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The effects of temperature (100–370 K) and pressure (0–6 GPa) on the non-localized two-electron multicentric covalent bonds (`pancake bonding') in closely bound radical dimers were studied using single-crystal X-ray diffraction on a 4-cyano-N-methyl­pyridinium salt of 5,6-di­chloro-2,3-di­cyano­semi­quinone radical anion (DDQ) as the sample compound. On cooling, the anisotropic structural compression was accompanied by continuous changes in molecular stacking; the discontinuities in the changes in volume and b and c cell parameters suggest that a phase transition occurs between 210 and 240 K. At a pressure of 2.55 GPa, distances between radical dimers shortened to 2.9 Å, which corresponds to distances observed in extended π-bonded polymers. Increasing pressure further to 6 GPa reduced the interplanar separation of the radicals to 2.75 Å. This may indicate that the covalent component of the interaction significantly increased, in accordance with the results of DFT calculations reported elsewhere [Molčanov et al. (2019), Cryst. Growth Des. 19, 391–402].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620002772/xk5067sup1.cif
Contains datablocks global, 100K_v2_a, 120K_v2, 150K, 180K, 210K, 240K, 270K, 293K, 310K, 340K, 370K, 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

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067100K_v2_asup2.hkl
Contains datablock 100K_v2_a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067120K_v2sup3.hkl
Contains datablock 120K_v2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067150Ksup4.hkl
Contains datablock 150K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067180Ksup5.hkl
Contains datablock 180K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067210Ksup6.hkl
Contains datablock 210K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067240Ksup7.hkl
Contains datablock 240K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067270Ksup8.hkl
Contains datablock 270K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067293Ksup9.hkl
Contains datablock 293K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067310Ksup10.hkl
Contains datablock 310K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067340Ksup11.hkl
Contains datablock 340K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067370Ksup12.hkl
Contains datablock 370K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_ddq_4cnsup13.hkl
Contains datablock test3_ddq_4cn

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.25GPasup14.hkl
Contains datablock test3_0.25GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.49GPasup15.hkl
Contains datablock test3_0.49GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_0.86GPasup16.hkl
Contains datablock test3_0.86GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_1.42GPasup17.hkl
Contains datablock test3_1.42GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_1.85GPasup18.hkl
Contains datablock test3_1.85GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_2.55GPasup19.hkl
Contains datablock test3_2.55GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_3.09GPasup20.hkl
Contains datablock test3_3.09GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_3.95GPasup21.hkl
Contains datablock test3_3.95GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_4.80GPasup22.hkl
Contains datablock test3_4.80GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_5.48GPasup23.hkl
Contains datablock test3_5.48GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620002772/xk5067test3_6.00GPasup24.hkl
Contains datablock test3_6.00GPa

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620002772/xk5067sup25.pdf
Tables S1 to S5

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

Computing details top

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).

(100K_v2_a) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.665 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.7437 (1) ÅCell parameters from 4986 reflections
b = 10.0558 (2) Åθ = 2.0–28.1°
c = 20.4325 (4) ŵ = 0.49 mm1
β = 94.828 (2)°T = 100 K
V = 1380.68 (4) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3025 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 78
Tmin = 0.958, Tmax = 1.000k = 1212
8958 measured reflectionsl = 2625
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-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 reflectionsΔρmax = 0.42 e Å3
209 parametersΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20839 (6)0.11213 (4)0.00692 (2)0.01412 (10)
N40.9971 (2)1.20526 (15)0.24921 (7)0.0199 (3)
Cl20.11858 (6)0.28111 (4)0.11765 (2)0.01427 (10)
C150.8453 (3)1.15719 (16)0.23625 (8)0.0160 (3)
O10.13549 (16)0.56748 (11)0.09454 (5)0.0141 (2)
O20.29019 (17)0.27739 (11)0.11898 (5)0.0157 (2)
N10.2964 (2)0.81495 (14)0.00674 (7)0.0171 (3)
N20.4174 (2)0.59870 (14)0.16878 (7)0.0173 (3)
C10.1808 (2)0.50059 (16)0.04682 (7)0.0110 (3)
C20.2475 (2)0.56100 (15)0.01202 (7)0.0112 (3)
C30.2886 (2)0.48723 (16)0.06644 (7)0.0117 (3)
C40.2644 (2)0.34343 (16)0.06915 (7)0.0119 (3)
C50.2144 (2)0.28256 (15)0.00757 (7)0.0115 (3)
C60.1752 (2)0.35472 (16)0.04580 (7)0.0116 (3)
C70.2746 (2)0.70222 (16)0.00955 (7)0.0123 (3)
C80.3593 (2)0.55030 (16)0.12323 (8)0.0128 (3)
N30.3182 (2)0.95368 (13)0.18261 (7)0.0149 (3)
C90.3503 (2)0.99969 (16)0.24440 (8)0.0149 (3)
H90.2542260.9842620.2750010.018*
C100.5213 (2)1.06895 (16)0.26355 (8)0.0143 (3)
H100.5445761.1014180.3071810.017*
C110.6593 (2)1.09053 (15)0.21786 (8)0.0138 (3)
C120.6227 (3)1.04289 (17)0.15402 (8)0.0164 (3)
H120.7150771.0582970.1222330.020*
C130.4509 (3)0.97341 (16)0.13793 (8)0.0171 (3)
H130.4251390.9387720.0947990.021*
C140.1367 (3)0.87596 (19)0.16300 (9)0.0241 (4)
H14A0.0605010.9206360.1263910.036*
H14B0.0549630.8690760.2003130.036*
H14C0.1742360.7866920.1492960.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0199 (2)0.00834 (18)0.01423 (19)0.00039 (14)0.00207 (15)0.00020 (13)
N40.0230 (8)0.0209 (8)0.0163 (7)0.0036 (6)0.0038 (6)0.0025 (6)
Cl20.0189 (2)0.01392 (19)0.01031 (18)0.00114 (14)0.00294 (14)0.00226 (13)
C150.0226 (9)0.0146 (8)0.0115 (8)0.0017 (7)0.0052 (6)0.0017 (6)
O10.0166 (6)0.0145 (6)0.0116 (5)0.0010 (4)0.0023 (4)0.0032 (4)
O20.0227 (6)0.0134 (6)0.0114 (5)0.0022 (5)0.0037 (5)0.0016 (4)
N10.0186 (7)0.0136 (8)0.0191 (7)0.0011 (6)0.0007 (6)0.0003 (6)
N20.0202 (7)0.0170 (7)0.0149 (7)0.0025 (6)0.0027 (6)0.0006 (6)
C10.0090 (7)0.0121 (8)0.0118 (7)0.0002 (6)0.0003 (6)0.0003 (6)
C20.0102 (7)0.0097 (7)0.0134 (7)0.0006 (6)0.0009 (6)0.0005 (6)
C30.0110 (7)0.0137 (8)0.0105 (7)0.0009 (6)0.0007 (6)0.0011 (6)
C40.0110 (7)0.0123 (8)0.0123 (7)0.0021 (6)0.0001 (6)0.0000 (6)
C50.0127 (7)0.0081 (7)0.0132 (7)0.0007 (6)0.0008 (6)0.0014 (6)
C60.0121 (8)0.0128 (8)0.0099 (7)0.0004 (6)0.0013 (6)0.0028 (6)
C70.0102 (7)0.0167 (9)0.0099 (7)0.0002 (6)0.0012 (6)0.0004 (6)
C80.0139 (8)0.0103 (7)0.0141 (8)0.0012 (6)0.0000 (6)0.0026 (6)
N30.0167 (7)0.0109 (7)0.0166 (7)0.0017 (5)0.0025 (5)0.0000 (5)
C90.0171 (8)0.0132 (8)0.0145 (8)0.0030 (6)0.0016 (6)0.0022 (6)
C100.0189 (8)0.0128 (8)0.0112 (7)0.0031 (6)0.0007 (6)0.0001 (6)
C110.0168 (8)0.0100 (7)0.0145 (8)0.0024 (6)0.0001 (6)0.0017 (6)
C120.0210 (9)0.0167 (8)0.0118 (8)0.0022 (7)0.0036 (6)0.0019 (6)
C130.0254 (9)0.0141 (8)0.0115 (8)0.0055 (7)0.0007 (6)0.0006 (6)
C140.0219 (9)0.0220 (9)0.0272 (10)0.0037 (7)0.0051 (7)0.0026 (7)
Geometric parameters (Å, º) top
Cl1—C51.7145 (15)C5—C61.354 (2)
N4—C151.143 (2)N3—C91.345 (2)
Cl2—C61.7157 (15)N3—C131.346 (2)
C15—C111.444 (2)N3—C141.479 (2)
O1—C11.2437 (18)C9—C101.376 (2)
O2—C41.2402 (19)C9—H90.9500
N1—C71.144 (2)C10—C111.390 (2)
N2—C81.148 (2)C10—H100.9500
C1—C21.452 (2)C11—C121.392 (2)
C1—C61.467 (2)C12—C131.369 (2)
C2—C31.384 (2)C12—H120.9500
C2—C71.432 (2)C13—H130.9500
C3—C81.438 (2)C14—H14A0.9800
C3—C41.456 (2)C14—H14B0.9800
C4—C51.464 (2)C14—H14C0.9800
N4—C15—C11176.66 (18)C13—N3—C14118.46 (14)
O1—C1—C2122.45 (14)N3—C9—C10120.37 (15)
O1—C1—C6122.96 (14)N3—C9—H9119.8
C2—C1—C6114.58 (13)C10—C9—H9119.8
C3—C2—C7121.75 (14)C9—C10—C11118.75 (15)
C3—C2—C1122.55 (14)C9—C10—H10120.6
C7—C2—C1115.67 (14)C11—C10—H10120.6
C2—C3—C8120.95 (14)C10—C11—C12119.96 (15)
C2—C3—C4122.24 (14)C10—C11—C15120.93 (14)
C8—C3—C4116.81 (14)C12—C11—C15119.05 (15)
O2—C4—C3122.68 (14)C13—C12—C11118.73 (15)
O2—C4—C5122.70 (14)C13—C12—H12120.6
C3—C4—C5114.58 (13)C11—C12—H12120.6
C6—C5—C4122.87 (14)N3—C13—C12120.65 (15)
C6—C5—Cl1121.54 (12)N3—C13—H13119.7
C4—C5—Cl1115.59 (11)C12—C13—H13119.7
C5—C6—C1122.72 (14)N3—C14—H14A109.5
C5—C6—Cl2122.04 (12)N3—C14—H14B109.5
C1—C6—Cl2115.24 (11)H14A—C14—H14B109.5
N1—C7—C2179.14 (17)N3—C14—H14C109.5
N2—C8—C3178.86 (17)H14A—C14—H14C109.5
C9—N3—C13121.52 (15)H14B—C14—H14C109.5
C9—N3—C14119.99 (14)
O1—C1—C2—C3176.73 (15)Cl1—C5—C6—C1179.51 (12)
C6—C1—C2—C34.4 (2)C4—C5—C6—Cl2179.56 (12)
O1—C1—C2—C75.2 (2)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.62 (13)O1—C1—C6—C5176.38 (15)
C7—C2—C3—C80.4 (2)C2—C1—C6—C54.8 (2)
C1—C2—C3—C8178.39 (14)O1—C1—C6—Cl24.5 (2)
C7—C2—C3—C4179.11 (14)C2—C1—C6—Cl2174.34 (11)
C1—C2—C3—C41.2 (2)C13—N3—C9—C100.1 (2)
C2—C3—C4—O2175.89 (15)C14—N3—C9—C10178.23 (15)
C8—C3—C4—O24.5 (2)N3—C9—C10—C110.2 (2)
C2—C3—C4—C56.3 (2)C9—C10—C11—C120.3 (2)
C8—C3—C4—C5173.27 (13)C9—C10—C11—C15177.09 (15)
O2—C4—C5—C6176.20 (15)C10—C11—C12—C131.0 (2)
C3—C4—C5—C66.0 (2)C15—C11—C12—C13176.46 (15)
O2—C4—C5—Cl13.8 (2)C9—N3—C13—C120.8 (2)
C3—C4—C5—Cl1174.00 (11)C14—N3—C13—C12178.98 (15)
C4—C5—C6—C10.5 (2)C11—C12—C13—N31.2 (2)
(120K_v2) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.659 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.75559 (15) ÅCell parameters from 4912 reflections
b = 10.0647 (2) Åθ = 2.0–28.1°
c = 20.4519 (4) ŵ = 0.48 mm1
β = 94.8065 (19)°T = 120 K
V = 1385.70 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
2682 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 87
Tmin = 0.928, Tmax = 1.000k = 1312
9214 measured reflectionsl = 2627
3171 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-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 reflectionsΔρmax = 0.34 e Å3
209 parametersΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20801 (6)0.11224 (4)0.00695 (2)0.01622 (10)
N40.9964 (2)1.20498 (16)0.24907 (7)0.0231 (3)
Cl20.11839 (6)0.28113 (4)0.11756 (2)0.01644 (10)
C150.8447 (3)1.15698 (17)0.23615 (8)0.0182 (3)
O10.13554 (16)0.56741 (11)0.09448 (5)0.0160 (2)
O20.29025 (18)0.27754 (11)0.11887 (5)0.0180 (3)
N10.2964 (2)0.81469 (14)0.00683 (7)0.0193 (3)
N20.4171 (2)0.59868 (14)0.16860 (7)0.0195 (3)
C10.1807 (2)0.50043 (16)0.04676 (7)0.0125 (3)
C20.2471 (2)0.56082 (15)0.01188 (7)0.0124 (3)
C30.2887 (2)0.48719 (16)0.06634 (7)0.0125 (3)
C40.2643 (2)0.34338 (16)0.06908 (7)0.0128 (3)
C50.2140 (2)0.28270 (15)0.00759 (7)0.0124 (3)
C60.1751 (2)0.35481 (16)0.04578 (7)0.0126 (3)
C70.2751 (2)0.70206 (16)0.00946 (7)0.0138 (3)
C80.3594 (2)0.55007 (16)0.12305 (8)0.0139 (3)
N30.3181 (2)0.95345 (13)0.18273 (7)0.0169 (3)
C90.3504 (2)0.99976 (16)0.24430 (8)0.0170 (3)
H90.2544730.9845560.2748750.020*
C100.5207 (2)1.06883 (16)0.26352 (8)0.0158 (3)
H100.5439861.1012870.3071070.019*
C110.6587 (2)1.09025 (16)0.21764 (8)0.0156 (3)
C120.6221 (3)1.04258 (17)0.15410 (8)0.0189 (4)
H120.7145171.0577950.1223570.023*
C130.4507 (3)0.97332 (17)0.13796 (8)0.0193 (4)
H130.4249360.9389010.0948350.023*
C140.1370 (3)0.87598 (19)0.16316 (10)0.0273 (4)
H14A0.0556130.8688720.2004850.041*
H14B0.1744240.7868690.1493220.041*
H14C0.0608130.9208090.1266920.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0224 (2)0.00946 (19)0.0170 (2)0.00043 (15)0.00266 (15)0.00033 (14)
N40.0258 (8)0.0250 (8)0.0188 (7)0.0050 (7)0.0036 (6)0.0023 (6)
Cl20.0214 (2)0.0161 (2)0.01220 (19)0.00100 (15)0.00350 (14)0.00277 (14)
C150.0243 (9)0.0171 (8)0.0137 (8)0.0006 (7)0.0052 (7)0.0024 (6)
O10.0185 (6)0.0167 (6)0.0130 (5)0.0003 (5)0.0029 (4)0.0040 (4)
O20.0262 (6)0.0142 (6)0.0140 (6)0.0029 (5)0.0040 (5)0.0020 (4)
N10.0209 (8)0.0159 (8)0.0211 (7)0.0013 (6)0.0013 (6)0.0010 (6)
N20.0223 (8)0.0191 (8)0.0173 (7)0.0016 (6)0.0027 (6)0.0015 (6)
C10.0117 (7)0.0130 (8)0.0126 (7)0.0005 (6)0.0000 (6)0.0006 (6)
C20.0118 (7)0.0117 (7)0.0137 (7)0.0001 (6)0.0008 (6)0.0004 (6)
C30.0120 (7)0.0137 (8)0.0119 (7)0.0002 (6)0.0009 (6)0.0018 (6)
C40.0121 (7)0.0136 (8)0.0127 (7)0.0027 (6)0.0007 (6)0.0000 (6)
C50.0129 (7)0.0093 (7)0.0147 (8)0.0001 (6)0.0003 (6)0.0006 (6)
C60.0125 (7)0.0139 (8)0.0115 (7)0.0005 (6)0.0019 (6)0.0023 (6)
C70.0128 (8)0.0171 (9)0.0118 (7)0.0002 (6)0.0017 (6)0.0000 (6)
C80.0144 (8)0.0121 (8)0.0150 (8)0.0012 (6)0.0005 (6)0.0028 (6)
N30.0187 (7)0.0128 (7)0.0184 (7)0.0015 (6)0.0031 (5)0.0004 (5)
C90.0191 (8)0.0161 (8)0.0160 (8)0.0034 (7)0.0026 (6)0.0020 (6)
C100.0193 (8)0.0162 (8)0.0120 (7)0.0038 (6)0.0015 (6)0.0002 (6)
C110.0184 (8)0.0118 (8)0.0167 (8)0.0022 (6)0.0014 (6)0.0023 (6)
C120.0237 (9)0.0185 (9)0.0148 (8)0.0041 (7)0.0035 (7)0.0015 (6)
C130.0275 (9)0.0169 (8)0.0128 (8)0.0049 (7)0.0017 (7)0.0012 (6)
C140.0243 (10)0.0249 (10)0.0313 (10)0.0049 (8)0.0063 (8)0.0043 (8)
Geometric parameters (Å, º) top
Cl1—C51.7161 (16)C5—C61.355 (2)
N4—C151.144 (2)N3—C91.343 (2)
Cl2—C61.7163 (15)N3—C131.349 (2)
C15—C111.447 (2)N3—C141.478 (2)
O1—C11.2448 (18)C9—C101.373 (2)
O2—C41.2396 (19)C9—H90.9500
N1—C71.143 (2)C10—C111.394 (2)
N2—C81.149 (2)C10—H100.9500
C1—C21.449 (2)C11—C121.388 (2)
C1—C61.466 (2)C12—C131.368 (2)
C2—C31.386 (2)C12—H120.9500
C2—C71.434 (2)C13—H130.9500
C3—C81.438 (2)C14—H14A0.9800
C3—C41.457 (2)C14—H14B0.9800
C4—C51.463 (2)C14—H14C0.9800
N4—C15—C11176.56 (18)C13—N3—C14118.45 (14)
O1—C1—C2122.34 (14)N3—C9—C10120.69 (15)
O1—C1—C6122.98 (14)N3—C9—H9119.7
C2—C1—C6114.66 (13)C10—C9—H9119.7
C3—C2—C7121.51 (14)C9—C10—C11118.50 (15)
C3—C2—C1122.59 (14)C9—C10—H10120.8
C7—C2—C1115.86 (14)C11—C10—H10120.8
C2—C3—C8121.09 (14)C12—C11—C10120.02 (16)
C2—C3—C4122.15 (14)C12—C11—C15119.22 (15)
C8—C3—C4116.76 (14)C10—C11—C15120.71 (15)
O2—C4—C3122.63 (14)C13—C12—C11118.87 (16)
O2—C4—C5122.80 (14)C13—C12—H12120.6
C3—C4—C5114.53 (13)C11—C12—H12120.6
C6—C5—C4122.92 (14)N3—C13—C12120.58 (15)
C6—C5—Cl1121.53 (12)N3—C13—H13119.7
C4—C5—Cl1115.55 (11)C12—C13—H13119.7
C5—C6—C1122.68 (14)N3—C14—H14A109.5
C5—C6—Cl2122.00 (13)N3—C14—H14B109.5
C1—C6—Cl2115.31 (11)H14A—C14—H14B109.5
N1—C7—C2179.17 (18)N3—C14—H14C109.5
N2—C8—C3179.05 (18)H14A—C14—H14C109.5
C9—N3—C13121.33 (15)H14B—C14—H14C109.5
C9—N3—C14120.19 (14)
O1—C1—C2—C3176.93 (15)Cl1—C5—C6—C1179.52 (12)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.47 (12)
O1—C1—C2—C75.4 (2)Cl1—C5—C6—Cl20.3 (2)
C6—C1—C2—C7173.35 (13)O1—C1—C6—C5176.36 (15)
C7—C2—C3—C80.8 (2)C2—C1—C6—C54.9 (2)
C1—C2—C3—C8178.32 (14)O1—C1—C6—Cl24.4 (2)
C7—C2—C3—C4178.88 (14)C2—C1—C6—Cl2174.38 (11)
C1—C2—C3—C41.4 (2)C13—N3—C9—C100.1 (2)
C2—C3—C4—O2175.79 (15)C14—N3—C9—C10178.26 (15)
C8—C3—C4—O24.5 (2)N3—C9—C10—C110.3 (2)
C2—C3—C4—C56.3 (2)C9—C10—C11—C120.2 (2)
C8—C3—C4—C5173.35 (13)C9—C10—C11—C15177.09 (15)
O2—C4—C5—C6176.31 (15)C10—C11—C12—C130.9 (2)
C3—C4—C5—C65.8 (2)C15—C11—C12—C13176.50 (15)
O2—C4—C5—Cl13.9 (2)C9—N3—C13—C120.5 (2)
C3—C4—C5—Cl1173.96 (11)C14—N3—C13—C12178.95 (16)
C4—C5—C6—C10.3 (2)C11—C12—C13—N31.0 (2)
(150K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.654 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.77203 (15) ÅCell parameters from 4725 reflections
b = 10.0679 (2) Åθ = 2.0–28.1°
c = 20.4627 (4) ŵ = 0.48 mm1
β = 94.7855 (19)°T = 150 K
V = 1390.28 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3178 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2695 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 87
Tmin = 0.955, Tmax = 1.000k = 1312
9239 measured reflectionsl = 2627
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-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 reflectionsΔρmax = 0.34 e Å3
209 parametersΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20742 (6)0.11236 (4)0.00699 (2)0.01950 (11)
N40.9950 (2)1.20447 (16)0.24893 (7)0.0275 (3)
Cl20.11795 (6)0.28112 (4)0.11743 (2)0.01970 (11)
C150.8438 (3)1.15665 (17)0.23606 (8)0.0217 (4)
O10.13550 (16)0.56728 (11)0.09448 (5)0.0188 (2)
O20.29016 (18)0.27743 (11)0.11873 (5)0.0215 (3)
N10.2973 (2)0.81416 (14)0.00682 (7)0.0233 (3)
N20.4170 (2)0.59857 (14)0.16819 (7)0.0231 (3)
C10.1807 (2)0.50057 (15)0.04683 (7)0.0143 (3)
C20.2472 (2)0.56055 (15)0.01192 (7)0.0145 (3)
C30.2884 (2)0.48710 (16)0.06628 (7)0.0146 (3)
C40.2646 (2)0.34355 (16)0.06889 (7)0.0154 (3)
C50.2143 (2)0.28288 (15)0.00756 (7)0.0146 (3)
C60.1748 (2)0.35486 (16)0.04581 (7)0.0148 (3)
C70.2752 (2)0.70175 (16)0.00939 (7)0.0162 (3)
C80.3598 (2)0.54994 (15)0.12282 (7)0.0159 (3)
N30.3187 (2)0.95345 (13)0.18278 (7)0.0200 (3)
C90.3513 (2)0.99941 (16)0.24432 (8)0.0203 (3)
H90.2558960.9839290.2749660.024*
C100.5211 (2)1.06857 (16)0.26338 (8)0.0190 (3)
H100.5441041.1011560.3069180.023*
C110.6586 (2)1.09001 (16)0.21778 (8)0.0184 (3)
C120.6214 (3)1.04238 (17)0.15422 (8)0.0227 (4)
H120.7134831.0575960.1224420.027*
C130.4504 (3)0.97326 (17)0.13803 (8)0.0225 (4)
H130.4244250.9390300.0949090.027*
C140.1377 (3)0.8760 (2)0.16333 (10)0.0329 (4)
H14A0.0604700.9216430.1274330.049*
H14B0.0578840.8676730.2009180.049*
H14C0.1749350.7874220.1487660.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0274 (2)0.01124 (19)0.0201 (2)0.00040 (15)0.00313 (16)0.00030 (14)
N40.0304 (9)0.0302 (8)0.0222 (8)0.0069 (7)0.0042 (6)0.0031 (6)
Cl20.0262 (2)0.0191 (2)0.01427 (19)0.00147 (15)0.00402 (15)0.00307 (14)
C150.0293 (10)0.0203 (9)0.0162 (8)0.0010 (7)0.0058 (7)0.0029 (6)
O10.0232 (6)0.0183 (6)0.0153 (6)0.0001 (5)0.0041 (5)0.0041 (4)
O20.0326 (7)0.0168 (6)0.0157 (6)0.0043 (5)0.0058 (5)0.0024 (4)
N10.0253 (8)0.0175 (8)0.0269 (8)0.0020 (6)0.0016 (6)0.0018 (6)
N20.0263 (8)0.0241 (8)0.0193 (7)0.0027 (6)0.0045 (6)0.0015 (6)
C10.0140 (7)0.0150 (8)0.0137 (7)0.0005 (6)0.0006 (6)0.0006 (6)
C20.0144 (7)0.0124 (7)0.0167 (8)0.0010 (6)0.0007 (6)0.0009 (6)
C30.0137 (7)0.0160 (8)0.0141 (7)0.0002 (6)0.0015 (6)0.0015 (6)
C40.0149 (7)0.0152 (8)0.0160 (8)0.0029 (6)0.0003 (6)0.0001 (6)
C50.0170 (8)0.0101 (7)0.0165 (8)0.0004 (6)0.0003 (6)0.0017 (6)
C60.0151 (7)0.0164 (8)0.0130 (7)0.0004 (6)0.0019 (6)0.0021 (6)
C70.0164 (8)0.0188 (8)0.0135 (7)0.0003 (6)0.0023 (6)0.0004 (6)
C80.0177 (8)0.0135 (8)0.0163 (8)0.0012 (6)0.0007 (6)0.0018 (6)
N30.0228 (7)0.0143 (7)0.0219 (7)0.0021 (6)0.0039 (6)0.0001 (5)
C90.0230 (9)0.0196 (8)0.0183 (8)0.0046 (7)0.0019 (7)0.0025 (6)
C100.0228 (8)0.0192 (8)0.0148 (8)0.0028 (7)0.0009 (6)0.0005 (6)
C110.0229 (8)0.0142 (8)0.0182 (8)0.0022 (6)0.0017 (6)0.0020 (6)
C120.0291 (9)0.0233 (9)0.0164 (8)0.0030 (7)0.0055 (7)0.0019 (6)
C130.0311 (9)0.0200 (8)0.0158 (8)0.0068 (7)0.0018 (7)0.0034 (6)
C140.0305 (10)0.0291 (10)0.0374 (11)0.0056 (8)0.0067 (8)0.0038 (8)
Geometric parameters (Å, º) top
Cl1—C51.7174 (15)C5—C61.356 (2)
N4—C151.142 (2)N3—C91.342 (2)
Cl2—C61.7150 (15)N3—C131.345 (2)
C15—C111.444 (2)N3—C141.479 (2)
O1—C11.2432 (18)C9—C101.373 (2)
O2—C41.2420 (18)C9—H90.9500
N1—C71.142 (2)C10—C111.389 (2)
N2—C81.145 (2)C10—H100.9500
C1—C21.450 (2)C11—C121.389 (2)
C1—C61.468 (2)C12—C131.368 (2)
C2—C31.383 (2)C12—H120.9500
C2—C71.435 (2)C13—H130.9500
C3—C81.437 (2)C14—H14A0.9800
C3—C41.455 (2)C14—H14B0.9800
C4—C51.461 (2)C14—H14C0.9800
N4—C15—C11176.59 (19)C13—N3—C14118.46 (14)
O1—C1—C2122.62 (14)N3—C9—C10120.63 (15)
O1—C1—C6122.88 (14)N3—C9—H9119.7
C2—C1—C6114.48 (13)C10—C9—H9119.7
C3—C2—C7121.58 (14)C9—C10—C11118.73 (15)
C3—C2—C1122.78 (14)C9—C10—H10120.6
C7—C2—C1115.60 (13)C11—C10—H10120.6
C2—C3—C8121.06 (14)C10—C11—C12119.72 (16)
C2—C3—C4122.09 (14)C10—C11—C15120.99 (15)
C8—C3—C4116.85 (13)C12—C11—C15119.25 (15)
O2—C4—C3122.68 (14)C13—C12—C11119.07 (15)
O2—C4—C5122.65 (14)C13—C12—H12120.5
C3—C4—C5114.64 (13)C11—C12—H12120.5
C6—C5—C4122.96 (14)N3—C13—C12120.43 (15)
C6—C5—Cl1121.44 (12)N3—C13—H13119.8
C4—C5—Cl1115.60 (11)C12—C13—H13119.8
C5—C6—C1122.60 (14)N3—C14—H14A109.5
C5—C6—Cl2122.03 (12)N3—C14—H14B109.5
C1—C6—Cl2115.36 (11)H14A—C14—H14B109.5
N1—C7—C2179.41 (17)N3—C14—H14C109.5
N2—C8—C3179.19 (17)H14A—C14—H14C109.5
C9—N3—C13121.41 (15)H14B—C14—H14C109.5
C9—N3—C14120.10 (15)
O1—C1—C2—C3176.76 (14)Cl1—C5—C6—C1179.62 (12)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.49 (12)
O1—C1—C2—C75.5 (2)Cl1—C5—C6—Cl20.7 (2)
C6—C1—C2—C7173.44 (13)O1—C1—C6—C5176.46 (15)
C7—C2—C3—C80.5 (2)C2—C1—C6—C54.6 (2)
C1—C2—C3—C8178.07 (14)O1—C1—C6—Cl24.5 (2)
C7—C2—C3—C4178.68 (14)C2—C1—C6—Cl2174.45 (11)
C1—C2—C3—C41.1 (2)C13—N3—C9—C100.1 (2)
C2—C3—C4—O2175.76 (15)C14—N3—C9—C10178.38 (15)
C8—C3—C4—O25.0 (2)N3—C9—C10—C110.0 (2)
C2—C3—C4—C56.1 (2)C9—C10—C11—C120.5 (2)
C8—C3—C4—C5173.13 (13)C9—C10—C11—C15177.06 (15)
O2—C4—C5—C6176.01 (15)C10—C11—C12—C131.0 (2)
C3—C4—C5—C65.8 (2)C15—C11—C12—C13176.64 (15)
O2—C4—C5—Cl13.8 (2)C9—N3—C13—C120.6 (2)
C3—C4—C5—Cl1174.31 (11)C14—N3—C13—C12178.89 (16)
C4—C5—C6—C10.5 (2)C11—C12—C13—N31.0 (2)
(180K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.649 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.78877 (15) ÅCell parameters from 4533 reflections
b = 10.07003 (19) Åθ = 2.0–27.9°
c = 20.4706 (4) ŵ = 0.48 mm1
β = 94.7503 (18)°T = 180 K
V = 1394.62 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3194 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2651 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 97
Tmin = 0.927, Tmax = 1.000k = 1312
9309 measured reflectionsl = 2626
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-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 reflectionsΔρmax = 0.30 e Å3
209 parametersΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20675 (6)0.11253 (4)0.00703 (2)0.02296 (11)
N40.9938 (2)1.20410 (17)0.24875 (7)0.0327 (4)
Cl20.11771 (6)0.28107 (4)0.11733 (2)0.02312 (11)
C150.8427 (3)1.15624 (17)0.23597 (8)0.0248 (4)
O10.13519 (17)0.56711 (11)0.09447 (5)0.0222 (3)
O20.29018 (18)0.27763 (11)0.11858 (5)0.0253 (3)
N10.2974 (2)0.81371 (14)0.00674 (7)0.0270 (3)
N20.4169 (2)0.59838 (15)0.16795 (7)0.0272 (3)
C10.1807 (2)0.50017 (15)0.04681 (7)0.0166 (3)
C20.2473 (2)0.56039 (15)0.01182 (7)0.0166 (3)
C30.2884 (2)0.48686 (16)0.06607 (7)0.0168 (3)
C40.2643 (2)0.34370 (16)0.06888 (7)0.0177 (3)
C50.2135 (2)0.28306 (15)0.00759 (7)0.0172 (3)
C60.1746 (2)0.35454 (16)0.04583 (7)0.0170 (3)
C70.2753 (2)0.70147 (16)0.00923 (7)0.0184 (3)
C80.3593 (2)0.54977 (16)0.12270 (7)0.0186 (3)
N30.3191 (2)0.95319 (13)0.18284 (7)0.0235 (3)
C90.3518 (3)0.99934 (17)0.24427 (8)0.0242 (4)
H90.2564560.9842270.2749200.029*
C100.5213 (2)1.06812 (16)0.26331 (8)0.0222 (3)
H100.5447961.1003970.3068690.027*
C110.6579 (2)1.08951 (16)0.21757 (8)0.0211 (3)
C120.6206 (3)1.04205 (18)0.15417 (8)0.0266 (4)
H120.7122781.0573470.1223420.032*
C130.4504 (3)0.97304 (17)0.13815 (8)0.0269 (4)
H130.4245740.9387460.0950560.032*
C140.1383 (3)0.8760 (2)0.16358 (11)0.0388 (5)
H14A0.0601190.9223390.1282220.058*
H14B0.0599430.8665230.2014140.058*
H14C0.1751830.7878350.1483400.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0323 (2)0.01302 (19)0.0238 (2)0.00067 (15)0.00413 (16)0.00045 (14)
N40.0349 (9)0.0355 (9)0.0282 (8)0.0081 (7)0.0057 (7)0.0045 (6)
Cl20.0306 (2)0.0222 (2)0.01695 (19)0.00181 (16)0.00479 (15)0.00360 (14)
C150.0333 (10)0.0225 (9)0.0195 (8)0.0005 (8)0.0071 (7)0.0030 (6)
O10.0277 (6)0.0210 (6)0.0183 (6)0.0008 (5)0.0047 (5)0.0051 (4)
O20.0387 (7)0.0185 (6)0.0194 (6)0.0045 (5)0.0068 (5)0.0028 (4)
N10.0303 (8)0.0191 (8)0.0313 (8)0.0022 (6)0.0015 (6)0.0017 (6)
N20.0324 (8)0.0270 (8)0.0228 (8)0.0035 (6)0.0060 (6)0.0030 (6)
C10.0155 (7)0.0176 (8)0.0166 (7)0.0008 (6)0.0002 (6)0.0009 (6)
C20.0163 (7)0.0148 (7)0.0188 (7)0.0014 (6)0.0006 (6)0.0002 (6)
C30.0173 (7)0.0175 (8)0.0156 (7)0.0004 (6)0.0018 (6)0.0016 (6)
C40.0180 (8)0.0170 (8)0.0182 (8)0.0038 (6)0.0014 (6)0.0001 (6)
C50.0184 (8)0.0133 (7)0.0197 (8)0.0003 (6)0.0005 (6)0.0016 (6)
C60.0174 (8)0.0185 (8)0.0151 (7)0.0002 (6)0.0016 (6)0.0025 (6)
C70.0181 (8)0.0214 (9)0.0160 (7)0.0004 (6)0.0021 (6)0.0002 (6)
C80.0205 (8)0.0161 (8)0.0191 (8)0.0017 (6)0.0014 (6)0.0029 (6)
N30.0273 (8)0.0171 (7)0.0248 (7)0.0029 (6)0.0046 (6)0.0006 (5)
C90.0270 (9)0.0240 (9)0.0217 (8)0.0030 (7)0.0027 (7)0.0028 (7)
C100.0271 (9)0.0226 (8)0.0170 (8)0.0041 (7)0.0015 (6)0.0005 (6)
C110.0267 (9)0.0162 (8)0.0204 (8)0.0032 (6)0.0025 (7)0.0023 (6)
C120.0332 (10)0.0282 (9)0.0191 (8)0.0041 (8)0.0059 (7)0.0019 (7)
C130.0379 (10)0.0240 (9)0.0182 (8)0.0063 (8)0.0014 (7)0.0027 (6)
C140.0344 (11)0.0349 (11)0.0451 (12)0.0075 (9)0.0084 (9)0.0061 (9)
Geometric parameters (Å, º) top
Cl1—C51.7179 (15)C5—C61.353 (2)
N4—C151.144 (2)N3—C131.344 (2)
Cl2—C61.7124 (15)N3—C91.342 (2)
C15—C111.445 (2)N3—C141.478 (2)
O1—C11.2458 (18)C9—C101.372 (2)
O2—C41.2401 (18)C9—H90.9500
N1—C71.141 (2)C10—C111.388 (2)
N2—C81.145 (2)C10—H100.9500
C1—C21.450 (2)C11—C121.386 (2)
C1—C61.467 (2)C12—C131.365 (3)
C2—C31.382 (2)C12—H120.9500
C2—C71.434 (2)C13—H130.9500
C3—C81.438 (2)C14—H14A0.9800
C3—C41.452 (2)C14—H14B0.9800
C4—C51.462 (2)C14—H14C0.9800
N4—C15—C11176.43 (19)C9—N3—C14120.09 (15)
O1—C1—C2122.45 (14)N3—C9—C10120.72 (15)
O1—C1—C6122.89 (14)N3—C9—H9119.6
C2—C1—C6114.66 (13)C10—C9—H9119.6
C3—C2—C7121.70 (14)C9—C10—C11118.57 (15)
C3—C2—C1122.58 (14)C9—C10—H10120.7
C7—C2—C1115.68 (13)C11—C10—H10120.7
C2—C3—C8120.99 (14)C12—C11—C10119.86 (16)
C2—C3—C4122.30 (14)C12—C11—C15119.42 (15)
C8—C3—C4116.71 (13)C10—C11—C15120.67 (15)
O2—C4—C3122.84 (14)C13—C12—C11119.05 (16)
O2—C4—C5122.64 (14)C13—C12—H12120.5
C3—C4—C5114.49 (13)C11—C12—H12120.5
C6—C5—C4123.16 (14)N3—C13—C12120.54 (15)
C6—C5—Cl1121.28 (12)N3—C13—H13119.7
C4—C5—Cl1115.56 (11)C12—C13—H13119.7
C5—C6—C1122.38 (14)N3—C14—H14A109.5
C5—C6—Cl2122.26 (13)N3—C14—H14B109.5
C1—C6—Cl2115.36 (11)H14A—C14—H14B109.5
N1—C7—C2179.55 (17)N3—C14—H14C109.5
N2—C8—C3179.14 (18)H14A—C14—H14C109.5
C13—N3—C9121.25 (15)H14B—C14—H14C109.5
C13—N3—C14118.64 (15)
O1—C1—C2—C3176.64 (14)Cl1—C5—C6—C1179.55 (12)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.35 (12)
O1—C1—C2—C75.6 (2)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.44 (13)O1—C1—C6—C5176.13 (15)
C7—C2—C3—C80.7 (2)C2—C1—C6—C54.8 (2)
C1—C2—C3—C8178.29 (14)O1—C1—C6—Cl24.6 (2)
C7—C2—C3—C4178.80 (14)C2—C1—C6—Cl2174.42 (11)
C1—C2—C3—C41.2 (2)C13—N3—C9—C100.2 (2)
C2—C3—C4—O2175.89 (15)C14—N3—C9—C10178.25 (16)
C8—C3—C4—O24.6 (2)N3—C9—C10—C110.3 (2)
C2—C3—C4—C56.0 (2)C9—C10—C11—C120.2 (2)
C8—C3—C4—C5173.45 (13)C9—C10—C11—C15177.25 (16)
O2—C4—C5—C6176.35 (15)C10—C11—C12—C130.9 (2)
C3—C4—C5—C65.6 (2)C15—C11—C12—C13176.58 (16)
O2—C4—C5—Cl13.9 (2)C9—N3—C13—C120.5 (2)
C3—C4—C5—Cl1174.16 (11)C14—N3—C13—C12179.00 (17)
C4—C5—C6—C10.2 (2)C11—C12—C13—N31.1 (3)
(210K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.644 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.80352 (17) ÅCell parameters from 4285 reflections
b = 10.0725 (2) Åθ = 2.0–27.9°
c = 20.4774 (4) ŵ = 0.48 mm1
β = 94.754 (2)°T = 210 K
V = 1398.45 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3199 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 79
Tmin = 0.932, Tmax = 1.000k = 1312
9343 measured reflectionsl = 2726
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-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 reflectionsΔρmax = 0.29 e Å3
209 parametersΔρmin = 0.23 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20616 (7)0.11275 (4)0.00708 (2)0.02676 (12)
N40.9921 (3)1.20339 (18)0.24850 (8)0.0382 (4)
Cl20.11731 (6)0.28110 (4)0.11722 (2)0.02697 (12)
C150.8419 (3)1.15576 (19)0.23570 (9)0.0293 (4)
O10.13556 (18)0.56682 (12)0.09442 (5)0.0255 (3)
O20.29002 (19)0.27781 (12)0.11834 (6)0.0291 (3)
N10.2976 (2)0.81332 (15)0.00675 (8)0.0316 (4)
N20.4172 (2)0.59824 (16)0.16752 (7)0.0315 (4)
C10.1807 (2)0.50016 (16)0.04675 (8)0.0194 (3)
C20.2471 (2)0.56018 (16)0.01166 (8)0.0190 (3)
C30.2886 (2)0.48704 (16)0.06601 (8)0.0192 (3)
C40.2641 (2)0.34358 (16)0.06871 (8)0.0204 (3)
C50.2135 (2)0.28302 (16)0.00758 (8)0.0198 (3)
C60.1746 (2)0.35484 (16)0.04577 (8)0.0199 (3)
C70.2757 (2)0.70120 (17)0.00908 (8)0.0211 (3)
C80.3596 (2)0.54999 (17)0.12232 (8)0.0221 (4)
N30.3193 (2)0.95323 (14)0.18294 (7)0.0274 (3)
C90.3524 (3)0.99933 (18)0.24437 (8)0.0273 (4)
H90.2586580.9843560.2748070.033*
C100.5213 (3)1.06792 (17)0.26309 (8)0.0258 (4)
H100.5444631.1000750.3061370.031*
C110.6573 (3)1.08913 (17)0.21769 (8)0.0245 (4)
C120.6202 (3)1.04183 (19)0.15427 (8)0.0300 (4)
H120.7106471.0569240.1227820.036*
C130.4507 (3)0.97321 (18)0.13836 (9)0.0316 (4)
H130.4251440.9393750.0957230.038*
C140.1395 (3)0.8758 (2)0.16371 (12)0.0454 (5)
H14A0.0628930.9210260.1283280.068*
H14B0.0612030.8673770.2009930.068*
H14C0.1761210.7882810.1491830.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0378 (3)0.0152 (2)0.0276 (2)0.00082 (17)0.00461 (18)0.00053 (15)
N40.0420 (10)0.0416 (10)0.0316 (9)0.0103 (8)0.0064 (7)0.0051 (7)
Cl20.0358 (3)0.0260 (2)0.0196 (2)0.00214 (18)0.00562 (17)0.00438 (16)
C150.0387 (11)0.0275 (10)0.0224 (9)0.0000 (8)0.0071 (8)0.0034 (7)
O10.0331 (7)0.0244 (6)0.0196 (6)0.0001 (5)0.0055 (5)0.0056 (5)
O20.0450 (8)0.0217 (7)0.0215 (6)0.0048 (6)0.0084 (5)0.0035 (5)
N10.0367 (9)0.0218 (9)0.0364 (9)0.0027 (7)0.0027 (7)0.0017 (6)
N20.0374 (9)0.0316 (9)0.0261 (8)0.0039 (7)0.0067 (7)0.0036 (6)
C10.0188 (8)0.0207 (8)0.0185 (8)0.0004 (6)0.0001 (6)0.0002 (6)
C20.0188 (8)0.0170 (8)0.0210 (8)0.0008 (6)0.0004 (6)0.0005 (6)
C30.0191 (8)0.0200 (8)0.0185 (8)0.0001 (6)0.0025 (6)0.0019 (6)
C40.0216 (8)0.0192 (8)0.0206 (8)0.0033 (6)0.0018 (6)0.0004 (6)
C50.0221 (8)0.0151 (8)0.0220 (8)0.0001 (6)0.0004 (6)0.0015 (6)
C60.0207 (8)0.0209 (8)0.0182 (8)0.0003 (6)0.0027 (6)0.0023 (6)
C70.0204 (8)0.0232 (9)0.0199 (8)0.0001 (7)0.0031 (6)0.0009 (6)
C80.0237 (9)0.0199 (9)0.0226 (9)0.0014 (7)0.0018 (7)0.0025 (7)
N30.0309 (8)0.0210 (8)0.0288 (8)0.0031 (6)0.0052 (6)0.0014 (6)
C90.0307 (10)0.0276 (10)0.0236 (9)0.0032 (8)0.0021 (7)0.0022 (7)
C100.0321 (10)0.0258 (9)0.0196 (8)0.0033 (7)0.0025 (7)0.0011 (7)
C110.0318 (10)0.0195 (9)0.0223 (9)0.0026 (7)0.0017 (7)0.0021 (6)
C120.0379 (10)0.0321 (10)0.0208 (9)0.0034 (8)0.0067 (8)0.0001 (7)
C130.0454 (11)0.0270 (10)0.0216 (9)0.0088 (8)0.0023 (8)0.0047 (7)
C140.0404 (12)0.0400 (12)0.0536 (14)0.0072 (10)0.0088 (10)0.0065 (10)
Geometric parameters (Å, º) top
Cl1—C51.7158 (16)C5—C61.354 (2)
N4—C151.139 (2)N3—C91.342 (2)
Cl2—C61.7142 (16)N3—C131.345 (2)
C15—C111.445 (3)N3—C141.476 (2)
O1—C11.2441 (19)C9—C101.368 (3)
O2—C41.2380 (19)C9—H90.9400
N1—C71.140 (2)C10—C111.382 (2)
N2—C81.143 (2)C10—H100.9400
C1—C21.446 (2)C11—C121.387 (2)
C1—C61.464 (2)C12—C131.361 (3)
C2—C31.383 (2)C12—H120.9400
C2—C71.434 (2)C13—H130.9400
C3—C81.434 (2)C14—H14A0.9700
C3—C41.455 (2)C14—H14B0.9700
C4—C51.459 (2)C14—H14C0.9700
N4—C15—C11176.7 (2)C13—N3—C14118.74 (16)
O1—C1—C2122.54 (15)N3—C9—C10120.59 (16)
O1—C1—C6122.79 (15)N3—C9—H9119.7
C2—C1—C6114.66 (14)C10—C9—H9119.7
C3—C2—C7121.40 (14)C9—C10—C11118.90 (16)
C3—C2—C1122.79 (15)C9—C10—H10120.5
C7—C2—C1115.75 (14)C11—C10—H10120.5
C2—C3—C8121.07 (15)C10—C11—C12119.81 (17)
C2—C3—C4121.94 (14)C10—C11—C15121.10 (16)
C8—C3—C4116.99 (14)C12—C11—C15119.05 (16)
O2—C4—C3122.60 (15)C13—C12—C11118.92 (17)
O2—C4—C5122.72 (15)C13—C12—H12120.5
C3—C4—C5114.65 (14)C11—C12—H12120.5
C6—C5—C4122.98 (15)N3—C13—C12120.76 (16)
C6—C5—Cl1121.43 (13)N3—C13—H13119.6
C4—C5—Cl1115.59 (12)C12—C13—H13119.6
C5—C6—C1122.52 (15)N3—C14—H14A109.5
C5—C6—Cl2122.03 (13)N3—C14—H14B109.5
C1—C6—Cl2115.45 (12)H14A—C14—H14B109.5
N1—C7—C2179.6 (2)N3—C14—H14C109.5
N2—C8—C3178.90 (19)H14A—C14—H14C109.5
C9—N3—C13121.01 (16)H14B—C14—H14C109.5
C9—N3—C14120.22 (16)
O1—C1—C2—C3176.86 (15)Cl1—C5—C6—C1179.72 (12)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.50 (12)
O1—C1—C2—C75.6 (2)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.24 (14)O1—C1—C6—C5176.28 (16)
C7—C2—C3—C80.8 (2)C2—C1—C6—C54.9 (2)
C1—C2—C3—C8178.20 (15)O1—C1—C6—Cl24.4 (2)
C7—C2—C3—C4178.71 (15)C2—C1—C6—Cl2174.48 (11)
C1—C2—C3—C41.3 (2)C13—N3—C9—C100.0 (3)
C2—C3—C4—O2175.85 (16)C14—N3—C9—C10178.15 (17)
C8—C3—C4—O24.6 (2)N3—C9—C10—C110.1 (3)
C2—C3—C4—C56.2 (2)C9—C10—C11—C120.5 (3)
C8—C3—C4—C5173.30 (14)C9—C10—C11—C15177.22 (17)
O2—C4—C5—C6176.38 (16)C10—C11—C12—C131.0 (3)
C3—C4—C5—C65.7 (2)C15—C11—C12—C13176.69 (17)
O2—C4—C5—Cl13.7 (2)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.19 (11)C14—N3—C13—C12178.78 (18)
C4—C5—C6—C10.2 (3)C11—C12—C13—N31.1 (3)
(240K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.632 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.83004 (15) ÅCell parameters from 4069 reflections
b = 10.08887 (19) Åθ = 2.0–27.8°
c = 20.5119 (4) ŵ = 0.48 mm1
β = 94.7341 (18)°T = 240 K
V = 1408.60 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3218 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2597 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 79
Tmin = 0.953, Tmax = 1.000k = 1312
9373 measured reflectionsl = 2626
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-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 reflectionsΔρmax = 0.29 e Å3
209 parametersΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20550 (7)0.11296 (4)0.00711 (2)0.03081 (13)
N40.9903 (3)1.20316 (19)0.24822 (8)0.0438 (4)
Cl20.11695 (7)0.28108 (4)0.11712 (2)0.03079 (13)
C150.8405 (3)1.1551 (2)0.23559 (9)0.0335 (4)
O10.13561 (18)0.56679 (12)0.09447 (6)0.0291 (3)
O20.2899 (2)0.27785 (12)0.11820 (6)0.0334 (3)
N10.2980 (2)0.81298 (16)0.00668 (8)0.0362 (4)
N20.4169 (3)0.59838 (17)0.16717 (8)0.0369 (4)
C10.1806 (2)0.49992 (17)0.04684 (8)0.0220 (3)
C20.2474 (2)0.56018 (17)0.01156 (8)0.0219 (3)
C30.2882 (2)0.48681 (17)0.06584 (8)0.0219 (3)
C40.2642 (2)0.34373 (17)0.06852 (8)0.0229 (4)
C50.2129 (2)0.28316 (16)0.00745 (8)0.0217 (3)
C60.1743 (2)0.35483 (17)0.04572 (8)0.0221 (4)
C70.2756 (3)0.70122 (18)0.00907 (8)0.0243 (4)
C80.3592 (2)0.54964 (17)0.12210 (8)0.0252 (4)
N30.3200 (2)0.95327 (15)0.18300 (7)0.0313 (4)
C90.3528 (3)0.99914 (19)0.24424 (9)0.0312 (4)
H90.2594500.9839750.2746090.037*
C100.5209 (3)1.06789 (18)0.26304 (8)0.0290 (4)
H100.5438141.1000900.3059950.035*
C110.6569 (3)1.08911 (17)0.21748 (9)0.0280 (4)
C120.6198 (3)1.0414 (2)0.15439 (9)0.0346 (4)
H120.7100951.0559960.1229620.042*
C130.4506 (3)0.97288 (19)0.13846 (9)0.0354 (5)
H130.4251290.9390410.0959080.042*
C140.1403 (3)0.8762 (2)0.16393 (12)0.0510 (6)
H14A0.0614270.8692970.2009960.077*
H14B0.1764030.7881790.1501570.077*
H14C0.0652190.9206000.1281270.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0438 (3)0.0170 (2)0.0321 (2)0.00105 (18)0.00549 (19)0.00061 (16)
N40.0489 (11)0.0477 (11)0.0354 (10)0.0117 (9)0.0069 (8)0.0060 (8)
Cl20.0413 (3)0.0298 (3)0.0219 (2)0.00272 (19)0.00638 (18)0.00484 (16)
C150.0431 (12)0.0318 (11)0.0266 (10)0.0018 (9)0.0083 (8)0.0036 (8)
O10.0375 (7)0.0276 (7)0.0228 (6)0.0009 (6)0.0066 (5)0.0070 (5)
O20.0517 (9)0.0253 (7)0.0243 (7)0.0055 (6)0.0095 (6)0.0040 (5)
N10.0420 (10)0.0236 (9)0.0429 (10)0.0031 (7)0.0033 (8)0.0014 (7)
N20.0438 (10)0.0375 (10)0.0301 (9)0.0059 (8)0.0078 (7)0.0048 (7)
C10.0223 (8)0.0224 (9)0.0210 (8)0.0006 (7)0.0002 (6)0.0003 (7)
C20.0222 (8)0.0205 (9)0.0230 (8)0.0005 (7)0.0018 (7)0.0005 (6)
C30.0234 (8)0.0215 (9)0.0210 (8)0.0010 (7)0.0029 (6)0.0014 (6)
C40.0257 (9)0.0213 (9)0.0220 (8)0.0037 (7)0.0031 (7)0.0010 (6)
C50.0245 (9)0.0161 (8)0.0243 (9)0.0009 (7)0.0017 (7)0.0011 (6)
C60.0236 (9)0.0231 (9)0.0198 (8)0.0003 (7)0.0023 (7)0.0027 (6)
C70.0246 (9)0.0260 (10)0.0223 (9)0.0000 (7)0.0023 (7)0.0004 (7)
C80.0276 (9)0.0217 (9)0.0260 (9)0.0006 (7)0.0012 (7)0.0018 (7)
N30.0363 (9)0.0236 (8)0.0328 (9)0.0038 (7)0.0045 (7)0.0013 (6)
C90.0344 (10)0.0318 (10)0.0275 (10)0.0034 (8)0.0029 (8)0.0021 (8)
C100.0347 (10)0.0323 (10)0.0200 (9)0.0048 (8)0.0023 (7)0.0009 (7)
C110.0349 (10)0.0225 (9)0.0267 (9)0.0031 (7)0.0030 (8)0.0025 (7)
C120.0444 (12)0.0361 (11)0.0242 (9)0.0035 (9)0.0085 (8)0.0001 (8)
C130.0495 (12)0.0325 (11)0.0230 (9)0.0089 (9)0.0030 (8)0.0056 (8)
C140.0454 (13)0.0476 (14)0.0574 (15)0.0089 (11)0.0113 (11)0.0065 (11)
Geometric parameters (Å, º) top
Cl1—C51.7178 (16)C5—C61.352 (2)
N4—C151.142 (3)N3—C91.340 (2)
Cl2—C61.7168 (17)N3—C131.343 (2)
C15—C111.442 (3)N3—C141.478 (3)
O1—C11.2466 (19)C9—C101.369 (3)
O2—C41.241 (2)C9—H90.9400
N1—C71.138 (2)C10—C111.387 (2)
N2—C81.145 (2)C10—H100.9400
C1—C21.450 (2)C11—C121.385 (3)
C1—C61.465 (2)C12—C131.362 (3)
C2—C31.384 (2)C12—H120.9400
C2—C71.436 (2)C13—H130.9400
C3—C81.436 (2)C14—H14A0.9700
C3—C41.453 (2)C14—H14B0.9700
C4—C51.462 (2)C14—H14C0.9700
N4—C15—C11176.8 (2)C13—N3—C14118.75 (17)
O1—C1—C2122.36 (16)N3—C9—C10120.68 (17)
O1—C1—C6122.99 (15)N3—C9—H9119.7
C2—C1—C6114.64 (14)C10—C9—H9119.7
C3—C2—C7121.55 (15)C9—C10—C11118.74 (17)
C3—C2—C1122.54 (16)C9—C10—H10120.6
C7—C2—C1115.88 (15)C11—C10—H10120.6
C2—C3—C8120.94 (15)C12—C11—C10119.67 (18)
C2—C3—C4122.16 (15)C12—C11—C15119.32 (17)
C8—C3—C4116.90 (14)C10—C11—C15120.95 (16)
O2—C4—C3122.68 (15)C13—C12—C11119.12 (18)
O2—C4—C5122.66 (16)C13—C12—H12120.4
C3—C4—C5114.64 (14)C11—C12—H12120.4
C6—C5—C4122.94 (15)N3—C13—C12120.60 (17)
C6—C5—Cl1121.55 (13)N3—C13—H13119.7
C4—C5—Cl1115.50 (12)C12—C13—H13119.7
C5—C6—C1122.66 (15)N3—C14—H14A109.5
C5—C6—Cl2121.98 (13)N3—C14—H14B109.5
C1—C6—Cl2115.36 (12)H14A—C14—H14B109.5
N1—C7—C2179.57 (19)N3—C14—H14C109.5
N2—C8—C3179.2 (2)H14A—C14—H14C109.5
C9—N3—C13121.18 (17)H14B—C14—H14C109.5
C9—N3—C14120.04 (17)
O1—C1—C2—C3176.67 (16)Cl1—C5—C6—C1179.68 (13)
C6—C1—C2—C34.5 (2)C4—C5—C6—Cl2179.30 (13)
O1—C1—C2—C75.4 (2)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.47 (14)O1—C1—C6—C5176.25 (16)
C7—C2—C3—C80.4 (2)C2—C1—C6—C54.9 (2)
C1—C2—C3—C8178.26 (15)O1—C1—C6—Cl24.4 (2)
C7—C2—C3—C4178.70 (16)C2—C1—C6—Cl2174.40 (12)
C1—C2—C3—C40.9 (3)C13—N3—C9—C100.2 (3)
C2—C3—C4—O2175.92 (17)C14—N3—C9—C10178.40 (18)
C8—C3—C4—O24.9 (3)N3—C9—C10—C110.0 (3)
C2—C3—C4—C55.7 (2)C9—C10—C11—C120.3 (3)
C8—C3—C4—C5173.44 (15)C9—C10—C11—C15176.89 (18)
O2—C4—C5—C6176.29 (17)C10—C11—C12—C130.7 (3)
C3—C4—C5—C65.3 (2)C15—C11—C12—C13176.52 (18)
O2—C4—C5—Cl14.0 (2)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.39 (12)C14—N3—C13—C12178.85 (19)
C4—C5—C6—C10.0 (3)C11—C12—C13—N30.9 (3)
(270K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.626 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.84899 (17) ÅCell parameters from 3845 reflections
b = 10.0928 (2) Åθ = 2.0–27.8°
c = 20.5226 (4) ŵ = 0.47 mm1
β = 94.715 (2)°T = 270 K
V = 1413.83 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3225 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 79
Tmin = 0.926, Tmax = 1.000k = 1312
9414 measured reflectionsl = 2626
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-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 reflectionsΔρmax = 0.28 e Å3
209 parametersΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20489 (7)0.11321 (4)0.00712 (2)0.03500 (13)
N40.9890 (3)1.20268 (19)0.24804 (8)0.0493 (5)
Cl20.11661 (7)0.28116 (5)0.11697 (2)0.03491 (13)
C150.8397 (3)1.1552 (2)0.23537 (9)0.0377 (4)
O10.13567 (18)0.56664 (12)0.09449 (6)0.0326 (3)
O20.2899 (2)0.27787 (12)0.11795 (6)0.0378 (3)
N10.2984 (2)0.81252 (16)0.00660 (8)0.0407 (4)
N20.4170 (3)0.59821 (16)0.16682 (8)0.0407 (4)
C10.1803 (2)0.49997 (17)0.04689 (8)0.0248 (4)
C20.2470 (2)0.55998 (16)0.01139 (8)0.0238 (3)
C30.2884 (2)0.48669 (16)0.06561 (8)0.0238 (3)
C40.2641 (2)0.34373 (17)0.06845 (8)0.0261 (4)
C50.2126 (2)0.28310 (16)0.00744 (8)0.0247 (4)
C60.1742 (2)0.35464 (17)0.04563 (8)0.0249 (4)
C70.2759 (2)0.70081 (18)0.00900 (8)0.0273 (4)
C80.3591 (3)0.54982 (17)0.12183 (8)0.0279 (4)
N30.3205 (2)0.95322 (15)0.18318 (7)0.0352 (4)
C90.3536 (3)0.99919 (19)0.24421 (9)0.0351 (4)
H90.2615620.9844320.2743010.042*
C100.5209 (3)1.06753 (18)0.26280 (9)0.0327 (4)
H100.5434731.0994470.3052620.039*
C110.6561 (3)1.08850 (17)0.21750 (8)0.0309 (4)
C120.6191 (3)1.0410 (2)0.15442 (9)0.0391 (5)
H120.7081901.0554810.1233130.047*
C130.4507 (3)0.97289 (19)0.13863 (9)0.0397 (5)
H130.4252990.9395530.0965400.048*
C140.1411 (3)0.8761 (2)0.16426 (13)0.0585 (6)
H14A0.0645780.8679980.2011950.088*
H14B0.1767090.7895020.1499210.088*
H14C0.0656860.9207360.1293770.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0497 (3)0.0194 (2)0.0364 (3)0.00091 (19)0.0064 (2)0.00062 (17)
N40.0518 (11)0.0567 (12)0.0399 (10)0.0136 (10)0.0079 (8)0.0071 (8)
Cl20.0465 (3)0.0337 (3)0.0252 (2)0.0030 (2)0.00737 (19)0.00588 (17)
C150.0476 (12)0.0376 (11)0.0291 (10)0.0006 (10)0.0094 (9)0.0040 (8)
O10.0422 (7)0.0307 (7)0.0257 (6)0.0006 (6)0.0075 (5)0.0074 (5)
O20.0588 (9)0.0285 (7)0.0273 (7)0.0058 (6)0.0105 (6)0.0056 (5)
N10.0480 (10)0.0268 (9)0.0472 (10)0.0041 (8)0.0033 (8)0.0024 (7)
N20.0493 (10)0.0403 (10)0.0334 (9)0.0054 (8)0.0094 (8)0.0045 (7)
C10.0250 (9)0.0261 (9)0.0233 (8)0.0014 (7)0.0013 (7)0.0012 (7)
C20.0250 (9)0.0216 (8)0.0246 (8)0.0016 (7)0.0005 (7)0.0013 (6)
C30.0250 (8)0.0239 (9)0.0227 (8)0.0005 (7)0.0030 (6)0.0012 (6)
C40.0280 (9)0.0242 (9)0.0262 (9)0.0049 (7)0.0026 (7)0.0006 (7)
C50.0285 (9)0.0195 (8)0.0258 (9)0.0018 (7)0.0008 (7)0.0013 (6)
C60.0270 (9)0.0265 (9)0.0213 (8)0.0008 (7)0.0033 (7)0.0025 (6)
C70.0275 (9)0.0286 (10)0.0261 (9)0.0003 (7)0.0028 (7)0.0004 (7)
C80.0317 (9)0.0246 (9)0.0273 (9)0.0014 (7)0.0020 (7)0.0016 (7)
N30.0396 (9)0.0269 (8)0.0375 (9)0.0037 (7)0.0056 (7)0.0015 (7)
C90.0393 (11)0.0368 (11)0.0292 (10)0.0039 (9)0.0026 (8)0.0028 (8)
C100.0395 (11)0.0350 (10)0.0236 (9)0.0042 (8)0.0023 (8)0.0018 (7)
C110.0396 (11)0.0255 (9)0.0277 (9)0.0040 (8)0.0030 (8)0.0020 (7)
C120.0502 (12)0.0415 (12)0.0266 (9)0.0036 (10)0.0093 (9)0.0004 (8)
C130.0547 (13)0.0369 (11)0.0265 (9)0.0112 (10)0.0022 (9)0.0058 (8)
C140.0520 (14)0.0526 (15)0.0683 (17)0.0093 (12)0.0112 (12)0.0067 (12)
Geometric parameters (Å, º) top
Cl1—C51.7155 (17)C5—C61.350 (2)
N4—C151.140 (3)N3—C91.337 (2)
Cl2—C61.7160 (16)N3—C131.343 (2)
C15—C111.447 (3)N3—C141.479 (3)
O1—C11.2450 (19)C9—C101.365 (3)
O2—C41.2388 (19)C9—H90.9300
N1—C71.138 (2)C10—C111.381 (2)
N2—C81.144 (2)C10—H100.9300
C1—C21.448 (2)C11—C121.384 (2)
C1—C61.468 (2)C12—C131.359 (3)
C2—C31.385 (2)C12—H120.9300
C2—C71.435 (2)C13—H130.9300
C3—C81.437 (2)C14—H14A0.9600
C3—C41.453 (2)C14—H14B0.9600
C4—C51.463 (2)C14—H14C0.9600
N4—C15—C11176.6 (2)C13—N3—C14118.86 (17)
O1—C1—C2122.46 (16)N3—C9—C10120.73 (17)
O1—C1—C6123.06 (15)N3—C9—H9119.6
C2—C1—C6114.46 (14)C10—C9—H9119.6
C3—C2—C7121.32 (15)C9—C10—C11118.89 (17)
C3—C2—C1122.66 (15)C9—C10—H10120.6
C7—C2—C1115.97 (14)C11—C10—H10120.6
C2—C3—C8120.88 (15)C10—C11—C12119.68 (18)
C2—C3—C4122.17 (15)C10—C11—C15121.17 (16)
C8—C3—C4116.95 (14)C12—C11—C15119.11 (17)
O2—C4—C3122.83 (15)C13—C12—C11118.98 (18)
O2—C4—C5122.57 (16)C13—C12—H12120.5
C3—C4—C5114.57 (14)C11—C12—H12120.5
C6—C5—C4122.91 (15)N3—C13—C12120.70 (17)
C6—C5—Cl1121.56 (13)N3—C13—H13119.7
C4—C5—Cl1115.53 (12)C12—C13—H13119.7
C5—C6—C1122.79 (15)N3—C14—H14A109.5
C5—C6—Cl2122.05 (13)N3—C14—H14B109.5
C1—C6—Cl2115.16 (12)H14A—C14—H14B109.5
N1—C7—C2179.5 (2)N3—C14—H14C109.5
N2—C8—C3178.87 (19)H14A—C14—H14C109.5
C9—N3—C13121.01 (17)H14B—C14—H14C109.5
C9—N3—C14120.10 (17)
O1—C1—C2—C3176.99 (16)Cl1—C5—C6—C1179.78 (13)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.31 (13)
O1—C1—C2—C75.4 (2)Cl1—C5—C6—Cl20.3 (2)
C6—C1—C2—C7173.26 (14)O1—C1—C6—C5176.30 (16)
C7—C2—C3—C80.9 (2)C2—C1—C6—C55.0 (2)
C1—C2—C3—C8178.38 (15)O1—C1—C6—Cl24.2 (2)
C7—C2—C3—C4178.69 (15)C2—C1—C6—Cl2174.46 (11)
C1—C2—C3—C41.2 (3)C13—N3—C9—C100.0 (3)
C2—C3—C4—O2175.81 (16)C14—N3—C9—C10178.28 (18)
C8—C3—C4—O24.6 (2)N3—C9—C10—C110.0 (3)
C2—C3—C4—C56.0 (2)C9—C10—C11—C120.5 (3)
C8—C3—C4—C5173.60 (14)C9—C10—C11—C15177.26 (18)
O2—C4—C5—C6176.45 (17)C10—C11—C12—C130.9 (3)
C3—C4—C5—C65.4 (2)C15—C11—C12—C13176.91 (18)
O2—C4—C5—Cl13.9 (2)C9—N3—C13—C120.5 (3)
C3—C4—C5—Cl1174.29 (12)C14—N3—C13—C12178.72 (19)
C4—C5—C6—C10.1 (3)C11—C12—C13—N30.9 (3)
(293K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.622 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.86364 (18) ÅCell parameters from 3676 reflections
b = 10.0969 (2) Åθ = 2.0–27.3°
c = 20.5284 (4) ŵ = 0.47 mm1
β = 94.703 (2)°T = 293 K
V = 1417.86 (5) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3235 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 97
Tmin = 0.956, Tmax = 1.000k = 1312
9438 measured reflectionsl = 2627
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.26 e Å3
209 parametersΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20442 (8)0.11340 (4)0.00715 (2)0.03848 (14)
N40.9875 (3)1.2023 (2)0.24795 (9)0.0539 (5)
Cl20.11641 (7)0.28119 (5)0.11692 (2)0.03839 (14)
C150.8391 (3)1.1547 (2)0.23541 (9)0.0413 (5)
O10.13604 (19)0.56657 (13)0.09443 (6)0.0354 (3)
O20.2898 (2)0.27812 (13)0.11782 (6)0.0413 (3)
N10.2985 (3)0.81196 (17)0.00661 (9)0.0440 (4)
N20.4168 (3)0.59814 (17)0.16661 (8)0.0440 (4)
C10.1810 (2)0.49968 (18)0.04692 (8)0.0271 (4)
C20.2470 (2)0.56022 (17)0.01128 (8)0.0264 (4)
C30.2880 (2)0.48656 (17)0.06545 (8)0.0261 (4)
C40.2638 (3)0.34397 (18)0.06828 (8)0.0285 (4)
C50.2125 (3)0.28326 (17)0.00744 (8)0.0270 (4)
C60.1734 (2)0.35462 (18)0.04562 (8)0.0271 (4)
C70.2760 (3)0.70050 (19)0.00887 (8)0.0296 (4)
C80.3594 (3)0.54937 (18)0.12160 (9)0.0305 (4)
N30.3207 (2)0.95306 (16)0.18317 (8)0.0382 (4)
C90.3538 (3)0.9991 (2)0.24416 (9)0.0383 (5)
H90.2619570.9844470.2742510.046*
C100.5209 (3)1.06728 (19)0.26276 (9)0.0351 (4)
H100.5433291.0990870.3052240.042*
C110.6563 (3)1.08840 (18)0.21747 (9)0.0341 (4)
C120.6191 (3)1.0409 (2)0.15453 (9)0.0423 (5)
H120.7076791.0554310.1233470.051*
C130.4503 (3)0.9725 (2)0.13885 (10)0.0446 (5)
H130.4250560.9388850.0968220.054*
C140.1423 (4)0.8759 (3)0.16434 (14)0.0641 (7)
H14A0.0684440.9193210.1287620.096*
H14B0.0643980.8695730.2009780.096*
H14C0.1779750.7886800.1510220.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0549 (3)0.0215 (2)0.0396 (3)0.0013 (2)0.0070 (2)0.00094 (18)
N40.0570 (12)0.0604 (13)0.0450 (11)0.0147 (10)0.0090 (9)0.0068 (9)
Cl20.0519 (3)0.0367 (3)0.0274 (2)0.0031 (2)0.0082 (2)0.00623 (18)
C150.0518 (13)0.0411 (12)0.0320 (11)0.0026 (10)0.0106 (10)0.0050 (9)
O10.0461 (8)0.0342 (7)0.0266 (7)0.0006 (6)0.0080 (6)0.0075 (5)
O20.0640 (10)0.0296 (7)0.0316 (7)0.0062 (7)0.0114 (7)0.0052 (6)
N10.0509 (11)0.0283 (10)0.0527 (11)0.0048 (8)0.0031 (8)0.0020 (8)
N20.0535 (11)0.0438 (11)0.0358 (10)0.0065 (8)0.0100 (8)0.0050 (8)
C10.0281 (9)0.0279 (10)0.0252 (9)0.0011 (7)0.0021 (7)0.0016 (7)
C20.0282 (9)0.0230 (9)0.0279 (9)0.0016 (7)0.0017 (7)0.0021 (7)
C30.0267 (9)0.0263 (9)0.0255 (9)0.0022 (7)0.0026 (7)0.0020 (7)
C40.0321 (10)0.0259 (9)0.0275 (9)0.0044 (8)0.0031 (7)0.0008 (7)
C50.0302 (9)0.0205 (9)0.0302 (9)0.0018 (7)0.0013 (7)0.0015 (7)
C60.0302 (9)0.0277 (9)0.0238 (9)0.0005 (7)0.0041 (7)0.0024 (7)
C70.0309 (10)0.0293 (10)0.0287 (9)0.0005 (8)0.0028 (7)0.0007 (7)
C80.0334 (10)0.0277 (10)0.0302 (10)0.0012 (8)0.0021 (8)0.0016 (8)
N30.0441 (10)0.0293 (9)0.0395 (9)0.0033 (7)0.0061 (8)0.0018 (7)
C90.0420 (11)0.0400 (12)0.0330 (10)0.0033 (9)0.0037 (9)0.0025 (8)
C100.0422 (11)0.0369 (11)0.0264 (10)0.0040 (9)0.0037 (8)0.0025 (8)
C110.0438 (11)0.0274 (10)0.0310 (10)0.0040 (8)0.0036 (8)0.0029 (7)
C120.0545 (13)0.0442 (13)0.0293 (10)0.0052 (10)0.0090 (9)0.0004 (9)
C130.0620 (14)0.0400 (12)0.0308 (10)0.0108 (11)0.0025 (10)0.0072 (9)
C140.0557 (15)0.0596 (16)0.0740 (18)0.0116 (13)0.0135 (13)0.0091 (13)
Geometric parameters (Å, º) top
Cl1—C51.7160 (17)C5—C61.351 (2)
N4—C151.136 (3)N3—C91.337 (2)
Cl2—C61.7144 (17)N3—C131.338 (3)
C15—C111.443 (3)N3—C141.476 (3)
O1—C11.246 (2)C9—C101.365 (3)
O2—C41.240 (2)C9—H90.9300
N1—C71.136 (2)C10—C111.384 (3)
N2—C81.145 (2)C10—H100.9300
C1—C21.448 (2)C11—C121.382 (3)
C1—C61.466 (2)C12—C131.365 (3)
C2—C31.386 (2)C12—H120.9300
C2—C71.431 (2)C13—H130.9300
C3—C81.436 (2)C14—H14A0.9600
C3—C41.450 (3)C14—H14B0.9600
C4—C51.460 (2)C14—H14C0.9600
N4—C15—C11176.7 (2)C13—N3—C14118.87 (18)
O1—C1—C2122.12 (16)N3—C9—C10120.79 (18)
O1—C1—C6123.05 (16)N3—C9—H9119.6
C2—C1—C6114.83 (15)C10—C9—H9119.6
C3—C2—C7121.49 (16)C9—C10—C11119.01 (18)
C3—C2—C1122.25 (16)C9—C10—H10120.5
C7—C2—C1116.21 (15)C11—C10—H10120.5
C2—C3—C8120.79 (16)C12—C11—C10119.43 (19)
C2—C3—C4122.35 (15)C12—C11—C15119.32 (18)
C8—C3—C4116.85 (15)C10—C11—C15121.20 (17)
O2—C4—C3122.79 (16)C13—C12—C11118.98 (19)
O2—C4—C5122.51 (17)C13—C12—H12120.5
C3—C4—C5114.67 (15)C11—C12—H12120.5
C6—C5—C4122.92 (16)N3—C13—C12120.85 (18)
C6—C5—Cl1121.44 (14)N3—C13—H13119.6
C4—C5—Cl1115.64 (13)C12—C13—H13119.6
C5—C6—C1122.59 (16)N3—C14—H14A109.5
C5—C6—Cl2122.14 (14)N3—C14—H14B109.5
C1—C6—Cl2115.26 (13)H14A—C14—H14B109.5
N1—C7—C2179.6 (2)N3—C14—H14C109.5
N2—C8—C3179.3 (2)H14A—C14—H14C109.5
C9—N3—C13120.93 (18)H14B—C14—H14C109.5
C9—N3—C14120.17 (19)
O1—C1—C2—C3176.79 (16)Cl1—C5—C6—C1179.41 (13)
C6—C1—C2—C33.8 (2)C4—C5—C6—Cl2179.16 (13)
O1—C1—C2—C75.8 (3)Cl1—C5—C6—Cl20.9 (2)
C6—C1—C2—C7173.58 (15)O1—C1—C6—C5176.41 (17)
C7—C2—C3—C80.7 (3)C2—C1—C6—C54.2 (2)
C1—C2—C3—C8177.95 (16)O1—C1—C6—Cl25.0 (2)
C7—C2—C3—C4178.58 (16)C2—C1—C6—Cl2174.46 (12)
C1—C2—C3—C41.4 (3)C13—N3—C9—C100.1 (3)
C2—C3—C4—O2175.91 (17)C14—N3—C9—C10178.10 (19)
C8—C3—C4—O24.8 (3)N3—C9—C10—C110.0 (3)
C2—C3—C4—C56.0 (2)C9—C10—C11—C120.4 (3)
C8—C3—C4—C5173.36 (15)C9—C10—C11—C15177.20 (19)
O2—C4—C5—C6176.24 (17)C10—C11—C12—C131.0 (3)
C3—C4—C5—C65.6 (3)C15—C11—C12—C13176.71 (19)
O2—C4—C5—Cl13.7 (2)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.40 (12)C14—N3—C13—C12178.7 (2)
C4—C5—C6—C10.6 (3)C11—C12—C13—N31.1 (3)
(310K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.617 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.87524 (18) ÅCell parameters from 3535 reflections
b = 10.1004 (2) Åθ = 2.0–27.3°
c = 20.5391 (4) ŵ = 0.47 mm1
β = 94.709 (2)°T = 310 K
V = 1421.47 (6) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3240 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 97
Tmin = 0.935, Tmax = 1.000k = 1312
9454 measured reflectionsl = 2627
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.29 e Å3
209 parametersΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20418 (8)0.11356 (4)0.00714 (2)0.04083 (14)
N40.9864 (3)1.2019 (2)0.24776 (9)0.0586 (5)
Cl20.11636 (7)0.28123 (5)0.11686 (2)0.04084 (14)
C150.8386 (3)1.1540 (2)0.23528 (10)0.0440 (5)
O10.13615 (19)0.56638 (12)0.09440 (6)0.0379 (3)
O20.2894 (2)0.27842 (13)0.11771 (6)0.0435 (3)
N10.2991 (3)0.81168 (17)0.00660 (9)0.0475 (4)
N20.4169 (3)0.59787 (18)0.16625 (8)0.0475 (4)
C10.1807 (2)0.49981 (17)0.04688 (8)0.0291 (4)
C20.2473 (2)0.55983 (17)0.01123 (8)0.0283 (4)
C30.2884 (2)0.48655 (17)0.06549 (8)0.0282 (4)
C40.2641 (3)0.34420 (17)0.06819 (8)0.0301 (4)
C50.2121 (3)0.28340 (16)0.00733 (8)0.0287 (4)
C60.1738 (2)0.35467 (17)0.04569 (8)0.0287 (4)
C70.2762 (3)0.70045 (19)0.00863 (8)0.0321 (4)
C80.3590 (3)0.54931 (18)0.12146 (9)0.0320 (4)
N30.3212 (2)0.95320 (15)0.18324 (8)0.0403 (4)
C90.3538 (3)0.9990 (2)0.24407 (9)0.0406 (5)
H90.2619580.9844040.2741180.049*
C100.5209 (3)1.06724 (19)0.26265 (9)0.0379 (4)
H100.5433981.0990300.3050920.046*
C110.6558 (3)1.08828 (18)0.21744 (9)0.0366 (4)
C120.6181 (3)1.0407 (2)0.15444 (9)0.0459 (5)
H120.7064051.0552070.1232280.055*
C130.4501 (3)0.9724 (2)0.13883 (9)0.0459 (5)
H130.4247120.9388020.0968460.055*
C140.1424 (4)0.8763 (3)0.16438 (14)0.0679 (7)
H14A0.0691680.9195990.1286950.102*
H14B0.0643650.8704720.2009470.102*
H14C0.1776450.7888780.1512630.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0580 (3)0.0227 (2)0.0423 (3)0.0014 (2)0.0074 (2)0.00052 (18)
N40.0637 (13)0.0657 (13)0.0473 (11)0.0182 (11)0.0092 (10)0.0072 (9)
Cl20.0547 (3)0.0395 (3)0.0292 (2)0.0034 (2)0.0089 (2)0.00669 (18)
C150.0560 (14)0.0425 (12)0.0347 (11)0.0035 (11)0.0108 (10)0.0056 (9)
O10.0501 (8)0.0358 (7)0.0289 (7)0.0006 (6)0.0087 (6)0.0085 (5)
O20.0676 (10)0.0328 (7)0.0317 (7)0.0077 (7)0.0126 (6)0.0050 (6)
N10.0556 (11)0.0296 (10)0.0570 (11)0.0049 (8)0.0038 (9)0.0028 (8)
N20.0558 (11)0.0484 (11)0.0391 (10)0.0079 (9)0.0098 (8)0.0062 (8)
C10.0311 (9)0.0288 (9)0.0271 (9)0.0009 (7)0.0020 (7)0.0019 (7)
C20.0305 (9)0.0249 (9)0.0295 (9)0.0009 (7)0.0029 (7)0.0006 (7)
C30.0303 (9)0.0279 (9)0.0266 (9)0.0017 (7)0.0033 (7)0.0019 (7)
C40.0348 (10)0.0284 (9)0.0274 (9)0.0053 (8)0.0042 (7)0.0003 (7)
C50.0330 (9)0.0223 (9)0.0306 (9)0.0017 (7)0.0011 (7)0.0013 (7)
C60.0322 (9)0.0302 (9)0.0239 (8)0.0012 (7)0.0040 (7)0.0032 (7)
C70.0331 (10)0.0321 (11)0.0312 (10)0.0009 (8)0.0029 (7)0.0006 (7)
C80.0352 (10)0.0294 (10)0.0315 (9)0.0010 (8)0.0036 (8)0.0005 (8)
N30.0468 (10)0.0312 (9)0.0413 (10)0.0035 (7)0.0065 (8)0.0009 (7)
C90.0448 (12)0.0425 (12)0.0348 (10)0.0038 (9)0.0042 (9)0.0029 (8)
C100.0451 (11)0.0423 (11)0.0262 (9)0.0056 (9)0.0024 (8)0.0028 (8)
C110.0475 (12)0.0303 (10)0.0322 (10)0.0040 (8)0.0051 (8)0.0018 (7)
C120.0570 (13)0.0502 (13)0.0316 (10)0.0049 (11)0.0108 (9)0.0004 (9)
C130.0642 (14)0.0429 (12)0.0295 (10)0.0096 (11)0.0031 (10)0.0070 (9)
C140.0629 (16)0.0578 (16)0.0795 (18)0.0114 (13)0.0155 (13)0.0086 (13)
Geometric parameters (Å, º) top
Cl1—C51.7163 (17)C5—C61.349 (2)
N4—C151.135 (3)N3—C91.334 (2)
Cl2—C61.7141 (17)N3—C131.337 (3)
C15—C111.442 (3)N3—C141.478 (3)
O1—C11.2440 (19)C9—C101.367 (3)
O2—C41.239 (2)C9—H90.9300
N1—C71.135 (2)C10—C111.382 (3)
N2—C81.142 (2)C10—H100.9300
C1—C21.446 (2)C11—C121.385 (3)
C1—C61.467 (2)C12—C131.361 (3)
C2—C31.386 (2)C12—H120.9300
C2—C71.434 (2)C13—H130.9300
C3—C81.432 (2)C14—H14A0.9600
C3—C41.448 (2)C14—H14B0.9600
C4—C51.463 (2)C14—H14C0.9600
N4—C15—C11177.1 (2)C13—N3—C14118.76 (18)
O1—C1—C2122.41 (16)N3—C9—C10120.60 (18)
O1—C1—C6122.93 (16)N3—C9—H9119.7
C2—C1—C6114.65 (15)C10—C9—H9119.7
C3—C2—C7121.47 (15)C9—C10—C11119.04 (18)
C3—C2—C1122.61 (16)C9—C10—H10120.5
C7—C2—C1115.87 (15)C11—C10—H10120.5
C2—C3—C8120.93 (16)C10—C11—C12119.33 (19)
C2—C3—C4122.04 (15)C10—C11—C15121.30 (17)
C8—C3—C4117.03 (15)C12—C11—C15119.32 (18)
O2—C4—C3122.71 (16)C13—C12—C11119.10 (19)
O2—C4—C5122.47 (16)C13—C12—H12120.5
C3—C4—C5114.81 (14)C11—C12—H12120.5
C6—C5—C4122.89 (16)N3—C13—C12120.69 (18)
C6—C5—Cl1121.54 (14)N3—C13—H13119.7
C4—C5—Cl1115.56 (12)C12—C13—H13119.7
C5—C6—C1122.59 (15)N3—C14—H14A109.5
C5—C6—Cl2122.09 (14)N3—C14—H14B109.5
C1—C6—Cl2115.31 (12)H14A—C14—H14B109.5
N1—C7—C2179.9 (3)N3—C14—H14C109.5
N2—C8—C3179.1 (2)H14A—C14—H14C109.5
C9—N3—C13121.24 (18)H14B—C14—H14C109.5
C9—N3—C14119.98 (18)
O1—C1—C2—C3176.91 (16)Cl1—C5—C6—C1179.64 (13)
C6—C1—C2—C34.3 (2)C4—C5—C6—Cl2179.11 (13)
O1—C1—C2—C75.5 (2)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.37 (15)O1—C1—C6—C5176.28 (17)
C7—C2—C3—C80.8 (3)C2—C1—C6—C54.9 (2)
C1—C2—C3—C8178.33 (16)O1—C1—C6—Cl24.4 (2)
C7—C2—C3—C4178.60 (16)C2—C1—C6—Cl2174.41 (12)
C1—C2—C3—C41.1 (3)C13—N3—C9—C100.0 (3)
C2—C3—C4—O2175.73 (17)C14—N3—C9—C10178.26 (19)
C8—C3—C4—O24.8 (3)N3—C9—C10—C110.1 (3)
C2—C3—C4—C55.8 (2)C9—C10—C11—C120.4 (3)
C8—C3—C4—C5173.68 (15)C9—C10—C11—C15176.99 (19)
O2—C4—C5—C6176.31 (17)C10—C11—C12—C131.0 (3)
C3—C4—C5—C65.2 (3)C15—C11—C12—C13176.47 (19)
O2—C4—C5—Cl14.2 (2)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.33 (12)C14—N3—C13—C12178.9 (2)
C4—C5—C6—C10.1 (3)C11—C12—C13—N31.1 (3)
(340K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.610 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.8983 (2) ÅCell parameters from 3314 reflections
b = 10.1074 (2) Åθ = 2.0–26.7°
c = 20.5530 (4) ŵ = 0.47 mm1
β = 94.690 (2)°T = 340 K
V = 1428.23 (6) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
3257 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 79
Tmin = 0.944, Tmax = 1.000k = 1312
9495 measured reflectionsl = 2726
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.24 e Å3
209 parametersΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20362 (8)0.11394 (5)0.00713 (2)0.04606 (15)
N40.9854 (3)1.2014 (2)0.24749 (9)0.0645 (6)
Cl20.11624 (8)0.28136 (5)0.11675 (2)0.04566 (15)
C150.8373 (4)1.1540 (2)0.23510 (10)0.0487 (5)
O10.1365 (2)0.56633 (13)0.09451 (6)0.0430 (3)
O20.2895 (2)0.27844 (13)0.11746 (6)0.0487 (4)
N10.2993 (3)0.81123 (18)0.00653 (9)0.0530 (5)
N20.4163 (3)0.59816 (18)0.16611 (9)0.0525 (5)
C10.1812 (3)0.49967 (18)0.04711 (8)0.0321 (4)
C20.2473 (2)0.55989 (17)0.01105 (8)0.0305 (4)
C30.2882 (2)0.48642 (18)0.06520 (8)0.0309 (4)
C40.2636 (3)0.34431 (18)0.06801 (9)0.0329 (4)
C50.2123 (3)0.28353 (17)0.00716 (8)0.0320 (4)
C60.1739 (3)0.35503 (18)0.04580 (8)0.0320 (4)
C70.2762 (3)0.7002 (2)0.00866 (9)0.0357 (4)
C80.3589 (3)0.54916 (19)0.12116 (9)0.0357 (4)
N30.3216 (2)0.95297 (16)0.18331 (8)0.0451 (4)
C90.3548 (3)0.9990 (2)0.24414 (10)0.0454 (5)
H90.2634970.9845930.2742510.054*
C100.5212 (3)1.0671 (2)0.26262 (9)0.0422 (5)
H100.5439891.0988960.3050120.051*
C110.6551 (3)1.08784 (19)0.21737 (9)0.0402 (5)
C120.6176 (3)1.0400 (2)0.15450 (10)0.0502 (5)
H120.7056631.0541320.1232930.060*
C130.4505 (3)0.9723 (2)0.13911 (10)0.0520 (6)
H130.4251360.9387090.0971470.062*
C140.1434 (4)0.8761 (3)0.16463 (14)0.0754 (8)
H14A0.0714880.9183100.1284360.113*
H14B0.0646090.8717860.2009740.113*
H14C0.1784180.7881400.1523630.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0656 (4)0.0258 (2)0.0475 (3)0.0013 (2)0.0089 (2)0.0007 (2)
N40.0687 (14)0.0738 (15)0.0517 (12)0.0195 (12)0.0096 (10)0.0101 (10)
Cl20.0613 (3)0.0441 (3)0.0327 (3)0.0034 (2)0.0099 (2)0.0071 (2)
C150.0613 (15)0.0480 (13)0.0381 (12)0.0030 (12)0.0120 (11)0.0058 (9)
O10.0570 (9)0.0404 (8)0.0326 (7)0.0015 (7)0.0097 (6)0.0092 (6)
O20.0755 (10)0.0361 (8)0.0359 (8)0.0069 (7)0.0140 (7)0.0060 (6)
N10.0630 (12)0.0330 (11)0.0628 (12)0.0057 (9)0.0047 (9)0.0035 (8)
N20.0632 (12)0.0526 (12)0.0428 (10)0.0080 (9)0.0116 (9)0.0067 (8)
C10.0355 (10)0.0318 (10)0.0288 (9)0.0020 (8)0.0022 (8)0.0011 (7)
C20.0327 (10)0.0272 (9)0.0315 (9)0.0020 (8)0.0029 (7)0.0004 (7)
C30.0332 (10)0.0300 (10)0.0297 (9)0.0022 (8)0.0035 (7)0.0025 (7)
C40.0374 (10)0.0304 (10)0.0312 (10)0.0057 (8)0.0038 (8)0.0012 (7)
C50.0362 (10)0.0246 (9)0.0351 (10)0.0023 (8)0.0027 (8)0.0027 (7)
C60.0362 (10)0.0317 (10)0.0284 (9)0.0008 (8)0.0043 (8)0.0033 (7)
C70.0382 (11)0.0350 (11)0.0338 (10)0.0009 (8)0.0026 (8)0.0001 (8)
C80.0395 (11)0.0327 (10)0.0348 (10)0.0006 (8)0.0019 (8)0.0014 (8)
N30.0518 (11)0.0353 (10)0.0464 (10)0.0050 (8)0.0065 (8)0.0024 (8)
C90.0499 (13)0.0475 (13)0.0389 (11)0.0037 (10)0.0051 (9)0.0029 (9)
C100.0520 (13)0.0448 (12)0.0298 (10)0.0046 (10)0.0044 (9)0.0020 (8)
C110.0522 (13)0.0335 (11)0.0349 (11)0.0036 (9)0.0042 (9)0.0028 (8)
C120.0634 (15)0.0543 (14)0.0343 (11)0.0029 (12)0.0115 (10)0.0002 (10)
C130.0714 (16)0.0482 (14)0.0351 (11)0.0115 (12)0.0032 (11)0.0082 (10)
C140.0694 (18)0.0661 (18)0.087 (2)0.0152 (14)0.0142 (15)0.0113 (14)
Geometric parameters (Å, º) top
Cl1—C51.7152 (18)C5—C61.351 (2)
N4—C151.138 (3)N3—C131.336 (3)
Cl2—C61.7129 (17)N3—C91.336 (2)
C15—C111.445 (3)N3—C141.478 (3)
O1—C11.244 (2)C9—C101.365 (3)
O2—C41.240 (2)C9—H90.9300
N1—C71.134 (2)C10—C111.379 (3)
N2—C81.147 (2)C10—H100.9300
C1—C21.448 (2)C11—C121.384 (3)
C1—C61.463 (3)C12—C131.356 (3)
C2—C31.386 (2)C12—H120.9300
C2—C71.433 (3)C13—H130.9300
C3—C81.434 (2)C14—H14A0.9600
C3—C41.447 (3)C14—H14B0.9600
C4—C51.462 (2)C14—H14C0.9600
N4—C15—C11176.6 (2)C9—N3—C14120.1 (2)
O1—C1—C2122.26 (17)N3—C9—C10120.79 (19)
O1—C1—C6123.05 (16)N3—C9—H9119.6
C2—C1—C6114.68 (15)C10—C9—H9119.6
C3—C2—C7121.41 (16)C9—C10—C11118.89 (19)
C3—C2—C1122.43 (16)C9—C10—H10120.6
C7—C2—C1116.11 (16)C11—C10—H10120.6
C2—C3—C8120.82 (16)C10—C11—C12119.5 (2)
C2—C3—C4122.20 (16)C10—C11—C15121.15 (18)
C8—C3—C4116.98 (16)C12—C11—C15119.32 (19)
O2—C4—C3122.78 (17)C13—C12—C11119.0 (2)
O2—C4—C5122.44 (17)C13—C12—H12120.5
C3—C4—C5114.75 (15)C11—C12—H12120.5
C6—C5—C4122.79 (17)N3—C13—C12121.02 (19)
C6—C5—Cl1121.68 (14)N3—C13—H13119.5
C4—C5—Cl1115.54 (13)C12—C13—H13119.5
C5—C6—C1122.73 (16)N3—C14—H14A109.5
C5—C6—Cl2121.87 (15)N3—C14—H14B109.5
C1—C6—Cl2115.39 (13)H14A—C14—H14B109.5
N1—C7—C2179.7 (2)N3—C14—H14C109.5
N2—C8—C3179.3 (2)H14A—C14—H14C109.5
C13—N3—C9120.82 (19)H14B—C14—H14C109.5
C13—N3—C14119.05 (19)
O1—C1—C2—C3176.80 (17)Cl1—C5—C6—C1179.71 (14)
C6—C1—C2—C33.9 (3)C4—C5—C6—Cl2179.43 (14)
O1—C1—C2—C75.7 (3)Cl1—C5—C6—Cl20.6 (2)
C6—C1—C2—C7173.53 (16)O1—C1—C6—C5176.25 (18)
C7—C2—C3—C80.8 (3)C2—C1—C6—C54.5 (3)
C1—C2—C3—C8178.09 (16)O1—C1—C6—Cl24.6 (2)
C7—C2—C3—C4178.76 (17)C2—C1—C6—Cl2174.66 (12)
C1—C2—C3—C41.4 (3)C13—N3—C9—C100.1 (3)
C2—C3—C4—O2175.93 (18)C14—N3—C9—C10178.2 (2)
C8—C3—C4—O24.5 (3)N3—C9—C10—C110.1 (3)
C2—C3—C4—C56.1 (3)C9—C10—C11—C120.3 (3)
C8—C3—C4—C5173.43 (16)C9—C10—C11—C15177.2 (2)
O2—C4—C5—C6176.43 (18)C10—C11—C12—C130.8 (3)
C3—C4—C5—C65.6 (3)C15—C11—C12—C13176.8 (2)
O2—C4—C5—Cl13.5 (2)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.44 (13)C14—N3—C13—C12178.7 (2)
C4—C5—C6—C10.3 (3)C11—C12—C13—N30.9 (3)
(370K) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.601 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.9227 (2) ÅCell parameters from 3098 reflections
b = 10.1152 (2) Åθ = 2.0–26.7°
c = 20.5732 (5) ŵ = 0.47 mm1
β = 94.691 (3)°T = 370 K
V = 1435.81 (7) Å3Block, black
Z = 40.40 × 0.15 × 0.07 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
2318 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 97
Tmin = 0.939, Tmax = 1.000k = 1312
9538 measured reflectionsl = 2627
3278 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-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 reflectionsΔρmax = 0.21 e Å3
209 parametersΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20329 (8)0.11434 (5)0.00714 (3)0.05121 (17)
N40.9835 (3)1.2008 (2)0.24711 (10)0.0718 (6)
Cl20.11629 (8)0.28167 (5)0.11673 (2)0.05103 (16)
C150.8364 (4)1.1537 (2)0.23493 (11)0.0546 (6)
O10.1370 (2)0.56620 (14)0.09453 (6)0.0482 (4)
O20.2896 (2)0.27898 (14)0.11726 (6)0.0540 (4)
N10.2995 (3)0.81096 (19)0.00651 (9)0.0587 (5)
N20.4158 (3)0.59791 (19)0.16570 (9)0.0585 (5)
C10.1814 (3)0.50002 (19)0.04716 (9)0.0358 (4)
C20.2479 (3)0.55989 (18)0.01088 (9)0.0345 (4)
C30.2888 (3)0.48661 (18)0.06500 (8)0.0341 (4)
C40.2641 (3)0.34441 (19)0.06768 (9)0.0370 (4)
C50.2119 (3)0.28391 (18)0.00713 (9)0.0356 (4)
C60.1740 (3)0.35534 (18)0.04582 (9)0.0353 (4)
C70.2762 (3)0.7001 (2)0.00859 (9)0.0395 (5)
C80.3589 (3)0.54945 (19)0.12087 (9)0.0400 (5)
N30.3222 (3)0.95302 (17)0.18346 (9)0.0502 (5)
C90.3554 (3)0.9990 (2)0.24421 (10)0.0497 (5)
H90.2646580.9845990.2743680.060*
C100.5211 (3)1.0669 (2)0.26237 (10)0.0463 (5)
H100.5436691.0990220.3046700.056*
C110.6548 (3)1.08754 (19)0.21738 (10)0.0445 (5)
C120.6171 (4)1.0396 (2)0.15467 (10)0.0548 (6)
H120.7049891.0535770.1235000.066*
C130.4509 (4)0.9721 (2)0.13920 (11)0.0566 (6)
H130.4257700.9386130.0972710.068*
C140.1442 (4)0.8762 (3)0.16488 (15)0.0835 (9)
H14A0.0744150.9169500.1279110.125*
H14B0.0639860.8743170.2008000.125*
H14C0.1786590.7875150.1538950.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0736 (4)0.0280 (3)0.0528 (3)0.0014 (2)0.0099 (3)0.0010 (2)
N40.0777 (15)0.0817 (16)0.0569 (13)0.0218 (13)0.0119 (11)0.0108 (11)
Cl20.0689 (4)0.0492 (3)0.0361 (3)0.0039 (3)0.0110 (2)0.0080 (2)
C150.0680 (16)0.0545 (14)0.0426 (13)0.0060 (13)0.0133 (12)0.0068 (10)
O10.0657 (9)0.0456 (8)0.0344 (7)0.0013 (7)0.0114 (7)0.0095 (6)
O20.0859 (11)0.0394 (8)0.0386 (8)0.0087 (8)0.0157 (7)0.0052 (6)
N10.0703 (13)0.0360 (11)0.0695 (13)0.0061 (9)0.0037 (10)0.0035 (9)
N20.0716 (13)0.0603 (13)0.0450 (11)0.0094 (10)0.0131 (10)0.0065 (9)
C10.0400 (11)0.0353 (11)0.0321 (10)0.0026 (8)0.0031 (8)0.0008 (8)
C20.0372 (11)0.0293 (10)0.0368 (10)0.0017 (8)0.0027 (8)0.0004 (8)
C30.0379 (10)0.0329 (10)0.0318 (9)0.0032 (8)0.0035 (8)0.0026 (7)
C40.0435 (11)0.0339 (10)0.0339 (10)0.0072 (9)0.0050 (8)0.0010 (8)
C50.0428 (11)0.0273 (10)0.0368 (10)0.0023 (8)0.0034 (8)0.0021 (8)
C60.0410 (11)0.0345 (10)0.0305 (10)0.0008 (8)0.0044 (8)0.0041 (7)
C70.0434 (11)0.0367 (12)0.0386 (11)0.0010 (9)0.0042 (9)0.0008 (8)
C80.0451 (12)0.0367 (11)0.0383 (11)0.0030 (9)0.0040 (9)0.0015 (9)
N30.0581 (12)0.0391 (10)0.0515 (11)0.0047 (9)0.0069 (9)0.0016 (8)
C90.0558 (14)0.0520 (13)0.0415 (12)0.0047 (11)0.0058 (10)0.0030 (10)
C100.0563 (13)0.0505 (13)0.0323 (11)0.0049 (11)0.0050 (10)0.0034 (9)
C110.0571 (14)0.0369 (11)0.0399 (11)0.0054 (10)0.0063 (10)0.0031 (8)
C120.0672 (15)0.0619 (15)0.0365 (12)0.0043 (13)0.0122 (11)0.0011 (10)
C130.0762 (17)0.0543 (15)0.0378 (12)0.0129 (13)0.0043 (12)0.0101 (10)
C140.0752 (19)0.075 (2)0.096 (2)0.0159 (15)0.0167 (16)0.0124 (16)
Geometric parameters (Å, º) top
Cl1—C51.7162 (19)C5—C61.351 (2)
N4—C151.134 (3)N3—C91.336 (3)
Cl2—C61.7143 (18)N3—C131.339 (3)
C15—C111.444 (3)N3—C141.481 (3)
O1—C11.242 (2)C9—C101.363 (3)
O2—C41.241 (2)C9—H90.9300
N1—C71.133 (2)C10—C111.377 (3)
N2—C81.143 (2)C10—H100.9300
C1—C21.447 (2)C11—C121.383 (3)
C1—C61.465 (3)C12—C131.353 (3)
C2—C31.386 (2)C12—H120.9300
C2—C71.432 (3)C13—H130.9300
C3—C81.433 (3)C14—H14A0.9600
C3—C41.449 (3)C14—H14B0.9600
C4—C51.460 (2)C14—H14C0.9600
N4—C15—C11176.6 (3)C13—N3—C14119.1 (2)
O1—C1—C2122.55 (17)N3—C9—C10120.6 (2)
O1—C1—C6122.88 (17)N3—C9—H9119.7
C2—C1—C6114.56 (16)C10—C9—H9119.7
C3—C2—C7121.31 (17)C9—C10—C11119.26 (19)
C3—C2—C1122.60 (17)C9—C10—H10120.4
C7—C2—C1116.06 (16)C11—C10—H10120.4
C2—C3—C8120.81 (17)C10—C11—C12119.2 (2)
C2—C3—C4122.03 (16)C10—C11—C15121.42 (19)
C8—C3—C4117.16 (16)C12—C11—C15119.31 (19)
O2—C4—C3122.46 (17)C13—C12—C11119.2 (2)
O2—C4—C5122.66 (18)C13—C12—H12120.4
C3—C4—C5114.86 (16)C11—C12—H12120.4
C6—C5—C4122.82 (17)N3—C13—C12120.9 (2)
C6—C5—Cl1121.72 (14)N3—C13—H13119.6
C4—C5—Cl1115.46 (13)C12—C13—H13119.6
C5—C6—C1122.75 (17)N3—C14—H14A109.5
C5—C6—Cl2121.87 (15)N3—C14—H14B109.5
C1—C6—Cl2115.38 (13)H14A—C14—H14B109.5
N1—C7—C2179.6 (2)N3—C14—H14C109.5
N2—C8—C3179.0 (2)H14A—C14—H14C109.5
C9—N3—C13120.8 (2)H14B—C14—H14C109.5
C9—N3—C14120.0 (2)
O1—C1—C2—C3176.90 (18)Cl1—C5—C6—C1179.65 (14)
C6—C1—C2—C34.1 (3)C4—C5—C6—Cl2179.06 (14)
O1—C1—C2—C75.3 (3)Cl1—C5—C6—Cl20.4 (2)
C6—C1—C2—C7173.73 (16)O1—C1—C6—C5176.16 (19)
C7—C2—C3—C80.8 (3)C2—C1—C6—C54.8 (3)
C1—C2—C3—C8178.44 (17)O1—C1—C6—Cl24.5 (3)
C7—C2—C3—C4178.90 (17)C2—C1—C6—Cl2174.51 (13)
C1—C2—C3—C41.2 (3)C13—N3—C9—C100.2 (3)
C2—C3—C4—O2175.71 (18)C14—N3—C9—C10178.3 (2)
C8—C3—C4—O24.6 (3)N3—C9—C10—C110.1 (3)
C2—C3—C4—C55.7 (3)C9—C10—C11—C120.4 (3)
C8—C3—C4—C5173.93 (16)C9—C10—C11—C15177.2 (2)
O2—C4—C5—C6176.39 (19)C10—C11—C12—C130.8 (3)
C3—C4—C5—C65.1 (3)C15—C11—C12—C13176.9 (2)
O2—C4—C5—Cl14.1 (3)C9—N3—C13—C120.6 (3)
C3—C4—C5—Cl1174.41 (13)C14—N3—C13—C12178.7 (2)
C4—C5—C6—C10.2 (3)C11—C12—C13—N30.9 (3)
(test3_ddq_4cn) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.618 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.8687 (6) ÅCell parameters from 1546 reflections
b = 10.105 (2) Åθ = 2.0–23.5°
c = 20.5426 (19) ŵ = 0.47 mm1
β = 94.681 (7)°T = 293 K
V = 1421.1 (4) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1558 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 88
Tmin = 0.360, Tmax = 0.450k = 88
7420 measured reflectionsl = 2323
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-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 reflectionsΔρmax = 0.28 e Å3
209 parametersΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20423 (15)0.11377 (18)0.00716 (5)0.0440 (6)
N40.9885 (5)1.2027 (5)0.24780 (16)0.0539 (18)
Cl20.11620 (14)0.28082 (16)0.11688 (5)0.0418 (5)
C150.8390 (7)1.1550 (6)0.23521 (19)0.0423 (19)
O10.1359 (4)0.5662 (4)0.09452 (13)0.0407 (13)
O20.2899 (4)0.2777 (4)0.11775 (13)0.0453 (14)
N10.2994 (7)0.8128 (7)0.00668 (18)0.049 (2)
N20.4167 (5)0.5980 (5)0.16687 (18)0.0484 (19)
C10.1801 (6)0.4993 (7)0.04724 (18)0.0309 (16)
C20.2475 (6)0.5612 (7)0.01107 (18)0.0315 (17)
C30.2877 (6)0.4856 (7)0.06535 (18)0.0307 (16)
C40.2638 (6)0.3461 (7)0.0688 (2)0.0332 (16)
C50.2125 (5)0.2846 (7)0.00726 (18)0.0284 (15)
C60.1743 (6)0.3566 (7)0.04548 (18)0.0310 (16)
C70.2762 (7)0.6997 (9)0.00885 (18)0.031 (2)
C80.3590 (5)0.5495 (6)0.1216 (2)0.0329 (19)
N30.3207 (4)0.9538 (5)0.18291 (17)0.0438 (17)
C90.3545 (6)1.0012 (7)0.2442 (2)0.042 (2)
H90.2618380.9883490.2741150.051*
C100.5202 (5)1.0669 (6)0.26252 (18)0.0365 (18)
H100.5437021.0970980.3051990.044*
C110.6557 (5)1.0892 (6)0.21732 (19)0.038 (2)
C120.6175 (6)1.0409 (7)0.1545 (2)0.044 (2)
H120.7056981.0555480.1232440.053*
C130.4501 (6)0.9718 (6)0.1387 (2)0.048 (2)
H130.4259090.9370430.0968830.058*
C140.1423 (6)0.8783 (8)0.1642 (2)0.069 (3)
H14A0.0641440.8728630.2007970.103*
H14B0.1767300.7906990.1511190.103*
H14C0.0694590.9218180.1285500.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0577 (7)0.033 (2)0.0426 (8)0.0008 (8)0.0091 (5)0.0010 (6)
N40.060 (2)0.057 (7)0.046 (3)0.020 (3)0.0120 (19)0.004 (2)
Cl20.0536 (7)0.0411 (18)0.0315 (7)0.0026 (7)0.0089 (5)0.0066 (6)
C150.055 (3)0.045 (7)0.028 (3)0.003 (3)0.010 (2)0.004 (2)
O10.0512 (16)0.042 (5)0.0302 (19)0.004 (2)0.0090 (13)0.0083 (16)
O20.0666 (19)0.037 (5)0.034 (2)0.006 (2)0.0132 (14)0.0069 (16)
N10.061 (3)0.036 (7)0.051 (3)0.004 (4)0.0042 (18)0.000 (3)
N20.055 (2)0.047 (7)0.044 (3)0.012 (3)0.0123 (18)0.003 (2)
C10.030 (2)0.036 (6)0.026 (3)0.001 (3)0.0032 (17)0.003 (2)
C20.027 (2)0.036 (6)0.031 (3)0.001 (3)0.0008 (18)0.002 (2)
C30.031 (2)0.033 (6)0.030 (3)0.005 (3)0.0066 (17)0.002 (2)
C40.034 (2)0.036 (6)0.030 (3)0.014 (3)0.0046 (18)0.001 (2)
C50.031 (2)0.017 (5)0.037 (3)0.001 (3)0.0029 (18)0.001 (2)
C60.032 (2)0.039 (5)0.022 (2)0.004 (3)0.0045 (17)0.002 (2)
C70.031 (2)0.037 (7)0.027 (3)0.003 (5)0.0051 (17)0.002 (3)
C80.034 (2)0.030 (7)0.035 (3)0.005 (3)0.0018 (19)0.005 (2)
N30.043 (2)0.046 (6)0.040 (2)0.002 (2)0.0066 (17)0.004 (2)
C90.044 (2)0.046 (7)0.037 (3)0.007 (3)0.0051 (19)0.000 (2)
C100.040 (2)0.044 (7)0.025 (3)0.006 (3)0.0011 (18)0.000 (2)
C110.042 (2)0.037 (7)0.034 (3)0.001 (3)0.0047 (19)0.007 (2)
C120.052 (2)0.049 (7)0.032 (3)0.003 (3)0.009 (2)0.002 (2)
C130.062 (3)0.050 (7)0.033 (3)0.009 (3)0.002 (2)0.002 (2)
C140.071 (3)0.049 (10)0.084 (4)0.016 (4)0.008 (3)0.012 (3)
Geometric parameters (Å, º) top
Cl1—C51.727 (7)C5—C61.349 (6)
N4—C151.145 (5)N3—C131.334 (5)
Cl2—C61.730 (5)N3—C91.349 (5)
C15—C111.444 (6)N3—C141.468 (6)
O1—C11.241 (5)C9—C101.345 (6)
O2—C41.246 (6)C9—H90.9300
N1—C71.155 (8)C10—C111.386 (5)
N2—C81.150 (5)C10—H100.9300
C1—C61.443 (8)C11—C121.385 (6)
C1—C21.460 (6)C12—C131.361 (6)
C2—C31.398 (7)C12—H120.9300
C2—C71.413 (8)C13—H130.9300
C3—C41.420 (8)C14—H14A0.9600
C3—C81.444 (6)C14—H14B0.9600
C4—C51.476 (6)C14—H14C0.9600
N4—C15—C11176.8 (6)C9—N3—C14120.3 (4)
O1—C1—C6123.8 (4)C10—C9—N3121.0 (4)
O1—C1—C2121.5 (6)C10—C9—H9119.5
C6—C1—C2114.7 (4)N3—C9—H9119.5
C3—C2—C7122.0 (5)C9—C10—C11119.5 (4)
C3—C2—C1121.1 (6)C9—C10—H10120.3
C7—C2—C1116.8 (4)C11—C10—H10120.3
C2—C3—C4123.5 (5)C12—C11—C10118.7 (4)
C2—C3—C8119.7 (6)C12—C11—C15119.7 (4)
C4—C3—C8116.7 (4)C10—C11—C15121.6 (4)
O2—C4—C3124.5 (5)C13—C12—C11119.7 (4)
O2—C4—C5121.2 (6)C13—C12—H12120.1
C3—C4—C5114.2 (4)C11—C12—H12120.1
C6—C5—C4122.4 (6)N3—C13—C12120.3 (4)
C6—C5—Cl1122.0 (4)N3—C13—H13119.9
C4—C5—Cl1115.6 (4)C12—C13—H13119.9
C5—C6—C1123.6 (5)N3—C14—H14A109.5
C5—C6—Cl2121.0 (5)N3—C14—H14B109.5
C1—C6—Cl2115.4 (3)H14A—C14—H14B109.5
N1—C7—C2179.6 (5)N3—C14—H14C109.5
N2—C8—C3178.6 (6)H14A—C14—H14C109.5
C13—N3—C9120.9 (4)H14B—C14—H14C109.5
C13—N3—C14118.8 (4)
O1—C1—C2—C3176.8 (4)Cl1—C5—C6—C1179.9 (3)
C6—C1—C2—C34.6 (6)C4—C5—C6—Cl2179.6 (3)
O1—C1—C2—C75.4 (6)Cl1—C5—C6—Cl20.5 (5)
C6—C1—C2—C7173.3 (4)O1—C1—C6—C5176.4 (3)
C7—C2—C3—C4178.9 (4)C2—C1—C6—C55.0 (6)
C1—C2—C3—C41.2 (7)O1—C1—C6—Cl24.2 (6)
C7—C2—C3—C80.7 (6)C2—C1—C6—Cl2174.4 (2)
C1—C2—C3—C8178.4 (3)C13—N3—C9—C100.6 (8)
C2—C3—C4—O2176.4 (4)C14—N3—C9—C10177.8 (6)
C8—C3—C4—O24.0 (7)N3—C9—C10—C111.8 (8)
C2—C3—C4—C56.2 (6)C9—C10—C11—C121.1 (8)
C8—C3—C4—C5173.3 (3)C9—C10—C11—C15177.7 (6)
O2—C4—C5—C6176.8 (4)C10—C11—C12—C130.7 (8)
C3—C4—C5—C65.8 (6)C15—C11—C12—C13176.0 (6)
O2—C4—C5—Cl13.2 (5)C9—N3—C13—C121.2 (8)
C3—C4—C5—Cl1174.3 (3)C14—N3—C13—C12179.7 (6)
C4—C5—C6—C10.2 (6)C11—C12—C13—N31.9 (8)
(test3_0.25GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.632 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.8312 (4) ÅCell parameters from 1555 reflections
b = 10.0839 (16) Åθ = 2.0–22.5°
c = 20.5232 (15) ŵ = 0.48 mm1
β = 94.635 (6)°T = 293 K
V = 1409.1 (3) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1542 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source922 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 88
Tmin = 0.361, Tmax = 0.450k = 88
7278 measured reflectionsl = 2323
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 reflectionsΔρmax = 0.21 e Å3
208 parametersΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20496 (16)0.11322 (18)0.00723 (5)0.0405 (5)
Cl20.11722 (15)0.28077 (17)0.11705 (5)0.0392 (5)
O10.1366 (4)0.5671 (4)0.09439 (13)0.0362 (13)
O20.2907 (4)0.2775 (4)0.11802 (13)0.0425 (15)
N10.2986 (7)0.8138 (7)0.00673 (19)0.047 (2)
N20.4175 (5)0.5977 (6)0.16718 (19)0.0455 (19)
N30.3199 (5)0.9541 (5)0.18265 (18)0.0376 (16)
N40.9898 (6)1.2036 (6)0.24820 (17)0.058 (2)
C10.1809 (6)0.4994 (7)0.0471 (2)0.0287 (16)
C20.2483 (6)0.5615 (7)0.01178 (19)0.0258 (16)
C30.2895 (6)0.4861 (7)0.0655 (2)0.0268 (16)
C40.2639 (6)0.3450 (7)0.0686 (2)0.0311 (16)
C50.2130 (6)0.2834 (7)0.00737 (19)0.0259 (15)
C60.1743 (6)0.3548 (7)0.04544 (19)0.0281 (15)
C70.2761 (7)0.7011 (9)0.0093 (2)0.0282 (19)
C80.3596 (5)0.5494 (6)0.1218 (2)0.0277 (18)
C90.3539 (6)1.0006 (6)0.2441 (2)0.036 (2)
H90.2611830.9866660.2741770.043*
C100.5202 (6)1.0669 (6)0.2625 (2)0.0365 (19)
H100.5434281.0969760.3053120.044*
C110.6562 (6)1.0901 (6)0.2176 (2)0.037 (2)
C120.6193 (7)1.0417 (7)0.1546 (2)0.043 (2)
H120.7088291.0559970.1234840.052*
C130.4504 (6)0.9729 (7)0.1387 (2)0.046 (2)
H130.4260070.9387110.0967060.055*
C140.1404 (7)0.8770 (7)0.1641 (3)0.066 (3)
H14A0.0613700.8719930.2006050.099*
H14B0.0671070.9196410.1280750.099*
H14C0.1758910.7890800.1514210.099*
C150.8396 (7)1.1542 (7)0.2353 (2)0.040 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0550 (7)0.026 (2)0.0412 (9)0.0006 (9)0.0087 (5)0.0010 (6)
Cl20.0526 (7)0.0359 (19)0.0301 (8)0.0039 (8)0.0104 (5)0.0073 (6)
O10.0502 (17)0.031 (5)0.028 (2)0.002 (2)0.0078 (14)0.0083 (16)
O20.063 (2)0.037 (5)0.028 (2)0.009 (2)0.0111 (15)0.0071 (17)
N10.058 (3)0.036 (7)0.048 (3)0.002 (4)0.0051 (19)0.006 (3)
N20.051 (2)0.047 (7)0.041 (3)0.004 (3)0.0134 (19)0.001 (2)
N30.046 (2)0.029 (6)0.037 (3)0.004 (2)0.0024 (18)0.000 (2)
N40.059 (3)0.075 (7)0.040 (3)0.018 (3)0.009 (2)0.006 (2)
C10.029 (2)0.033 (6)0.023 (3)0.005 (3)0.0018 (19)0.001 (2)
C20.024 (2)0.024 (6)0.029 (3)0.004 (3)0.0039 (19)0.002 (2)
C30.027 (2)0.027 (6)0.028 (3)0.004 (3)0.0095 (19)0.000 (2)
C40.032 (2)0.032 (6)0.029 (3)0.009 (3)0.004 (2)0.004 (2)
C50.035 (2)0.012 (6)0.031 (3)0.002 (3)0.0043 (19)0.002 (2)
C60.028 (2)0.031 (5)0.026 (3)0.000 (3)0.0042 (19)0.003 (2)
C70.029 (3)0.027 (7)0.029 (3)0.006 (5)0.0052 (19)0.001 (3)
C80.031 (2)0.018 (7)0.035 (3)0.002 (3)0.006 (2)0.004 (2)
C90.045 (3)0.029 (7)0.035 (3)0.009 (3)0.012 (2)0.000 (2)
C100.038 (2)0.046 (7)0.025 (3)0.003 (3)0.002 (2)0.002 (2)
C110.044 (2)0.039 (7)0.029 (3)0.007 (3)0.006 (2)0.006 (2)
C120.052 (3)0.045 (8)0.034 (3)0.003 (3)0.012 (2)0.002 (3)
C130.060 (3)0.048 (7)0.028 (3)0.011 (3)0.003 (2)0.005 (2)
C140.071 (3)0.043 (10)0.083 (5)0.014 (4)0.005 (3)0.010 (3)
C150.054 (3)0.041 (7)0.027 (3)0.002 (3)0.009 (2)0.005 (2)
Geometric parameters (Å, º) top
Cl1—C51.717 (7)C3—C81.437 (6)
Cl2—C61.721 (5)C4—C51.468 (7)
O1—C11.244 (6)C5—C61.345 (7)
O2—C41.248 (6)C9—C101.346 (6)
N1—C71.147 (8)C9—H90.9300
N2—C81.149 (5)C10—C111.381 (5)
N3—C131.333 (5)C10—H100.9300
N3—C91.348 (5)C11—C121.386 (6)
N3—C141.476 (6)C11—C151.430 (7)
N4—C151.152 (6)C12—C131.364 (7)
C1—C61.460 (8)C12—H120.9300
C1—C21.467 (7)C13—H130.9300
C2—C31.386 (7)C14—H14A0.9600
C2—C71.421 (8)C14—H14B0.9600
C3—C41.434 (8)C14—H14C0.9600
C13—N3—C9120.7 (4)C10—C9—N3120.9 (4)
C13—N3—C14119.2 (4)C10—C9—H9119.5
C9—N3—C14120.1 (4)N3—C9—H9119.5
O1—C1—C6123.9 (5)C9—C10—C11119.6 (4)
O1—C1—C2121.4 (6)C9—C10—H10120.2
C6—C1—C2114.7 (4)C11—C10—H10120.2
C3—C2—C7122.5 (5)C10—C11—C12118.8 (5)
C3—C2—C1121.2 (6)C10—C11—C15122.0 (4)
C7—C2—C1116.3 (4)C12—C11—C15119.0 (4)
C2—C3—C4123.2 (5)C13—C12—C11119.3 (4)
C2—C3—C8119.9 (6)C13—C12—H12120.4
C4—C3—C8116.9 (4)C11—C12—H12120.4
O2—C4—C3123.5 (5)N3—C13—C12120.7 (4)
O2—C4—C5121.7 (6)N3—C13—H13119.7
C3—C4—C5114.7 (4)C12—C13—H13119.7
C6—C5—C4122.6 (6)N3—C14—H14A109.5
C6—C5—Cl1121.7 (4)N3—C14—H14B109.5
C4—C5—Cl1115.8 (4)H14A—C14—H14B109.5
C5—C6—C1123.1 (5)N3—C14—H14C109.5
C5—C6—Cl2121.9 (5)H14A—C14—H14C109.5
C1—C6—Cl2115.0 (3)H14B—C14—H14C109.5
N1—C7—C2179.5 (5)N4—C15—C11178.1 (6)
N2—C8—C3178.6 (6)
O1—C1—C2—C3177.2 (4)Cl1—C5—C6—C1179.7 (3)
C6—C1—C2—C33.8 (6)C4—C5—C6—Cl2179.4 (3)
O1—C1—C2—C75.3 (6)Cl1—C5—C6—Cl20.9 (5)
C6—C1—C2—C7173.7 (4)O1—C1—C6—C5176.5 (4)
C7—C2—C3—C4179.5 (4)C2—C1—C6—C54.6 (6)
C1—C2—C3—C42.1 (7)O1—C1—C6—Cl24.6 (6)
C7—C2—C3—C81.2 (7)C2—C1—C6—Cl2174.3 (3)
C1—C2—C3—C8178.5 (4)C13—N3—C9—C100.1 (8)
C2—C3—C4—O2176.1 (4)C14—N3—C9—C10177.6 (6)
C8—C3—C4—O23.3 (7)N3—C9—C10—C111.3 (8)
C2—C3—C4—C57.1 (7)C9—C10—C11—C121.3 (8)
C8—C3—C4—C5173.6 (3)C9—C10—C11—C15176.8 (6)
O2—C4—C5—C6176.7 (4)C10—C11—C12—C130.1 (8)
C3—C4—C5—C66.3 (6)C15—C11—C12—C13175.7 (6)
O2—C4—C5—Cl13.1 (6)C9—N3—C13—C121.2 (8)
C3—C4—C5—Cl1173.9 (3)C14—N3—C13—C12178.9 (6)
C4—C5—C6—C10.6 (7)C11—C12—C13—N31.2 (9)
(test3_0.49GPa) top
Crystal data top
C15H7Cl2N4O2F(000) = 700
Mr = 346.15Dx = 1.664 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.7445 (3) ÅCell parameters from 1864 reflections
b = 10.0486 (12) Åθ = 2.0–25.4°
c = 20.4539 (11) ŵ = 0.49 mm1
β = 94.589 (4)°T = 293 K
V = 1381.77 (19) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1500 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source995 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 88
Tmin = 0.364, Tmax = 0.450k = 88
7093 measured reflectionsl = 2323
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.29 e Å3
209 parametersΔρmin = 0.22 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20679 (15)0.11222 (17)0.00714 (5)0.0355 (5)
Cl20.11879 (15)0.28046 (16)0.11746 (5)0.0345 (5)
O10.1374 (4)0.5672 (4)0.09451 (13)0.0308 (12)
O20.2924 (4)0.2769 (4)0.11835 (13)0.0350 (13)
N10.2986 (7)0.8156 (7)0.00721 (18)0.0415 (18)
N20.4176 (5)0.5979 (5)0.16858 (18)0.0379 (17)
N30.3175 (5)0.9551 (5)0.18243 (17)0.0329 (15)
N40.9944 (6)1.2060 (6)0.24859 (17)0.0495 (18)
C10.1831 (5)0.4984 (7)0.04660 (19)0.0234 (15)
C20.2485 (5)0.5624 (7)0.01190 (19)0.0246 (15)
C30.2900 (5)0.4855 (7)0.06599 (18)0.0226 (15)
C40.2666 (6)0.3443 (7)0.0684 (2)0.0274 (16)
C50.2150 (5)0.2822 (7)0.00754 (18)0.0216 (14)
C60.1751 (6)0.3538 (6)0.04551 (19)0.0231 (14)
C70.2761 (7)0.7021 (9)0.00957 (18)0.0231 (17)
C80.3599 (5)0.5504 (6)0.1228 (2)0.0241 (17)
C90.3509 (6)1.0004 (6)0.2437 (2)0.0332 (19)
H90.2569930.9852380.2737620.040*
C100.5195 (5)1.0682 (6)0.26280 (19)0.0315 (18)
H100.5419211.0989610.3056340.038*
C110.6574 (6)1.0908 (6)0.2177 (2)0.0327 (18)
C120.6206 (6)1.0421 (7)0.1544 (2)0.0383 (19)
H120.7122261.0558710.1234720.046*
C130.4507 (6)0.9746 (6)0.1381 (2)0.0390 (18)
H130.4259030.9413400.0958200.047*
C140.1374 (6)0.8761 (8)0.1629 (2)0.057 (2)
H14A0.1757650.7892160.1489950.086*
H14B0.0617900.9199360.1273690.086*
H14C0.0577540.8679020.1995050.086*
C150.8418 (7)1.1565 (6)0.23604 (19)0.0362 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0473 (6)0.0218 (18)0.0378 (9)0.0000 (8)0.0068 (5)0.0008 (5)
Cl20.0470 (6)0.0314 (17)0.0262 (7)0.0020 (7)0.0090 (5)0.0065 (5)
O10.0421 (15)0.023 (4)0.0280 (19)0.0008 (19)0.0081 (13)0.0067 (15)
O20.0546 (18)0.023 (5)0.029 (2)0.006 (2)0.0084 (13)0.0054 (15)
N10.047 (2)0.028 (6)0.049 (3)0.008 (4)0.0061 (17)0.002 (3)
N20.046 (2)0.031 (6)0.038 (3)0.003 (3)0.0111 (17)0.000 (2)
N30.0379 (19)0.025 (5)0.034 (2)0.003 (2)0.0045 (16)0.0011 (18)
N40.053 (2)0.057 (7)0.039 (3)0.013 (3)0.0094 (19)0.004 (2)
C10.022 (2)0.025 (5)0.024 (3)0.000 (3)0.0014 (17)0.0014 (19)
C20.022 (2)0.024 (5)0.028 (3)0.004 (3)0.0035 (17)0.002 (2)
C30.022 (2)0.021 (5)0.025 (3)0.006 (3)0.0035 (16)0.000 (2)
C40.027 (2)0.027 (5)0.029 (3)0.004 (3)0.0053 (18)0.001 (2)
C50.0246 (19)0.007 (5)0.033 (3)0.003 (3)0.0038 (17)0.002 (2)
C60.025 (2)0.020 (5)0.024 (3)0.003 (3)0.0048 (17)0.0024 (19)
C70.024 (2)0.020 (6)0.025 (3)0.001 (4)0.0018 (16)0.001 (2)
C80.029 (2)0.016 (6)0.028 (3)0.000 (3)0.0043 (18)0.002 (2)
C90.040 (2)0.030 (7)0.031 (3)0.009 (3)0.0056 (19)0.002 (2)
C100.034 (2)0.039 (7)0.021 (3)0.002 (3)0.0014 (17)0.000 (2)
C110.035 (2)0.035 (7)0.027 (3)0.003 (3)0.0032 (18)0.005 (2)
C120.042 (2)0.044 (7)0.030 (3)0.003 (3)0.009 (2)0.002 (2)
C130.051 (3)0.039 (7)0.026 (3)0.009 (3)0.002 (2)0.002 (2)
C140.052 (3)0.044 (9)0.073 (4)0.008 (3)0.013 (2)0.005 (3)
C150.051 (3)0.032 (7)0.027 (3)0.007 (3)0.011 (2)0.006 (2)
Geometric parameters (Å, º) top
Cl1—C51.709 (6)C3—C81.444 (6)
Cl2—C61.716 (5)C4—C51.459 (6)
O1—C11.257 (5)C5—C61.347 (7)
O2—C41.250 (6)C9—C101.356 (6)
N1—C71.151 (8)C9—H90.9300
N2—C81.147 (5)C10—C111.379 (5)
N3—C91.335 (5)C10—H100.9300
N3—C131.341 (5)C11—C121.388 (6)
N3—C141.479 (6)C11—C151.431 (7)
N4—C151.153 (5)C12—C131.350 (6)
C1—C61.454 (8)C12—H120.9300
C1—C21.458 (6)C13—H130.9300
C2—C31.396 (7)C14—H14A0.9600
C2—C71.417 (8)C14—H14B0.9600
C3—C41.428 (8)C14—H14C0.9600
C9—N3—C13120.8 (4)N3—C9—C10121.1 (4)
C9—N3—C14120.7 (4)N3—C9—H9119.5
C13—N3—C14118.4 (4)C10—C9—H9119.5
O1—C1—C6123.4 (4)C9—C10—C11119.0 (4)
O1—C1—C2120.4 (6)C9—C10—H10120.5
C6—C1—C2116.2 (4)C11—C10—H10120.5
C3—C2—C7122.8 (4)C10—C11—C12119.1 (4)
C3—C2—C1120.0 (6)C10—C11—C15121.3 (4)
C7—C2—C1117.2 (4)C12—C11—C15119.6 (4)
C2—C3—C4123.3 (4)C13—C12—C11119.5 (4)
C2—C3—C8119.1 (6)C13—C12—H12120.2
C4—C3—C8117.6 (4)C11—C12—H12120.2
O2—C4—C3123.0 (4)N3—C13—C12120.5 (4)
O2—C4—C5121.5 (6)N3—C13—H13119.7
C3—C4—C5115.4 (4)C12—C13—H13119.7
C6—C5—C4122.3 (6)N3—C14—H14A109.5
C6—C5—Cl1121.4 (4)N3—C14—H14B109.5
C4—C5—Cl1116.2 (4)H14A—C14—H14B109.5
C5—C6—C1122.5 (4)N3—C14—H14C109.5
C5—C6—Cl2122.2 (5)H14A—C14—H14C109.5
C1—C6—Cl2115.3 (3)H14B—C14—H14C109.5
N1—C7—C2179.5 (4)N4—C15—C11176.8 (5)
N2—C8—C3177.7 (6)
O1—C1—C2—C3177.0 (4)Cl1—C5—C6—C1179.4 (3)
C6—C1—C2—C33.1 (5)C4—C5—C6—Cl2178.8 (3)
O1—C1—C2—C75.9 (5)Cl1—C5—C6—Cl21.4 (5)
C6—C1—C2—C7174.0 (4)O1—C1—C6—C5176.6 (3)
C7—C2—C3—C4178.7 (4)C2—C1—C6—C53.5 (6)
C1—C2—C3—C41.8 (6)O1—C1—C6—Cl25.3 (5)
C7—C2—C3—C81.3 (6)C2—C1—C6—Cl2174.5 (3)
C1—C2—C3—C8178.3 (3)C13—N3—C9—C100.5 (8)
C2—C3—C4—O2175.6 (4)C14—N3—C9—C10177.2 (6)
C8—C3—C4—O24.4 (6)N3—C9—C10—C110.3 (8)
C2—C3—C4—C56.0 (6)C9—C10—C11—C120.8 (8)
C8—C3—C4—C5174.1 (3)C9—C10—C11—C15177.2 (6)
O2—C4—C5—C6176.0 (4)C10—C11—C12—C130.4 (8)
C3—C4—C5—C65.5 (6)C15—C11—C12—C13176.9 (6)
O2—C4—C5—Cl13.8 (5)C9—N3—C13—C120.9 (8)
C3—C4—C5—Cl1174.7 (3)C14—N3—C13—C12177.7 (6)
C4—C5—C6—C10.9 (6)C11—C12—C13—N30.4 (8)
(test3_0.86GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.710 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.6277 (4) ÅCell parameters from 1833 reflections
b = 10.0050 (17) Åθ = 2.0–26.4°
c = 20.3418 (16) ŵ = 0.50 mm1
β = 94.609 (5)°T = 293 K
V = 1344.5 (3) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1457 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source980 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.364, Tmax = 0.450k = 88
6881 measured reflectionsl = 2323
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-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 reflectionsΔρmax = 0.27 e Å3
209 parametersΔρmin = 0.31 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.20949 (18)0.11052 (19)0.00704 (6)0.0330 (6)
Cl20.12077 (17)0.28017 (18)0.11832 (5)0.0326 (6)
O10.1399 (4)0.5688 (4)0.09474 (15)0.0304 (14)
O20.2954 (5)0.2756 (5)0.11898 (15)0.0346 (15)
N10.2959 (7)0.8166 (8)0.0078 (2)0.0377 (19)
N20.4178 (6)0.5986 (6)0.1704 (2)0.0375 (19)
N30.3154 (5)0.9561 (6)0.18186 (19)0.0324 (16)
N41.0016 (7)1.2095 (7)0.2502 (2)0.048 (2)
C10.1855 (6)0.4984 (8)0.0472 (2)0.0236 (16)
C20.2496 (6)0.5617 (8)0.0127 (2)0.0248 (16)
C30.2922 (7)0.4862 (8)0.0670 (2)0.0226 (16)
C40.2693 (7)0.3445 (8)0.0692 (2)0.0252 (16)
C50.2185 (6)0.2808 (7)0.0074 (2)0.0209 (15)
C60.1773 (6)0.3535 (7)0.0459 (2)0.0229 (15)
C70.2769 (8)0.7020 (10)0.0106 (2)0.0229 (18)
C80.3600 (6)0.5507 (7)0.1244 (2)0.0262 (19)
C90.3471 (7)0.9996 (7)0.2437 (2)0.032 (2)
H90.2522510.9820630.2738310.038*
C100.5175 (7)1.0697 (7)0.2629 (2)0.033 (2)
H100.5388291.1010480.3059120.040*
C110.6592 (7)1.0939 (7)0.2178 (2)0.031 (2)
C120.6233 (7)1.0460 (8)0.1542 (2)0.037 (2)
H120.7169941.0602060.1233070.045*
C130.4506 (7)0.9781 (8)0.1376 (2)0.039 (2)
H130.4252310.9462610.0947570.047*
C140.1322 (8)0.8774 (9)0.1614 (3)0.045 (2)
H14A0.1712210.7902840.1472020.068*
H14B0.0562440.9220970.1257050.068*
H14C0.0501920.8686520.1979650.068*
C150.8476 (8)1.1602 (7)0.2372 (2)0.0295 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0443 (7)0.022 (2)0.0335 (9)0.0000 (8)0.0078 (5)0.0005 (6)
Cl20.0444 (7)0.0300 (19)0.0246 (8)0.0025 (8)0.0091 (5)0.0059 (6)
O10.0391 (18)0.027 (5)0.026 (2)0.002 (2)0.0086 (14)0.0090 (17)
O20.053 (2)0.028 (5)0.024 (2)0.006 (2)0.0088 (15)0.0037 (16)
N10.044 (3)0.030 (6)0.040 (3)0.004 (4)0.0087 (19)0.002 (3)
N20.044 (2)0.038 (7)0.031 (3)0.004 (3)0.0095 (19)0.001 (2)
N30.034 (2)0.030 (6)0.032 (3)0.005 (2)0.0023 (17)0.002 (2)
N40.052 (3)0.057 (7)0.036 (3)0.012 (3)0.007 (2)0.004 (2)
C10.020 (2)0.027 (6)0.024 (3)0.001 (3)0.0042 (19)0.000 (2)
C20.025 (2)0.028 (6)0.023 (3)0.007 (3)0.0049 (19)0.002 (2)
C30.024 (2)0.021 (6)0.023 (3)0.000 (3)0.0048 (19)0.002 (2)
C40.027 (2)0.028 (6)0.021 (3)0.003 (3)0.0055 (19)0.000 (2)
C50.020 (2)0.016 (6)0.026 (3)0.001 (3)0.0004 (18)0.004 (2)
C60.023 (2)0.024 (5)0.022 (3)0.000 (3)0.0024 (18)0.000 (2)
C70.025 (3)0.022 (6)0.023 (3)0.013 (4)0.0050 (18)0.003 (3)
C80.030 (2)0.023 (7)0.026 (3)0.001 (3)0.006 (2)0.003 (2)
C90.038 (3)0.032 (8)0.026 (3)0.004 (3)0.006 (2)0.001 (2)
C100.032 (2)0.044 (7)0.023 (3)0.003 (3)0.004 (2)0.001 (2)
C110.036 (2)0.029 (7)0.027 (3)0.005 (3)0.006 (2)0.001 (2)
C120.040 (3)0.047 (8)0.025 (3)0.006 (3)0.008 (2)0.003 (3)
C130.047 (3)0.046 (8)0.025 (3)0.008 (3)0.001 (2)0.002 (2)
C140.051 (3)0.017 (9)0.065 (5)0.006 (3)0.010 (3)0.005 (3)
C150.044 (3)0.021 (7)0.025 (3)0.001 (3)0.010 (2)0.008 (2)
Geometric parameters (Å, º) top
Cl1—C51.705 (7)C3—C81.437 (7)
Cl2—C61.714 (5)C4—C51.473 (7)
O1—C11.252 (6)C5—C61.351 (8)
O2—C41.249 (6)C9—C101.360 (7)
N1—C71.155 (8)C9—H90.9300
N2—C81.145 (6)C10—C111.385 (6)
N3—C91.331 (6)C10—H100.9300
N3—C131.339 (6)C11—C121.382 (7)
N3—C141.479 (7)C11—C151.441 (8)
N4—C151.145 (6)C12—C131.350 (8)
C1—C61.451 (9)C12—H120.9300
C1—C21.467 (7)C13—H130.9300
C2—C31.386 (8)C14—H14A0.9600
C2—C71.415 (10)C14—H14B0.9600
C3—C41.426 (9)C14—H14C0.9600
C9—N3—C13121.2 (5)N3—C9—C10120.3 (4)
C9—N3—C14120.3 (4)N3—C9—H9119.8
C13—N3—C14118.5 (4)C10—C9—H9119.8
O1—C1—C6124.5 (5)C9—C10—C11119.4 (5)
O1—C1—C2120.2 (7)C9—C10—H10120.3
C6—C1—C2115.4 (5)C11—C10—H10120.3
C3—C2—C7122.1 (5)C12—C11—C10118.9 (5)
C3—C2—C1121.2 (7)C12—C11—C15119.8 (4)
C7—C2—C1116.6 (5)C10—C11—C15121.2 (4)
C2—C3—C4122.6 (5)C13—C12—C11119.2 (4)
C2—C3—C8119.9 (7)C13—C12—H12120.4
C4—C3—C8117.5 (5)C11—C12—H12120.4
O2—C4—C3123.5 (5)N3—C13—C12120.9 (5)
O2—C4—C5120.6 (7)N3—C13—H13119.6
C3—C4—C5115.8 (5)C12—C13—H13119.6
C6—C5—C4121.8 (7)N3—C14—H14A109.5
C6—C5—Cl1121.7 (4)N3—C14—H14B109.5
C4—C5—Cl1116.5 (4)H14A—C14—H14B109.5
C5—C6—C1122.9 (5)N3—C14—H14C109.5
C5—C6—Cl2122.1 (6)H14A—C14—H14C109.5
C1—C6—Cl2115.0 (4)H14B—C14—H14C109.5
N1—C7—C2178.4 (5)N4—C15—C11176.6 (6)
N2—C8—C3177.8 (7)
O1—C1—C2—C3177.1 (4)Cl1—C5—C6—C1179.4 (3)
C6—C1—C2—C32.0 (6)C4—C5—C6—Cl2179.3 (3)
O1—C1—C2—C76.5 (6)Cl1—C5—C6—Cl22.0 (6)
C6—C1—C2—C7174.4 (4)O1—C1—C6—C5176.8 (4)
C7—C2—C3—C4178.6 (4)C2—C1—C6—C52.3 (7)
C1—C2—C3—C42.5 (7)O1—C1—C6—Cl25.6 (6)
C7—C2—C3—C82.1 (7)C2—C1—C6—Cl2175.3 (3)
C1—C2—C3—C8178.3 (4)C13—N3—C9—C101.0 (9)
C2—C3—C4—O2175.6 (4)C14—N3—C9—C10178.6 (6)
C8—C3—C4—O23.6 (7)N3—C9—C10—C110.8 (10)
C2—C3—C4—C56.4 (7)C9—C10—C11—C120.0 (9)
C8—C3—C4—C5174.4 (4)C9—C10—C11—C15176.0 (6)
O2—C4—C5—C6175.9 (4)C10—C11—C12—C130.7 (9)
C3—C4—C5—C66.1 (6)C15—C11—C12—C13176.7 (7)
O2—C4—C5—Cl12.9 (6)C9—N3—C13—C120.4 (10)
C3—C4—C5—Cl1175.1 (3)C14—N3—C13—C12178.0 (7)
C4—C5—C6—C11.8 (7)C11—C12—C13—N30.5 (10)
(test3_1.42GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.760 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.5155 (3) ÅCell parameters from 1909 reflections
b = 9.9444 (12) Åθ = 2.0–26.6°
c = 20.2293 (11) ŵ = 0.51 mm1
β = 94.662 (4)°T = 293 K
V = 1306.37 (18) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1418 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source973 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.357, Tmax = 0.450k = 88
6645 measured reflectionsl = 2223
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-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 reflectionsΔρmax = 0.22 e Å3
209 parametersΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.21184 (14)0.10945 (16)0.00673 (5)0.0289 (5)
Cl20.12333 (14)0.27986 (15)0.11911 (4)0.0289 (5)
O10.1412 (4)0.5700 (4)0.09518 (12)0.0277 (12)
O20.2992 (4)0.2740 (4)0.11938 (12)0.0308 (13)
N10.2944 (6)0.8189 (7)0.00801 (16)0.0341 (17)
N20.4162 (5)0.6004 (5)0.17266 (17)0.0304 (16)
N30.3138 (4)0.9577 (5)0.18052 (15)0.0276 (14)
N41.0101 (5)1.2122 (5)0.25165 (15)0.0387 (16)
C10.1869 (5)0.4986 (7)0.04709 (18)0.0204 (15)
C20.2515 (5)0.5635 (7)0.01293 (18)0.0217 (15)
C30.2942 (5)0.4866 (6)0.06753 (18)0.0189 (14)
C40.2722 (5)0.3437 (7)0.06975 (19)0.0216 (15)
C50.2196 (5)0.2812 (7)0.00702 (17)0.0190 (14)
C60.1812 (6)0.3539 (6)0.04593 (18)0.0218 (14)
C70.2756 (6)0.7041 (9)0.01089 (18)0.0214 (17)
C80.3610 (5)0.5514 (6)0.1256 (2)0.0227 (17)
C90.3451 (6)1.0022 (6)0.24310 (19)0.0269 (17)
H90.2470380.9850790.2729630.032*
C100.5176 (5)1.0715 (5)0.26343 (18)0.0249 (16)
H100.5389781.1021010.3068920.030*
C110.6614 (5)1.0960 (6)0.21826 (19)0.0238 (17)
C120.6281 (6)1.0489 (6)0.15377 (19)0.0327 (18)
H120.7240541.0645460.1230320.039*
C130.4526 (6)0.9797 (6)0.13644 (19)0.0328 (17)
H130.4284410.9471150.0934210.039*
C140.1280 (6)0.8776 (7)0.1596 (2)0.046 (2)
H14A0.0452500.8671950.1964010.069*
H14B0.1688230.7906620.1447140.069*
H14C0.0496320.9230280.1240580.069*
C150.8530 (7)1.1629 (6)0.23809 (18)0.0259 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0373 (6)0.0203 (18)0.0297 (8)0.0005 (7)0.0059 (4)0.0003 (5)
Cl20.0367 (6)0.0283 (17)0.0224 (7)0.0033 (6)0.0067 (4)0.0057 (5)
O10.0388 (15)0.022 (4)0.0235 (18)0.0025 (18)0.0072 (12)0.0095 (14)
O20.0478 (17)0.023 (5)0.0231 (19)0.0055 (18)0.0089 (13)0.0049 (14)
N10.035 (2)0.030 (6)0.037 (3)0.005 (3)0.0024 (15)0.001 (2)
N20.0363 (19)0.028 (6)0.028 (2)0.003 (2)0.0062 (15)0.0023 (18)
N30.0322 (18)0.022 (5)0.027 (2)0.003 (2)0.0052 (14)0.0026 (17)
N40.044 (2)0.039 (6)0.034 (3)0.010 (3)0.0073 (18)0.0003 (19)
C10.0181 (18)0.024 (5)0.020 (2)0.003 (3)0.0054 (16)0.0023 (19)
C20.018 (2)0.025 (5)0.022 (2)0.003 (3)0.0024 (16)0.001 (2)
C30.0197 (19)0.015 (5)0.022 (3)0.001 (3)0.0025 (16)0.0019 (19)
C40.0182 (19)0.023 (5)0.024 (3)0.004 (3)0.0014 (16)0.001 (2)
C50.0216 (19)0.011 (5)0.024 (3)0.000 (2)0.0012 (16)0.0017 (18)
C60.022 (2)0.025 (5)0.019 (2)0.003 (3)0.0039 (16)0.0048 (18)
C70.020 (2)0.022 (6)0.023 (3)0.003 (4)0.0027 (16)0.002 (2)
C80.0207 (19)0.020 (6)0.027 (3)0.003 (2)0.0023 (17)0.003 (2)
C90.030 (2)0.025 (7)0.026 (3)0.003 (2)0.0080 (17)0.001 (2)
C100.029 (2)0.025 (6)0.020 (3)0.001 (2)0.0014 (16)0.0005 (18)
C110.028 (2)0.015 (6)0.028 (3)0.003 (2)0.0046 (17)0.0038 (19)
C120.039 (2)0.041 (7)0.019 (3)0.001 (3)0.0105 (18)0.000 (2)
C130.043 (2)0.033 (6)0.022 (3)0.010 (3)0.0022 (18)0.000 (2)
C140.042 (3)0.043 (8)0.051 (4)0.015 (3)0.014 (2)0.002 (3)
C150.040 (2)0.015 (6)0.024 (3)0.001 (3)0.0093 (19)0.0049 (19)
Geometric parameters (Å, º) top
Cl1—C51.709 (6)C3—C81.438 (6)
Cl2—C61.722 (4)C4—C51.478 (6)
O1—C11.259 (5)C5—C61.333 (6)
O2—C41.244 (5)C9—C101.354 (6)
N1—C71.149 (7)C9—H90.9300
N2—C81.152 (5)C10—C111.382 (5)
N3—C131.339 (5)C10—H100.9300
N3—C91.341 (5)C11—C121.386 (6)
N3—C141.482 (6)C11—C151.442 (6)
N4—C151.148 (5)C12—C131.356 (6)
C1—C61.439 (8)C12—H120.9300
C1—C21.467 (6)C13—H130.9300
C2—C31.390 (7)C14—H14A0.9600
C2—C71.407 (8)C14—H14B0.9600
C3—C41.429 (8)C14—H14C0.9600
C13—N3—C9121.0 (4)N3—C9—C10120.9 (3)
C13—N3—C14118.5 (3)N3—C9—H9119.5
C9—N3—C14120.4 (3)C10—C9—H9119.5
O1—C1—C6124.6 (4)C9—C10—C11118.6 (4)
O1—C1—C2119.6 (6)C9—C10—H10120.7
C6—C1—C2115.8 (4)C11—C10—H10120.7
C3—C2—C7122.7 (4)C10—C11—C12120.0 (4)
C3—C2—C1120.4 (6)C10—C11—C15121.0 (4)
C7—C2—C1116.9 (4)C12—C11—C15118.9 (3)
C2—C3—C4123.1 (4)C13—C12—C11118.6 (4)
C2—C3—C8119.8 (6)C13—C12—H12120.7
C4—C3—C8117.1 (4)C11—C12—H12120.7
O2—C4—C3124.0 (4)N3—C13—C12120.8 (4)
O2—C4—C5121.1 (6)N3—C13—H13119.6
C3—C4—C5114.9 (4)C12—C13—H13119.6
C6—C5—C4122.2 (6)N3—C14—H14A109.5
C6—C5—Cl1122.1 (4)N3—C14—H14B109.5
C4—C5—Cl1115.6 (4)H14A—C14—H14B109.5
C5—C6—C1123.3 (4)N3—C14—H14C109.5
C5—C6—Cl2121.8 (5)H14A—C14—H14C109.5
C1—C6—Cl2114.9 (3)H14B—C14—H14C109.5
N1—C7—C2178.7 (4)N4—C15—C11176.6 (5)
N2—C8—C3178.4 (6)
O1—C1—C2—C3177.3 (4)Cl1—C5—C6—C1179.9 (3)
C6—C1—C2—C32.8 (5)C4—C5—C6—Cl2179.1 (3)
O1—C1—C2—C75.3 (5)Cl1—C5—C6—Cl20.7 (5)
C6—C1—C2—C7174.6 (4)O1—C1—C6—C5176.2 (3)
C7—C2—C3—C4179.3 (4)C2—C1—C6—C53.8 (6)
C1—C2—C3—C42.1 (6)O1—C1—C6—Cl24.5 (5)
C7—C2—C3—C81.6 (6)C2—C1—C6—Cl2175.4 (2)
C1—C2—C3—C8178.9 (3)C13—N3—C9—C100.5 (7)
C2—C3—C4—O2176.0 (3)C14—N3—C9—C10177.7 (5)
C8—C3—C4—O23.0 (6)N3—C9—C10—C110.1 (8)
C2—C3—C4—C55.6 (5)C9—C10—C11—C120.4 (7)
C8—C3—C4—C5175.3 (3)C9—C10—C11—C15176.6 (5)
O2—C4—C5—C6177.0 (4)C10—C11—C12—C130.2 (7)
C3—C4—C5—C64.6 (5)C15—C11—C12—C13176.5 (5)
O2—C4—C5—Cl13.1 (5)C9—N3—C13—C120.7 (8)
C3—C4—C5—Cl1175.2 (3)C14—N3—C13—C12178.0 (5)
C4—C5—C6—C10.1 (6)C11—C12—C13—N30.3 (8)
(test3_1.85GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.795 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.4387 (2) ÅCell parameters from 1960 reflections
b = 9.9135 (11) Åθ = 2.0–26.7°
c = 20.1349 (10) ŵ = 0.52 mm1
β = 94.729 (3)°T = 293 K
V = 1280.83 (16) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1390 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.368, Tmax = 0.449k = 88
6531 measured reflectionsl = 2322
Refinement top
Refinement on F2192 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 reflectionsΔρmax = 0.25 e Å3
209 parametersΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.21350 (15)0.10860 (16)0.00654 (5)0.0268 (5)
Cl20.12508 (14)0.27982 (16)0.11979 (5)0.0273 (5)
O10.1434 (4)0.5710 (4)0.09558 (13)0.0260 (12)
O20.3017 (4)0.2726 (4)0.11992 (13)0.0273 (13)
N10.2928 (6)0.8197 (7)0.00807 (17)0.0312 (17)
N20.4153 (5)0.5997 (5)0.17377 (18)0.0283 (16)
N30.3128 (5)0.9582 (5)0.18015 (16)0.0249 (14)
N41.0157 (5)1.2133 (6)0.25263 (16)0.0387 (17)
C10.1889 (6)0.4985 (7)0.04704 (19)0.0181 (15)
C20.2522 (6)0.5641 (7)0.01311 (19)0.0197 (15)
C30.2950 (6)0.4863 (7)0.06818 (19)0.0200 (15)
C40.2730 (6)0.3437 (7)0.0702 (2)0.0206 (15)
C50.2210 (5)0.2807 (7)0.00712 (18)0.0167 (14)
C60.1830 (5)0.3534 (7)0.04636 (19)0.0157 (14)
C70.2752 (7)0.7045 (9)0.01127 (19)0.0194 (18)
C80.3606 (6)0.5516 (6)0.1268 (2)0.0191 (17)
C90.3434 (6)1.0026 (6)0.24299 (19)0.0241 (18)
H90.2441830.9849480.2728840.029*
C100.5165 (6)1.0727 (6)0.26342 (19)0.0265 (17)
H100.5371111.1031320.3071590.032*
C110.6642 (6)1.0990 (6)0.2183 (2)0.0251 (18)
C120.6307 (6)1.0506 (6)0.1540 (2)0.0295 (18)
H120.7284331.0657020.1232470.035*
C130.4534 (6)0.9805 (6)0.1360 (2)0.0284 (17)
H130.4295870.9478940.0927440.034*
C140.1251 (6)0.8773 (8)0.1588 (2)0.044 (2)
H14A0.0474050.9219010.1223820.066*
H14B0.0395360.8682050.1953650.066*
H14C0.1668950.7895890.1447190.066*
C150.8550 (7)1.1657 (6)0.23876 (19)0.0270 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0345 (6)0.0173 (18)0.0288 (8)0.0011 (7)0.0047 (4)0.0005 (5)
Cl20.0342 (6)0.0273 (17)0.0209 (7)0.0026 (6)0.0060 (4)0.0050 (5)
O10.0323 (15)0.022 (4)0.0243 (19)0.0028 (18)0.0060 (12)0.0070 (15)
O20.0435 (17)0.016 (5)0.023 (2)0.0046 (18)0.0079 (13)0.0025 (14)
N10.033 (2)0.025 (6)0.035 (3)0.001 (3)0.0023 (15)0.001 (2)
N20.036 (2)0.022 (6)0.028 (3)0.001 (2)0.0056 (16)0.0017 (19)
N30.0284 (18)0.019 (5)0.026 (2)0.005 (2)0.0046 (15)0.0015 (17)
N40.039 (2)0.045 (6)0.032 (3)0.010 (3)0.0052 (18)0.000 (2)
C10.0162 (19)0.019 (5)0.019 (3)0.004 (3)0.0002 (16)0.0003 (19)
C20.018 (2)0.016 (5)0.026 (3)0.003 (3)0.0017 (17)0.003 (2)
C30.0181 (19)0.019 (5)0.023 (3)0.001 (3)0.0011 (16)0.002 (2)
C40.017 (2)0.022 (5)0.023 (3)0.002 (3)0.0011 (17)0.003 (2)
C50.0202 (19)0.007 (5)0.023 (3)0.000 (2)0.0023 (17)0.0002 (19)
C60.0169 (19)0.009 (5)0.021 (3)0.002 (3)0.0008 (16)0.0026 (19)
C70.020 (2)0.017 (6)0.022 (3)0.001 (4)0.0059 (16)0.004 (3)
C80.021 (2)0.012 (6)0.025 (3)0.001 (2)0.0023 (17)0.002 (2)
C90.027 (2)0.022 (7)0.024 (3)0.002 (2)0.0022 (17)0.001 (2)
C100.028 (2)0.035 (6)0.016 (3)0.003 (3)0.0011 (17)0.000 (2)
C110.027 (2)0.024 (7)0.024 (3)0.000 (2)0.0033 (17)0.003 (2)
C120.032 (2)0.039 (7)0.017 (3)0.003 (3)0.0055 (17)0.002 (2)
C130.038 (2)0.028 (6)0.020 (3)0.013 (3)0.0006 (18)0.000 (2)
C140.039 (3)0.044 (9)0.046 (4)0.011 (3)0.012 (2)0.002 (3)
C150.036 (2)0.021 (7)0.024 (3)0.002 (3)0.0066 (19)0.006 (2)
Geometric parameters (Å, º) top
Cl1—C51.707 (6)C3—C81.440 (6)
Cl2—C61.717 (5)C4—C51.478 (6)
O1—C11.266 (6)C5—C61.335 (7)
O2—C41.251 (6)C9—C101.349 (6)
N1—C71.149 (7)C9—H90.9300
N2—C81.141 (5)C10—C111.393 (5)
N3—C131.338 (5)C10—H100.9300
N3—C91.339 (5)C11—C121.382 (6)
N3—C141.484 (6)C11—C151.426 (6)
N4—C151.150 (5)C12—C131.359 (7)
C1—C61.439 (8)C12—H120.9300
C1—C21.462 (6)C13—H130.9300
C2—C31.397 (7)C14—H14A0.9600
C2—C71.400 (8)C14—H14B0.9600
C3—C41.421 (8)C14—H14C0.9600
C13—N3—C9121.2 (4)N3—C9—C10120.7 (4)
C13—N3—C14118.4 (4)N3—C9—H9119.6
C9—N3—C14120.3 (3)C10—C9—H9119.6
O1—C1—C6124.5 (4)C9—C10—C11119.3 (4)
O1—C1—C2119.0 (6)C9—C10—H10120.4
C6—C1—C2116.5 (4)C11—C10—H10120.4
C3—C2—C7122.9 (4)C12—C11—C10119.0 (4)
C3—C2—C1119.9 (6)C12—C11—C15119.7 (3)
C7—C2—C1117.1 (4)C10—C11—C15121.1 (4)
C2—C3—C4123.1 (4)C13—C12—C11119.3 (4)
C2—C3—C8119.5 (6)C13—C12—H12120.3
C4—C3—C8117.4 (4)C11—C12—H12120.3
O2—C4—C3124.2 (4)N3—C13—C12120.5 (4)
O2—C4—C5120.6 (6)N3—C13—H13119.8
C3—C4—C5115.2 (4)C12—C13—H13119.8
C6—C5—C4122.3 (6)N3—C14—H14A109.5
C6—C5—Cl1121.8 (4)N3—C14—H14B109.5
C4—C5—Cl1115.9 (4)H14A—C14—H14B109.5
C5—C6—C1122.7 (4)N3—C14—H14C109.5
C5—C6—Cl2122.2 (5)H14A—C14—H14C109.5
C1—C6—Cl2115.1 (3)H14B—C14—H14C109.5
N1—C7—C2178.2 (4)N4—C15—C11175.3 (6)
N2—C8—C3177.9 (6)
O1—C1—C2—C3177.4 (4)Cl1—C5—C6—C1179.9 (3)
C6—C1—C2—C32.5 (5)C4—C5—C6—Cl2179.4 (3)
O1—C1—C2—C75.1 (5)Cl1—C5—C6—Cl20.4 (5)
C6—C1—C2—C7174.9 (4)O1—C1—C6—C5176.2 (3)
C7—C2—C3—C4179.7 (4)C2—C1—C6—C53.7 (6)
C1—C2—C3—C42.4 (6)O1—C1—C6—Cl24.3 (5)
C7—C2—C3—C81.7 (6)C2—C1—C6—Cl2175.8 (2)
C1—C2—C3—C8178.9 (3)C13—N3—C9—C100.7 (8)
C2—C3—C4—O2176.8 (4)C14—N3—C9—C10178.0 (5)
C8—C3—C4—O21.9 (6)N3—C9—C10—C110.2 (8)
C2—C3—C4—C55.8 (6)C9—C10—C11—C121.0 (8)
C8—C3—C4—C5175.5 (3)C9—C10—C11—C15176.2 (5)
O2—C4—C5—C6177.9 (4)C10—C11—C12—C131.1 (7)
C3—C4—C5—C64.6 (5)C15—C11—C12—C13176.3 (6)
O2—C4—C5—Cl12.4 (5)C9—N3—C13—C120.7 (8)
C3—C4—C5—Cl1175.2 (3)C14—N3—C13—C12178.0 (5)
C4—C5—C6—C10.1 (6)C11—C12—C13—N30.2 (8)
(test3_2.55GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.834 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.3580 (4) ÅCell parameters from 1653 reflections
b = 9.895 (2) Åθ = 2.0–26.9°
c = 20.0093 (18) ŵ = 0.54 mm1
β = 95.314 (7)°T = 293 K
V = 1253.5 (3) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1374 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source924 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.361, Tmax = 0.449k = 88
6405 measured reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.140H-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 reflectionsΔρmax = 1.50 e Å3
94 parametersΔρmin = 1.60 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2234 (4)0.1128 (4)0.00453 (13)0.0313 (10)*
Cl20.1324 (4)0.2836 (4)0.12234 (13)0.0295 (10)*
O10.1562 (11)0.5751 (11)0.0988 (4)0.034 (2)*
O20.3144 (11)0.2808 (11)0.1175 (4)0.035 (2)*
N10.2818 (12)0.8227 (19)0.0080 (4)0.032 (2)*
N20.4095 (12)0.6029 (13)0.1749 (5)0.032 (2)*
N30.3067 (12)0.9592 (13)0.1800 (4)0.030 (2)*
N41.0214 (12)1.2149 (13)0.2538 (4)0.032 (2)*
C10.2043 (14)0.5101 (18)0.0484 (5)0.028 (3)*
C20.2658 (13)0.5671 (17)0.0100 (5)0.025 (3)*
C30.3098 (14)0.4941 (17)0.0667 (5)0.026 (3)*
C40.2870 (13)0.3532 (17)0.0679 (5)0.024 (2)*
C50.2354 (13)0.2894 (17)0.0058 (5)0.024 (3)*
C60.1956 (14)0.3635 (17)0.0476 (5)0.025 (2)*
C70.2754 (14)0.706 (2)0.0105 (5)0.026 (3)*
C80.3631 (13)0.5566 (15)0.1261 (5)0.018 (2)*
C90.3403 (14)1.0026 (16)0.2426 (5)0.026 (3)*
H90.2418670.9826760.2727770.031*
C100.5148 (15)1.0756 (15)0.2641 (6)0.031 (3)*
H100.5345281.1080340.3078900.038*
C110.6646 (13)1.1006 (14)0.2180 (5)0.023 (2)*
C120.6309 (15)1.0473 (16)0.1538 (5)0.028 (3)*
H120.7316941.0584840.1234500.034*
C130.4518 (14)0.9796 (16)0.1359 (5)0.029 (3)*
H130.4272980.9462230.0924860.035*
C140.1202 (17)0.884 (2)0.1583 (7)0.052 (4)*
H14A0.1599560.7990050.1395600.077*
H14B0.0355800.9341510.1248180.077*
H14C0.0404530.8669100.1958850.077*
C150.8584 (15)1.1687 (17)0.2391 (5)0.031 (3)*
Geometric parameters (Å, º) top
Cl1—C51.749 (17)C3—C81.407 (16)
Cl2—C61.770 (12)C4—C51.458 (16)
O1—C11.257 (15)C5—C61.339 (17)
O2—C41.249 (15)C9—C101.360 (16)
N1—C71.156 (18)C9—H90.9300
N2—C81.142 (13)C10—C111.408 (14)
N3—C91.323 (13)C10—H100.9300
N3—C131.350 (12)C11—C121.385 (15)
N3—C141.435 (16)C11—C151.433 (15)
N4—C151.146 (13)C12—C131.341 (16)
C1—C21.386 (16)C12—H120.9300
C1—C61.45 (2)C13—H130.9300
C2—C71.38 (2)C14—H14A0.9600
C2—C31.395 (17)C14—H14B0.9600
C3—C41.40 (2)C14—H14C0.9600
C9—N3—C13120.6 (9)N3—C9—C10121.9 (9)
C9—N3—C14120.9 (9)N3—C9—H9119.1
C13—N3—C14118.4 (10)C10—C9—H9119.1
O1—C1—C2125.2 (15)C9—C10—C11117.8 (10)
O1—C1—C6120.5 (11)C9—C10—H10121.1
C2—C1—C6114.3 (11)C11—C10—H10121.1
C7—C2—C1115.4 (11)C12—C11—C10119.0 (10)
C7—C2—C3119.9 (10)C12—C11—C15120.4 (8)
C1—C2—C3124.7 (15)C10—C11—C15120.3 (9)
C2—C3—C4120.0 (11)C13—C12—C11119.5 (9)
C2—C3—C8122.8 (14)C13—C12—H12120.3
C4—C3—C8117.1 (10)C11—C12—H12120.3
O2—C4—C3124.1 (11)C12—C13—N3121.0 (10)
O2—C4—C5119.2 (14)C12—C13—H13119.5
C3—C4—C5116.6 (10)N3—C13—H13119.5
C6—C5—C4121.1 (14)N3—C14—H14A109.5
C6—C5—Cl1121.6 (10)N3—C14—H14B109.5
C4—C5—Cl1117.3 (9)H14A—C14—H14B109.5
C5—C6—C1123.1 (11)N3—C14—H14C109.5
C5—C6—Cl2120.2 (12)H14A—C14—H14C109.5
C1—C6—Cl2116.7 (8)H14B—C14—H14C109.5
N1—C7—C2177.0 (10)N4—C15—C11174.6 (15)
N2—C8—C3177.5 (14)
O1—C1—C2—C70.8 (14)Cl1—C5—C6—C1179.9 (7)
C6—C1—C2—C7180.0 (8)C4—C5—C6—Cl2179.8 (6)
O1—C1—C2—C3177.0 (9)Cl1—C5—C6—Cl20.9 (12)
C6—C1—C2—C32.2 (14)O1—C1—C6—C5176.8 (9)
C7—C2—C3—C4175.9 (8)C2—C1—C6—C52.5 (14)
C1—C2—C3—C41.8 (15)O1—C1—C6—Cl24.2 (12)
C7—C2—C3—C80.5 (14)C2—C1—C6—Cl2176.6 (7)
C1—C2—C3—C8177.2 (8)C13—N3—C9—C104 (2)
C2—C3—C4—O2176.9 (9)C14—N3—C9—C10179.3 (15)
C8—C3—C4—O21.3 (14)N3—C9—C10—C112 (2)
C2—C3—C4—C55.4 (13)C9—C10—C11—C121.6 (19)
C8—C3—C4—C5179.0 (8)C9—C10—C11—C15175.6 (13)
O2—C4—C5—C6177.0 (9)C10—C11—C12—C134 (2)
C3—C4—C5—C65.1 (13)C15—C11—C12—C13177.5 (14)
O2—C4—C5—Cl12.0 (12)C11—C12—C13—N32 (2)
C3—C4—C5—Cl1175.9 (7)C9—N3—C13—C122 (2)
C4—C5—C6—C11.2 (14)C14—N3—C13—C12178.7 (15)
(test3_3.09GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.887 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.2590 (2) ÅCell parameters from 1965 reflections
b = 9.8519 (12) Åθ = 2.1–27.2°
c = 19.8571 (11) ŵ = 0.55 mm1
β = 95.624 (4)°T = 293 K
V = 1218.56 (17) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1312 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.368, Tmax = 0.449k = 87
6137 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H-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 reflectionsΔρmax = 0.56 e Å3
94 parametersΔρmin = 0.72 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2320 (2)0.1163 (2)0.00400 (7)0.0230 (4)*
Cl20.1388 (2)0.2862 (2)0.12396 (7)0.0223 (4)*
O10.1674 (6)0.5777 (6)0.1016 (2)0.0236 (10)*
O20.3254 (6)0.2821 (6)0.1171 (2)0.0260 (11)*
N10.2653 (7)0.8311 (9)0.0089 (2)0.0241 (13)*
N20.4009 (7)0.6046 (8)0.1773 (3)0.0249 (13)*
N30.3035 (7)0.9609 (7)0.1792 (2)0.0241 (12)*
N41.0260 (8)1.2187 (8)0.2553 (3)0.0327 (14)*
C10.2132 (8)0.5102 (9)0.0517 (3)0.0169 (13)*
C20.2712 (8)0.5741 (9)0.0092 (3)0.0156 (13)*
C30.3157 (8)0.4961 (9)0.0652 (3)0.0161 (13)*
C40.2979 (8)0.3527 (9)0.0666 (3)0.0176 (14)*
C50.2441 (8)0.2892 (9)0.0034 (3)0.0158 (13)*
C60.2070 (8)0.3635 (9)0.0509 (3)0.0147 (13)*
C70.2702 (8)0.7140 (11)0.0094 (3)0.0140 (13)*
C80.3618 (8)0.5620 (8)0.1269 (3)0.0148 (13)*
C90.3369 (8)1.0069 (9)0.2431 (3)0.0220 (14)*
H90.2350650.9896960.2731490.026*
C100.5156 (8)1.0778 (9)0.2646 (3)0.0231 (15)*
H100.5374441.1096110.3088140.028*
C110.6658 (9)1.1019 (9)0.2190 (3)0.0225 (14)*
C120.6321 (9)1.0526 (9)0.1540 (3)0.0253 (15)*
H120.7322861.0685130.1233200.030*
C130.4514 (9)0.9803 (9)0.1352 (3)0.0269 (15)*
H130.4295940.9441190.0917650.032*
C140.1129 (9)0.8804 (11)0.1572 (3)0.0345 (17)*
H14A0.0254670.8710210.1940130.052*
H14B0.1560410.7921920.1430420.052*
H14C0.0321270.9251770.1200140.052*
C150.8638 (9)1.1706 (9)0.2398 (3)0.0225 (15)*
Geometric parameters (Å, º) top
Cl1—C51.705 (9)C3—C81.440 (8)
Cl2—C61.728 (6)C4—C51.471 (8)
O1—C11.249 (8)C5—C61.342 (9)
O2—C41.246 (8)C9—C101.351 (9)
N1—C71.154 (9)C9—H90.9300
N2—C81.134 (7)C10—C111.388 (8)
N3—C91.345 (8)C10—H100.9300
N3—C131.348 (7)C11—C121.374 (9)
N3—C141.463 (9)C11—C151.437 (9)
N4—C151.135 (8)C12—C131.358 (9)
C1—C21.441 (9)C12—H120.9300
C1—C61.446 (10)C13—H130.9300
C2—C71.378 (10)C14—H14A0.9600
C2—C31.403 (9)C14—H14B0.9600
C3—C41.417 (10)C14—H14C0.9600
C9—N3—C13120.8 (6)N3—C9—C10121.3 (5)
C9—N3—C14120.8 (5)N3—C9—H9119.4
C13—N3—C14118.3 (5)C10—C9—H9119.4
O1—C1—C2121.9 (7)C9—C10—C11118.4 (6)
O1—C1—C6122.2 (6)C9—C10—H10120.8
C2—C1—C6115.9 (5)C11—C10—H10120.8
C7—C2—C3123.2 (6)C12—C11—C10120.0 (6)
C7—C2—C1116.0 (5)C12—C11—C15119.0 (5)
C3—C2—C1120.8 (7)C10—C11—C15120.8 (5)
C2—C3—C4122.7 (5)C13—C12—C11119.4 (5)
C2—C3—C8119.9 (7)C13—C12—H12120.3
C4—C3—C8117.1 (5)C11—C12—H12120.3
O2—C4—C3123.7 (6)N3—C13—C12120.1 (6)
O2—C4—C5120.7 (7)N3—C13—H13119.9
C3—C4—C5115.6 (5)C12—C13—H13119.9
C6—C5—C4121.7 (7)N3—C14—H14A109.5
C6—C5—Cl1122.7 (5)N3—C14—H14B109.5
C4—C5—Cl1115.6 (5)H14A—C14—H14B109.5
C5—C6—C1123.2 (6)N3—C14—H14C109.5
C5—C6—Cl2120.6 (6)H14A—C14—H14C109.5
C1—C6—Cl2116.1 (4)H14B—C14—H14C109.5
N1—C7—C2178.5 (6)N4—C15—C11176.2 (8)
N2—C8—C3174.9 (8)
O1—C1—C2—C70.8 (7)Cl1—C5—C6—C1178.9 (4)
C6—C1—C2—C7177.9 (5)C4—C5—C6—Cl2178.7 (4)
O1—C1—C2—C3178.1 (5)Cl1—C5—C6—Cl21.3 (6)
C6—C1—C2—C30.7 (7)O1—C1—C6—C5176.2 (5)
C7—C2—C3—C4174.3 (5)C2—C1—C6—C52.5 (7)
C1—C2—C3—C42.8 (8)O1—C1—C6—Cl21.5 (7)
C7—C2—C3—C80.4 (7)C2—C1—C6—Cl2179.7 (4)
C1—C2—C3—C8176.6 (4)C13—N3—C9—C102.2 (11)
C2—C3—C4—O2176.0 (5)C14—N3—C9—C10178.0 (8)
C8—C3—C4—O22.0 (8)N3—C9—C10—C110.2 (12)
C2—C3—C4—C54.2 (7)C9—C10—C11—C120.9 (11)
C8—C3—C4—C5178.2 (4)C9—C10—C11—C15176.8 (8)
O2—C4—C5—C6177.9 (5)C10—C11—C12—C130.0 (12)
C3—C4—C5—C62.3 (7)C15—C11—C12—C13176.0 (8)
O2—C4—C5—Cl12.1 (7)C9—N3—C13—C123.1 (11)
C3—C4—C5—Cl1177.7 (4)C14—N3—C13—C12179.0 (8)
C4—C5—C6—C11.0 (8)C11—C12—C13—N32.0 (12)
(test3_3.95GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.916 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.2058 (3) ÅCell parameters from 1972 reflections
b = 9.8299 (15) Åθ = 2.1–27.3°
c = 19.7739 (13) ŵ = 0.56 mm1
β = 95.781 (5)°T = 293 K
V = 1200.1 (2) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1290 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source953 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.366, Tmax = 0.449k = 88
6073 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-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 reflectionsΔρmax = 0.54 e Å3
94 parametersΔρmin = 0.55 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.23248 (19)0.1157 (2)0.00366 (6)0.0213 (4)*
Cl20.13994 (19)0.2863 (2)0.12473 (6)0.0211 (4)*
O10.1688 (5)0.5782 (5)0.10216 (19)0.0228 (9)*
O20.3268 (6)0.2814 (6)0.11688 (18)0.0241 (10)*
N10.2655 (6)0.8307 (9)0.0091 (2)0.0213 (12)*
N20.3997 (7)0.6038 (7)0.1785 (2)0.0244 (12)*
N30.3044 (6)0.9610 (7)0.1788 (2)0.0218 (11)*
N41.0292 (7)1.2215 (7)0.2561 (2)0.0280 (13)*
C10.2139 (7)0.5102 (8)0.0523 (2)0.0150 (12)*
C20.2706 (7)0.5743 (8)0.0091 (2)0.0130 (12)*
C30.3142 (7)0.4967 (8)0.0656 (2)0.0154 (12)*
C40.2990 (7)0.3524 (8)0.0665 (3)0.0173 (13)*
C50.2453 (7)0.2881 (8)0.0032 (2)0.0129 (12)*
C60.2071 (7)0.3626 (8)0.0515 (2)0.0135 (12)*
C70.2700 (7)0.7143 (10)0.0097 (2)0.0121 (12)*
C80.3601 (7)0.5608 (8)0.1273 (3)0.0152 (12)*
C90.3339 (8)1.0074 (8)0.2426 (3)0.0190 (13)*
H90.2299280.9907850.2723200.023*
C100.5155 (8)1.0788 (8)0.2642 (3)0.0218 (14)*
H100.5372881.1105090.3086290.026*
C110.6672 (8)1.1037 (8)0.2191 (3)0.0224 (14)*
C120.6324 (9)1.0534 (9)0.1534 (3)0.0258 (14)*
H120.7326281.0695890.1223550.031*
C130.4520 (8)0.9809 (9)0.1349 (3)0.0259 (14)*
H130.4297730.9444520.0913360.031*
C140.1107 (9)0.8811 (10)0.1562 (3)0.0358 (17)*
H14A0.0251360.8687530.1935930.054*
H14B0.1533900.7938690.1402390.054*
H14C0.0268700.9282720.1200990.054*
C150.8665 (8)1.1736 (8)0.2408 (3)0.0218 (14)*
Geometric parameters (Å, º) top
Cl1—C51.697 (8)C3—C81.428 (8)
Cl2—C61.720 (6)C4—C51.469 (8)
O1—C11.245 (7)C5—C61.347 (8)
O2—C41.243 (7)C9—C101.359 (8)
N1—C71.144 (9)C9—H90.9300
N2—C81.145 (7)C10—C111.382 (7)
N3—C91.337 (7)C10—H100.9300
N3—C131.338 (7)C11—C121.388 (8)
N3—C141.467 (9)C11—C151.441 (8)
N4—C151.128 (7)C12—C131.346 (9)
C1—C21.443 (8)C12—H120.9300
C1—C61.451 (9)C13—H130.9300
C2—C71.376 (10)C14—H14A0.9600
C2—C31.402 (8)C14—H14B0.9600
C3—C41.421 (10)C14—H14C0.9600
C9—N3—C13121.6 (5)N3—C9—C10120.2 (5)
C9—N3—C14120.0 (4)N3—C9—H9119.9
C13—N3—C14118.3 (5)C10—C9—H9119.9
O1—C1—C2121.6 (7)C9—C10—C11119.1 (5)
O1—C1—C6122.5 (5)C9—C10—H10120.4
C2—C1—C6115.8 (5)C11—C10—H10120.4
C7—C2—C3122.5 (5)C10—C11—C12119.3 (6)
C7—C2—C1116.3 (5)C10—C11—C15120.8 (5)
C3—C2—C1121.1 (7)C12—C11—C15119.8 (5)
C2—C3—C4122.4 (5)C13—C12—C11119.3 (5)
C2—C3—C8120.8 (7)C13—C12—H12120.3
C4—C3—C8116.6 (5)C11—C12—H12120.3
O2—C4—C3123.8 (5)N3—C13—C12120.4 (6)
O2—C4—C5120.2 (7)N3—C13—H13119.8
C3—C4—C5116.0 (5)C12—C13—H13119.8
C6—C5—C4121.5 (7)N3—C14—H14A109.5
C6—C5—Cl1122.4 (5)N3—C14—H14B109.5
C4—C5—Cl1116.1 (4)H14A—C14—H14B109.5
C5—C6—C1123.1 (5)N3—C14—H14C109.5
C5—C6—Cl2121.1 (6)H14A—C14—H14C109.5
C1—C6—Cl2115.8 (4)H14B—C14—H14C109.5
N1—C7—C2178.2 (5)N4—C15—C11175.6 (8)
N2—C8—C3175.4 (7)
O1—C1—C2—C70.6 (7)Cl1—C5—C6—C1179.0 (4)
C6—C1—C2—C7177.8 (4)C4—C5—C6—Cl2178.9 (3)
O1—C1—C2—C3177.9 (4)Cl1—C5—C6—Cl20.6 (6)
C6—C1—C2—C30.4 (6)O1—C1—C6—C5176.7 (5)
C7—C2—C3—C4175.2 (4)C2—C1—C6—C51.6 (7)
C1—C2—C3—C41.9 (7)O1—C1—C6—Cl21.8 (6)
C7—C2—C3—C80.1 (7)C2—C1—C6—Cl2179.9 (3)
C1—C2—C3—C8177.0 (4)C13—N3—C9—C101.1 (10)
C2—C3—C4—O2176.5 (4)C14—N3—C9—C10178.5 (7)
C8—C3—C4—O21.2 (7)N3—C9—C10—C110.6 (11)
C2—C3—C4—C53.0 (7)C9—C10—C11—C121.0 (11)
C8—C3—C4—C5178.3 (4)C9—C10—C11—C15177.1 (7)
O2—C4—C5—C6177.7 (5)C10—C11—C12—C130.3 (11)
C3—C4—C5—C61.8 (6)C15—C11—C12—C13175.9 (7)
O2—C4—C5—Cl11.8 (6)C9—N3—C13—C122.5 (11)
C3—C4—C5—Cl1178.7 (3)C14—N3—C13—C12179.9 (7)
C4—C5—C6—C10.5 (7)C11—C12—C13—N32.0 (11)
(test3_4.80GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 346.15Dx = 1.965 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.1216 (6) ÅCell parameters from 781 reflections
b = 9.806 (4) Åθ = 2.1–25.4°
c = 19.603 (3) ŵ = 0.57 mm1
β = 96.013 (12)°T = 293 K
V = 1170.2 (5) Å3Block, black
Z = 40.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1271 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source651 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.157
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.367, Tmax = 0.449k = 87
5803 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.116H-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 reflectionsΔρmax = 0.85 e Å3
94 parametersΔρmin = 0.61 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2330 (4)0.1147 (5)0.00304 (14)0.0317 (11)*
Cl20.1409 (5)0.2868 (5)0.12592 (14)0.0322 (11)*
O10.1688 (13)0.5779 (12)0.1035 (4)0.034 (2)*
O20.3290 (12)0.2806 (13)0.1168 (4)0.032 (2)*
N10.2663 (14)0.833 (2)0.0083 (4)0.031 (3)*
N20.4022 (17)0.6025 (16)0.1796 (5)0.041 (3)*
N30.3073 (14)0.9631 (15)0.1777 (5)0.031 (3)*
N41.0364 (16)1.2243 (16)0.2584 (5)0.041 (3)*
C10.2130 (16)0.5100 (19)0.0533 (5)0.023 (3)*
C20.2692 (17)0.572 (2)0.0081 (5)0.028 (3)*
C30.3121 (15)0.4940 (18)0.0668 (5)0.021 (3)*
C40.2982 (16)0.3484 (18)0.0677 (5)0.020 (3)*
C50.2450 (15)0.2834 (18)0.0027 (5)0.019 (3)*
C60.2069 (15)0.3638 (17)0.0535 (5)0.017 (3)*
C70.2670 (16)0.717 (3)0.0095 (5)0.022 (3)*
C80.3582 (18)0.5587 (19)0.1276 (6)0.029 (3)*
C90.3299 (18)1.0085 (19)0.2412 (6)0.030 (3)*
H90.2242630.9886190.2705650.036*
C100.5143 (19)1.0869 (18)0.2643 (6)0.035 (3)*
H100.5310261.1248100.3079830.041*
C110.6672 (18)1.1050 (17)0.2198 (6)0.029 (3)*
C120.637 (2)1.059 (2)0.1534 (7)0.039 (3)*
H120.7378001.0789360.1224410.047*
C130.4545 (17)0.9846 (19)0.1348 (6)0.035 (3)*
H130.4331300.9479090.0908300.042*
C140.113 (2)0.879 (2)0.1549 (7)0.041 (4)*
H14A0.0368880.8558410.1937850.061*
H14B0.1589110.7970380.1337900.061*
H14C0.0162390.9294520.1224080.061*
C150.8699 (19)1.175 (2)0.2423 (6)0.036 (4)*
Geometric parameters (Å, º) top
Cl1—C51.656 (17)C3—C41.43 (2)
Cl2—C61.694 (12)C4—C51.491 (16)
O1—C11.239 (16)C5—C61.394 (18)
O2—C41.201 (15)C9—C101.401 (19)
N1—C71.14 (2)C9—H90.9300
N2—C81.163 (15)C10—C111.356 (17)
N3—C131.313 (14)C10—H100.9300
N3—C91.315 (15)C11—C121.369 (18)
N3—C141.479 (18)C11—C151.445 (19)
N4—C151.143 (15)C12—C131.354 (19)
C1—C21.423 (18)C12—H120.9300
C1—C61.43 (2)C13—H130.9300
C2—C71.42 (2)C14—H14A0.9600
C2—C31.428 (19)C14—H14B0.9600
C3—C81.405 (18)C14—H14C0.9600
C13—N3—C9122.8 (12)N3—C9—C10119.5 (11)
C13—N3—C14118.7 (11)N3—C9—H9120.3
C9—N3—C14118.4 (9)C10—C9—H9120.3
O1—C1—C2122.2 (17)C11—C10—C9116.8 (12)
O1—C1—C6121.8 (12)C11—C10—H10121.6
C2—C1—C6115.9 (12)C9—C10—H10121.6
C7—C2—C1116.2 (12)C10—C11—C12122.3 (12)
C7—C2—C3121.5 (11)C10—C11—C15119.6 (11)
C1—C2—C3122.3 (17)C12—C11—C15118.1 (10)
C8—C3—C2120.8 (15)C13—C12—C11117.3 (12)
C8—C3—C4117.2 (11)C13—C12—H12121.3
C2—C3—C4121.9 (11)C11—C12—H12121.3
O2—C4—C3123.3 (11)N3—C13—C12121.1 (12)
O2—C4—C5121.0 (15)N3—C13—H13119.5
C3—C4—C5115.7 (10)C12—C13—H13119.5
C6—C5—C4120.2 (15)N3—C14—H14A109.5
C6—C5—Cl1123.9 (10)N3—C14—H14B109.5
C4—C5—Cl1115.9 (9)H14A—C14—H14B109.5
C5—C6—C1123.9 (11)N3—C14—H14C109.5
C5—C6—Cl2119.0 (13)H14A—C14—H14C109.5
C1—C6—Cl2117.1 (8)H14B—C14—H14C109.5
N1—C7—C2177.8 (11)N4—C15—C11176.1 (17)
N2—C8—C3174.7 (17)
O1—C1—C2—C71.4 (15)Cl1—C5—C6—C1178.7 (8)
C6—C1—C2—C7177.6 (10)C4—C5—C6—Cl2178.6 (7)
O1—C1—C2—C3177.6 (10)Cl1—C5—C6—Cl20.8 (12)
C6—C1—C2—C31.4 (14)O1—C1—C6—C5176.9 (10)
C7—C2—C3—C81.3 (15)C2—C1—C6—C52.2 (15)
C1—C2—C3—C8177.3 (10)O1—C1—C6—Cl21.1 (14)
C7—C2—C3—C4175.2 (10)C2—C1—C6—Cl2179.9 (7)
C1—C2—C3—C40.9 (15)C13—N3—C9—C102 (2)
C8—C3—C4—O21.8 (15)C14—N3—C9—C10179.2 (15)
C2—C3—C4—O2178.4 (9)N3—C9—C10—C114 (2)
C8—C3—C4—C5178.9 (8)C9—C10—C11—C125 (2)
C2—C3—C4—C52.3 (14)C9—C10—C11—C15174.7 (15)
O2—C4—C5—C6179.1 (10)C10—C11—C12—C135 (2)
C3—C4—C5—C61.6 (13)C15—C11—C12—C13174.8 (16)
O2—C4—C5—Cl10.3 (13)C9—N3—C13—C122 (2)
C3—C4—C5—Cl1179.0 (8)C14—N3—C13—C12179.1 (16)
C4—C5—C6—C10.7 (15)C11—C12—C13—N33 (2)
(test3_5.48GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 276.92Dx = 1.989 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.0779 (9) ÅCell parameters from 654 reflections
b = 9.783 (6) Åθ = 2.1–22.9°
c = 19.555 (4) ŵ = 0.58 mm1
β = 96.225 (16)°T = 293 K
V = 1155.9 (7) Å3Block, black
Z = 50.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1257 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.173
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.362, Tmax = 0.449k = 77
5634 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.137H-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 reflectionsΔρmax = 0.90 e Å3
94 parametersΔρmin = 0.79 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2345 (5)0.1144 (6)0.00246 (16)0.0315 (12)*
Cl20.1426 (5)0.2870 (6)0.12660 (17)0.0339 (13)*
O10.1723 (14)0.5776 (14)0.1038 (5)0.033 (3)*
O20.3309 (14)0.2805 (16)0.1177 (4)0.033 (3)*
N10.2624 (16)0.835 (2)0.0086 (5)0.031 (3)*
N20.398 (2)0.604 (2)0.1807 (7)0.046 (4)*
N30.3047 (16)0.9615 (18)0.1772 (5)0.029 (3)*
N41.0406 (19)1.2265 (19)0.2604 (6)0.044 (4)*
C10.2136 (19)0.514 (2)0.0532 (7)0.026 (4)*
C20.2705 (18)0.571 (2)0.0088 (6)0.021 (4)*
C30.3133 (17)0.493 (2)0.0679 (6)0.020 (3)*
C40.3006 (18)0.348 (2)0.0666 (6)0.020 (3)*
C50.2456 (17)0.284 (2)0.0031 (5)0.016 (3)*
C60.2106 (19)0.367 (2)0.0551 (6)0.022 (3)*
C70.2667 (17)0.713 (3)0.0100 (5)0.015 (3)*
C80.355 (2)0.556 (2)0.1288 (7)0.026 (4)*
C90.332 (2)1.004 (2)0.2412 (7)0.029 (4)*
H90.2321360.9778410.2714840.034*
C100.511 (2)1.089 (2)0.2645 (8)0.038 (4)*
H100.5215011.1298640.3075810.046*
C110.671 (2)1.108 (2)0.2200 (8)0.038 (4)*
C120.643 (3)1.060 (2)0.1544 (8)0.045 (4)*
H120.7476411.0780000.1241130.054*
C130.458 (2)0.985 (2)0.1340 (7)0.043 (4)*
H130.4383080.9498460.0896120.051*
C140.112 (2)0.884 (2)0.1539 (8)0.042 (4)*
H14A0.0369930.9257530.1135400.051*
H14B0.0146270.8806390.1894000.051*
H14C0.1546930.7924020.1430780.051*
C150.872 (2)1.180 (2)0.2438 (7)0.037 (4)*
Geometric parameters (Å, º) top
Cl1—C51.66 (2)C3—C41.42 (2)
Cl2—C61.695 (15)C4—C51.465 (19)
O1—C11.218 (18)C5—C61.44 (2)
O2—C41.230 (18)C9—C101.40 (2)
N1—C71.19 (2)C9—H90.9300
N2—C81.170 (18)C10—C111.39 (2)
N3—C91.312 (17)C10—H100.9300
N3—C131.346 (17)C11—C121.36 (2)
N3—C141.43 (2)C11—C151.44 (2)
N4—C151.135 (18)C12—C131.36 (2)
C1—C21.41 (2)C12—H120.9300
C1—C61.43 (3)C13—H130.9300
C2—C71.39 (2)C14—H14A0.9600
C2—C31.43 (2)C14—H14B0.9600
C3—C81.39 (2)C14—H14C0.9600
C9—N3—C13121.2 (13)N3—C9—C10120.8 (13)
C9—N3—C14119.3 (11)N3—C9—H9119.6
C13—N3—C14119.5 (13)C10—C9—H9119.6
O1—C1—C2126 (2)C11—C10—C9116.6 (15)
O1—C1—C6119.0 (14)C11—C10—H10121.7
C2—C1—C6115.0 (14)C9—C10—H10121.7
C7—C2—C1113.8 (14)C12—C11—C10121.5 (16)
C7—C2—C3121.6 (13)C12—C11—C15119.1 (13)
C1—C2—C3124.4 (19)C10—C11—C15119.3 (14)
C8—C3—C4118.4 (13)C11—C12—C13118.3 (15)
C8—C3—C2121.3 (18)C11—C12—H12120.8
C4—C3—C2120.2 (13)C13—C12—H12120.8
O2—C4—C3120.7 (13)N3—C13—C12121.0 (15)
O2—C4—C5121.5 (17)N3—C13—H13119.5
C3—C4—C5117.8 (12)C12—C13—H13119.5
C6—C5—C4119.4 (17)N3—C14—H14A109.5
C6—C5—Cl1123.7 (11)N3—C14—H14B109.5
C4—C5—Cl1116.9 (11)H14A—C14—H14B109.5
C1—C6—C5123.2 (13)N3—C14—H14C109.5
C1—C6—Cl2119.4 (10)H14A—C14—H14C109.5
C5—C6—Cl2117.3 (15)H14B—C14—H14C109.5
N1—C7—C2177.7 (11)N4—C15—C11174 (2)
N2—C8—C3176.6 (19)
O1—C1—C2—C72.9 (18)C2—C1—C6—C54.6 (17)
C6—C1—C2—C7178.4 (11)O1—C1—C6—Cl21.7 (16)
O1—C1—C2—C3178.5 (12)C2—C1—C6—Cl2179.5 (9)
C6—C1—C2—C32.8 (17)C4—C5—C6—C13.8 (17)
C7—C2—C3—C80.7 (17)Cl1—C5—C6—C1178.0 (9)
C1—C2—C3—C8176.0 (12)C4—C5—C6—Cl2178.9 (8)
C7—C2—C3—C4175.5 (11)Cl1—C5—C6—Cl22.9 (14)
C1—C2—C3—C40.2 (17)C13—N3—C9—C107 (3)
C8—C3—C4—O21.6 (17)C14—N3—C9—C10175.4 (18)
C2—C3—C4—O2177.9 (10)N3—C9—C10—C119 (3)
C8—C3—C4—C5177.1 (10)C9—C10—C11—C128 (3)
C2—C3—C4—C50.7 (16)C9—C10—C11—C15172.6 (19)
O2—C4—C5—C6179.6 (11)C10—C11—C12—C134 (3)
C3—C4—C5—C61.0 (15)C15—C11—C12—C13176 (2)
O2—C4—C5—Cl12.0 (15)C9—N3—C13—C123 (3)
C3—C4—C5—Cl1179.3 (8)C14—N3—C13—C12179.4 (19)
O1—C1—C6—C5176.6 (11)C11—C12—C13—N32 (3)
(test3_6.00GPa) top
Crystal data top
C8Cl2N2O2·C7H7N2F(000) = 700
Mr = 276.92Dx = 2.017 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.0307 (11) ÅCell parameters from 616 reflections
b = 9.769 (6) Åθ = 2.1–25.7°
c = 19.465 (5) ŵ = 0.59 mm1
β = 96.336 (18)°T = 293 K
V = 1139.8 (8) Å3Block, black
Z = 50.25 × 0.10 × 0.05 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1226 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source543 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.171
Detector resolution: 10.3457 pixels mm-1θmax = 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 = 77
Tmin = 0.371, Tmax = 0.449k = 77
5596 measured reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.141H-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 reflectionsΔρmax = 0.99 e Å3
94 parametersΔρmin = 0.85 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2338 (6)0.1131 (6)0.00176 (18)0.0342 (13)*
Cl20.1432 (6)0.2879 (7)0.12747 (18)0.0359 (14)*
O10.1716 (16)0.5766 (16)0.1044 (5)0.039 (3)*
O20.3299 (15)0.2801 (17)0.1176 (5)0.035 (3)*
N10.2674 (19)0.838 (3)0.0094 (6)0.038 (4)*
N20.398 (2)0.605 (2)0.1823 (7)0.048 (4)*
N30.3007 (18)0.966 (2)0.1760 (6)0.035 (3)*
N41.040 (2)1.227 (2)0.2611 (7)0.050 (4)*
C10.217 (2)0.512 (2)0.0532 (7)0.026 (4)*
C20.268 (2)0.574 (3)0.0092 (7)0.030 (4)*
C30.312 (2)0.497 (2)0.0680 (7)0.027 (4)*
C40.294 (2)0.352 (2)0.0667 (7)0.030 (4)*
C50.2516 (19)0.285 (2)0.0028 (6)0.025 (4)*
C60.2075 (18)0.365 (2)0.0543 (6)0.015 (3)*
C70.2644 (19)0.722 (3)0.0105 (6)0.016 (4)*
C80.355 (2)0.558 (3)0.1295 (8)0.033 (4)*
C90.328 (2)1.007 (2)0.2407 (7)0.028 (4)*
H90.2270260.9810820.2710440.033*
C100.511 (2)1.092 (2)0.2639 (8)0.036 (4)*
H100.5242491.1328050.3073010.043*
C110.667 (2)1.110 (2)0.2198 (8)0.037 (5)*
C120.643 (2)1.065 (2)0.1533 (8)0.033 (4)*
H120.7448761.0866460.1225630.040*
C130.462 (2)0.988 (2)0.1347 (8)0.041 (5)*
H130.4478550.9470570.0912240.049*
C140.110 (3)0.883 (3)0.1514 (8)0.045 (5)*
H14A0.1596680.7938840.1393710.067*
H14B0.0318820.9257020.1113170.067*
H14C0.0129700.8755390.1869510.067*
C150.873 (2)1.180 (2)0.2436 (7)0.035 (4)*
Geometric parameters (Å, º) top
Cl1—C51.69 (2)C3—C41.42 (3)
Cl2—C61.694 (15)C4—C51.45 (2)
O1—C11.234 (19)C5—C61.41 (2)
O2—C41.25 (2)C9—C101.41 (2)
N1—C71.14 (2)C9—H90.9300
N2—C81.180 (19)C10—C111.35 (2)
N3—C91.317 (18)C10—H100.9300
N3—C131.345 (18)C11—C121.36 (2)
N3—C141.44 (2)C11—C151.45 (2)
N4—C151.123 (19)C12—C131.34 (2)
C1—C21.42 (2)C12—H120.9300
C1—C61.44 (3)C13—H130.9300
C2—C31.42 (2)C14—H14A0.9600
C2—C71.44 (3)C14—H14B0.9600
C3—C81.39 (2)C14—H14C0.9600
C9—N3—C13120.0 (14)N3—C9—C10119.8 (13)
C9—N3—C14120.1 (12)N3—C9—H9120.1
C13—N3—C14119.5 (14)C10—C9—H9120.1
O1—C1—C2124 (2)C11—C10—C9116.6 (16)
O1—C1—C6119.1 (15)C11—C10—H10121.7
C2—C1—C6116.7 (14)C9—C10—H10121.7
C3—C2—C1123 (2)C10—C11—C12123.5 (16)
C3—C2—C7121.3 (15)C10—C11—C15119.3 (15)
C1—C2—C7115.7 (14)C12—C11—C15117.1 (13)
C8—C3—C2123 (2)C13—C12—C11116.0 (14)
C8—C3—C4117.6 (14)C13—C12—H12122.0
C2—C3—C4119.4 (15)C11—C12—H12122.0
O2—C4—C3121.6 (15)C12—C13—N3123.2 (16)
O2—C4—C5119 (2)C12—C13—H13118.4
C3—C4—C5118.9 (14)N3—C13—H13118.4
C6—C5—C4119.7 (19)N3—C14—H14A109.5
C6—C5—Cl1121.8 (13)N3—C14—H14B109.5
C4—C5—Cl1118.4 (13)H14A—C14—H14B109.5
C5—C6—C1122.1 (14)N3—C14—H14C109.5
C5—C6—Cl2119.9 (16)H14A—C14—H14C109.5
C1—C6—Cl2118.0 (10)H14B—C14—H14C109.5
N1—C7—C2177.4 (14)N4—C15—C11176 (2)
N2—C8—C3177 (2)
O1—C1—C2—C3177.7 (13)Cl1—C5—C6—C1178.4 (10)
C6—C1—C2—C30.7 (18)C4—C5—C6—Cl2176.6 (9)
O1—C1—C2—C70.3 (19)Cl1—C5—C6—Cl22.1 (15)
C6—C1—C2—C7176.6 (12)O1—C1—C6—C5178.4 (12)
C1—C2—C3—C8177.9 (13)C2—C1—C6—C51.3 (18)
C7—C2—C3—C80.6 (19)O1—C1—C6—Cl22.1 (17)
C1—C2—C3—C43 (2)C2—C1—C6—Cl2179.2 (9)
C7—C2—C3—C4174.3 (12)C13—N3—C9—C109 (3)
C8—C3—C4—O24 (2)C14—N3—C9—C10177.9 (19)
C2—C3—C4—O2179.5 (12)N3—C9—C10—C119 (3)
C8—C3—C4—C5179.4 (11)C9—C10—C11—C127 (3)
C2—C3—C4—C55.4 (19)C9—C10—C11—C15171.7 (19)
O2—C4—C5—C6178.8 (12)C10—C11—C12—C136 (3)
C3—C4—C5—C65.9 (18)C15—C11—C12—C13173 (2)
O2—C4—C5—Cl14.2 (17)C11—C12—C13—N37 (3)
C3—C4—C5—Cl1179.4 (10)C9—N3—C13—C128 (3)
C4—C5—C6—C13.9 (18)C14—N3—C13—C12179 (2)
 

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