—C5—C6—C1 | 1.0 (8) | C11—C12—C13—N3 | 2.0 (12) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.916 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2058 (3) Å | Cell parameters from 1972 reflections |
b = 9.8299 (15) Å | θ = 2.1–27.3° |
c = 19.7739 (13) Å | µ = 0.56 mm−1 |
β = 95.781 (5)° | T = 293 K |
V = 1200.1 (2) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1290 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 953 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.3° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.371 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.366, Tmax = 0.449 | k = −8→8 |
6073 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0635P)2 + 3.3338P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1290 reflections | Δρmax = 0.54 e Å−3 |
94 parameters | Δρmin = −0.55 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 | ||
Cl1 | 0.23248 (19) | 0.1157 (2) | −0.00366 (6) | 0.0213 (4)* | |
Cl2 | 0.13994 (19) | 0.2863 (2) | 0.12473 (6) | 0.0211 (4)* | |
O1 | 0.1688 (5) | 0.5782 (5) | 0.10216 (19) | 0.0228 (9)* | |
O2 | 0.3268 (6) | 0.2814 (6) | −0.11688 (18) | 0.0241 (10)* | |
N1 | 0.2655 (6) | 0.8307 (9) | −0.0091 (2) | 0.0213 (12)* | |
N2 | 0.3997 (7) | 0.6038 (7) | −0.1785 (2) | 0.0244 (12)* | |
N3 | 0.3044 (6) | 0.9610 (7) | 0.1788 (2) | 0.0218 (11)* | |
N4 | 1.0292 (7) | 1.2215 (7) | 0.2561 (2) | 0.0280 (13)* | |
C1 | 0.2139 (7) | 0.5102 (8) | 0.0523 (2) | 0.0150 (12)* | |
C2 | 0.2706 (7) | 0.5743 (8) | −0.0091 (2) | 0.0130 (12)* | |
C3 | 0.3142 (7) | 0.4967 (8) | −0.0656 (2) | 0.0154 (12)* | |
C4 | 0.2990 (7) | 0.3524 (8) | −0.0665 (3) | 0.0173 (13)* | |
C5 | 0.2453 (7) | 0.2881 (8) | −0.0032 (2) | 0.0129 (12)* | |
C6 | 0.2071 (7) | 0.3626 (8) | 0.0515 (2) | 0.0135 (12)* | |
C7 | 0.2700 (7) | 0.7143 (10) | −0.0097 (2) | 0.0121 (12)* | |
C8 | 0.3601 (7) | 0.5608 (8) | −0.1273 (3) | 0.0152 (12)* | |
C9 | 0.3339 (8) | 1.0074 (8) | 0.2426 (3) | 0.0190 (13)* | |
H9 | 0.229928 | 0.990785 | 0.272320 | 0.023* | |
C10 | 0.5155 (8) | 1.0788 (8) | 0.2642 (3) | 0.0218 (14)* | |
H10 | 0.537288 | 1.110509 | 0.308629 | 0.026* | |
C11 | 0.6672 (8) | 1.1037 (8) | 0.2191 (3) | 0.0224 (14)* | |
C12 | 0.6324 (9) | 1.0534 (9) | 0.1534 (3) | 0.0258 (14)* | |
H12 | 0.732628 | 1.069589 | 0.122355 | 0.031* | |
C13 | 0.4520 (8) | 0.9809 (9) | 0.1349 (3) | 0.0259 (14)* | |
H13 | 0.429773 | 0.944452 | 0.091336 | 0.031* | |
C14 | 0.1107 (9) | 0.8811 (10) | 0.1562 (3) | 0.0358 (17)* | |
H14A | 0.025136 | 0.868753 | 0.193593 | 0.054* | |
H14B | 0.153390 | 0.793869 | 0.140239 | 0.054* | |
H14C | 0.026870 | 0.928272 | 0.120099 | 0.054* | |
C15 | 0.8665 (8) | 1.1736 (8) | 0.2408 (3) | 0.0218 (14)* |
Cl1—C5 | 1.697 (8) | C3—C8 | 1.428 (8) |
Cl2—C6 | 1.720 (6) | C4—C5 | 1.469 (8) |
O1—C1 | 1.245 (7) | C5—C6 | 1.347 (8) |
O2—C4 | 1.243 (7) | C9—C10 | 1.359 (8) |
N1—C7 | 1.144 (9) | C9—H9 | 0.9300 |
N2—C8 | 1.145 (7) | C10—C11 | 1.382 (7) |
N3—C9 | 1.337 (7) | C10—H10 | 0.9300 |
N3—C13 | 1.338 (7) | C11—C12 | 1.388 (8) |
N3—C14 | 1.467 (9) | C11—C15 | 1.441 (8) |
N4—C15 | 1.128 (7) | C12—C13 | 1.346 (9) |
C1—C2 | 1.443 (8) | C12—H12 | 0.9300 |
C1—C6 | 1.451 (9) | C13—H13 | 0.9300 |
C2—C7 | 1.376 (10) | C14—H14A | 0.9600 |
C2—C3 | 1.402 (8) | C14—H14B | 0.9600 |
C3—C4 | 1.421 (10) | C14—H14C | 0.9600 |
C9—N3—C13 | 121.6 (5) | N3—C9—C10 | 120.2 (5) |
C9—N3—C14 | 120.0 (4) | N3—C9—H9 | 119.9 |
C13—N3—C14 | 118.3 (5) | C10—C9—H9 | 119.9 |
O1—C1—C2 | 121.6 (7) | C9—C10—C11 | 119.1 (5) |
O1—C1—C6 | 122.5 (5) | C9—C10—H10 | 120.4 |
C2—C1—C6 | 115.8 (5) | C11—C10—H10 | 120.4 |
C7—C2—C3 | 122.5 (5) | C10—C11—C12 | 119.3 (6) |
C7—C2—C1 | 116.3 (5) | C10—C11—C15 | 120.8 (5) |
C3—C2—C1 | 121.1 (7) | C12—C11—C15 | 119.8 (5) |
C2—C3—C4 | 122.4 (5) | C13—C12—C11 | 119.3 (5) |
C2—C3—C8 | 120.8 (7) | C13—C12—H12 | 120.3 |
C4—C3—C8 | 116.6 (5) | C11—C12—H12 | 120.3 |
O2—C4—C3 | 123.8 (5) | N3—C13—C12 | 120.4 (6) |
O2—C4—C5 | 120.2 (7) | N3—C13—H13 | 119.8 |
C3—C4—C5 | 116.0 (5) | C12—C13—H13 | 119.8 |
C6—C5—C4 | 121.5 (7) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 122.4 (5) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 116.1 (4) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.1 (5) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 121.1 (6) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 115.8 (4) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 178.2 (5) | N4—C15—C11 | 175.6 (8) |
N2—C8—C3 | 175.4 (7) | ||
O1—C1—C2—C7 | −0.6 (7) | Cl1—C5—C6—C1 | −179.0 (4) |
C6—C1—C2—C7 | 177.8 (4) | C4—C5—C6—Cl2 | 178.9 (3) |
O1—C1—C2—C3 | −177.9 (4) | Cl1—C5—C6—Cl2 | −0.6 (6) |
C6—C1—C2—C3 | 0.4 (6) | O1—C1—C6—C5 | 176.7 (5) |
C7—C2—C3—C4 | −175.2 (4) | C2—C1—C6—C5 | −1.6 (7) |
C1—C2—C3—C4 | 1.9 (7) | O1—C1—C6—Cl2 | −1.8 (6) |
C7—C2—C3—C8 | −0.1 (7) | C2—C1—C6—Cl2 | 179.9 (3) |
C1—C2—C3—C8 | 177.0 (4) | C13—N3—C9—C10 | 1.1 (10) |
C2—C3—C4—O2 | 176.5 (4) | C14—N3—C9—C10 | 178.5 (7) |
C8—C3—C4—O2 | 1.2 (7) | N3—C9—C10—C11 | 0.6 (11) |
C2—C3—C4—C5 | −3.0 (7) | C9—C10—C11—C12 | −1.0 (11) |
C8—C3—C4—C5 | −178.3 (4) | C9—C10—C11—C15 | −177.1 (7) |
O2—C4—C5—C6 | −177.7 (5) | C10—C11—C12—C13 | −0.3 (11) |
C3—C4—C5—C6 | 1.8 (6) | C15—C11—C12—C13 | 175.9 (7) |
O2—C4—C5—Cl1 | 1.8 (6) | C9—N3—C13—C12 | −2.5 (11) |
C3—C4—C5—Cl1 | −178.7 (3) | C14—N3—C13—C12 | −179.9 (7) |
C4—C5—C6—C1 | 0.5 (7) | C11—C12—C13—N3 | 2.0 (11) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 346.15 | Dx = 1.965 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1216 (6) Å | Cell parameters from 781 reflections |
b = 9.806 (4) Å | θ = 2.1–25.4° |
c = 19.603 (3) Å | µ = 0.57 mm−1 |
β = 96.013 (12)° | T = 293 K |
V = 1170.2 (5) Å3 | Block, black |
Z = 4 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1271 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 651 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.157 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.4°, θmin = 2.1° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.372 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.367, Tmax = 0.449 | k = −8→7 |
5803 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.116 | H-atom parameters constrained |
wR(F2) = 0.348 | w = 1/[σ2(Fo2) + (0.1997P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1271 reflections | Δρmax = 0.85 e Å−3 |
94 parameters | Δρmin = −0.61 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 | ||
Cl1 | 0.2330 (4) | 0.1147 (5) | −0.00304 (14) | 0.0317 (11)* | |
Cl2 | 0.1409 (5) | 0.2868 (5) | 0.12592 (14) | 0.0322 (11)* | |
O1 | 0.1688 (13) | 0.5779 (12) | 0.1035 (4) | 0.034 (2)* | |
O2 | 0.3290 (12) | 0.2806 (13) | −0.1168 (4) | 0.032 (2)* | |
N1 | 0.2663 (14) | 0.833 (2) | −0.0083 (4) | 0.031 (3)* | |
N2 | 0.4022 (17) | 0.6025 (16) | −0.1796 (5) | 0.041 (3)* | |
N3 | 0.3073 (14) | 0.9631 (15) | 0.1777 (5) | 0.031 (3)* | |
N4 | 1.0364 (16) | 1.2243 (16) | 0.2584 (5) | 0.041 (3)* | |
C1 | 0.2130 (16) | 0.5100 (19) | 0.0533 (5) | 0.023 (3)* | |
C2 | 0.2692 (17) | 0.572 (2) | −0.0081 (5) | 0.028 (3)* | |
C3 | 0.3121 (15) | 0.4940 (18) | −0.0668 (5) | 0.021 (3)* | |
C4 | 0.2982 (16) | 0.3484 (18) | −0.0677 (5) | 0.020 (3)* | |
C5 | 0.2450 (15) | 0.2834 (18) | −0.0027 (5) | 0.019 (3)* | |
C6 | 0.2069 (15) | 0.3638 (17) | 0.0535 (5) | 0.017 (3)* | |
C7 | 0.2670 (16) | 0.717 (3) | −0.0095 (5) | 0.022 (3)* | |
C8 | 0.3582 (18) | 0.5587 (19) | −0.1276 (6) | 0.029 (3)* | |
C9 | 0.3299 (18) | 1.0085 (19) | 0.2412 (6) | 0.030 (3)* | |
H9 | 0.224263 | 0.988619 | 0.270565 | 0.036* | |
C10 | 0.5143 (19) | 1.0869 (18) | 0.2643 (6) | 0.035 (3)* | |
H10 | 0.531026 | 1.124810 | 0.307983 | 0.041* | |
C11 | 0.6672 (18) | 1.1050 (17) | 0.2198 (6) | 0.029 (3)* | |
C12 | 0.637 (2) | 1.059 (2) | 0.1534 (7) | 0.039 (3)* | |
H12 | 0.737800 | 1.078936 | 0.122441 | 0.047* | |
C13 | 0.4545 (17) | 0.9846 (19) | 0.1348 (6) | 0.035 (3)* | |
H13 | 0.433130 | 0.947909 | 0.090830 | 0.042* | |
C14 | 0.113 (2) | 0.879 (2) | 0.1549 (7) | 0.041 (4)* | |
H14A | 0.036888 | 0.855841 | 0.193785 | 0.061* | |
H14B | 0.158911 | 0.797038 | 0.133790 | 0.061* | |
H14C | 0.016239 | 0.929452 | 0.122408 | 0.061* | |
C15 | 0.8699 (19) | 1.175 (2) | 0.2423 (6) | 0.036 (4)* |
Cl1—C5 | 1.656 (17) | C3—C4 | 1.43 (2) |
Cl2—C6 | 1.694 (12) | C4—C5 | 1.491 (16) |
O1—C1 | 1.239 (16) | C5—C6 | 1.394 (18) |
O2—C4 | 1.201 (15) | C9—C10 | 1.401 (19) |
N1—C7 | 1.14 (2) | C9—H9 | 0.9300 |
N2—C8 | 1.163 (15) | C10—C11 | 1.356 (17) |
N3—C13 | 1.313 (14) | C10—H10 | 0.9300 |
N3—C9 | 1.315 (15) | C11—C12 | 1.369 (18) |
N3—C14 | 1.479 (18) | C11—C15 | 1.445 (19) |
N4—C15 | 1.143 (15) | C12—C13 | 1.354 (19) |
C1—C2 | 1.423 (18) | C12—H12 | 0.9300 |
C1—C6 | 1.43 (2) | C13—H13 | 0.9300 |
C2—C7 | 1.42 (2) | C14—H14A | 0.9600 |
C2—C3 | 1.428 (19) | C14—H14B | 0.9600 |
C3—C8 | 1.405 (18) | C14—H14C | 0.9600 |
C13—N3—C9 | 122.8 (12) | N3—C9—C10 | 119.5 (11) |
C13—N3—C14 | 118.7 (11) | N3—C9—H9 | 120.3 |
C9—N3—C14 | 118.4 (9) | C10—C9—H9 | 120.3 |
O1—C1—C2 | 122.2 (17) | C11—C10—C9 | 116.8 (12) |
O1—C1—C6 | 121.8 (12) | C11—C10—H10 | 121.6 |
C2—C1—C6 | 115.9 (12) | C9—C10—H10 | 121.6 |
C7—C2—C1 | 116.2 (12) | C10—C11—C12 | 122.3 (12) |
C7—C2—C3 | 121.5 (11) | C10—C11—C15 | 119.6 (11) |
C1—C2—C3 | 122.3 (17) | C12—C11—C15 | 118.1 (10) |
C8—C3—C2 | 120.8 (15) | C13—C12—C11 | 117.3 (12) |
C8—C3—C4 | 117.2 (11) | C13—C12—H12 | 121.3 |
C2—C3—C4 | 121.9 (11) | C11—C12—H12 | 121.3 |
O2—C4—C3 | 123.3 (11) | N3—C13—C12 | 121.1 (12) |
O2—C4—C5 | 121.0 (15) | N3—C13—H13 | 119.5 |
C3—C4—C5 | 115.7 (10) | C12—C13—H13 | 119.5 |
C6—C5—C4 | 120.2 (15) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 123.9 (10) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 115.9 (9) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 123.9 (11) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 119.0 (13) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 117.1 (8) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 177.8 (11) | N4—C15—C11 | 176.1 (17) |
N2—C8—C3 | 174.7 (17) | ||
O1—C1—C2—C7 | −1.4 (15) | Cl1—C5—C6—C1 | −178.7 (8) |
C6—C1—C2—C7 | 177.6 (10) | C4—C5—C6—Cl2 | 178.6 (7) |
O1—C1—C2—C3 | −177.6 (10) | Cl1—C5—C6—Cl2 | −0.8 (12) |
C6—C1—C2—C3 | 1.4 (14) | O1—C1—C6—C5 | 176.9 (10) |
C7—C2—C3—C8 | 1.3 (15) | C2—C1—C6—C5 | −2.2 (15) |
C1—C2—C3—C8 | 177.3 (10) | O1—C1—C6—Cl2 | −1.1 (14) |
C7—C2—C3—C4 | −175.2 (10) | C2—C1—C6—Cl2 | 179.9 (7) |
C1—C2—C3—C4 | 0.9 (15) | C13—N3—C9—C10 | 2 (2) |
C8—C3—C4—O2 | 1.8 (15) | C14—N3—C9—C10 | 179.2 (15) |
C2—C3—C4—O2 | 178.4 (9) | N3—C9—C10—C11 | −4 (2) |
C8—C3—C4—C5 | −178.9 (8) | C9—C10—C11—C12 | 5 (2) |
C2—C3—C4—C5 | −2.3 (14) | C9—C10—C11—C15 | −174.7 (15) |
O2—C4—C5—C6 | −179.1 (10) | C10—C11—C12—C13 | −5 (2) |
C3—C4—C5—C6 | 1.6 (13) | C15—C11—C12—C13 | 174.8 (16) |
O2—C4—C5—Cl1 | 0.3 (13) | C9—N3—C13—C12 | −2 (2) |
C3—C4—C5—Cl1 | −179.0 (8) | C14—N3—C13—C12 | −179.1 (16) |
C4—C5—C6—C1 | 0.7 (15) | C11—C12—C13—N3 | 3 (2) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 276.92 | Dx = 1.989 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0779 (9) Å | Cell parameters from 654 reflections |
b = 9.783 (6) Å | θ = 2.1–22.9° |
c = 19.555 (4) Å | µ = 0.58 mm−1 |
β = 96.225 (16)° | T = 293 K |
V = 1155.9 (7) Å3 | Block, black |
Z = 5 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1257 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 593 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.173 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.1° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.367 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.362, Tmax = 0.449 | k = −7→7 |
5634 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.137 | H-atom parameters constrained |
wR(F2) = 0.384 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1257 reflections | Δρmax = 0.90 e Å−3 |
94 parameters | Δρmin = −0.79 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 | ||
Cl1 | 0.2345 (5) | 0.1144 (6) | −0.00246 (16) | 0.0315 (12)* | |
Cl2 | 0.1426 (5) | 0.2870 (6) | 0.12660 (17) | 0.0339 (13)* | |
O1 | 0.1723 (14) | 0.5776 (14) | 0.1038 (5) | 0.033 (3)* | |
O2 | 0.3309 (14) | 0.2805 (16) | −0.1177 (4) | 0.033 (3)* | |
N1 | 0.2624 (16) | 0.835 (2) | −0.0086 (5) | 0.031 (3)* | |
N2 | 0.398 (2) | 0.604 (2) | −0.1807 (7) | 0.046 (4)* | |
N3 | 0.3047 (16) | 0.9615 (18) | 0.1772 (5) | 0.029 (3)* | |
N4 | 1.0406 (19) | 1.2265 (19) | 0.2604 (6) | 0.044 (4)* | |
C1 | 0.2136 (19) | 0.514 (2) | 0.0532 (7) | 0.026 (4)* | |
C2 | 0.2705 (18) | 0.571 (2) | −0.0088 (6) | 0.021 (4)* | |
C3 | 0.3133 (17) | 0.493 (2) | −0.0679 (6) | 0.020 (3)* | |
C4 | 0.3006 (18) | 0.348 (2) | −0.0666 (6) | 0.020 (3)* | |
C5 | 0.2456 (17) | 0.284 (2) | −0.0031 (5) | 0.016 (3)* | |
C6 | 0.2106 (19) | 0.367 (2) | 0.0551 (6) | 0.022 (3)* | |
C7 | 0.2667 (17) | 0.713 (3) | −0.0100 (5) | 0.015 (3)* | |
C8 | 0.355 (2) | 0.556 (2) | −0.1288 (7) | 0.026 (4)* | |
C9 | 0.332 (2) | 1.004 (2) | 0.2412 (7) | 0.029 (4)* | |
H9 | 0.232136 | 0.977841 | 0.271484 | 0.034* | |
C10 | 0.511 (2) | 1.089 (2) | 0.2645 (8) | 0.038 (4)* | |
H10 | 0.521501 | 1.129864 | 0.307581 | 0.046* | |
C11 | 0.671 (2) | 1.108 (2) | 0.2200 (8) | 0.038 (4)* | |
C12 | 0.643 (3) | 1.060 (2) | 0.1544 (8) | 0.045 (4)* | |
H12 | 0.747641 | 1.078000 | 0.124113 | 0.054* | |
C13 | 0.458 (2) | 0.985 (2) | 0.1340 (7) | 0.043 (4)* | |
H13 | 0.438308 | 0.949846 | 0.089612 | 0.051* | |
C14 | 0.112 (2) | 0.884 (2) | 0.1539 (8) | 0.042 (4)* | |
H14A | 0.036993 | 0.925753 | 0.113540 | 0.051* | |
H14B | 0.014627 | 0.880639 | 0.189400 | 0.051* | |
H14C | 0.154693 | 0.792402 | 0.143078 | 0.051* | |
C15 | 0.872 (2) | 1.180 (2) | 0.2438 (7) | 0.037 (4)* |
Cl1—C5 | 1.66 (2) | C3—C4 | 1.42 (2) |
Cl2—C6 | 1.695 (15) | C4—C5 | 1.465 (19) |
O1—C1 | 1.218 (18) | C5—C6 | 1.44 (2) |
O2—C4 | 1.230 (18) | C9—C10 | 1.40 (2) |
N1—C7 | 1.19 (2) | C9—H9 | 0.9300 |
N2—C8 | 1.170 (18) | C10—C11 | 1.39 (2) |
N3—C9 | 1.312 (17) | C10—H10 | 0.9300 |
N3—C13 | 1.346 (17) | C11—C12 | 1.36 (2) |
N3—C14 | 1.43 (2) | C11—C15 | 1.44 (2) |
N4—C15 | 1.135 (18) | C12—C13 | 1.36 (2) |
C1—C2 | 1.41 (2) | C12—H12 | 0.9300 |
C1—C6 | 1.43 (3) | C13—H13 | 0.9300 |
C2—C7 | 1.39 (2) | C14—H14A | 0.9600 |
C2—C3 | 1.43 (2) | C14—H14B | 0.9600 |
C3—C8 | 1.39 (2) | C14—H14C | 0.9600 |
C9—N3—C13 | 121.2 (13) | N3—C9—C10 | 120.8 (13) |
C9—N3—C14 | 119.3 (11) | N3—C9—H9 | 119.6 |
C13—N3—C14 | 119.5 (13) | C10—C9—H9 | 119.6 |
O1—C1—C2 | 126 (2) | C11—C10—C9 | 116.6 (15) |
O1—C1—C6 | 119.0 (14) | C11—C10—H10 | 121.7 |
C2—C1—C6 | 115.0 (14) | C9—C10—H10 | 121.7 |
C7—C2—C1 | 113.8 (14) | C12—C11—C10 | 121.5 (16) |
C7—C2—C3 | 121.6 (13) | C12—C11—C15 | 119.1 (13) |
C1—C2—C3 | 124.4 (19) | C10—C11—C15 | 119.3 (14) |
C8—C3—C4 | 118.4 (13) | C11—C12—C13 | 118.3 (15) |
C8—C3—C2 | 121.3 (18) | C11—C12—H12 | 120.8 |
C4—C3—C2 | 120.2 (13) | C13—C12—H12 | 120.8 |
O2—C4—C3 | 120.7 (13) | N3—C13—C12 | 121.0 (15) |
O2—C4—C5 | 121.5 (17) | N3—C13—H13 | 119.5 |
C3—C4—C5 | 117.8 (12) | C12—C13—H13 | 119.5 |
C6—C5—C4 | 119.4 (17) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 123.7 (11) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 116.9 (11) | H14A—C14—H14B | 109.5 |
C1—C6—C5 | 123.2 (13) | N3—C14—H14C | 109.5 |
C1—C6—Cl2 | 119.4 (10) | H14A—C14—H14C | 109.5 |
C5—C6—Cl2 | 117.3 (15) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 177.7 (11) | N4—C15—C11 | 174 (2) |
N2—C8—C3 | 176.6 (19) | ||
O1—C1—C2—C7 | −2.9 (18) | C2—C1—C6—C5 | −4.6 (17) |
C6—C1—C2—C7 | 178.4 (11) | O1—C1—C6—Cl2 | 1.7 (16) |
O1—C1—C2—C3 | −178.5 (12) | C2—C1—C6—Cl2 | −179.5 (9) |
C6—C1—C2—C3 | 2.8 (17) | C4—C5—C6—C1 | 3.8 (17) |
C7—C2—C3—C8 | 0.7 (17) | Cl1—C5—C6—C1 | −178.0 (9) |
C1—C2—C3—C8 | 176.0 (12) | C4—C5—C6—Cl2 | 178.9 (8) |
C7—C2—C3—C4 | −175.5 (11) | Cl1—C5—C6—Cl2 | −2.9 (14) |
C1—C2—C3—C4 | −0.2 (17) | C13—N3—C9—C10 | 7 (3) |
C8—C3—C4—O2 | 1.6 (17) | C14—N3—C9—C10 | −175.4 (18) |
C2—C3—C4—O2 | 177.9 (10) | N3—C9—C10—C11 | −9 (3) |
C8—C3—C4—C5 | −177.1 (10) | C9—C10—C11—C12 | 8 (3) |
C2—C3—C4—C5 | −0.7 (16) | C9—C10—C11—C15 | −172.6 (19) |
O2—C4—C5—C6 | −179.6 (11) | C10—C11—C12—C13 | −4 (3) |
C3—C4—C5—C6 | −1.0 (15) | C15—C11—C12—C13 | 176 (2) |
O2—C4—C5—Cl1 | 2.0 (15) | C9—N3—C13—C12 | −3 (3) |
C3—C4—C5—Cl1 | −179.3 (8) | C14—N3—C13—C12 | 179.4 (19) |
O1—C1—C6—C5 | 176.6 (11) | C11—C12—C13—N3 | 2 (3) |
C8Cl2N2O2·C7H7N2 | F(000) = 700 |
Mr = 276.92 | Dx = 2.017 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0307 (11) Å | Cell parameters from 616 reflections |
b = 9.769 (6) Å | θ = 2.1–25.7° |
c = 19.465 (5) Å | µ = 0.59 mm−1 |
β = 96.336 (18)° | T = 293 K |
V = 1139.8 (8) Å3 | Block, black |
Z = 5 | 0.25 × 0.10 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1226 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.171 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 25.3°, θmin = 2.1° |
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.376 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium | h = −7→7 |
Tmin = 0.371, Tmax = 0.449 | k = −7→7 |
5596 measured reflections | l = −22→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.141 | H-atom parameters constrained |
wR(F2) = 0.399 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1226 reflections | Δρmax = 0.99 e Å−3 |
94 parameters | Δρmin = −0.85 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 | ||
Cl1 | 0.2338 (6) | 0.1131 (6) | −0.00176 (18) | 0.0342 (13)* | |
Cl2 | 0.1432 (6) | 0.2879 (7) | 0.12747 (18) | 0.0359 (14)* | |
O1 | 0.1716 (16) | 0.5766 (16) | 0.1044 (5) | 0.039 (3)* | |
O2 | 0.3299 (15) | 0.2801 (17) | −0.1176 (5) | 0.035 (3)* | |
N1 | 0.2674 (19) | 0.838 (3) | −0.0094 (6) | 0.038 (4)* | |
N2 | 0.398 (2) | 0.605 (2) | −0.1823 (7) | 0.048 (4)* | |
N3 | 0.3007 (18) | 0.966 (2) | 0.1760 (6) | 0.035 (3)* | |
N4 | 1.040 (2) | 1.227 (2) | 0.2611 (7) | 0.050 (4)* | |
C1 | 0.217 (2) | 0.512 (2) | 0.0532 (7) | 0.026 (4)* | |
C2 | 0.268 (2) | 0.574 (3) | −0.0092 (7) | 0.030 (4)* | |
C3 | 0.312 (2) | 0.497 (2) | −0.0680 (7) | 0.027 (4)* | |
C4 | 0.294 (2) | 0.352 (2) | −0.0667 (7) | 0.030 (4)* | |
C5 | 0.2516 (19) | 0.285 (2) | −0.0028 (6) | 0.025 (4)* | |
C6 | 0.2075 (18) | 0.365 (2) | 0.0543 (6) | 0.015 (3)* | |
C7 | 0.2644 (19) | 0.722 (3) | −0.0105 (6) | 0.016 (4)* | |
C8 | 0.355 (2) | 0.558 (3) | −0.1295 (8) | 0.033 (4)* | |
C9 | 0.328 (2) | 1.007 (2) | 0.2407 (7) | 0.028 (4)* | |
H9 | 0.227026 | 0.981082 | 0.271044 | 0.033* | |
C10 | 0.511 (2) | 1.092 (2) | 0.2639 (8) | 0.036 (4)* | |
H10 | 0.524249 | 1.132805 | 0.307301 | 0.043* | |
C11 | 0.667 (2) | 1.110 (2) | 0.2198 (8) | 0.037 (5)* | |
C12 | 0.643 (2) | 1.065 (2) | 0.1533 (8) | 0.033 (4)* | |
H12 | 0.744876 | 1.086646 | 0.122563 | 0.040* | |
C13 | 0.462 (2) | 0.988 (2) | 0.1347 (8) | 0.041 (5)* | |
H13 | 0.447855 | 0.947057 | 0.091224 | 0.049* | |
C14 | 0.110 (3) | 0.883 (3) | 0.1514 (8) | 0.045 (5)* | |
H14A | 0.159668 | 0.793884 | 0.139371 | 0.067* | |
H14B | 0.031882 | 0.925702 | 0.111317 | 0.067* | |
H14C | 0.012970 | 0.875539 | 0.186951 | 0.067* | |
C15 | 0.873 (2) | 1.180 (2) | 0.2436 (7) | 0.035 (4)* |
Cl1—C5 | 1.69 (2) | C3—C4 | 1.42 (3) |
Cl2—C6 | 1.694 (15) | C4—C5 | 1.45 (2) |
O1—C1 | 1.234 (19) | C5—C6 | 1.41 (2) |
O2—C4 | 1.25 (2) | C9—C10 | 1.41 (2) |
N1—C7 | 1.14 (2) | C9—H9 | 0.9300 |
N2—C8 | 1.180 (19) | C10—C11 | 1.35 (2) |
N3—C9 | 1.317 (18) | C10—H10 | 0.9300 |
N3—C13 | 1.345 (18) | C11—C12 | 1.36 (2) |
N3—C14 | 1.44 (2) | C11—C15 | 1.45 (2) |
N4—C15 | 1.123 (19) | C12—C13 | 1.34 (2) |
C1—C2 | 1.42 (2) | C12—H12 | 0.9300 |
C1—C6 | 1.44 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.42 (2) | C14—H14A | 0.9600 |
C2—C7 | 1.44 (3) | C14—H14B | 0.9600 |
C3—C8 | 1.39 (2) | C14—H14C | 0.9600 |
C9—N3—C13 | 120.0 (14) | N3—C9—C10 | 119.8 (13) |
C9—N3—C14 | 120.1 (12) | N3—C9—H9 | 120.1 |
C13—N3—C14 | 119.5 (14) | C10—C9—H9 | 120.1 |
O1—C1—C2 | 124 (2) | C11—C10—C9 | 116.6 (16) |
O1—C1—C6 | 119.1 (15) | C11—C10—H10 | 121.7 |
C2—C1—C6 | 116.7 (14) | C9—C10—H10 | 121.7 |
C3—C2—C1 | 123 (2) | C10—C11—C12 | 123.5 (16) |
C3—C2—C7 | 121.3 (15) | C10—C11—C15 | 119.3 (15) |
C1—C2—C7 | 115.7 (14) | C12—C11—C15 | 117.1 (13) |
C8—C3—C2 | 123 (2) | C13—C12—C11 | 116.0 (14) |
C8—C3—C4 | 117.6 (14) | C13—C12—H12 | 122.0 |
C2—C3—C4 | 119.4 (15) | C11—C12—H12 | 122.0 |
O2—C4—C3 | 121.6 (15) | C12—C13—N3 | 123.2 (16) |
O2—C4—C5 | 119 (2) | C12—C13—H13 | 118.4 |
C3—C4—C5 | 118.9 (14) | N3—C13—H13 | 118.4 |
C6—C5—C4 | 119.7 (19) | N3—C14—H14A | 109.5 |
C6—C5—Cl1 | 121.8 (13) | N3—C14—H14B | 109.5 |
C4—C5—Cl1 | 118.4 (13) | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 122.1 (14) | N3—C14—H14C | 109.5 |
C5—C6—Cl2 | 119.9 (16) | H14A—C14—H14C | 109.5 |
C1—C6—Cl2 | 118.0 (10) | H14B—C14—H14C | 109.5 |
N1—C7—C2 | 177.4 (14) | N4—C15—C11 | 176 (2) |
N2—C8—C3 | 177 (2) | ||
O1—C1—C2—C3 | −177.7 (13) | Cl1—C5—C6—C1 | −178.4 (10) |
C6—C1—C2—C3 | −0.7 (18) | C4—C5—C6—Cl2 | 176.6 (9) |
O1—C1—C2—C7 | −0.3 (19) | Cl1—C5—C6—Cl2 | 2.1 (15) |
C6—C1—C2—C7 | 176.6 (12) | O1—C1—C6—C5 | 178.4 (12) |
C1—C2—C3—C8 | 177.9 (13) | C2—C1—C6—C5 | 1.3 (18) |
C7—C2—C3—C8 | 0.6 (19) | O1—C1—C6—Cl2 | −2.1 (17) |
C1—C2—C3—C4 | 3 (2) | C2—C1—C6—Cl2 | −179.2 (9) |
C7—C2—C3—C4 | −174.3 (12) | C13—N3—C9—C10 | 9 (3) |
C8—C3—C4—O2 | 4 (2) | C14—N3—C9—C10 | −177.9 (19) |
C2—C3—C4—O2 | 179.5 (12) | N3—C9—C10—C11 | −9 (3) |
C8—C3—C4—C5 | 179.4 (11) | C9—C10—C11—C12 | 7 (3) |
C2—C3—C4—C5 | −5.4 (19) | C9—C10—C11—C15 | −171.7 (19) |
O2—C4—C5—C6 | −178.8 (12) | C10—C11—C12—C13 | −6 (3) |
C3—C4—C5—C6 | 5.9 (18) | C15—C11—C12—C13 | 173 (2) |
O2—C4—C5—Cl1 | −4.2 (17) | C11—C12—C13—N3 | 7 (3) |
C3—C4—C5—Cl1 | −179.4 (10) | C9—N3—C13—C12 | −8 (3) |
C4—C5—C6—C1 | −3.9 (18) | C14—N3—C13—C12 | 179 (2) |