Pancake-bonding of semi­quinone radicals under variable temperature and pressure conditions

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].

Computing details

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)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.665 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7437 (1) Å	Cell parameters from 4986 reflections
b = 10.0558 (2) Å	θ = 2.0–28.1°
c = 20.4325 (4) Å	µ = 0.49 mm^−1
β = 94.828 (2)°	T = 100 K
V = 1380.68 (4) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3025 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2616 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.3457 pixels mm^-1	θmax = 27.1°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→8
Tmin = 0.958, Tmax = 1.000	k = −12→12
8958 measured reflections	l = −26→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 1.1138P] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
3025 reflections	Δρmax = 0.42 e Å^−3
209 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20839 (6)	0.11213 (4)	−0.00692 (2)	0.01412 (10)
N4	0.9971 (2)	1.20526 (15)	0.24921 (7)	0.0199 (3)
Cl2	0.11858 (6)	0.28111 (4)	0.11765 (2)	0.01427 (10)
C15	0.8453 (3)	1.15719 (16)	0.23625 (8)	0.0160 (3)
O1	0.13549 (16)	0.56748 (11)	0.09454 (5)	0.0141 (2)
O2	0.29019 (17)	0.27739 (11)	−0.11898 (5)	0.0157 (2)
N1	0.2964 (2)	0.81495 (14)	−0.00674 (7)	0.0171 (3)
N2	0.4174 (2)	0.59870 (14)	−0.16878 (7)	0.0173 (3)
C1	0.1808 (2)	0.50059 (16)	0.04682 (7)	0.0110 (3)
C2	0.2475 (2)	0.56100 (15)	−0.01202 (7)	0.0112 (3)
C3	0.2886 (2)	0.48723 (16)	−0.06644 (7)	0.0117 (3)
C4	0.2644 (2)	0.34343 (16)	−0.06915 (7)	0.0119 (3)
C5	0.2144 (2)	0.28256 (15)	−0.00757 (7)	0.0115 (3)
C6	0.1752 (2)	0.35472 (16)	0.04580 (7)	0.0116 (3)
C7	0.2746 (2)	0.70222 (16)	−0.00955 (7)	0.0123 (3)
C8	0.3593 (2)	0.55030 (16)	−0.12323 (8)	0.0128 (3)
N3	0.3182 (2)	0.95368 (13)	0.18261 (7)	0.0149 (3)
C9	0.3503 (2)	0.99969 (16)	0.24440 (8)	0.0149 (3)
H9	0.254226	0.984262	0.275001	0.018*
C10	0.5213 (2)	1.06895 (16)	0.26355 (8)	0.0143 (3)
H10	0.544576	1.101418	0.307181	0.017*
C11	0.6593 (2)	1.09053 (15)	0.21786 (8)	0.0138 (3)
C12	0.6227 (3)	1.04289 (17)	0.15402 (8)	0.0164 (3)
H12	0.715077	1.058297	0.122233	0.020*
C13	0.4509 (3)	0.97341 (16)	0.13793 (8)	0.0171 (3)
H13	0.425139	0.938772	0.094799	0.021*
C14	0.1367 (3)	0.87596 (19)	0.16300 (9)	0.0241 (4)
H14A	0.060501	0.920636	0.126391	0.036*
H14B	0.054963	0.869076	0.200313	0.036*
H14C	0.174236	0.786692	0.149296	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0199 (2)	0.00834 (18)	0.01423 (19)	0.00039 (14)	0.00207 (15)	0.00020 (13)
N4	0.0230 (8)	0.0209 (8)	0.0163 (7)	−0.0036 (6)	0.0038 (6)	0.0025 (6)
Cl2	0.0189 (2)	0.01392 (19)	0.01031 (18)	−0.00114 (14)	0.00294 (14)	0.00226 (13)
C15	0.0226 (9)	0.0146 (8)	0.0115 (8)	0.0017 (7)	0.0052 (6)	0.0017 (6)
O1	0.0166 (6)	0.0145 (6)	0.0116 (5)	0.0010 (4)	0.0023 (4)	−0.0032 (4)
O2	0.0227 (6)	0.0134 (6)	0.0114 (5)	0.0022 (5)	0.0037 (5)	−0.0016 (4)
N1	0.0186 (7)	0.0136 (8)	0.0191 (7)	−0.0011 (6)	0.0007 (6)	−0.0003 (6)
N2	0.0202 (7)	0.0170 (7)	0.0149 (7)	−0.0025 (6)	0.0027 (6)	0.0006 (6)
C1	0.0090 (7)	0.0121 (8)	0.0118 (7)	0.0002 (6)	−0.0003 (6)	0.0003 (6)
C2	0.0102 (7)	0.0097 (7)	0.0134 (7)	0.0006 (6)	−0.0009 (6)	0.0005 (6)
C3	0.0110 (7)	0.0137 (8)	0.0105 (7)	−0.0009 (6)	0.0007 (6)	0.0011 (6)
C4	0.0110 (7)	0.0123 (8)	0.0123 (7)	0.0021 (6)	0.0001 (6)	0.0000 (6)
C5	0.0127 (7)	0.0081 (7)	0.0132 (7)	0.0007 (6)	−0.0008 (6)	0.0014 (6)
C6	0.0121 (8)	0.0128 (8)	0.0099 (7)	−0.0004 (6)	0.0013 (6)	0.0028 (6)
C7	0.0102 (7)	0.0167 (9)	0.0099 (7)	0.0002 (6)	0.0012 (6)	−0.0004 (6)
C8	0.0139 (8)	0.0103 (7)	0.0141 (8)	0.0012 (6)	0.0000 (6)	−0.0026 (6)
N3	0.0167 (7)	0.0109 (7)	0.0166 (7)	0.0017 (5)	−0.0025 (5)	0.0000 (5)
C9	0.0171 (8)	0.0132 (8)	0.0145 (8)	0.0030 (6)	0.0016 (6)	0.0022 (6)
C10	0.0189 (8)	0.0128 (8)	0.0112 (7)	0.0031 (6)	0.0007 (6)	−0.0001 (6)
C11	0.0168 (8)	0.0100 (7)	0.0145 (8)	0.0024 (6)	0.0001 (6)	0.0017 (6)
C12	0.0210 (9)	0.0167 (8)	0.0118 (8)	0.0022 (7)	0.0036 (6)	0.0019 (6)
C13	0.0254 (9)	0.0141 (8)	0.0115 (8)	0.0055 (7)	−0.0007 (6)	−0.0006 (6)
C14	0.0219 (9)	0.0220 (9)	0.0272 (10)	−0.0037 (7)	−0.0051 (7)	−0.0026 (7)

Geometric parameters (Å, º)

Cl1—C5	1.7145 (15)	C5—C6	1.354 (2)
N4—C15	1.143 (2)	N3—C9	1.345 (2)
Cl2—C6	1.7157 (15)	N3—C13	1.346 (2)
C15—C11	1.444 (2)	N3—C14	1.479 (2)
O1—C1	1.2437 (18)	C9—C10	1.376 (2)
O2—C4	1.2402 (19)	C9—H9	0.9500
N1—C7	1.144 (2)	C10—C11	1.390 (2)
N2—C8	1.148 (2)	C10—H10	0.9500
C1—C2	1.452 (2)	C11—C12	1.392 (2)
C1—C6	1.467 (2)	C12—C13	1.369 (2)
C2—C3	1.384 (2)	C12—H12	0.9500
C2—C7	1.432 (2)	C13—H13	0.9500
C3—C8	1.438 (2)	C14—H14A	0.9800
C3—C4	1.456 (2)	C14—H14B	0.9800
C4—C5	1.464 (2)	C14—H14C	0.9800
N4—C15—C11	176.66 (18)	C13—N3—C14	118.46 (14)
O1—C1—C2	122.45 (14)	N3—C9—C10	120.37 (15)
O1—C1—C6	122.96 (14)	N3—C9—H9	119.8
C2—C1—C6	114.58 (13)	C10—C9—H9	119.8
C3—C2—C7	121.75 (14)	C9—C10—C11	118.75 (15)
C3—C2—C1	122.55 (14)	C9—C10—H10	120.6
C7—C2—C1	115.67 (14)	C11—C10—H10	120.6
C2—C3—C8	120.95 (14)	C10—C11—C12	119.96 (15)
C2—C3—C4	122.24 (14)	C10—C11—C15	120.93 (14)
C8—C3—C4	116.81 (14)	C12—C11—C15	119.05 (15)
O2—C4—C3	122.68 (14)	C13—C12—C11	118.73 (15)
O2—C4—C5	122.70 (14)	C13—C12—H12	120.6
C3—C4—C5	114.58 (13)	C11—C12—H12	120.6
C6—C5—C4	122.87 (14)	N3—C13—C12	120.65 (15)
C6—C5—Cl1	121.54 (12)	N3—C13—H13	119.7
C4—C5—Cl1	115.59 (11)	C12—C13—H13	119.7
C5—C6—C1	122.72 (14)	N3—C14—H14A	109.5
C5—C6—Cl2	122.04 (12)	N3—C14—H14B	109.5
C1—C6—Cl2	115.24 (11)	H14A—C14—H14B	109.5
N1—C7—C2	179.14 (17)	N3—C14—H14C	109.5
N2—C8—C3	178.86 (17)	H14A—C14—H14C	109.5
C9—N3—C13	121.52 (15)	H14B—C14—H14C	109.5
C9—N3—C14	119.99 (14)
O1—C1—C2—C3	−176.73 (15)	Cl1—C5—C6—C1	179.51 (12)
C6—C1—C2—C3	4.4 (2)	C4—C5—C6—Cl2	−179.56 (12)
O1—C1—C2—C7	5.2 (2)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.62 (13)	O1—C1—C6—C5	176.38 (15)
C7—C2—C3—C8	−0.4 (2)	C2—C1—C6—C5	−4.8 (2)
C1—C2—C3—C8	−178.39 (14)	O1—C1—C6—Cl2	−4.5 (2)
C7—C2—C3—C4	179.11 (14)	C2—C1—C6—Cl2	174.34 (11)
C1—C2—C3—C4	1.2 (2)	C13—N3—C9—C10	0.1 (2)
C2—C3—C4—O2	175.89 (15)	C14—N3—C9—C10	178.23 (15)
C8—C3—C4—O2	−4.5 (2)	N3—C9—C10—C11	0.2 (2)
C2—C3—C4—C5	−6.3 (2)	C9—C10—C11—C12	0.3 (2)
C8—C3—C4—C5	173.27 (13)	C9—C10—C11—C15	−177.09 (15)
O2—C4—C5—C6	−176.20 (15)	C10—C11—C12—C13	−1.0 (2)
C3—C4—C5—C6	6.0 (2)	C15—C11—C12—C13	176.46 (15)
O2—C4—C5—Cl1	3.8 (2)	C9—N3—C13—C12	−0.8 (2)
C3—C4—C5—Cl1	−174.00 (11)	C14—N3—C13—C12	−178.98 (15)
C4—C5—C6—C1	−0.5 (2)	C11—C12—C13—N3	1.2 (2)

(120K_v2)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.659 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.75559 (15) Å	Cell parameters from 4912 reflections
b = 10.0647 (2) Å	θ = 2.0–28.1°
c = 20.4519 (4) Å	µ = 0.48 mm^−1
β = 94.8065 (19)°	T = 120 K
V = 1385.70 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	2682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→7
Tmin = 0.928, Tmax = 1.000	k = −13→12
9214 measured reflections	l = −26→27
3171 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.8587P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
3171 reflections	Δρmax = 0.34 e Å^−3
209 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20801 (6)	0.11224 (4)	−0.00695 (2)	0.01622 (10)
N4	0.9964 (2)	1.20498 (16)	0.24907 (7)	0.0231 (3)
Cl2	0.11839 (6)	0.28113 (4)	0.11756 (2)	0.01644 (10)
C15	0.8447 (3)	1.15698 (17)	0.23615 (8)	0.0182 (3)
O1	0.13554 (16)	0.56741 (11)	0.09448 (5)	0.0160 (2)
O2	0.29025 (18)	0.27754 (11)	−0.11887 (5)	0.0180 (3)
N1	0.2964 (2)	0.81469 (14)	−0.00683 (7)	0.0193 (3)
N2	0.4171 (2)	0.59868 (14)	−0.16860 (7)	0.0195 (3)
C1	0.1807 (2)	0.50043 (16)	0.04676 (7)	0.0125 (3)
C2	0.2471 (2)	0.56082 (15)	−0.01188 (7)	0.0124 (3)
C3	0.2887 (2)	0.48719 (16)	−0.06634 (7)	0.0125 (3)
C4	0.2643 (2)	0.34338 (16)	−0.06908 (7)	0.0128 (3)
C5	0.2140 (2)	0.28270 (15)	−0.00759 (7)	0.0124 (3)
C6	0.1751 (2)	0.35481 (16)	0.04578 (7)	0.0126 (3)
C7	0.2751 (2)	0.70206 (16)	−0.00946 (7)	0.0138 (3)
C8	0.3594 (2)	0.55007 (16)	−0.12305 (8)	0.0139 (3)
N3	0.3181 (2)	0.95345 (13)	0.18273 (7)	0.0169 (3)
C9	0.3504 (2)	0.99976 (16)	0.24430 (8)	0.0170 (3)
H9	0.254473	0.984556	0.274875	0.020*
C10	0.5207 (2)	1.06883 (16)	0.26352 (8)	0.0158 (3)
H10	0.543986	1.101287	0.307107	0.019*
C11	0.6587 (2)	1.09025 (16)	0.21764 (8)	0.0156 (3)
C12	0.6221 (3)	1.04258 (17)	0.15410 (8)	0.0189 (4)
H12	0.714517	1.057795	0.122357	0.023*
C13	0.4507 (3)	0.97332 (17)	0.13796 (8)	0.0193 (4)
H13	0.424936	0.938901	0.094835	0.023*
C14	0.1370 (3)	0.87598 (19)	0.16316 (10)	0.0273 (4)
H14A	0.055613	0.868872	0.200485	0.041*
H14B	0.174424	0.786869	0.149322	0.041*
H14C	0.060813	0.920809	0.126692	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0224 (2)	0.00946 (19)	0.0170 (2)	0.00043 (15)	0.00266 (15)	0.00033 (14)
N4	0.0258 (8)	0.0250 (8)	0.0188 (7)	−0.0050 (7)	0.0036 (6)	0.0023 (6)
Cl2	0.0214 (2)	0.0161 (2)	0.01220 (19)	−0.00100 (15)	0.00350 (14)	0.00277 (14)
C15	0.0243 (9)	0.0171 (8)	0.0137 (8)	0.0006 (7)	0.0052 (7)	0.0024 (6)
O1	0.0185 (6)	0.0167 (6)	0.0130 (5)	0.0003 (5)	0.0029 (4)	−0.0040 (4)
O2	0.0262 (6)	0.0142 (6)	0.0140 (6)	0.0029 (5)	0.0040 (5)	−0.0020 (4)
N1	0.0209 (8)	0.0159 (8)	0.0211 (7)	−0.0013 (6)	0.0013 (6)	−0.0010 (6)
N2	0.0223 (8)	0.0191 (8)	0.0173 (7)	−0.0016 (6)	0.0027 (6)	0.0015 (6)
C1	0.0117 (7)	0.0130 (8)	0.0126 (7)	0.0005 (6)	0.0000 (6)	0.0006 (6)
C2	0.0118 (7)	0.0117 (7)	0.0137 (7)	0.0001 (6)	0.0008 (6)	−0.0004 (6)
C3	0.0120 (7)	0.0137 (8)	0.0119 (7)	−0.0002 (6)	0.0009 (6)	0.0018 (6)
C4	0.0121 (7)	0.0136 (8)	0.0127 (7)	0.0027 (6)	0.0007 (6)	0.0000 (6)
C5	0.0129 (7)	0.0093 (7)	0.0147 (8)	−0.0001 (6)	−0.0003 (6)	0.0006 (6)
C6	0.0125 (7)	0.0139 (8)	0.0115 (7)	−0.0005 (6)	0.0019 (6)	0.0023 (6)
C7	0.0128 (8)	0.0171 (9)	0.0118 (7)	−0.0002 (6)	0.0017 (6)	0.0000 (6)
C8	0.0144 (8)	0.0121 (8)	0.0150 (8)	0.0012 (6)	−0.0005 (6)	−0.0028 (6)
N3	0.0187 (7)	0.0128 (7)	0.0184 (7)	0.0015 (6)	−0.0031 (5)	−0.0004 (5)
C9	0.0191 (8)	0.0161 (8)	0.0160 (8)	0.0034 (7)	0.0026 (6)	0.0020 (6)
C10	0.0193 (8)	0.0162 (8)	0.0120 (7)	0.0038 (6)	0.0015 (6)	0.0002 (6)
C11	0.0184 (8)	0.0118 (8)	0.0167 (8)	0.0022 (6)	0.0014 (6)	0.0023 (6)
C12	0.0237 (9)	0.0185 (9)	0.0148 (8)	0.0041 (7)	0.0035 (7)	0.0015 (6)
C13	0.0275 (9)	0.0169 (8)	0.0128 (8)	0.0049 (7)	−0.0017 (7)	−0.0012 (6)
C14	0.0243 (10)	0.0249 (10)	0.0313 (10)	−0.0049 (8)	−0.0063 (8)	−0.0043 (8)

Geometric parameters (Å, º)

Cl1—C5	1.7161 (16)	C5—C6	1.355 (2)
N4—C15	1.144 (2)	N3—C9	1.343 (2)
Cl2—C6	1.7163 (15)	N3—C13	1.349 (2)
C15—C11	1.447 (2)	N3—C14	1.478 (2)
O1—C1	1.2448 (18)	C9—C10	1.373 (2)
O2—C4	1.2396 (19)	C9—H9	0.9500
N1—C7	1.143 (2)	C10—C11	1.394 (2)
N2—C8	1.149 (2)	C10—H10	0.9500
C1—C2	1.449 (2)	C11—C12	1.388 (2)
C1—C6	1.466 (2)	C12—C13	1.368 (2)
C2—C3	1.386 (2)	C12—H12	0.9500
C2—C7	1.434 (2)	C13—H13	0.9500
C3—C8	1.438 (2)	C14—H14A	0.9800
C3—C4	1.457 (2)	C14—H14B	0.9800
C4—C5	1.463 (2)	C14—H14C	0.9800
N4—C15—C11	176.56 (18)	C13—N3—C14	118.45 (14)
O1—C1—C2	122.34 (14)	N3—C9—C10	120.69 (15)
O1—C1—C6	122.98 (14)	N3—C9—H9	119.7
C2—C1—C6	114.66 (13)	C10—C9—H9	119.7
C3—C2—C7	121.51 (14)	C9—C10—C11	118.50 (15)
C3—C2—C1	122.59 (14)	C9—C10—H10	120.8
C7—C2—C1	115.86 (14)	C11—C10—H10	120.8
C2—C3—C8	121.09 (14)	C12—C11—C10	120.02 (16)
C2—C3—C4	122.15 (14)	C12—C11—C15	119.22 (15)
C8—C3—C4	116.76 (14)	C10—C11—C15	120.71 (15)
O2—C4—C3	122.63 (14)	C13—C12—C11	118.87 (16)
O2—C4—C5	122.80 (14)	C13—C12—H12	120.6
C3—C4—C5	114.53 (13)	C11—C12—H12	120.6
C6—C5—C4	122.92 (14)	N3—C13—C12	120.58 (15)
C6—C5—Cl1	121.53 (12)	N3—C13—H13	119.7
C4—C5—Cl1	115.55 (11)	C12—C13—H13	119.7
C5—C6—C1	122.68 (14)	N3—C14—H14A	109.5
C5—C6—Cl2	122.00 (13)	N3—C14—H14B	109.5
C1—C6—Cl2	115.31 (11)	H14A—C14—H14B	109.5
N1—C7—C2	179.17 (18)	N3—C14—H14C	109.5
N2—C8—C3	179.05 (18)	H14A—C14—H14C	109.5
C9—N3—C13	121.33 (15)	H14B—C14—H14C	109.5
C9—N3—C14	120.19 (14)
O1—C1—C2—C3	−176.93 (15)	Cl1—C5—C6—C1	179.52 (12)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.47 (12)
O1—C1—C2—C7	5.4 (2)	Cl1—C5—C6—Cl2	0.3 (2)
C6—C1—C2—C7	−173.35 (13)	O1—C1—C6—C5	176.36 (15)
C7—C2—C3—C8	−0.8 (2)	C2—C1—C6—C5	−4.9 (2)
C1—C2—C3—C8	−178.32 (14)	O1—C1—C6—Cl2	−4.4 (2)
C7—C2—C3—C4	178.88 (14)	C2—C1—C6—Cl2	174.38 (11)
C1—C2—C3—C4	1.4 (2)	C13—N3—C9—C10	−0.1 (2)
C2—C3—C4—O2	175.79 (15)	C14—N3—C9—C10	178.26 (15)
C8—C3—C4—O2	−4.5 (2)	N3—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	−6.3 (2)	C9—C10—C11—C12	0.2 (2)
C8—C3—C4—C5	173.35 (13)	C9—C10—C11—C15	−177.09 (15)
O2—C4—C5—C6	−176.31 (15)	C10—C11—C12—C13	−0.9 (2)
C3—C4—C5—C6	5.8 (2)	C15—C11—C12—C13	176.50 (15)
O2—C4—C5—Cl1	3.9 (2)	C9—N3—C13—C12	−0.5 (2)
C3—C4—C5—Cl1	−173.96 (11)	C14—N3—C13—C12	−178.95 (16)
C4—C5—C6—C1	−0.3 (2)	C11—C12—C13—N3	1.0 (2)

(150K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.654 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.77203 (15) Å	Cell parameters from 4725 reflections
b = 10.0679 (2) Å	θ = 2.0–28.1°
c = 20.4627 (4) Å	µ = 0.48 mm^−1
β = 94.7855 (19)°	T = 150 K
V = 1390.28 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3178 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2695 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −8→7
Tmin = 0.955, Tmax = 1.000	k = −13→12
9239 measured reflections	l = −26→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 0.5503P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3178 reflections	Δρmax = 0.34 e Å^−3
209 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20742 (6)	0.11236 (4)	−0.00699 (2)	0.01950 (11)
N4	0.9950 (2)	1.20447 (16)	0.24893 (7)	0.0275 (3)
Cl2	0.11795 (6)	0.28112 (4)	0.11743 (2)	0.01970 (11)
C15	0.8438 (3)	1.15665 (17)	0.23606 (8)	0.0217 (4)
O1	0.13550 (16)	0.56728 (11)	0.09448 (5)	0.0188 (2)
O2	0.29016 (18)	0.27743 (11)	−0.11873 (5)	0.0215 (3)
N1	0.2973 (2)	0.81416 (14)	−0.00682 (7)	0.0233 (3)
N2	0.4170 (2)	0.59857 (14)	−0.16819 (7)	0.0231 (3)
C1	0.1807 (2)	0.50057 (15)	0.04683 (7)	0.0143 (3)
C2	0.2472 (2)	0.56055 (15)	−0.01192 (7)	0.0145 (3)
C3	0.2884 (2)	0.48710 (16)	−0.06628 (7)	0.0146 (3)
C4	0.2646 (2)	0.34355 (16)	−0.06889 (7)	0.0154 (3)
C5	0.2143 (2)	0.28288 (15)	−0.00756 (7)	0.0146 (3)
C6	0.1748 (2)	0.35486 (16)	0.04581 (7)	0.0148 (3)
C7	0.2752 (2)	0.70175 (16)	−0.00939 (7)	0.0162 (3)
C8	0.3598 (2)	0.54994 (15)	−0.12282 (7)	0.0159 (3)
N3	0.3187 (2)	0.95345 (13)	0.18278 (7)	0.0200 (3)
C9	0.3513 (2)	0.99941 (16)	0.24432 (8)	0.0203 (3)
H9	0.255896	0.983929	0.274966	0.024*
C10	0.5211 (2)	1.06857 (16)	0.26338 (8)	0.0190 (3)
H10	0.544104	1.101156	0.306918	0.023*
C11	0.6586 (2)	1.09001 (16)	0.21778 (8)	0.0184 (3)
C12	0.6214 (3)	1.04238 (17)	0.15422 (8)	0.0227 (4)
H12	0.713483	1.057596	0.122442	0.027*
C13	0.4504 (3)	0.97326 (17)	0.13803 (8)	0.0225 (4)
H13	0.424425	0.939030	0.094909	0.027*
C14	0.1377 (3)	0.8760 (2)	0.16333 (10)	0.0329 (4)
H14A	0.060470	0.921643	0.127433	0.049*
H14B	0.057884	0.867673	0.200918	0.049*
H14C	0.174935	0.787422	0.148766	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0274 (2)	0.01124 (19)	0.0201 (2)	0.00040 (15)	0.00313 (16)	0.00030 (14)
N4	0.0304 (9)	0.0302 (8)	0.0222 (8)	−0.0069 (7)	0.0042 (6)	0.0031 (6)
Cl2	0.0262 (2)	0.0191 (2)	0.01427 (19)	−0.00147 (15)	0.00402 (15)	0.00307 (14)
C15	0.0293 (10)	0.0203 (9)	0.0162 (8)	0.0010 (7)	0.0058 (7)	0.0029 (6)
O1	0.0232 (6)	0.0183 (6)	0.0153 (6)	0.0001 (5)	0.0041 (5)	−0.0041 (4)
O2	0.0326 (7)	0.0168 (6)	0.0157 (6)	0.0043 (5)	0.0058 (5)	−0.0024 (4)
N1	0.0253 (8)	0.0175 (8)	0.0269 (8)	−0.0020 (6)	0.0016 (6)	−0.0018 (6)
N2	0.0263 (8)	0.0241 (8)	0.0193 (7)	−0.0027 (6)	0.0045 (6)	0.0015 (6)
C1	0.0140 (7)	0.0150 (8)	0.0137 (7)	0.0005 (6)	0.0006 (6)	−0.0006 (6)
C2	0.0144 (7)	0.0124 (7)	0.0167 (8)	0.0010 (6)	0.0007 (6)	−0.0009 (6)
C3	0.0137 (7)	0.0160 (8)	0.0141 (7)	0.0002 (6)	0.0015 (6)	0.0015 (6)
C4	0.0149 (7)	0.0152 (8)	0.0160 (8)	0.0029 (6)	0.0003 (6)	0.0001 (6)
C5	0.0170 (8)	0.0101 (7)	0.0165 (8)	−0.0004 (6)	0.0003 (6)	0.0017 (6)
C6	0.0151 (7)	0.0164 (8)	0.0130 (7)	0.0004 (6)	0.0019 (6)	0.0021 (6)
C7	0.0164 (8)	0.0188 (8)	0.0135 (7)	0.0003 (6)	0.0023 (6)	−0.0004 (6)
C8	0.0177 (8)	0.0135 (8)	0.0163 (8)	0.0012 (6)	0.0007 (6)	−0.0018 (6)
N3	0.0228 (7)	0.0143 (7)	0.0219 (7)	0.0021 (6)	−0.0039 (6)	−0.0001 (5)
C9	0.0230 (9)	0.0196 (8)	0.0183 (8)	0.0046 (7)	0.0019 (7)	0.0025 (6)
C10	0.0228 (8)	0.0192 (8)	0.0148 (8)	0.0028 (7)	0.0009 (6)	−0.0005 (6)
C11	0.0229 (8)	0.0142 (8)	0.0182 (8)	0.0022 (6)	0.0017 (6)	0.0020 (6)
C12	0.0291 (9)	0.0233 (9)	0.0164 (8)	0.0030 (7)	0.0055 (7)	0.0019 (6)
C13	0.0311 (9)	0.0200 (8)	0.0158 (8)	0.0068 (7)	−0.0018 (7)	−0.0034 (6)
C14	0.0305 (10)	0.0291 (10)	0.0374 (11)	−0.0056 (8)	−0.0067 (8)	−0.0038 (8)

Geometric parameters (Å, º)

Cl1—C5	1.7174 (15)	C5—C6	1.356 (2)
N4—C15	1.142 (2)	N3—C9	1.342 (2)
Cl2—C6	1.7150 (15)	N3—C13	1.345 (2)
C15—C11	1.444 (2)	N3—C14	1.479 (2)
O1—C1	1.2432 (18)	C9—C10	1.373 (2)
O2—C4	1.2420 (18)	C9—H9	0.9500
N1—C7	1.142 (2)	C10—C11	1.389 (2)
N2—C8	1.145 (2)	C10—H10	0.9500
C1—C2	1.450 (2)	C11—C12	1.389 (2)
C1—C6	1.468 (2)	C12—C13	1.368 (2)
C2—C3	1.383 (2)	C12—H12	0.9500
C2—C7	1.435 (2)	C13—H13	0.9500
C3—C8	1.437 (2)	C14—H14A	0.9800
C3—C4	1.455 (2)	C14—H14B	0.9800
C4—C5	1.461 (2)	C14—H14C	0.9800
N4—C15—C11	176.59 (19)	C13—N3—C14	118.46 (14)
O1—C1—C2	122.62 (14)	N3—C9—C10	120.63 (15)
O1—C1—C6	122.88 (14)	N3—C9—H9	119.7
C2—C1—C6	114.48 (13)	C10—C9—H9	119.7
C3—C2—C7	121.58 (14)	C9—C10—C11	118.73 (15)
C3—C2—C1	122.78 (14)	C9—C10—H10	120.6
C7—C2—C1	115.60 (13)	C11—C10—H10	120.6
C2—C3—C8	121.06 (14)	C10—C11—C12	119.72 (16)
C2—C3—C4	122.09 (14)	C10—C11—C15	120.99 (15)
C8—C3—C4	116.85 (13)	C12—C11—C15	119.25 (15)
O2—C4—C3	122.68 (14)	C13—C12—C11	119.07 (15)
O2—C4—C5	122.65 (14)	C13—C12—H12	120.5
C3—C4—C5	114.64 (13)	C11—C12—H12	120.5
C6—C5—C4	122.96 (14)	N3—C13—C12	120.43 (15)
C6—C5—Cl1	121.44 (12)	N3—C13—H13	119.8
C4—C5—Cl1	115.60 (11)	C12—C13—H13	119.8
C5—C6—C1	122.60 (14)	N3—C14—H14A	109.5
C5—C6—Cl2	122.03 (12)	N3—C14—H14B	109.5
C1—C6—Cl2	115.36 (11)	H14A—C14—H14B	109.5
N1—C7—C2	179.41 (17)	N3—C14—H14C	109.5
N2—C8—C3	179.19 (17)	H14A—C14—H14C	109.5
C9—N3—C13	121.41 (15)	H14B—C14—H14C	109.5
C9—N3—C14	120.10 (15)
O1—C1—C2—C3	−176.76 (14)	Cl1—C5—C6—C1	179.62 (12)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.49 (12)
O1—C1—C2—C7	5.5 (2)	Cl1—C5—C6—Cl2	0.7 (2)
C6—C1—C2—C7	−173.44 (13)	O1—C1—C6—C5	176.46 (15)
C7—C2—C3—C8	−0.5 (2)	C2—C1—C6—C5	−4.6 (2)
C1—C2—C3—C8	−178.07 (14)	O1—C1—C6—Cl2	−4.5 (2)
C7—C2—C3—C4	178.68 (14)	C2—C1—C6—Cl2	174.45 (11)
C1—C2—C3—C4	1.1 (2)	C13—N3—C9—C10	0.1 (2)
C2—C3—C4—O2	175.76 (15)	C14—N3—C9—C10	178.38 (15)
C8—C3—C4—O2	−5.0 (2)	N3—C9—C10—C11	0.0 (2)
C2—C3—C4—C5	−6.1 (2)	C9—C10—C11—C12	0.5 (2)
C8—C3—C4—C5	173.13 (13)	C9—C10—C11—C15	−177.06 (15)
O2—C4—C5—C6	−176.01 (15)	C10—C11—C12—C13	−1.0 (2)
C3—C4—C5—C6	5.8 (2)	C15—C11—C12—C13	176.64 (15)
O2—C4—C5—Cl1	3.8 (2)	C9—N3—C13—C12	−0.6 (2)
C3—C4—C5—Cl1	−174.31 (11)	C14—N3—C13—C12	−178.89 (16)
C4—C5—C6—C1	−0.5 (2)	C11—C12—C13—N3	1.0 (2)

(180K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.649 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.78877 (15) Å	Cell parameters from 4533 reflections
b = 10.07003 (19) Å	θ = 2.0–27.9°
c = 20.4706 (4) Å	µ = 0.48 mm^−1
β = 94.7503 (18)°	T = 180 K
V = 1394.62 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3194 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→7
Tmin = 0.927, Tmax = 1.000	k = −13→12
9309 measured reflections	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0347P)^2 + 0.5717P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3194 reflections	Δρmax = 0.30 e Å^−3
209 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20675 (6)	0.11253 (4)	−0.00703 (2)	0.02296 (11)
N4	0.9938 (2)	1.20410 (17)	0.24875 (7)	0.0327 (4)
Cl2	0.11771 (6)	0.28107 (4)	0.11733 (2)	0.02312 (11)
C15	0.8427 (3)	1.15624 (17)	0.23597 (8)	0.0248 (4)
O1	0.13519 (17)	0.56711 (11)	0.09447 (5)	0.0222 (3)
O2	0.29018 (18)	0.27763 (11)	−0.11858 (5)	0.0253 (3)
N1	0.2974 (2)	0.81371 (14)	−0.00674 (7)	0.0270 (3)
N2	0.4169 (2)	0.59838 (15)	−0.16795 (7)	0.0272 (3)
C1	0.1807 (2)	0.50017 (15)	0.04681 (7)	0.0166 (3)
C2	0.2473 (2)	0.56039 (15)	−0.01182 (7)	0.0166 (3)
C3	0.2884 (2)	0.48686 (16)	−0.06607 (7)	0.0168 (3)
C4	0.2643 (2)	0.34370 (16)	−0.06888 (7)	0.0177 (3)
C5	0.2135 (2)	0.28306 (15)	−0.00759 (7)	0.0172 (3)
C6	0.1746 (2)	0.35454 (16)	0.04583 (7)	0.0170 (3)
C7	0.2753 (2)	0.70147 (16)	−0.00923 (7)	0.0184 (3)
C8	0.3593 (2)	0.54977 (16)	−0.12270 (7)	0.0186 (3)
N3	0.3191 (2)	0.95319 (13)	0.18284 (7)	0.0235 (3)
C9	0.3518 (3)	0.99934 (17)	0.24427 (8)	0.0242 (4)
H9	0.256456	0.984227	0.274920	0.029*
C10	0.5213 (2)	1.06812 (16)	0.26331 (8)	0.0222 (3)
H10	0.544796	1.100397	0.306869	0.027*
C11	0.6579 (2)	1.08951 (16)	0.21757 (8)	0.0211 (3)
C12	0.6206 (3)	1.04205 (18)	0.15417 (8)	0.0266 (4)
H12	0.712278	1.057347	0.122342	0.032*
C13	0.4504 (3)	0.97304 (17)	0.13815 (8)	0.0269 (4)
H13	0.424574	0.938746	0.095056	0.032*
C14	0.1383 (3)	0.8760 (2)	0.16358 (11)	0.0388 (5)
H14A	0.060119	0.922339	0.128222	0.058*
H14B	0.059943	0.866523	0.201414	0.058*
H14C	0.175183	0.787835	0.148340	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0323 (2)	0.01302 (19)	0.0238 (2)	0.00067 (15)	0.00413 (16)	0.00045 (14)
N4	0.0349 (9)	0.0355 (9)	0.0282 (8)	−0.0081 (7)	0.0057 (7)	0.0045 (6)
Cl2	0.0306 (2)	0.0222 (2)	0.01695 (19)	−0.00181 (16)	0.00479 (15)	0.00360 (14)
C15	0.0333 (10)	0.0225 (9)	0.0195 (8)	0.0005 (8)	0.0071 (7)	0.0030 (6)
O1	0.0277 (6)	0.0210 (6)	0.0183 (6)	0.0008 (5)	0.0047 (5)	−0.0051 (4)
O2	0.0387 (7)	0.0185 (6)	0.0194 (6)	0.0045 (5)	0.0068 (5)	−0.0028 (4)
N1	0.0303 (8)	0.0191 (8)	0.0313 (8)	−0.0022 (6)	0.0015 (6)	−0.0017 (6)
N2	0.0324 (8)	0.0270 (8)	0.0228 (8)	−0.0035 (6)	0.0060 (6)	0.0030 (6)
C1	0.0155 (7)	0.0176 (8)	0.0166 (7)	0.0008 (6)	−0.0002 (6)	−0.0009 (6)
C2	0.0163 (7)	0.0148 (7)	0.0188 (7)	0.0014 (6)	0.0006 (6)	0.0002 (6)
C3	0.0173 (7)	0.0175 (8)	0.0156 (7)	0.0004 (6)	0.0018 (6)	0.0016 (6)
C4	0.0180 (8)	0.0170 (8)	0.0182 (8)	0.0038 (6)	0.0014 (6)	0.0001 (6)
C5	0.0184 (8)	0.0133 (7)	0.0197 (8)	0.0003 (6)	0.0005 (6)	0.0016 (6)
C6	0.0174 (8)	0.0185 (8)	0.0151 (7)	−0.0002 (6)	0.0016 (6)	0.0025 (6)
C7	0.0181 (8)	0.0214 (9)	0.0160 (7)	0.0004 (6)	0.0021 (6)	−0.0002 (6)
C8	0.0205 (8)	0.0161 (8)	0.0191 (8)	0.0017 (6)	0.0014 (6)	−0.0029 (6)
N3	0.0273 (8)	0.0171 (7)	0.0248 (7)	0.0029 (6)	−0.0046 (6)	−0.0006 (5)
C9	0.0270 (9)	0.0240 (9)	0.0217 (8)	0.0030 (7)	0.0027 (7)	0.0028 (7)
C10	0.0271 (9)	0.0226 (8)	0.0170 (8)	0.0041 (7)	0.0015 (6)	−0.0005 (6)
C11	0.0267 (9)	0.0162 (8)	0.0204 (8)	0.0032 (6)	0.0025 (7)	0.0023 (6)
C12	0.0332 (10)	0.0282 (9)	0.0191 (8)	0.0041 (8)	0.0059 (7)	0.0019 (7)
C13	0.0379 (10)	0.0240 (9)	0.0182 (8)	0.0063 (8)	−0.0014 (7)	−0.0027 (6)
C14	0.0344 (11)	0.0349 (11)	0.0451 (12)	−0.0075 (9)	−0.0084 (9)	−0.0061 (9)

Geometric parameters (Å, º)

Cl1—C5	1.7179 (15)	C5—C6	1.353 (2)
N4—C15	1.144 (2)	N3—C13	1.344 (2)
Cl2—C6	1.7124 (15)	N3—C9	1.342 (2)
C15—C11	1.445 (2)	N3—C14	1.478 (2)
O1—C1	1.2458 (18)	C9—C10	1.372 (2)
O2—C4	1.2401 (18)	C9—H9	0.9500
N1—C7	1.141 (2)	C10—C11	1.388 (2)
N2—C8	1.145 (2)	C10—H10	0.9500
C1—C2	1.450 (2)	C11—C12	1.386 (2)
C1—C6	1.467 (2)	C12—C13	1.365 (3)
C2—C3	1.382 (2)	C12—H12	0.9500
C2—C7	1.434 (2)	C13—H13	0.9500
C3—C8	1.438 (2)	C14—H14A	0.9800
C3—C4	1.452 (2)	C14—H14B	0.9800
C4—C5	1.462 (2)	C14—H14C	0.9800
N4—C15—C11	176.43 (19)	C9—N3—C14	120.09 (15)
O1—C1—C2	122.45 (14)	N3—C9—C10	120.72 (15)
O1—C1—C6	122.89 (14)	N3—C9—H9	119.6
C2—C1—C6	114.66 (13)	C10—C9—H9	119.6
C3—C2—C7	121.70 (14)	C9—C10—C11	118.57 (15)
C3—C2—C1	122.58 (14)	C9—C10—H10	120.7
C7—C2—C1	115.68 (13)	C11—C10—H10	120.7
C2—C3—C8	120.99 (14)	C12—C11—C10	119.86 (16)
C2—C3—C4	122.30 (14)	C12—C11—C15	119.42 (15)
C8—C3—C4	116.71 (13)	C10—C11—C15	120.67 (15)
O2—C4—C3	122.84 (14)	C13—C12—C11	119.05 (16)
O2—C4—C5	122.64 (14)	C13—C12—H12	120.5
C3—C4—C5	114.49 (13)	C11—C12—H12	120.5
C6—C5—C4	123.16 (14)	N3—C13—C12	120.54 (15)
C6—C5—Cl1	121.28 (12)	N3—C13—H13	119.7
C4—C5—Cl1	115.56 (11)	C12—C13—H13	119.7
C5—C6—C1	122.38 (14)	N3—C14—H14A	109.5
C5—C6—Cl2	122.26 (13)	N3—C14—H14B	109.5
C1—C6—Cl2	115.36 (11)	H14A—C14—H14B	109.5
N1—C7—C2	179.55 (17)	N3—C14—H14C	109.5
N2—C8—C3	179.14 (18)	H14A—C14—H14C	109.5
C13—N3—C9	121.25 (15)	H14B—C14—H14C	109.5
C13—N3—C14	118.64 (15)
O1—C1—C2—C3	−176.64 (14)	Cl1—C5—C6—C1	179.55 (12)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.35 (12)
O1—C1—C2—C7	5.6 (2)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.44 (13)	O1—C1—C6—C5	176.13 (15)
C7—C2—C3—C8	−0.7 (2)	C2—C1—C6—C5	−4.8 (2)
C1—C2—C3—C8	−178.29 (14)	O1—C1—C6—Cl2	−4.6 (2)
C7—C2—C3—C4	178.80 (14)	C2—C1—C6—Cl2	174.42 (11)
C1—C2—C3—C4	1.2 (2)	C13—N3—C9—C10	−0.2 (2)
C2—C3—C4—O2	175.89 (15)	C14—N3—C9—C10	178.25 (16)
C8—C3—C4—O2	−4.6 (2)	N3—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	−6.0 (2)	C9—C10—C11—C12	0.2 (2)
C8—C3—C4—C5	173.45 (13)	C9—C10—C11—C15	−177.25 (16)
O2—C4—C5—C6	−176.35 (15)	C10—C11—C12—C13	−0.9 (2)
C3—C4—C5—C6	5.6 (2)	C15—C11—C12—C13	176.58 (16)
O2—C4—C5—Cl1	3.9 (2)	C9—N3—C13—C12	−0.5 (2)
C3—C4—C5—Cl1	−174.16 (11)	C14—N3—C13—C12	−179.00 (17)
C4—C5—C6—C1	−0.2 (2)	C11—C12—C13—N3	1.1 (3)

(210K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.644 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.80352 (17) Å	Cell parameters from 4285 reflections
b = 10.0725 (2) Å	θ = 2.0–27.9°
c = 20.4774 (4) Å	µ = 0.48 mm^−1
β = 94.754 (2)°	T = 210 K
V = 1398.45 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3199 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2633 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→9
Tmin = 0.932, Tmax = 1.000	k = −13→12
9343 measured reflections	l = −27→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.4275P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3199 reflections	Δρmax = 0.29 e Å^−3
209 parameters	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20616 (7)	0.11275 (4)	−0.00708 (2)	0.02676 (12)
N4	0.9921 (3)	1.20339 (18)	0.24850 (8)	0.0382 (4)
Cl2	0.11731 (6)	0.28110 (4)	0.11722 (2)	0.02697 (12)
C15	0.8419 (3)	1.15576 (19)	0.23570 (9)	0.0293 (4)
O1	0.13556 (18)	0.56682 (12)	0.09442 (5)	0.0255 (3)
O2	0.29002 (19)	0.27781 (12)	−0.11834 (6)	0.0291 (3)
N1	0.2976 (2)	0.81332 (15)	−0.00675 (8)	0.0316 (4)
N2	0.4172 (2)	0.59824 (16)	−0.16752 (7)	0.0315 (4)
C1	0.1807 (2)	0.50016 (16)	0.04675 (8)	0.0194 (3)
C2	0.2471 (2)	0.56018 (16)	−0.01166 (8)	0.0190 (3)
C3	0.2886 (2)	0.48704 (16)	−0.06601 (8)	0.0192 (3)
C4	0.2641 (2)	0.34358 (16)	−0.06871 (8)	0.0204 (3)
C5	0.2135 (2)	0.28302 (16)	−0.00758 (8)	0.0198 (3)
C6	0.1746 (2)	0.35484 (16)	0.04577 (8)	0.0199 (3)
C7	0.2757 (2)	0.70120 (17)	−0.00908 (8)	0.0211 (3)
C8	0.3596 (2)	0.54999 (17)	−0.12232 (8)	0.0221 (4)
N3	0.3193 (2)	0.95323 (14)	0.18294 (7)	0.0274 (3)
C9	0.3524 (3)	0.99933 (18)	0.24437 (8)	0.0273 (4)
H9	0.258658	0.984356	0.274807	0.033*
C10	0.5213 (3)	1.06792 (17)	0.26309 (8)	0.0258 (4)
H10	0.544463	1.100075	0.306137	0.031*
C11	0.6573 (3)	1.08913 (17)	0.21769 (8)	0.0245 (4)
C12	0.6202 (3)	1.04183 (19)	0.15427 (8)	0.0300 (4)
H12	0.710647	1.056924	0.122782	0.036*
C13	0.4507 (3)	0.97321 (18)	0.13836 (9)	0.0316 (4)
H13	0.425144	0.939375	0.095723	0.038*
C14	0.1395 (3)	0.8758 (2)	0.16371 (12)	0.0454 (5)
H14A	0.062893	0.921026	0.128328	0.068*
H14B	0.061203	0.867377	0.200993	0.068*
H14C	0.176121	0.788281	0.149183	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0378 (3)	0.0152 (2)	0.0276 (2)	0.00082 (17)	0.00461 (18)	0.00053 (15)
N4	0.0420 (10)	0.0416 (10)	0.0316 (9)	−0.0103 (8)	0.0064 (7)	0.0051 (7)
Cl2	0.0358 (3)	0.0260 (2)	0.0196 (2)	−0.00214 (18)	0.00562 (17)	0.00438 (16)
C15	0.0387 (11)	0.0275 (10)	0.0224 (9)	0.0000 (8)	0.0071 (8)	0.0034 (7)
O1	0.0331 (7)	0.0244 (6)	0.0196 (6)	0.0001 (5)	0.0055 (5)	−0.0056 (5)
O2	0.0450 (8)	0.0217 (7)	0.0215 (6)	0.0048 (6)	0.0084 (5)	−0.0035 (5)
N1	0.0367 (9)	0.0218 (9)	0.0364 (9)	−0.0027 (7)	0.0027 (7)	−0.0017 (6)
N2	0.0374 (9)	0.0316 (9)	0.0261 (8)	−0.0039 (7)	0.0067 (7)	0.0036 (6)
C1	0.0188 (8)	0.0207 (8)	0.0185 (8)	0.0004 (6)	0.0001 (6)	−0.0002 (6)
C2	0.0188 (8)	0.0170 (8)	0.0210 (8)	0.0008 (6)	0.0004 (6)	0.0005 (6)
C3	0.0191 (8)	0.0200 (8)	0.0185 (8)	0.0001 (6)	0.0025 (6)	0.0019 (6)
C4	0.0216 (8)	0.0192 (8)	0.0206 (8)	0.0033 (6)	0.0018 (6)	−0.0004 (6)
C5	0.0221 (8)	0.0151 (8)	0.0220 (8)	0.0001 (6)	0.0004 (6)	0.0015 (6)
C6	0.0207 (8)	0.0209 (8)	0.0182 (8)	0.0003 (6)	0.0027 (6)	0.0023 (6)
C7	0.0204 (8)	0.0232 (9)	0.0199 (8)	−0.0001 (7)	0.0031 (6)	−0.0009 (6)
C8	0.0237 (9)	0.0199 (9)	0.0226 (9)	0.0014 (7)	0.0018 (7)	−0.0025 (7)
N3	0.0309 (8)	0.0210 (8)	0.0288 (8)	0.0031 (6)	−0.0052 (6)	−0.0014 (6)
C9	0.0307 (10)	0.0276 (10)	0.0236 (9)	0.0032 (8)	0.0021 (7)	0.0022 (7)
C10	0.0321 (10)	0.0258 (9)	0.0196 (8)	0.0033 (7)	0.0025 (7)	−0.0011 (7)
C11	0.0318 (10)	0.0195 (9)	0.0223 (9)	0.0026 (7)	0.0017 (7)	0.0021 (6)
C12	0.0379 (10)	0.0321 (10)	0.0208 (9)	0.0034 (8)	0.0067 (8)	0.0001 (7)
C13	0.0454 (11)	0.0270 (10)	0.0216 (9)	0.0088 (8)	−0.0023 (8)	−0.0047 (7)
C14	0.0404 (12)	0.0400 (12)	0.0536 (14)	−0.0072 (10)	−0.0088 (10)	−0.0065 (10)

Geometric parameters (Å, º)

Cl1—C5	1.7158 (16)	C5—C6	1.354 (2)
N4—C15	1.139 (2)	N3—C9	1.342 (2)
Cl2—C6	1.7142 (16)	N3—C13	1.345 (2)
C15—C11	1.445 (3)	N3—C14	1.476 (2)
O1—C1	1.2441 (19)	C9—C10	1.368 (3)
O2—C4	1.2380 (19)	C9—H9	0.9400
N1—C7	1.140 (2)	C10—C11	1.382 (2)
N2—C8	1.143 (2)	C10—H10	0.9400
C1—C2	1.446 (2)	C11—C12	1.387 (2)
C1—C6	1.464 (2)	C12—C13	1.361 (3)
C2—C3	1.383 (2)	C12—H12	0.9400
C2—C7	1.434 (2)	C13—H13	0.9400
C3—C8	1.434 (2)	C14—H14A	0.9700
C3—C4	1.455 (2)	C14—H14B	0.9700
C4—C5	1.459 (2)	C14—H14C	0.9700
N4—C15—C11	176.7 (2)	C13—N3—C14	118.74 (16)
O1—C1—C2	122.54 (15)	N3—C9—C10	120.59 (16)
O1—C1—C6	122.79 (15)	N3—C9—H9	119.7
C2—C1—C6	114.66 (14)	C10—C9—H9	119.7
C3—C2—C7	121.40 (14)	C9—C10—C11	118.90 (16)
C3—C2—C1	122.79 (15)	C9—C10—H10	120.5
C7—C2—C1	115.75 (14)	C11—C10—H10	120.5
C2—C3—C8	121.07 (15)	C10—C11—C12	119.81 (17)
C2—C3—C4	121.94 (14)	C10—C11—C15	121.10 (16)
C8—C3—C4	116.99 (14)	C12—C11—C15	119.05 (16)
O2—C4—C3	122.60 (15)	C13—C12—C11	118.92 (17)
O2—C4—C5	122.72 (15)	C13—C12—H12	120.5
C3—C4—C5	114.65 (14)	C11—C12—H12	120.5
C6—C5—C4	122.98 (15)	N3—C13—C12	120.76 (16)
C6—C5—Cl1	121.43 (13)	N3—C13—H13	119.6
C4—C5—Cl1	115.59 (12)	C12—C13—H13	119.6
C5—C6—C1	122.52 (15)	N3—C14—H14A	109.5
C5—C6—Cl2	122.03 (13)	N3—C14—H14B	109.5
C1—C6—Cl2	115.45 (12)	H14A—C14—H14B	109.5
N1—C7—C2	179.6 (2)	N3—C14—H14C	109.5
N2—C8—C3	178.90 (19)	H14A—C14—H14C	109.5
C9—N3—C13	121.01 (16)	H14B—C14—H14C	109.5
C9—N3—C14	120.22 (16)
O1—C1—C2—C3	−176.86 (15)	Cl1—C5—C6—C1	179.72 (12)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.50 (12)
O1—C1—C2—C7	5.6 (2)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.24 (14)	O1—C1—C6—C5	176.28 (16)
C7—C2—C3—C8	−0.8 (2)	C2—C1—C6—C5	−4.9 (2)
C1—C2—C3—C8	−178.20 (15)	O1—C1—C6—Cl2	−4.4 (2)
C7—C2—C3—C4	178.71 (15)	C2—C1—C6—Cl2	174.48 (11)
C1—C2—C3—C4	1.3 (2)	C13—N3—C9—C10	0.0 (3)
C2—C3—C4—O2	175.85 (16)	C14—N3—C9—C10	178.15 (17)
C8—C3—C4—O2	−4.6 (2)	N3—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	−6.2 (2)	C9—C10—C11—C12	0.5 (3)
C8—C3—C4—C5	173.30 (14)	C9—C10—C11—C15	−177.22 (17)
O2—C4—C5—C6	−176.38 (16)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	5.7 (2)	C15—C11—C12—C13	176.69 (17)
O2—C4—C5—Cl1	3.7 (2)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.19 (11)	C14—N3—C13—C12	−178.78 (18)
C4—C5—C6—C1	−0.2 (3)	C11—C12—C13—N3	1.1 (3)

(240K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.632 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.83004 (15) Å	Cell parameters from 4069 reflections
b = 10.08887 (19) Å	θ = 2.0–27.8°
c = 20.5119 (4) Å	µ = 0.48 mm^−1
β = 94.7341 (18)°	T = 240 K
V = 1408.60 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3218 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2597 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→9
Tmin = 0.953, Tmax = 1.000	k = −13→12
9373 measured reflections	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 0.3774P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3218 reflections	Δρmax = 0.29 e Å^−3
209 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20550 (7)	0.11296 (4)	−0.00711 (2)	0.03081 (13)
N4	0.9903 (3)	1.20316 (19)	0.24822 (8)	0.0438 (4)
Cl2	0.11695 (7)	0.28108 (4)	0.11712 (2)	0.03079 (13)
C15	0.8405 (3)	1.1551 (2)	0.23559 (9)	0.0335 (4)
O1	0.13561 (18)	0.56679 (12)	0.09447 (6)	0.0291 (3)
O2	0.2899 (2)	0.27785 (12)	−0.11820 (6)	0.0334 (3)
N1	0.2980 (2)	0.81298 (16)	−0.00668 (8)	0.0362 (4)
N2	0.4169 (3)	0.59838 (17)	−0.16717 (8)	0.0369 (4)
C1	0.1806 (2)	0.49992 (17)	0.04684 (8)	0.0220 (3)
C2	0.2474 (2)	0.56018 (17)	−0.01156 (8)	0.0219 (3)
C3	0.2882 (2)	0.48681 (17)	−0.06584 (8)	0.0219 (3)
C4	0.2642 (2)	0.34373 (17)	−0.06852 (8)	0.0229 (4)
C5	0.2129 (2)	0.28316 (16)	−0.00745 (8)	0.0217 (3)
C6	0.1743 (2)	0.35483 (17)	0.04572 (8)	0.0221 (4)
C7	0.2756 (3)	0.70122 (18)	−0.00907 (8)	0.0243 (4)
C8	0.3592 (2)	0.54964 (17)	−0.12210 (8)	0.0252 (4)
N3	0.3200 (2)	0.95327 (15)	0.18300 (7)	0.0313 (4)
C9	0.3528 (3)	0.99914 (19)	0.24424 (9)	0.0312 (4)
H9	0.259450	0.983975	0.274609	0.037*
C10	0.5209 (3)	1.06789 (18)	0.26304 (8)	0.0290 (4)
H10	0.543814	1.100090	0.305995	0.035*
C11	0.6569 (3)	1.08911 (17)	0.21748 (9)	0.0280 (4)
C12	0.6198 (3)	1.0414 (2)	0.15439 (9)	0.0346 (4)
H12	0.710095	1.055996	0.122962	0.042*
C13	0.4506 (3)	0.97288 (19)	0.13846 (9)	0.0354 (5)
H13	0.425129	0.939041	0.095908	0.042*
C14	0.1403 (3)	0.8762 (2)	0.16393 (12)	0.0510 (6)
H14A	0.061427	0.869297	0.200996	0.077*
H14B	0.176403	0.788179	0.150157	0.077*
H14C	0.065219	0.920600	0.128127	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0438 (3)	0.0170 (2)	0.0321 (2)	0.00105 (18)	0.00549 (19)	0.00061 (16)
N4	0.0489 (11)	0.0477 (11)	0.0354 (10)	−0.0117 (9)	0.0069 (8)	0.0060 (8)
Cl2	0.0413 (3)	0.0298 (3)	0.0219 (2)	−0.00272 (19)	0.00638 (18)	0.00484 (16)
C15	0.0431 (12)	0.0318 (11)	0.0266 (10)	−0.0018 (9)	0.0083 (8)	0.0036 (8)
O1	0.0375 (7)	0.0276 (7)	0.0228 (6)	0.0009 (6)	0.0066 (5)	−0.0070 (5)
O2	0.0517 (9)	0.0253 (7)	0.0243 (7)	0.0055 (6)	0.0095 (6)	−0.0040 (5)
N1	0.0420 (10)	0.0236 (9)	0.0429 (10)	−0.0031 (7)	0.0033 (8)	−0.0014 (7)
N2	0.0438 (10)	0.0375 (10)	0.0301 (9)	−0.0059 (8)	0.0078 (7)	0.0048 (7)
C1	0.0223 (8)	0.0224 (9)	0.0210 (8)	0.0006 (7)	0.0002 (6)	−0.0003 (7)
C2	0.0222 (8)	0.0205 (9)	0.0230 (8)	0.0005 (7)	0.0018 (7)	−0.0005 (6)
C3	0.0234 (8)	0.0215 (9)	0.0210 (8)	0.0010 (7)	0.0029 (6)	0.0014 (6)
C4	0.0257 (9)	0.0213 (9)	0.0220 (8)	0.0037 (7)	0.0031 (7)	−0.0010 (6)
C5	0.0245 (9)	0.0161 (8)	0.0243 (9)	0.0009 (7)	0.0017 (7)	0.0011 (6)
C6	0.0236 (9)	0.0231 (9)	0.0198 (8)	0.0003 (7)	0.0023 (7)	0.0027 (6)
C7	0.0246 (9)	0.0260 (10)	0.0223 (9)	0.0000 (7)	0.0023 (7)	−0.0004 (7)
C8	0.0276 (9)	0.0217 (9)	0.0260 (9)	0.0006 (7)	0.0012 (7)	−0.0018 (7)
N3	0.0363 (9)	0.0236 (8)	0.0328 (9)	0.0038 (7)	−0.0045 (7)	−0.0013 (6)
C9	0.0344 (10)	0.0318 (10)	0.0275 (10)	0.0034 (8)	0.0029 (8)	0.0021 (8)
C10	0.0347 (10)	0.0323 (10)	0.0200 (9)	0.0048 (8)	0.0023 (7)	−0.0009 (7)
C11	0.0349 (10)	0.0225 (9)	0.0267 (9)	0.0031 (7)	0.0030 (8)	0.0025 (7)
C12	0.0444 (12)	0.0361 (11)	0.0242 (9)	0.0035 (9)	0.0085 (8)	0.0001 (8)
C13	0.0495 (12)	0.0325 (11)	0.0230 (9)	0.0089 (9)	−0.0030 (8)	−0.0056 (8)
C14	0.0454 (13)	0.0476 (14)	0.0574 (15)	−0.0089 (11)	−0.0113 (11)	−0.0065 (11)

Geometric parameters (Å, º)

Cl1—C5	1.7178 (16)	C5—C6	1.352 (2)
N4—C15	1.142 (3)	N3—C9	1.340 (2)
Cl2—C6	1.7168 (17)	N3—C13	1.343 (2)
C15—C11	1.442 (3)	N3—C14	1.478 (3)
O1—C1	1.2466 (19)	C9—C10	1.369 (3)
O2—C4	1.241 (2)	C9—H9	0.9400
N1—C7	1.138 (2)	C10—C11	1.387 (2)
N2—C8	1.145 (2)	C10—H10	0.9400
C1—C2	1.450 (2)	C11—C12	1.385 (3)
C1—C6	1.465 (2)	C12—C13	1.362 (3)
C2—C3	1.384 (2)	C12—H12	0.9400
C2—C7	1.436 (2)	C13—H13	0.9400
C3—C8	1.436 (2)	C14—H14A	0.9700
C3—C4	1.453 (2)	C14—H14B	0.9700
C4—C5	1.462 (2)	C14—H14C	0.9700
N4—C15—C11	176.8 (2)	C13—N3—C14	118.75 (17)
O1—C1—C2	122.36 (16)	N3—C9—C10	120.68 (17)
O1—C1—C6	122.99 (15)	N3—C9—H9	119.7
C2—C1—C6	114.64 (14)	C10—C9—H9	119.7
C3—C2—C7	121.55 (15)	C9—C10—C11	118.74 (17)
C3—C2—C1	122.54 (16)	C9—C10—H10	120.6
C7—C2—C1	115.88 (15)	C11—C10—H10	120.6
C2—C3—C8	120.94 (15)	C12—C11—C10	119.67 (18)
C2—C3—C4	122.16 (15)	C12—C11—C15	119.32 (17)
C8—C3—C4	116.90 (14)	C10—C11—C15	120.95 (16)
O2—C4—C3	122.68 (15)	C13—C12—C11	119.12 (18)
O2—C4—C5	122.66 (16)	C13—C12—H12	120.4
C3—C4—C5	114.64 (14)	C11—C12—H12	120.4
C6—C5—C4	122.94 (15)	N3—C13—C12	120.60 (17)
C6—C5—Cl1	121.55 (13)	N3—C13—H13	119.7
C4—C5—Cl1	115.50 (12)	C12—C13—H13	119.7
C5—C6—C1	122.66 (15)	N3—C14—H14A	109.5
C5—C6—Cl2	121.98 (13)	N3—C14—H14B	109.5
C1—C6—Cl2	115.36 (12)	H14A—C14—H14B	109.5
N1—C7—C2	179.57 (19)	N3—C14—H14C	109.5
N2—C8—C3	179.2 (2)	H14A—C14—H14C	109.5
C9—N3—C13	121.18 (17)	H14B—C14—H14C	109.5
C9—N3—C14	120.04 (17)
O1—C1—C2—C3	−176.67 (16)	Cl1—C5—C6—C1	179.68 (13)
C6—C1—C2—C3	4.5 (2)	C4—C5—C6—Cl2	−179.30 (13)
O1—C1—C2—C7	5.4 (2)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.47 (14)	O1—C1—C6—C5	176.25 (16)
C7—C2—C3—C8	−0.4 (2)	C2—C1—C6—C5	−4.9 (2)
C1—C2—C3—C8	−178.26 (15)	O1—C1—C6—Cl2	−4.4 (2)
C7—C2—C3—C4	178.70 (16)	C2—C1—C6—Cl2	174.40 (12)
C1—C2—C3—C4	0.9 (3)	C13—N3—C9—C10	0.2 (3)
C2—C3—C4—O2	175.92 (17)	C14—N3—C9—C10	178.40 (18)
C8—C3—C4—O2	−4.9 (3)	N3—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−5.7 (2)	C9—C10—C11—C12	0.3 (3)
C8—C3—C4—C5	173.44 (15)	C9—C10—C11—C15	−176.89 (18)
O2—C4—C5—C6	−176.29 (17)	C10—C11—C12—C13	−0.7 (3)
C3—C4—C5—C6	5.3 (2)	C15—C11—C12—C13	176.52 (18)
O2—C4—C5—Cl1	4.0 (2)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.39 (12)	C14—N3—C13—C12	−178.85 (19)
C4—C5—C6—C1	0.0 (3)	C11—C12—C13—N3	0.9 (3)

(270K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.626 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.84899 (17) Å	Cell parameters from 3845 reflections
b = 10.0928 (2) Å	θ = 2.0–27.8°
c = 20.5226 (4) Å	µ = 0.47 mm^−1
β = 94.715 (2)°	T = 270 K
V = 1413.83 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3225 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2539 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→9
Tmin = 0.926, Tmax = 1.000	k = −13→12
9414 measured reflections	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0318P)^2 + 0.3721P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3225 reflections	Δρmax = 0.28 e Å^−3
209 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20489 (7)	0.11321 (4)	−0.00712 (2)	0.03500 (13)
N4	0.9890 (3)	1.20268 (19)	0.24804 (8)	0.0493 (5)
Cl2	0.11661 (7)	0.28116 (5)	0.11697 (2)	0.03491 (13)
C15	0.8397 (3)	1.1552 (2)	0.23537 (9)	0.0377 (4)
O1	0.13567 (18)	0.56664 (12)	0.09449 (6)	0.0326 (3)
O2	0.2899 (2)	0.27787 (12)	−0.11795 (6)	0.0378 (3)
N1	0.2984 (2)	0.81252 (16)	−0.00660 (8)	0.0407 (4)
N2	0.4170 (3)	0.59821 (16)	−0.16682 (8)	0.0407 (4)
C1	0.1803 (2)	0.49997 (17)	0.04689 (8)	0.0248 (4)
C2	0.2470 (2)	0.55998 (16)	−0.01139 (8)	0.0238 (3)
C3	0.2884 (2)	0.48669 (16)	−0.06561 (8)	0.0238 (3)
C4	0.2641 (2)	0.34373 (17)	−0.06845 (8)	0.0261 (4)
C5	0.2126 (2)	0.28310 (16)	−0.00744 (8)	0.0247 (4)
C6	0.1742 (2)	0.35464 (17)	0.04563 (8)	0.0249 (4)
C7	0.2759 (2)	0.70081 (18)	−0.00900 (8)	0.0273 (4)
C8	0.3591 (3)	0.54982 (17)	−0.12183 (8)	0.0279 (4)
N3	0.3205 (2)	0.95322 (15)	0.18318 (7)	0.0352 (4)
C9	0.3536 (3)	0.99919 (19)	0.24421 (9)	0.0351 (4)
H9	0.261562	0.984432	0.274301	0.042*
C10	0.5209 (3)	1.06753 (18)	0.26280 (9)	0.0327 (4)
H10	0.543473	1.099447	0.305262	0.039*
C11	0.6561 (3)	1.08850 (17)	0.21750 (8)	0.0309 (4)
C12	0.6191 (3)	1.0410 (2)	0.15442 (9)	0.0391 (5)
H12	0.708190	1.055481	0.123313	0.047*
C13	0.4507 (3)	0.97289 (19)	0.13863 (9)	0.0397 (5)
H13	0.425299	0.939553	0.096540	0.048*
C14	0.1411 (3)	0.8761 (2)	0.16426 (13)	0.0585 (6)
H14A	0.064578	0.867998	0.201195	0.088*
H14B	0.176709	0.789502	0.149921	0.088*
H14C	0.065686	0.920736	0.129377	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0497 (3)	0.0194 (2)	0.0364 (3)	0.00091 (19)	0.0064 (2)	0.00062 (17)
N4	0.0518 (11)	0.0567 (12)	0.0399 (10)	−0.0136 (10)	0.0079 (8)	0.0071 (8)
Cl2	0.0465 (3)	0.0337 (3)	0.0252 (2)	−0.0030 (2)	0.00737 (19)	0.00588 (17)
C15	0.0476 (12)	0.0376 (11)	0.0291 (10)	−0.0006 (10)	0.0094 (9)	0.0040 (8)
O1	0.0422 (7)	0.0307 (7)	0.0257 (6)	0.0006 (6)	0.0075 (5)	−0.0074 (5)
O2	0.0588 (9)	0.0285 (7)	0.0273 (7)	0.0058 (6)	0.0105 (6)	−0.0056 (5)
N1	0.0480 (10)	0.0268 (9)	0.0472 (10)	−0.0041 (8)	0.0033 (8)	−0.0024 (7)
N2	0.0493 (10)	0.0403 (10)	0.0334 (9)	−0.0054 (8)	0.0094 (8)	0.0045 (7)
C1	0.0250 (9)	0.0261 (9)	0.0233 (8)	0.0014 (7)	0.0013 (7)	−0.0012 (7)
C2	0.0250 (9)	0.0216 (8)	0.0246 (8)	0.0016 (7)	0.0005 (7)	−0.0013 (6)
C3	0.0250 (8)	0.0239 (9)	0.0227 (8)	0.0005 (7)	0.0030 (6)	0.0012 (6)
C4	0.0280 (9)	0.0242 (9)	0.0262 (9)	0.0049 (7)	0.0026 (7)	−0.0006 (7)
C5	0.0285 (9)	0.0195 (8)	0.0258 (9)	0.0018 (7)	0.0008 (7)	0.0013 (6)
C6	0.0270 (9)	0.0265 (9)	0.0213 (8)	0.0008 (7)	0.0033 (7)	0.0025 (6)
C7	0.0275 (9)	0.0286 (10)	0.0261 (9)	0.0003 (7)	0.0028 (7)	−0.0004 (7)
C8	0.0317 (9)	0.0246 (9)	0.0273 (9)	0.0014 (7)	0.0020 (7)	−0.0016 (7)
N3	0.0396 (9)	0.0269 (8)	0.0375 (9)	0.0037 (7)	−0.0056 (7)	−0.0015 (7)
C9	0.0393 (11)	0.0368 (11)	0.0292 (10)	0.0039 (9)	0.0026 (8)	0.0028 (8)
C10	0.0395 (11)	0.0350 (10)	0.0236 (9)	0.0042 (8)	0.0023 (8)	−0.0018 (7)
C11	0.0396 (11)	0.0255 (9)	0.0277 (9)	0.0040 (8)	0.0030 (8)	0.0020 (7)
C12	0.0502 (12)	0.0415 (12)	0.0266 (9)	0.0036 (10)	0.0093 (9)	0.0004 (8)
C13	0.0547 (13)	0.0369 (11)	0.0265 (9)	0.0112 (10)	−0.0022 (9)	−0.0058 (8)
C14	0.0520 (14)	0.0526 (15)	0.0683 (17)	−0.0093 (12)	−0.0112 (12)	−0.0067 (12)

Geometric parameters (Å, º)

Cl1—C5	1.7155 (17)	C5—C6	1.350 (2)
N4—C15	1.140 (3)	N3—C9	1.337 (2)
Cl2—C6	1.7160 (16)	N3—C13	1.343 (2)
C15—C11	1.447 (3)	N3—C14	1.479 (3)
O1—C1	1.2450 (19)	C9—C10	1.365 (3)
O2—C4	1.2388 (19)	C9—H9	0.9300
N1—C7	1.138 (2)	C10—C11	1.381 (2)
N2—C8	1.144 (2)	C10—H10	0.9300
C1—C2	1.448 (2)	C11—C12	1.384 (2)
C1—C6	1.468 (2)	C12—C13	1.359 (3)
C2—C3	1.385 (2)	C12—H12	0.9300
C2—C7	1.435 (2)	C13—H13	0.9300
C3—C8	1.437 (2)	C14—H14A	0.9600
C3—C4	1.453 (2)	C14—H14B	0.9600
C4—C5	1.463 (2)	C14—H14C	0.9600
N4—C15—C11	176.6 (2)	C13—N3—C14	118.86 (17)
O1—C1—C2	122.46 (16)	N3—C9—C10	120.73 (17)
O1—C1—C6	123.06 (15)	N3—C9—H9	119.6
C2—C1—C6	114.46 (14)	C10—C9—H9	119.6
C3—C2—C7	121.32 (15)	C9—C10—C11	118.89 (17)
C3—C2—C1	122.66 (15)	C9—C10—H10	120.6
C7—C2—C1	115.97 (14)	C11—C10—H10	120.6
C2—C3—C8	120.88 (15)	C10—C11—C12	119.68 (18)
C2—C3—C4	122.17 (15)	C10—C11—C15	121.17 (16)
C8—C3—C4	116.95 (14)	C12—C11—C15	119.11 (17)
O2—C4—C3	122.83 (15)	C13—C12—C11	118.98 (18)
O2—C4—C5	122.57 (16)	C13—C12—H12	120.5
C3—C4—C5	114.57 (14)	C11—C12—H12	120.5
C6—C5—C4	122.91 (15)	N3—C13—C12	120.70 (17)
C6—C5—Cl1	121.56 (13)	N3—C13—H13	119.7
C4—C5—Cl1	115.53 (12)	C12—C13—H13	119.7
C5—C6—C1	122.79 (15)	N3—C14—H14A	109.5
C5—C6—Cl2	122.05 (13)	N3—C14—H14B	109.5
C1—C6—Cl2	115.16 (12)	H14A—C14—H14B	109.5
N1—C7—C2	179.5 (2)	N3—C14—H14C	109.5
N2—C8—C3	178.87 (19)	H14A—C14—H14C	109.5
C9—N3—C13	121.01 (17)	H14B—C14—H14C	109.5
C9—N3—C14	120.10 (17)
O1—C1—C2—C3	−176.99 (16)	Cl1—C5—C6—C1	179.78 (13)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.31 (13)
O1—C1—C2—C7	5.4 (2)	Cl1—C5—C6—Cl2	0.3 (2)
C6—C1—C2—C7	−173.26 (14)	O1—C1—C6—C5	176.30 (16)
C7—C2—C3—C8	−0.9 (2)	C2—C1—C6—C5	−5.0 (2)
C1—C2—C3—C8	−178.38 (15)	O1—C1—C6—Cl2	−4.2 (2)
C7—C2—C3—C4	178.69 (15)	C2—C1—C6—Cl2	174.46 (11)
C1—C2—C3—C4	1.2 (3)	C13—N3—C9—C10	0.0 (3)
C2—C3—C4—O2	175.81 (16)	C14—N3—C9—C10	178.28 (18)
C8—C3—C4—O2	−4.6 (2)	N3—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−6.0 (2)	C9—C10—C11—C12	0.5 (3)
C8—C3—C4—C5	173.60 (14)	C9—C10—C11—C15	−177.26 (18)
O2—C4—C5—C6	−176.45 (17)	C10—C11—C12—C13	−0.9 (3)
C3—C4—C5—C6	5.4 (2)	C15—C11—C12—C13	176.91 (18)
O2—C4—C5—Cl1	3.9 (2)	C9—N3—C13—C12	−0.5 (3)
C3—C4—C5—Cl1	−174.29 (12)	C14—N3—C13—C12	−178.72 (19)
C4—C5—C6—C1	0.1 (3)	C11—C12—C13—N3	0.9 (3)

(293K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.622 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.86364 (18) Å	Cell parameters from 3676 reflections
b = 10.0969 (2) Å	θ = 2.0–27.3°
c = 20.5284 (4) Å	µ = 0.47 mm^−1
β = 94.703 (2)°	T = 293 K
V = 1417.86 (5) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3235 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→7
Tmin = 0.956, Tmax = 1.000	k = −13→12
9438 measured reflections	l = −26→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.3465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3235 reflections	Δρmax = 0.26 e Å^−3
209 parameters	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20442 (8)	0.11340 (4)	−0.00715 (2)	0.03848 (14)
N4	0.9875 (3)	1.2023 (2)	0.24795 (9)	0.0539 (5)
Cl2	0.11641 (7)	0.28119 (5)	0.11692 (2)	0.03839 (14)
C15	0.8391 (3)	1.1547 (2)	0.23541 (9)	0.0413 (5)
O1	0.13604 (19)	0.56657 (13)	0.09443 (6)	0.0354 (3)
O2	0.2898 (2)	0.27812 (13)	−0.11782 (6)	0.0413 (3)
N1	0.2985 (3)	0.81196 (17)	−0.00661 (9)	0.0440 (4)
N2	0.4168 (3)	0.59814 (17)	−0.16661 (8)	0.0440 (4)
C1	0.1810 (2)	0.49968 (18)	0.04692 (8)	0.0271 (4)
C2	0.2470 (2)	0.56022 (17)	−0.01128 (8)	0.0264 (4)
C3	0.2880 (2)	0.48656 (17)	−0.06545 (8)	0.0261 (4)
C4	0.2638 (3)	0.34397 (18)	−0.06828 (8)	0.0285 (4)
C5	0.2125 (3)	0.28326 (17)	−0.00744 (8)	0.0270 (4)
C6	0.1734 (2)	0.35462 (18)	0.04562 (8)	0.0271 (4)
C7	0.2760 (3)	0.70050 (19)	−0.00887 (8)	0.0296 (4)
C8	0.3594 (3)	0.54937 (18)	−0.12160 (9)	0.0305 (4)
N3	0.3207 (2)	0.95306 (16)	0.18317 (8)	0.0382 (4)
C9	0.3538 (3)	0.9991 (2)	0.24416 (9)	0.0383 (5)
H9	0.261957	0.984447	0.274251	0.046*
C10	0.5209 (3)	1.06728 (19)	0.26276 (9)	0.0351 (4)
H10	0.543329	1.099087	0.305224	0.042*
C11	0.6563 (3)	1.08840 (18)	0.21747 (9)	0.0341 (4)
C12	0.6191 (3)	1.0409 (2)	0.15453 (9)	0.0423 (5)
H12	0.707679	1.055431	0.123347	0.051*
C13	0.4503 (3)	0.9725 (2)	0.13885 (10)	0.0446 (5)
H13	0.425056	0.938885	0.096822	0.054*
C14	0.1423 (4)	0.8759 (3)	0.16434 (14)	0.0641 (7)
H14A	0.068444	0.919321	0.128762	0.096*
H14B	0.064398	0.869573	0.200978	0.096*
H14C	0.177975	0.788680	0.151022	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0549 (3)	0.0215 (2)	0.0396 (3)	0.0013 (2)	0.0070 (2)	0.00094 (18)
N4	0.0570 (12)	0.0604 (13)	0.0450 (11)	−0.0147 (10)	0.0090 (9)	0.0068 (9)
Cl2	0.0519 (3)	0.0367 (3)	0.0274 (2)	−0.0031 (2)	0.0082 (2)	0.00623 (18)
C15	0.0518 (13)	0.0411 (12)	0.0320 (11)	−0.0026 (10)	0.0106 (10)	0.0050 (9)
O1	0.0461 (8)	0.0342 (7)	0.0266 (7)	0.0006 (6)	0.0080 (6)	−0.0075 (5)
O2	0.0640 (10)	0.0296 (7)	0.0316 (7)	0.0062 (7)	0.0114 (7)	−0.0052 (6)
N1	0.0509 (11)	0.0283 (10)	0.0527 (11)	−0.0048 (8)	0.0031 (8)	−0.0020 (8)
N2	0.0535 (11)	0.0438 (11)	0.0358 (10)	−0.0065 (8)	0.0100 (8)	0.0050 (8)
C1	0.0281 (9)	0.0279 (10)	0.0252 (9)	0.0011 (7)	0.0021 (7)	−0.0016 (7)
C2	0.0282 (9)	0.0230 (9)	0.0279 (9)	0.0016 (7)	0.0017 (7)	−0.0021 (7)
C3	0.0267 (9)	0.0263 (9)	0.0255 (9)	0.0022 (7)	0.0026 (7)	0.0020 (7)
C4	0.0321 (10)	0.0259 (9)	0.0275 (9)	0.0044 (8)	0.0031 (7)	−0.0008 (7)
C5	0.0302 (9)	0.0205 (9)	0.0302 (9)	0.0018 (7)	0.0013 (7)	0.0015 (7)
C6	0.0302 (9)	0.0277 (9)	0.0238 (9)	0.0005 (7)	0.0041 (7)	0.0024 (7)
C7	0.0309 (10)	0.0293 (10)	0.0287 (9)	0.0005 (8)	0.0028 (7)	−0.0007 (7)
C8	0.0334 (10)	0.0277 (10)	0.0302 (10)	0.0012 (8)	0.0021 (8)	−0.0016 (8)
N3	0.0441 (10)	0.0293 (9)	0.0395 (9)	0.0033 (7)	−0.0061 (8)	−0.0018 (7)
C9	0.0420 (11)	0.0400 (12)	0.0330 (10)	0.0033 (9)	0.0037 (9)	0.0025 (8)
C10	0.0422 (11)	0.0369 (11)	0.0264 (10)	0.0040 (9)	0.0037 (8)	−0.0025 (8)
C11	0.0438 (11)	0.0274 (10)	0.0310 (10)	0.0040 (8)	0.0036 (8)	0.0029 (7)
C12	0.0545 (13)	0.0442 (13)	0.0293 (10)	0.0052 (10)	0.0090 (9)	0.0004 (9)
C13	0.0620 (14)	0.0400 (12)	0.0308 (10)	0.0108 (11)	−0.0025 (10)	−0.0072 (9)
C14	0.0557 (15)	0.0596 (16)	0.0740 (18)	−0.0116 (13)	−0.0135 (13)	−0.0091 (13)

Geometric parameters (Å, º)

Cl1—C5	1.7160 (17)	C5—C6	1.351 (2)
N4—C15	1.136 (3)	N3—C9	1.337 (2)
Cl2—C6	1.7144 (17)	N3—C13	1.338 (3)
C15—C11	1.443 (3)	N3—C14	1.476 (3)
O1—C1	1.246 (2)	C9—C10	1.365 (3)
O2—C4	1.240 (2)	C9—H9	0.9300
N1—C7	1.136 (2)	C10—C11	1.384 (3)
N2—C8	1.145 (2)	C10—H10	0.9300
C1—C2	1.448 (2)	C11—C12	1.382 (3)
C1—C6	1.466 (2)	C12—C13	1.365 (3)
C2—C3	1.386 (2)	C12—H12	0.9300
C2—C7	1.431 (2)	C13—H13	0.9300
C3—C8	1.436 (2)	C14—H14A	0.9600
C3—C4	1.450 (3)	C14—H14B	0.9600
C4—C5	1.460 (2)	C14—H14C	0.9600
N4—C15—C11	176.7 (2)	C13—N3—C14	118.87 (18)
O1—C1—C2	122.12 (16)	N3—C9—C10	120.79 (18)
O1—C1—C6	123.05 (16)	N3—C9—H9	119.6
C2—C1—C6	114.83 (15)	C10—C9—H9	119.6
C3—C2—C7	121.49 (16)	C9—C10—C11	119.01 (18)
C3—C2—C1	122.25 (16)	C9—C10—H10	120.5
C7—C2—C1	116.21 (15)	C11—C10—H10	120.5
C2—C3—C8	120.79 (16)	C12—C11—C10	119.43 (19)
C2—C3—C4	122.35 (15)	C12—C11—C15	119.32 (18)
C8—C3—C4	116.85 (15)	C10—C11—C15	121.20 (17)
O2—C4—C3	122.79 (16)	C13—C12—C11	118.98 (19)
O2—C4—C5	122.51 (17)	C13—C12—H12	120.5
C3—C4—C5	114.67 (15)	C11—C12—H12	120.5
C6—C5—C4	122.92 (16)	N3—C13—C12	120.85 (18)
C6—C5—Cl1	121.44 (14)	N3—C13—H13	119.6
C4—C5—Cl1	115.64 (13)	C12—C13—H13	119.6
C5—C6—C1	122.59 (16)	N3—C14—H14A	109.5
C5—C6—Cl2	122.14 (14)	N3—C14—H14B	109.5
C1—C6—Cl2	115.26 (13)	H14A—C14—H14B	109.5
N1—C7—C2	179.6 (2)	N3—C14—H14C	109.5
N2—C8—C3	179.3 (2)	H14A—C14—H14C	109.5
C9—N3—C13	120.93 (18)	H14B—C14—H14C	109.5
C9—N3—C14	120.17 (19)
O1—C1—C2—C3	−176.79 (16)	Cl1—C5—C6—C1	179.41 (13)
C6—C1—C2—C3	3.8 (2)	C4—C5—C6—Cl2	−179.16 (13)
O1—C1—C2—C7	5.8 (3)	Cl1—C5—C6—Cl2	0.9 (2)
C6—C1—C2—C7	−173.58 (15)	O1—C1—C6—C5	176.41 (17)
C7—C2—C3—C8	−0.7 (3)	C2—C1—C6—C5	−4.2 (2)
C1—C2—C3—C8	−177.95 (16)	O1—C1—C6—Cl2	−5.0 (2)
C7—C2—C3—C4	178.58 (16)	C2—C1—C6—Cl2	174.46 (12)
C1—C2—C3—C4	1.4 (3)	C13—N3—C9—C10	0.1 (3)
C2—C3—C4—O2	175.91 (17)	C14—N3—C9—C10	178.10 (19)
C8—C3—C4—O2	−4.8 (3)	N3—C9—C10—C11	0.0 (3)
C2—C3—C4—C5	−6.0 (2)	C9—C10—C11—C12	0.4 (3)
C8—C3—C4—C5	173.36 (15)	C9—C10—C11—C15	−177.20 (19)
O2—C4—C5—C6	−176.24 (17)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	5.6 (3)	C15—C11—C12—C13	176.71 (19)
O2—C4—C5—Cl1	3.7 (2)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.40 (12)	C14—N3—C13—C12	−178.7 (2)
C4—C5—C6—C1	−0.6 (3)	C11—C12—C13—N3	1.1 (3)

(310K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.617 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.87524 (18) Å	Cell parameters from 3535 reflections
b = 10.1004 (2) Å	θ = 2.0–27.3°
c = 20.5391 (4) Å	µ = 0.47 mm^−1
β = 94.709 (2)°	T = 310 K
V = 1421.47 (6) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3240 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→7
Tmin = 0.935, Tmax = 1.000	k = −13→12
9454 measured reflections	l = −26→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.2983P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3240 reflections	Δρmax = 0.29 e Å^−3
209 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20418 (8)	0.11356 (4)	−0.00714 (2)	0.04083 (14)
N4	0.9864 (3)	1.2019 (2)	0.24776 (9)	0.0586 (5)
Cl2	0.11636 (7)	0.28123 (5)	0.11686 (2)	0.04084 (14)
C15	0.8386 (3)	1.1540 (2)	0.23528 (10)	0.0440 (5)
O1	0.13615 (19)	0.56638 (12)	0.09440 (6)	0.0379 (3)
O2	0.2894 (2)	0.27842 (13)	−0.11771 (6)	0.0435 (3)
N1	0.2991 (3)	0.81168 (17)	−0.00660 (9)	0.0475 (4)
N2	0.4169 (3)	0.59787 (18)	−0.16625 (8)	0.0475 (4)
C1	0.1807 (2)	0.49981 (17)	0.04688 (8)	0.0291 (4)
C2	0.2473 (2)	0.55983 (17)	−0.01123 (8)	0.0283 (4)
C3	0.2884 (2)	0.48655 (17)	−0.06549 (8)	0.0282 (4)
C4	0.2641 (3)	0.34420 (17)	−0.06819 (8)	0.0301 (4)
C5	0.2121 (3)	0.28340 (16)	−0.00733 (8)	0.0287 (4)
C6	0.1738 (2)	0.35467 (17)	0.04569 (8)	0.0287 (4)
C7	0.2762 (3)	0.70045 (19)	−0.00863 (8)	0.0321 (4)
C8	0.3590 (3)	0.54931 (18)	−0.12146 (9)	0.0320 (4)
N3	0.3212 (2)	0.95320 (15)	0.18324 (8)	0.0403 (4)
C9	0.3538 (3)	0.9990 (2)	0.24407 (9)	0.0406 (5)
H9	0.261958	0.984404	0.274118	0.049*
C10	0.5209 (3)	1.06724 (19)	0.26265 (9)	0.0379 (4)
H10	0.543398	1.099030	0.305092	0.046*
C11	0.6558 (3)	1.08828 (18)	0.21744 (9)	0.0366 (4)
C12	0.6181 (3)	1.0407 (2)	0.15444 (9)	0.0459 (5)
H12	0.706405	1.055207	0.123228	0.055*
C13	0.4501 (3)	0.9724 (2)	0.13883 (9)	0.0459 (5)
H13	0.424712	0.938802	0.096846	0.055*
C14	0.1424 (4)	0.8763 (3)	0.16438 (14)	0.0679 (7)
H14A	0.069168	0.919599	0.128695	0.102*
H14B	0.064365	0.870472	0.200947	0.102*
H14C	0.177645	0.788878	0.151263	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0580 (3)	0.0227 (2)	0.0423 (3)	0.0014 (2)	0.0074 (2)	0.00052 (18)
N4	0.0637 (13)	0.0657 (13)	0.0473 (11)	−0.0182 (11)	0.0092 (10)	0.0072 (9)
Cl2	0.0547 (3)	0.0395 (3)	0.0292 (2)	−0.0034 (2)	0.0089 (2)	0.00669 (18)
C15	0.0560 (14)	0.0425 (12)	0.0347 (11)	−0.0035 (11)	0.0108 (10)	0.0056 (9)
O1	0.0501 (8)	0.0358 (7)	0.0289 (7)	0.0006 (6)	0.0087 (6)	−0.0085 (5)
O2	0.0676 (10)	0.0328 (7)	0.0317 (7)	0.0077 (7)	0.0126 (6)	−0.0050 (6)
N1	0.0556 (11)	0.0296 (10)	0.0570 (11)	−0.0049 (8)	0.0038 (9)	−0.0028 (8)
N2	0.0558 (11)	0.0484 (11)	0.0391 (10)	−0.0079 (9)	0.0098 (8)	0.0062 (8)
C1	0.0311 (9)	0.0288 (9)	0.0271 (9)	0.0009 (7)	0.0020 (7)	−0.0019 (7)
C2	0.0305 (9)	0.0249 (9)	0.0295 (9)	0.0009 (7)	0.0029 (7)	−0.0006 (7)
C3	0.0303 (9)	0.0279 (9)	0.0266 (9)	0.0017 (7)	0.0033 (7)	0.0019 (7)
C4	0.0348 (10)	0.0284 (9)	0.0274 (9)	0.0053 (8)	0.0042 (7)	−0.0003 (7)
C5	0.0330 (9)	0.0223 (9)	0.0306 (9)	0.0017 (7)	0.0011 (7)	0.0013 (7)
C6	0.0322 (9)	0.0302 (9)	0.0239 (8)	0.0012 (7)	0.0040 (7)	0.0032 (7)
C7	0.0331 (10)	0.0321 (11)	0.0312 (10)	0.0009 (8)	0.0029 (7)	−0.0006 (7)
C8	0.0352 (10)	0.0294 (10)	0.0315 (9)	0.0010 (8)	0.0036 (8)	−0.0005 (8)
N3	0.0468 (10)	0.0312 (9)	0.0413 (10)	0.0035 (7)	−0.0065 (8)	−0.0009 (7)
C9	0.0448 (12)	0.0425 (12)	0.0348 (10)	0.0038 (9)	0.0042 (9)	0.0029 (8)
C10	0.0451 (11)	0.0423 (11)	0.0262 (9)	0.0056 (9)	0.0024 (8)	−0.0028 (8)
C11	0.0475 (12)	0.0303 (10)	0.0322 (10)	0.0040 (8)	0.0051 (8)	0.0018 (7)
C12	0.0570 (13)	0.0502 (13)	0.0316 (10)	0.0049 (11)	0.0108 (9)	−0.0004 (9)
C13	0.0642 (14)	0.0429 (12)	0.0295 (10)	0.0096 (11)	−0.0031 (10)	−0.0070 (9)
C14	0.0629 (16)	0.0578 (16)	0.0795 (18)	−0.0114 (13)	−0.0155 (13)	−0.0086 (13)

Geometric parameters (Å, º)

Cl1—C5	1.7163 (17)	C5—C6	1.349 (2)
N4—C15	1.135 (3)	N3—C9	1.334 (2)
Cl2—C6	1.7141 (17)	N3—C13	1.337 (3)
C15—C11	1.442 (3)	N3—C14	1.478 (3)
O1—C1	1.2440 (19)	C9—C10	1.367 (3)
O2—C4	1.239 (2)	C9—H9	0.9300
N1—C7	1.135 (2)	C10—C11	1.382 (3)
N2—C8	1.142 (2)	C10—H10	0.9300
C1—C2	1.446 (2)	C11—C12	1.385 (3)
C1—C6	1.467 (2)	C12—C13	1.361 (3)
C2—C3	1.386 (2)	C12—H12	0.9300
C2—C7	1.434 (2)	C13—H13	0.9300
C3—C8	1.432 (2)	C14—H14A	0.9600
C3—C4	1.448 (2)	C14—H14B	0.9600
C4—C5	1.463 (2)	C14—H14C	0.9600
N4—C15—C11	177.1 (2)	C13—N3—C14	118.76 (18)
O1—C1—C2	122.41 (16)	N3—C9—C10	120.60 (18)
O1—C1—C6	122.93 (16)	N3—C9—H9	119.7
C2—C1—C6	114.65 (15)	C10—C9—H9	119.7
C3—C2—C7	121.47 (15)	C9—C10—C11	119.04 (18)
C3—C2—C1	122.61 (16)	C9—C10—H10	120.5
C7—C2—C1	115.87 (15)	C11—C10—H10	120.5
C2—C3—C8	120.93 (16)	C10—C11—C12	119.33 (19)
C2—C3—C4	122.04 (15)	C10—C11—C15	121.30 (17)
C8—C3—C4	117.03 (15)	C12—C11—C15	119.32 (18)
O2—C4—C3	122.71 (16)	C13—C12—C11	119.10 (19)
O2—C4—C5	122.47 (16)	C13—C12—H12	120.5
C3—C4—C5	114.81 (14)	C11—C12—H12	120.5
C6—C5—C4	122.89 (16)	N3—C13—C12	120.69 (18)
C6—C5—Cl1	121.54 (14)	N3—C13—H13	119.7
C4—C5—Cl1	115.56 (12)	C12—C13—H13	119.7
C5—C6—C1	122.59 (15)	N3—C14—H14A	109.5
C5—C6—Cl2	122.09 (14)	N3—C14—H14B	109.5
C1—C6—Cl2	115.31 (12)	H14A—C14—H14B	109.5
N1—C7—C2	179.9 (3)	N3—C14—H14C	109.5
N2—C8—C3	179.1 (2)	H14A—C14—H14C	109.5
C9—N3—C13	121.24 (18)	H14B—C14—H14C	109.5
C9—N3—C14	119.98 (18)
O1—C1—C2—C3	−176.91 (16)	Cl1—C5—C6—C1	179.64 (13)
C6—C1—C2—C3	4.3 (2)	C4—C5—C6—Cl2	−179.11 (13)
O1—C1—C2—C7	5.5 (2)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.37 (15)	O1—C1—C6—C5	176.28 (17)
C7—C2—C3—C8	−0.8 (3)	C2—C1—C6—C5	−4.9 (2)
C1—C2—C3—C8	−178.33 (16)	O1—C1—C6—Cl2	−4.4 (2)
C7—C2—C3—C4	178.60 (16)	C2—C1—C6—Cl2	174.41 (12)
C1—C2—C3—C4	1.1 (3)	C13—N3—C9—C10	0.0 (3)
C2—C3—C4—O2	175.73 (17)	C14—N3—C9—C10	178.26 (19)
C8—C3—C4—O2	−4.8 (3)	N3—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	−5.8 (2)	C9—C10—C11—C12	0.4 (3)
C8—C3—C4—C5	173.68 (15)	C9—C10—C11—C15	−176.99 (19)
O2—C4—C5—C6	−176.31 (17)	C10—C11—C12—C13	−1.0 (3)
C3—C4—C5—C6	5.2 (3)	C15—C11—C12—C13	176.47 (19)
O2—C4—C5—Cl1	4.2 (2)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.33 (12)	C14—N3—C13—C12	−178.9 (2)
C4—C5—C6—C1	0.1 (3)	C11—C12—C13—N3	1.1 (3)

(340K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.610 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8983 (2) Å	Cell parameters from 3314 reflections
b = 10.1074 (2) Å	θ = 2.0–26.7°
c = 20.5530 (4) Å	µ = 0.47 mm^−1
β = 94.690 (2)°	T = 340 K
V = 1428.23 (6) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3257 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→9
Tmin = 0.944, Tmax = 1.000	k = −13→12
9495 measured reflections	l = −27→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0319P)^2 + 0.2909P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3257 reflections	Δρmax = 0.24 e Å^−3
209 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20362 (8)	0.11394 (5)	−0.00713 (2)	0.04606 (15)
N4	0.9854 (3)	1.2014 (2)	0.24749 (9)	0.0645 (6)
Cl2	0.11624 (8)	0.28136 (5)	0.11675 (2)	0.04566 (15)
C15	0.8373 (4)	1.1540 (2)	0.23510 (10)	0.0487 (5)
O1	0.1365 (2)	0.56633 (13)	0.09451 (6)	0.0430 (3)
O2	0.2895 (2)	0.27844 (13)	−0.11746 (6)	0.0487 (4)
N1	0.2993 (3)	0.81123 (18)	−0.00653 (9)	0.0530 (5)
N2	0.4163 (3)	0.59816 (18)	−0.16611 (9)	0.0525 (5)
C1	0.1812 (3)	0.49967 (18)	0.04711 (8)	0.0321 (4)
C2	0.2473 (2)	0.55989 (17)	−0.01105 (8)	0.0305 (4)
C3	0.2882 (2)	0.48642 (18)	−0.06520 (8)	0.0309 (4)
C4	0.2636 (3)	0.34431 (18)	−0.06801 (9)	0.0329 (4)
C5	0.2123 (3)	0.28353 (17)	−0.00716 (8)	0.0320 (4)
C6	0.1739 (3)	0.35503 (18)	0.04580 (8)	0.0320 (4)
C7	0.2762 (3)	0.7002 (2)	−0.00866 (9)	0.0357 (4)
C8	0.3589 (3)	0.54916 (19)	−0.12116 (9)	0.0357 (4)
N3	0.3216 (2)	0.95297 (16)	0.18331 (8)	0.0451 (4)
C9	0.3548 (3)	0.9990 (2)	0.24414 (10)	0.0454 (5)
H9	0.263497	0.984593	0.274251	0.054*
C10	0.5212 (3)	1.0671 (2)	0.26262 (9)	0.0422 (5)
H10	0.543989	1.098896	0.305012	0.051*
C11	0.6551 (3)	1.08784 (19)	0.21737 (9)	0.0402 (5)
C12	0.6176 (3)	1.0400 (2)	0.15450 (10)	0.0502 (5)
H12	0.705663	1.054132	0.123293	0.060*
C13	0.4505 (3)	0.9723 (2)	0.13911 (10)	0.0520 (6)
H13	0.425136	0.938709	0.097147	0.062*
C14	0.1434 (4)	0.8761 (3)	0.16463 (14)	0.0754 (8)
H14A	0.071488	0.918310	0.128436	0.113*
H14B	0.064609	0.871786	0.200974	0.113*
H14C	0.178418	0.788140	0.152363	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0656 (4)	0.0258 (2)	0.0475 (3)	0.0013 (2)	0.0089 (2)	0.0007 (2)
N4	0.0687 (14)	0.0738 (15)	0.0517 (12)	−0.0195 (12)	0.0096 (10)	0.0101 (10)
Cl2	0.0613 (3)	0.0441 (3)	0.0327 (3)	−0.0034 (2)	0.0099 (2)	0.0071 (2)
C15	0.0613 (15)	0.0480 (13)	0.0381 (12)	−0.0030 (12)	0.0120 (11)	0.0058 (9)
O1	0.0570 (9)	0.0404 (8)	0.0326 (7)	0.0015 (7)	0.0097 (6)	−0.0092 (6)
O2	0.0755 (10)	0.0361 (8)	0.0359 (8)	0.0069 (7)	0.0140 (7)	−0.0060 (6)
N1	0.0630 (12)	0.0330 (11)	0.0628 (12)	−0.0057 (9)	0.0047 (9)	−0.0035 (8)
N2	0.0632 (12)	0.0526 (12)	0.0428 (10)	−0.0080 (9)	0.0116 (9)	0.0067 (8)
C1	0.0355 (10)	0.0318 (10)	0.0288 (9)	0.0020 (8)	0.0022 (8)	−0.0011 (7)
C2	0.0327 (10)	0.0272 (9)	0.0315 (9)	0.0020 (8)	0.0029 (7)	−0.0004 (7)
C3	0.0332 (10)	0.0300 (10)	0.0297 (9)	0.0022 (8)	0.0035 (7)	0.0025 (7)
C4	0.0374 (10)	0.0304 (10)	0.0312 (10)	0.0057 (8)	0.0038 (8)	−0.0012 (7)
C5	0.0362 (10)	0.0246 (9)	0.0351 (10)	0.0023 (8)	0.0027 (8)	0.0027 (7)
C6	0.0362 (10)	0.0317 (10)	0.0284 (9)	0.0008 (8)	0.0043 (8)	0.0033 (7)
C7	0.0382 (11)	0.0350 (11)	0.0338 (10)	−0.0009 (8)	0.0026 (8)	0.0001 (8)
C8	0.0395 (11)	0.0327 (10)	0.0348 (10)	0.0006 (8)	0.0019 (8)	−0.0014 (8)
N3	0.0518 (11)	0.0353 (10)	0.0464 (10)	0.0050 (8)	−0.0065 (8)	−0.0024 (8)
C9	0.0499 (13)	0.0475 (13)	0.0389 (11)	0.0037 (10)	0.0051 (9)	0.0029 (9)
C10	0.0520 (13)	0.0448 (12)	0.0298 (10)	0.0046 (10)	0.0044 (9)	−0.0020 (8)
C11	0.0522 (13)	0.0335 (11)	0.0349 (11)	0.0036 (9)	0.0042 (9)	0.0028 (8)
C12	0.0634 (15)	0.0543 (14)	0.0343 (11)	0.0029 (12)	0.0115 (10)	0.0002 (10)
C13	0.0714 (16)	0.0482 (14)	0.0351 (11)	0.0115 (12)	−0.0032 (11)	−0.0082 (10)
C14	0.0694 (18)	0.0661 (18)	0.087 (2)	−0.0152 (14)	−0.0142 (15)	−0.0113 (14)

Geometric parameters (Å, º)

Cl1—C5	1.7152 (18)	C5—C6	1.351 (2)
N4—C15	1.138 (3)	N3—C13	1.336 (3)
Cl2—C6	1.7129 (17)	N3—C9	1.336 (2)
C15—C11	1.445 (3)	N3—C14	1.478 (3)
O1—C1	1.244 (2)	C9—C10	1.365 (3)
O2—C4	1.240 (2)	C9—H9	0.9300
N1—C7	1.134 (2)	C10—C11	1.379 (3)
N2—C8	1.147 (2)	C10—H10	0.9300
C1—C2	1.448 (2)	C11—C12	1.384 (3)
C1—C6	1.463 (3)	C12—C13	1.356 (3)
C2—C3	1.386 (2)	C12—H12	0.9300
C2—C7	1.433 (3)	C13—H13	0.9300
C3—C8	1.434 (2)	C14—H14A	0.9600
C3—C4	1.447 (3)	C14—H14B	0.9600
C4—C5	1.462 (2)	C14—H14C	0.9600
N4—C15—C11	176.6 (2)	C9—N3—C14	120.1 (2)
O1—C1—C2	122.26 (17)	N3—C9—C10	120.79 (19)
O1—C1—C6	123.05 (16)	N3—C9—H9	119.6
C2—C1—C6	114.68 (15)	C10—C9—H9	119.6
C3—C2—C7	121.41 (16)	C9—C10—C11	118.89 (19)
C3—C2—C1	122.43 (16)	C9—C10—H10	120.6
C7—C2—C1	116.11 (16)	C11—C10—H10	120.6
C2—C3—C8	120.82 (16)	C10—C11—C12	119.5 (2)
C2—C3—C4	122.20 (16)	C10—C11—C15	121.15 (18)
C8—C3—C4	116.98 (16)	C12—C11—C15	119.32 (19)
O2—C4—C3	122.78 (17)	C13—C12—C11	119.0 (2)
O2—C4—C5	122.44 (17)	C13—C12—H12	120.5
C3—C4—C5	114.75 (15)	C11—C12—H12	120.5
C6—C5—C4	122.79 (17)	N3—C13—C12	121.02 (19)
C6—C5—Cl1	121.68 (14)	N3—C13—H13	119.5
C4—C5—Cl1	115.54 (13)	C12—C13—H13	119.5
C5—C6—C1	122.73 (16)	N3—C14—H14A	109.5
C5—C6—Cl2	121.87 (15)	N3—C14—H14B	109.5
C1—C6—Cl2	115.39 (13)	H14A—C14—H14B	109.5
N1—C7—C2	179.7 (2)	N3—C14—H14C	109.5
N2—C8—C3	179.3 (2)	H14A—C14—H14C	109.5
C13—N3—C9	120.82 (19)	H14B—C14—H14C	109.5
C13—N3—C14	119.05 (19)
O1—C1—C2—C3	−176.80 (17)	Cl1—C5—C6—C1	179.71 (14)
C6—C1—C2—C3	3.9 (3)	C4—C5—C6—Cl2	−179.43 (14)
O1—C1—C2—C7	5.7 (3)	Cl1—C5—C6—Cl2	0.6 (2)
C6—C1—C2—C7	−173.53 (16)	O1—C1—C6—C5	176.25 (18)
C7—C2—C3—C8	−0.8 (3)	C2—C1—C6—C5	−4.5 (3)
C1—C2—C3—C8	−178.09 (16)	O1—C1—C6—Cl2	−4.6 (2)
C7—C2—C3—C4	178.76 (17)	C2—C1—C6—Cl2	174.66 (12)
C1—C2—C3—C4	1.4 (3)	C13—N3—C9—C10	0.1 (3)
C2—C3—C4—O2	175.93 (18)	C14—N3—C9—C10	178.2 (2)
C8—C3—C4—O2	−4.5 (3)	N3—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	−6.1 (3)	C9—C10—C11—C12	0.3 (3)
C8—C3—C4—C5	173.43 (16)	C9—C10—C11—C15	−177.2 (2)
O2—C4—C5—C6	−176.43 (18)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—C6	5.6 (3)	C15—C11—C12—C13	176.8 (2)
O2—C4—C5—Cl1	3.5 (2)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.44 (13)	C14—N3—C13—C12	−178.7 (2)
C4—C5—C6—C1	−0.3 (3)	C11—C12—C13—N3	0.9 (3)

(370K)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.601 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.9227 (2) Å	Cell parameters from 3098 reflections
b = 10.1152 (2) Å	θ = 2.0–26.7°
c = 20.5732 (5) Å	µ = 0.47 mm^−1
β = 94.691 (3)°	T = 370 K
V = 1435.81 (7) Å^3	Block, black
Z = 4	0.40 × 0.15 × 0.07 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	2318 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 10.3457 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −9→7
Tmin = 0.939, Tmax = 1.000	k = −13→12
9538 measured reflections	l = −26→27
3278 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0336P)^2 + 0.2488P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3278 reflections	Δρmax = 0.21 e Å^−3
209 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20329 (8)	0.11434 (5)	−0.00714 (3)	0.05121 (17)
N4	0.9835 (3)	1.2008 (2)	0.24711 (10)	0.0718 (6)
Cl2	0.11629 (8)	0.28167 (5)	0.11673 (2)	0.05103 (16)
C15	0.8364 (4)	1.1537 (2)	0.23493 (11)	0.0546 (6)
O1	0.1370 (2)	0.56620 (14)	0.09453 (6)	0.0482 (4)
O2	0.2896 (2)	0.27898 (14)	−0.11726 (6)	0.0540 (4)
N1	0.2995 (3)	0.81096 (19)	−0.00651 (9)	0.0587 (5)
N2	0.4158 (3)	0.59791 (19)	−0.16570 (9)	0.0585 (5)
C1	0.1814 (3)	0.50002 (19)	0.04716 (9)	0.0358 (4)
C2	0.2479 (3)	0.55989 (18)	−0.01088 (9)	0.0345 (4)
C3	0.2888 (3)	0.48661 (18)	−0.06500 (8)	0.0341 (4)
C4	0.2641 (3)	0.34441 (19)	−0.06768 (9)	0.0370 (4)
C5	0.2119 (3)	0.28391 (18)	−0.00713 (9)	0.0356 (4)
C6	0.1740 (3)	0.35534 (18)	0.04582 (9)	0.0353 (4)
C7	0.2762 (3)	0.7001 (2)	−0.00859 (9)	0.0395 (5)
C8	0.3589 (3)	0.54945 (19)	−0.12087 (9)	0.0400 (5)
N3	0.3222 (3)	0.95302 (17)	0.18346 (9)	0.0502 (5)
C9	0.3554 (3)	0.9990 (2)	0.24421 (10)	0.0497 (5)
H9	0.264658	0.984599	0.274368	0.060*
C10	0.5211 (3)	1.0669 (2)	0.26237 (10)	0.0463 (5)
H10	0.543669	1.099022	0.304670	0.056*
C11	0.6548 (3)	1.08754 (19)	0.21738 (10)	0.0445 (5)
C12	0.6171 (4)	1.0396 (2)	0.15467 (10)	0.0548 (6)
H12	0.704989	1.053577	0.123500	0.066*
C13	0.4509 (4)	0.9721 (2)	0.13920 (11)	0.0566 (6)
H13	0.425770	0.938613	0.097271	0.068*
C14	0.1442 (4)	0.8762 (3)	0.16488 (15)	0.0835 (9)
H14A	0.074415	0.916950	0.127911	0.125*
H14B	0.063986	0.874317	0.200800	0.125*
H14C	0.178659	0.787515	0.153895	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0736 (4)	0.0280 (3)	0.0528 (3)	0.0014 (2)	0.0099 (3)	0.0010 (2)
N4	0.0777 (15)	0.0817 (16)	0.0569 (13)	−0.0218 (13)	0.0119 (11)	0.0108 (11)
Cl2	0.0689 (4)	0.0492 (3)	0.0361 (3)	−0.0039 (3)	0.0110 (2)	0.0080 (2)
C15	0.0680 (16)	0.0545 (14)	0.0426 (13)	−0.0060 (13)	0.0133 (12)	0.0068 (10)
O1	0.0657 (9)	0.0456 (8)	0.0344 (7)	0.0013 (7)	0.0114 (7)	−0.0095 (6)
O2	0.0859 (11)	0.0394 (8)	0.0386 (8)	0.0087 (8)	0.0157 (7)	−0.0052 (6)
N1	0.0703 (13)	0.0360 (11)	0.0695 (13)	−0.0061 (9)	0.0037 (10)	−0.0035 (9)
N2	0.0716 (13)	0.0603 (13)	0.0450 (11)	−0.0094 (10)	0.0131 (10)	0.0065 (9)
C1	0.0400 (11)	0.0353 (11)	0.0321 (10)	0.0026 (8)	0.0031 (8)	−0.0008 (8)
C2	0.0372 (11)	0.0293 (10)	0.0368 (10)	0.0017 (8)	0.0027 (8)	−0.0004 (8)
C3	0.0379 (10)	0.0329 (10)	0.0318 (9)	0.0032 (8)	0.0035 (8)	0.0026 (7)
C4	0.0435 (11)	0.0339 (10)	0.0339 (10)	0.0072 (9)	0.0050 (8)	−0.0010 (8)
C5	0.0428 (11)	0.0273 (10)	0.0368 (10)	0.0023 (8)	0.0034 (8)	0.0021 (8)
C6	0.0410 (11)	0.0345 (10)	0.0305 (10)	0.0008 (8)	0.0044 (8)	0.0041 (7)
C7	0.0434 (11)	0.0367 (12)	0.0386 (11)	0.0010 (9)	0.0042 (9)	−0.0008 (8)
C8	0.0451 (12)	0.0367 (11)	0.0383 (11)	0.0030 (9)	0.0040 (9)	−0.0015 (9)
N3	0.0581 (12)	0.0391 (10)	0.0515 (11)	0.0047 (9)	−0.0069 (9)	−0.0016 (8)
C9	0.0558 (14)	0.0520 (13)	0.0415 (12)	0.0047 (11)	0.0058 (10)	0.0030 (10)
C10	0.0563 (13)	0.0505 (13)	0.0323 (11)	0.0049 (11)	0.0050 (10)	−0.0034 (9)
C11	0.0571 (14)	0.0369 (11)	0.0399 (11)	0.0054 (10)	0.0063 (10)	0.0031 (8)
C12	0.0672 (15)	0.0619 (15)	0.0365 (12)	0.0043 (13)	0.0122 (11)	−0.0011 (10)
C13	0.0762 (17)	0.0543 (15)	0.0378 (12)	0.0129 (13)	−0.0043 (12)	−0.0101 (10)
C14	0.0752 (19)	0.075 (2)	0.096 (2)	−0.0159 (15)	−0.0167 (16)	−0.0124 (16)

Geometric parameters (Å, º)

Cl1—C5	1.7162 (19)	C5—C6	1.351 (2)
N4—C15	1.134 (3)	N3—C9	1.336 (3)
Cl2—C6	1.7143 (18)	N3—C13	1.339 (3)
C15—C11	1.444 (3)	N3—C14	1.481 (3)
O1—C1	1.242 (2)	C9—C10	1.363 (3)
O2—C4	1.241 (2)	C9—H9	0.9300
N1—C7	1.133 (2)	C10—C11	1.377 (3)
N2—C8	1.143 (2)	C10—H10	0.9300
C1—C2	1.447 (2)	C11—C12	1.383 (3)
C1—C6	1.465 (3)	C12—C13	1.353 (3)
C2—C3	1.386 (2)	C12—H12	0.9300
C2—C7	1.432 (3)	C13—H13	0.9300
C3—C8	1.433 (3)	C14—H14A	0.9600
C3—C4	1.449 (3)	C14—H14B	0.9600
C4—C5	1.460 (2)	C14—H14C	0.9600
N4—C15—C11	176.6 (3)	C13—N3—C14	119.1 (2)
O1—C1—C2	122.55 (17)	N3—C9—C10	120.6 (2)
O1—C1—C6	122.88 (17)	N3—C9—H9	119.7
C2—C1—C6	114.56 (16)	C10—C9—H9	119.7
C3—C2—C7	121.31 (17)	C9—C10—C11	119.26 (19)
C3—C2—C1	122.60 (17)	C9—C10—H10	120.4
C7—C2—C1	116.06 (16)	C11—C10—H10	120.4
C2—C3—C8	120.81 (17)	C10—C11—C12	119.2 (2)
C2—C3—C4	122.03 (16)	C10—C11—C15	121.42 (19)
C8—C3—C4	117.16 (16)	C12—C11—C15	119.31 (19)
O2—C4—C3	122.46 (17)	C13—C12—C11	119.2 (2)
O2—C4—C5	122.66 (18)	C13—C12—H12	120.4
C3—C4—C5	114.86 (16)	C11—C12—H12	120.4
C6—C5—C4	122.82 (17)	N3—C13—C12	120.9 (2)
C6—C5—Cl1	121.72 (14)	N3—C13—H13	119.6
C4—C5—Cl1	115.46 (13)	C12—C13—H13	119.6
C5—C6—C1	122.75 (17)	N3—C14—H14A	109.5
C5—C6—Cl2	121.87 (15)	N3—C14—H14B	109.5
C1—C6—Cl2	115.38 (13)	H14A—C14—H14B	109.5
N1—C7—C2	179.6 (2)	N3—C14—H14C	109.5
N2—C8—C3	179.0 (2)	H14A—C14—H14C	109.5
C9—N3—C13	120.8 (2)	H14B—C14—H14C	109.5
C9—N3—C14	120.0 (2)
O1—C1—C2—C3	−176.90 (18)	Cl1—C5—C6—C1	179.65 (14)
C6—C1—C2—C3	4.1 (3)	C4—C5—C6—Cl2	−179.06 (14)
O1—C1—C2—C7	5.3 (3)	Cl1—C5—C6—Cl2	0.4 (2)
C6—C1—C2—C7	−173.73 (16)	O1—C1—C6—C5	176.16 (19)
C7—C2—C3—C8	−0.8 (3)	C2—C1—C6—C5	−4.8 (3)
C1—C2—C3—C8	−178.44 (17)	O1—C1—C6—Cl2	−4.5 (3)
C7—C2—C3—C4	178.90 (17)	C2—C1—C6—Cl2	174.51 (13)
C1—C2—C3—C4	1.2 (3)	C13—N3—C9—C10	0.2 (3)
C2—C3—C4—O2	175.71 (18)	C14—N3—C9—C10	178.3 (2)
C8—C3—C4—O2	−4.6 (3)	N3—C9—C10—C11	−0.1 (3)
C2—C3—C4—C5	−5.7 (3)	C9—C10—C11—C12	0.4 (3)
C8—C3—C4—C5	173.93 (16)	C9—C10—C11—C15	−177.2 (2)
O2—C4—C5—C6	−176.39 (19)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—C6	5.1 (3)	C15—C11—C12—C13	176.9 (2)
O2—C4—C5—Cl1	4.1 (3)	C9—N3—C13—C12	−0.6 (3)
C3—C4—C5—Cl1	−174.41 (13)	C14—N3—C13—C12	−178.7 (2)
C4—C5—C6—C1	0.2 (3)	C11—C12—C13—N3	0.9 (3)

(test3_ddq_4cn)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.618 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8687 (6) Å	Cell parameters from 1546 reflections
b = 10.105 (2) Å	θ = 2.0–23.5°
c = 20.5426 (19) Å	µ = 0.47 mm^−1
β = 94.681 (7)°	T = 293 K
V = 1421.1 (4) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1558 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.364 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −8→8
Tmin = 0.360, Tmax = 0.450	k = −8→8
7420 measured reflections	l = −23→23

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0391P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
1558 reflections	Δρmax = 0.28 e Å^−3
209 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20423 (15)	0.11377 (18)	−0.00716 (5)	0.0440 (6)
N4	0.9885 (5)	1.2027 (5)	0.24780 (16)	0.0539 (18)
Cl2	0.11620 (14)	0.28082 (16)	0.11688 (5)	0.0418 (5)
C15	0.8390 (7)	1.1550 (6)	0.23521 (19)	0.0423 (19)
O1	0.1359 (4)	0.5662 (4)	0.09452 (13)	0.0407 (13)
O2	0.2899 (4)	0.2777 (4)	−0.11775 (13)	0.0453 (14)
N1	0.2994 (7)	0.8128 (7)	−0.00668 (18)	0.049 (2)
N2	0.4167 (5)	0.5980 (5)	−0.16687 (18)	0.0484 (19)
C1	0.1801 (6)	0.4993 (7)	0.04724 (18)	0.0309 (16)
C2	0.2475 (6)	0.5612 (7)	−0.01107 (18)	0.0315 (17)
C3	0.2877 (6)	0.4856 (7)	−0.06535 (18)	0.0307 (16)
C4	0.2638 (6)	0.3461 (7)	−0.0688 (2)	0.0332 (16)
C5	0.2125 (5)	0.2846 (7)	−0.00726 (18)	0.0284 (15)
C6	0.1743 (6)	0.3566 (7)	0.04548 (18)	0.0310 (16)
C7	0.2762 (7)	0.6997 (9)	−0.00885 (18)	0.031 (2)
C8	0.3590 (5)	0.5495 (6)	−0.1216 (2)	0.0329 (19)
N3	0.3207 (4)	0.9538 (5)	0.18291 (17)	0.0438 (17)
C9	0.3545 (6)	1.0012 (7)	0.2442 (2)	0.042 (2)
H9	0.261838	0.988349	0.274115	0.051*
C10	0.5202 (5)	1.0669 (6)	0.26252 (18)	0.0365 (18)
H10	0.543702	1.097098	0.305199	0.044*
C11	0.6557 (5)	1.0892 (6)	0.21732 (19)	0.038 (2)
C12	0.6175 (6)	1.0409 (7)	0.1545 (2)	0.044 (2)
H12	0.705698	1.055548	0.123244	0.053*
C13	0.4501 (6)	0.9718 (6)	0.1387 (2)	0.048 (2)
H13	0.425909	0.937043	0.096883	0.058*
C14	0.1423 (6)	0.8783 (8)	0.1642 (2)	0.069 (3)
H14A	0.064144	0.872863	0.200797	0.103*
H14B	0.176730	0.790699	0.151119	0.103*
H14C	0.069459	0.921818	0.128550	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0577 (7)	0.033 (2)	0.0426 (8)	0.0008 (8)	0.0091 (5)	0.0010 (6)
N4	0.060 (2)	0.057 (7)	0.046 (3)	−0.020 (3)	0.0120 (19)	0.004 (2)
Cl2	0.0536 (7)	0.0411 (18)	0.0315 (7)	−0.0026 (7)	0.0089 (5)	0.0066 (6)
C15	0.055 (3)	0.045 (7)	0.028 (3)	−0.003 (3)	0.010 (2)	0.004 (2)
O1	0.0512 (16)	0.042 (5)	0.0302 (19)	0.004 (2)	0.0090 (13)	−0.0083 (16)
O2	0.0666 (19)	0.037 (5)	0.034 (2)	0.006 (2)	0.0132 (14)	−0.0069 (16)
N1	0.061 (3)	0.036 (7)	0.051 (3)	−0.004 (4)	0.0042 (18)	0.000 (3)
N2	0.055 (2)	0.047 (7)	0.044 (3)	−0.012 (3)	0.0123 (18)	0.003 (2)
C1	0.030 (2)	0.036 (6)	0.026 (3)	0.001 (3)	0.0032 (17)	−0.003 (2)
C2	0.027 (2)	0.036 (6)	0.031 (3)	0.001 (3)	0.0008 (18)	−0.002 (2)
C3	0.031 (2)	0.033 (6)	0.030 (3)	0.005 (3)	0.0066 (17)	0.002 (2)
C4	0.034 (2)	0.036 (6)	0.030 (3)	0.014 (3)	0.0046 (18)	0.001 (2)
C5	0.031 (2)	0.017 (5)	0.037 (3)	−0.001 (3)	0.0029 (18)	0.001 (2)
C6	0.032 (2)	0.039 (5)	0.022 (2)	0.004 (3)	0.0045 (17)	0.002 (2)
C7	0.031 (2)	0.037 (7)	0.027 (3)	0.003 (5)	0.0051 (17)	0.002 (3)
C8	0.034 (2)	0.030 (7)	0.035 (3)	−0.005 (3)	0.0018 (19)	−0.005 (2)
N3	0.043 (2)	0.046 (6)	0.040 (2)	0.002 (2)	−0.0066 (17)	−0.004 (2)
C9	0.044 (2)	0.046 (7)	0.037 (3)	0.007 (3)	0.0051 (19)	0.000 (2)
C10	0.040 (2)	0.044 (7)	0.025 (3)	0.006 (3)	0.0011 (18)	0.000 (2)
C11	0.042 (2)	0.037 (7)	0.034 (3)	0.001 (3)	0.0047 (19)	0.007 (2)
C12	0.052 (2)	0.049 (7)	0.032 (3)	−0.003 (3)	0.009 (2)	−0.002 (2)
C13	0.062 (3)	0.050 (7)	0.033 (3)	0.009 (3)	0.002 (2)	−0.002 (2)
C14	0.071 (3)	0.049 (10)	0.084 (4)	−0.016 (4)	−0.008 (3)	−0.012 (3)

Geometric parameters (Å, º)

Cl1—C5	1.727 (7)	C5—C6	1.349 (6)
N4—C15	1.145 (5)	N3—C13	1.334 (5)
Cl2—C6	1.730 (5)	N3—C9	1.349 (5)
C15—C11	1.444 (6)	N3—C14	1.468 (6)
O1—C1	1.241 (5)	C9—C10	1.345 (6)
O2—C4	1.246 (6)	C9—H9	0.9300
N1—C7	1.155 (8)	C10—C11	1.386 (5)
N2—C8	1.150 (5)	C10—H10	0.9300
C1—C6	1.443 (8)	C11—C12	1.385 (6)
C1—C2	1.460 (6)	C12—C13	1.361 (6)
C2—C3	1.398 (7)	C12—H12	0.9300
C2—C7	1.413 (8)	C13—H13	0.9300
C3—C4	1.420 (8)	C14—H14A	0.9600
C3—C8	1.444 (6)	C14—H14B	0.9600
C4—C5	1.476 (6)	C14—H14C	0.9600
N4—C15—C11	176.8 (6)	C9—N3—C14	120.3 (4)
O1—C1—C6	123.8 (4)	C10—C9—N3	121.0 (4)
O1—C1—C2	121.5 (6)	C10—C9—H9	119.5
C6—C1—C2	114.7 (4)	N3—C9—H9	119.5
C3—C2—C7	122.0 (5)	C9—C10—C11	119.5 (4)
C3—C2—C1	121.1 (6)	C9—C10—H10	120.3
C7—C2—C1	116.8 (4)	C11—C10—H10	120.3
C2—C3—C4	123.5 (5)	C12—C11—C10	118.7 (4)
C2—C3—C8	119.7 (6)	C12—C11—C15	119.7 (4)
C4—C3—C8	116.7 (4)	C10—C11—C15	121.6 (4)
O2—C4—C3	124.5 (5)	C13—C12—C11	119.7 (4)
O2—C4—C5	121.2 (6)	C13—C12—H12	120.1
C3—C4—C5	114.2 (4)	C11—C12—H12	120.1
C6—C5—C4	122.4 (6)	N3—C13—C12	120.3 (4)
C6—C5—Cl1	122.0 (4)	N3—C13—H13	119.9
C4—C5—Cl1	115.6 (4)	C12—C13—H13	119.9
C5—C6—C1	123.6 (5)	N3—C14—H14A	109.5
C5—C6—Cl2	121.0 (5)	N3—C14—H14B	109.5
C1—C6—Cl2	115.4 (3)	H14A—C14—H14B	109.5
N1—C7—C2	179.6 (5)	N3—C14—H14C	109.5
N2—C8—C3	178.6 (6)	H14A—C14—H14C	109.5
C13—N3—C9	120.9 (4)	H14B—C14—H14C	109.5
C13—N3—C14	118.8 (4)
O1—C1—C2—C3	−176.8 (4)	Cl1—C5—C6—C1	179.9 (3)
C6—C1—C2—C3	4.6 (6)	C4—C5—C6—Cl2	−179.6 (3)
O1—C1—C2—C7	5.4 (6)	Cl1—C5—C6—Cl2	0.5 (5)
C6—C1—C2—C7	−173.3 (4)	O1—C1—C6—C5	176.4 (3)
C7—C2—C3—C4	178.9 (4)	C2—C1—C6—C5	−5.0 (6)
C1—C2—C3—C4	1.2 (7)	O1—C1—C6—Cl2	−4.2 (6)
C7—C2—C3—C8	−0.7 (6)	C2—C1—C6—Cl2	174.4 (2)
C1—C2—C3—C8	−178.4 (3)	C13—N3—C9—C10	−0.6 (8)
C2—C3—C4—O2	176.4 (4)	C14—N3—C9—C10	177.8 (6)
C8—C3—C4—O2	−4.0 (7)	N3—C9—C10—C11	1.8 (8)
C2—C3—C4—C5	−6.2 (6)	C9—C10—C11—C12	−1.1 (8)
C8—C3—C4—C5	173.3 (3)	C9—C10—C11—C15	−177.7 (6)
O2—C4—C5—C6	−176.8 (4)	C10—C11—C12—C13	−0.7 (8)
C3—C4—C5—C6	5.8 (6)	C15—C11—C12—C13	176.0 (6)
O2—C4—C5—Cl1	3.2 (5)	C9—N3—C13—C12	−1.2 (8)
C3—C4—C5—Cl1	−174.3 (3)	C14—N3—C13—C12	−179.7 (6)
C4—C5—C6—C1	−0.2 (6)	C11—C12—C13—N3	1.9 (8)

(test3_0.25GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.632 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8312 (4) Å	Cell parameters from 1555 reflections
b = 10.0839 (16) Å	θ = 2.0–22.5°
c = 20.5232 (15) Å	µ = 0.48 mm^−1
β = 94.635 (6)°	T = 293 K
V = 1409.1 (3) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1542 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	922 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.365 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −8→8
Tmin = 0.361, Tmax = 0.450	k = −8→8
7278 measured reflections	l = −23→23

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0326P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
1542 reflections	Δρmax = 0.21 e Å^−3
208 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20496 (16)	0.11322 (18)	−0.00723 (5)	0.0405 (5)
Cl2	0.11722 (15)	0.28077 (17)	0.11705 (5)	0.0392 (5)
O1	0.1366 (4)	0.5671 (4)	0.09439 (13)	0.0362 (13)
O2	0.2907 (4)	0.2775 (4)	−0.11802 (13)	0.0425 (15)
N1	0.2986 (7)	0.8138 (7)	−0.00673 (19)	0.047 (2)
N2	0.4175 (5)	0.5977 (6)	−0.16718 (19)	0.0455 (19)
N3	0.3199 (5)	0.9541 (5)	0.18265 (18)	0.0376 (16)
N4	0.9898 (6)	1.2036 (6)	0.24820 (17)	0.058 (2)
C1	0.1809 (6)	0.4994 (7)	0.0471 (2)	0.0287 (16)
C2	0.2483 (6)	0.5615 (7)	−0.01178 (19)	0.0258 (16)
C3	0.2895 (6)	0.4861 (7)	−0.0655 (2)	0.0268 (16)
C4	0.2639 (6)	0.3450 (7)	−0.0686 (2)	0.0311 (16)
C5	0.2130 (6)	0.2834 (7)	−0.00737 (19)	0.0259 (15)
C6	0.1743 (6)	0.3548 (7)	0.04544 (19)	0.0281 (15)
C7	0.2761 (7)	0.7011 (9)	−0.0093 (2)	0.0282 (19)
C8	0.3596 (5)	0.5494 (6)	−0.1218 (2)	0.0277 (18)
C9	0.3539 (6)	1.0006 (6)	0.2441 (2)	0.036 (2)
H9	0.261183	0.986666	0.274177	0.043*
C10	0.5202 (6)	1.0669 (6)	0.2625 (2)	0.0365 (19)
H10	0.543428	1.096976	0.305312	0.044*
C11	0.6562 (6)	1.0901 (6)	0.2176 (2)	0.037 (2)
C12	0.6193 (7)	1.0417 (7)	0.1546 (2)	0.043 (2)
H12	0.708829	1.055997	0.123484	0.052*
C13	0.4504 (6)	0.9729 (7)	0.1387 (2)	0.046 (2)
H13	0.426007	0.938711	0.096706	0.055*
C14	0.1404 (7)	0.8770 (7)	0.1641 (3)	0.066 (3)
H14A	0.061370	0.871993	0.200605	0.099*
H14B	0.067107	0.919641	0.128075	0.099*
H14C	0.175891	0.789080	0.151421	0.099*
C15	0.8396 (7)	1.1542 (7)	0.2353 (2)	0.040 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0550 (7)	0.026 (2)	0.0412 (9)	0.0006 (9)	0.0087 (5)	0.0010 (6)
Cl2	0.0526 (7)	0.0359 (19)	0.0301 (8)	−0.0039 (8)	0.0104 (5)	0.0073 (6)
O1	0.0502 (17)	0.031 (5)	0.028 (2)	0.002 (2)	0.0078 (14)	−0.0083 (16)
O2	0.063 (2)	0.037 (5)	0.028 (2)	0.009 (2)	0.0111 (15)	−0.0071 (17)
N1	0.058 (3)	0.036 (7)	0.048 (3)	−0.002 (4)	0.0051 (19)	−0.006 (3)
N2	0.051 (2)	0.047 (7)	0.041 (3)	−0.004 (3)	0.0134 (19)	0.001 (2)
N3	0.046 (2)	0.029 (6)	0.037 (3)	0.004 (2)	−0.0024 (18)	0.000 (2)
N4	0.059 (3)	0.075 (7)	0.040 (3)	−0.018 (3)	0.009 (2)	0.006 (2)
C1	0.029 (2)	0.033 (6)	0.023 (3)	0.005 (3)	−0.0018 (19)	0.001 (2)
C2	0.024 (2)	0.024 (6)	0.029 (3)	0.004 (3)	0.0039 (19)	0.002 (2)
C3	0.027 (2)	0.027 (6)	0.028 (3)	0.004 (3)	0.0095 (19)	0.000 (2)
C4	0.032 (2)	0.032 (6)	0.029 (3)	0.009 (3)	0.004 (2)	0.004 (2)
C5	0.035 (2)	0.012 (6)	0.031 (3)	−0.002 (3)	0.0043 (19)	0.002 (2)
C6	0.028 (2)	0.031 (5)	0.026 (3)	0.000 (3)	0.0042 (19)	0.003 (2)
C7	0.029 (3)	0.027 (7)	0.029 (3)	0.006 (5)	0.0052 (19)	−0.001 (3)
C8	0.031 (2)	0.018 (7)	0.035 (3)	−0.002 (3)	0.006 (2)	−0.004 (2)
C9	0.045 (3)	0.029 (7)	0.035 (3)	0.009 (3)	0.012 (2)	0.000 (2)
C10	0.038 (2)	0.046 (7)	0.025 (3)	0.003 (3)	0.002 (2)	0.002 (2)
C11	0.044 (2)	0.039 (7)	0.029 (3)	0.007 (3)	0.006 (2)	0.006 (2)
C12	0.052 (3)	0.045 (8)	0.034 (3)	−0.003 (3)	0.012 (2)	−0.002 (3)
C13	0.060 (3)	0.048 (7)	0.028 (3)	0.011 (3)	0.003 (2)	−0.005 (2)
C14	0.071 (3)	0.043 (10)	0.083 (5)	−0.014 (4)	−0.005 (3)	−0.010 (3)
C15	0.054 (3)	0.041 (7)	0.027 (3)	−0.002 (3)	0.009 (2)	0.005 (2)

Geometric parameters (Å, º)

Cl1—C5	1.717 (7)	C3—C8	1.437 (6)
Cl2—C6	1.721 (5)	C4—C5	1.468 (7)
O1—C1	1.244 (6)	C5—C6	1.345 (7)
O2—C4	1.248 (6)	C9—C10	1.346 (6)
N1—C7	1.147 (8)	C9—H9	0.9300
N2—C8	1.149 (5)	C10—C11	1.381 (5)
N3—C13	1.333 (5)	C10—H10	0.9300
N3—C9	1.348 (5)	C11—C12	1.386 (6)
N3—C14	1.476 (6)	C11—C15	1.430 (7)
N4—C15	1.152 (6)	C12—C13	1.364 (7)
C1—C6	1.460 (8)	C12—H12	0.9300
C1—C2	1.467 (7)	C13—H13	0.9300
C2—C3	1.386 (7)	C14—H14A	0.9600
C2—C7	1.421 (8)	C14—H14B	0.9600
C3—C4	1.434 (8)	C14—H14C	0.9600
C13—N3—C9	120.7 (4)	C10—C9—N3	120.9 (4)
C13—N3—C14	119.2 (4)	C10—C9—H9	119.5
C9—N3—C14	120.1 (4)	N3—C9—H9	119.5
O1—C1—C6	123.9 (5)	C9—C10—C11	119.6 (4)
O1—C1—C2	121.4 (6)	C9—C10—H10	120.2
C6—C1—C2	114.7 (4)	C11—C10—H10	120.2
C3—C2—C7	122.5 (5)	C10—C11—C12	118.8 (5)
C3—C2—C1	121.2 (6)	C10—C11—C15	122.0 (4)
C7—C2—C1	116.3 (4)	C12—C11—C15	119.0 (4)
C2—C3—C4	123.2 (5)	C13—C12—C11	119.3 (4)
C2—C3—C8	119.9 (6)	C13—C12—H12	120.4
C4—C3—C8	116.9 (4)	C11—C12—H12	120.4
O2—C4—C3	123.5 (5)	N3—C13—C12	120.7 (4)
O2—C4—C5	121.7 (6)	N3—C13—H13	119.7
C3—C4—C5	114.7 (4)	C12—C13—H13	119.7
C6—C5—C4	122.6 (6)	N3—C14—H14A	109.5
C6—C5—Cl1	121.7 (4)	N3—C14—H14B	109.5
C4—C5—Cl1	115.8 (4)	H14A—C14—H14B	109.5
C5—C6—C1	123.1 (5)	N3—C14—H14C	109.5
C5—C6—Cl2	121.9 (5)	H14A—C14—H14C	109.5
C1—C6—Cl2	115.0 (3)	H14B—C14—H14C	109.5
N1—C7—C2	179.5 (5)	N4—C15—C11	178.1 (6)
N2—C8—C3	178.6 (6)
O1—C1—C2—C3	−177.2 (4)	Cl1—C5—C6—C1	179.7 (3)
C6—C1—C2—C3	3.8 (6)	C4—C5—C6—Cl2	−179.4 (3)
O1—C1—C2—C7	5.3 (6)	Cl1—C5—C6—Cl2	0.9 (5)
C6—C1—C2—C7	−173.7 (4)	O1—C1—C6—C5	176.5 (4)
C7—C2—C3—C4	179.5 (4)	C2—C1—C6—C5	−4.6 (6)
C1—C2—C3—C4	2.1 (7)	O1—C1—C6—Cl2	−4.6 (6)
C7—C2—C3—C8	−1.2 (7)	C2—C1—C6—Cl2	174.3 (3)
C1—C2—C3—C8	−178.5 (4)	C13—N3—C9—C10	−0.1 (8)
C2—C3—C4—O2	176.1 (4)	C14—N3—C9—C10	177.6 (6)
C8—C3—C4—O2	−3.3 (7)	N3—C9—C10—C11	1.3 (8)
C2—C3—C4—C5	−7.1 (7)	C9—C10—C11—C12	−1.3 (8)
C8—C3—C4—C5	173.6 (3)	C9—C10—C11—C15	−176.8 (6)
O2—C4—C5—C6	−176.7 (4)	C10—C11—C12—C13	0.1 (8)
C3—C4—C5—C6	6.3 (6)	C15—C11—C12—C13	175.7 (6)
O2—C4—C5—Cl1	3.1 (6)	C9—N3—C13—C12	−1.2 (8)
C3—C4—C5—Cl1	−173.9 (3)	C14—N3—C13—C12	−178.9 (6)
C4—C5—C6—C1	−0.6 (7)	C11—C12—C13—N3	1.2 (9)

(test3_0.49GPa)

Crystal data

C15H7Cl2N4O2	F(000) = 700
Mr = 346.15	Dx = 1.664 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7445 (3) Å	Cell parameters from 1864 reflections
b = 10.0486 (12) Å	θ = 2.0–25.4°
c = 20.4539 (11) Å	µ = 0.49 mm^−1
β = 94.589 (4)°	T = 293 K
V = 1381.77 (19) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1500 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	995 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.368 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −8→8
Tmin = 0.364, Tmax = 0.450	k = −8→8
7093 measured reflections	l = −23→23

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 0.2564P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1500 reflections	Δρmax = 0.29 e Å^−3
209 parameters	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20679 (15)	0.11222 (17)	−0.00714 (5)	0.0355 (5)
Cl2	0.11879 (15)	0.28046 (16)	0.11746 (5)	0.0345 (5)
O1	0.1374 (4)	0.5672 (4)	0.09451 (13)	0.0308 (12)
O2	0.2924 (4)	0.2769 (4)	−0.11835 (13)	0.0350 (13)
N1	0.2986 (7)	0.8156 (7)	−0.00721 (18)	0.0415 (18)
N2	0.4176 (5)	0.5979 (5)	−0.16858 (18)	0.0379 (17)
N3	0.3175 (5)	0.9551 (5)	0.18243 (17)	0.0329 (15)
N4	0.9944 (6)	1.2060 (6)	0.24859 (17)	0.0495 (18)
C1	0.1831 (5)	0.4984 (7)	0.04660 (19)	0.0234 (15)
C2	0.2485 (5)	0.5624 (7)	−0.01190 (19)	0.0246 (15)
C3	0.2900 (5)	0.4855 (7)	−0.06599 (18)	0.0226 (15)
C4	0.2666 (6)	0.3443 (7)	−0.0684 (2)	0.0274 (16)
C5	0.2150 (5)	0.2822 (7)	−0.00754 (18)	0.0216 (14)
C6	0.1751 (6)	0.3538 (6)	0.04551 (19)	0.0231 (14)
C7	0.2761 (7)	0.7021 (9)	−0.00957 (18)	0.0231 (17)
C8	0.3599 (5)	0.5504 (6)	−0.1228 (2)	0.0241 (17)
C9	0.3509 (6)	1.0004 (6)	0.2437 (2)	0.0332 (19)
H9	0.256993	0.985238	0.273762	0.040*
C10	0.5195 (5)	1.0682 (6)	0.26280 (19)	0.0315 (18)
H10	0.541921	1.098961	0.305634	0.038*
C11	0.6574 (6)	1.0908 (6)	0.2177 (2)	0.0327 (18)
C12	0.6206 (6)	1.0421 (7)	0.1544 (2)	0.0383 (19)
H12	0.712226	1.055871	0.123472	0.046*
C13	0.4507 (6)	0.9746 (6)	0.1381 (2)	0.0390 (18)
H13	0.425903	0.941340	0.095820	0.047*
C14	0.1374 (6)	0.8761 (8)	0.1629 (2)	0.057 (2)
H14A	0.175765	0.789216	0.148995	0.086*
H14B	0.061790	0.919936	0.127369	0.086*
H14C	0.057754	0.867902	0.199505	0.086*
C15	0.8418 (7)	1.1565 (6)	0.23604 (19)	0.0362 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0473 (6)	0.0218 (18)	0.0378 (9)	0.0000 (8)	0.0068 (5)	0.0008 (5)
Cl2	0.0470 (6)	0.0314 (17)	0.0262 (7)	−0.0020 (7)	0.0090 (5)	0.0065 (5)
O1	0.0421 (15)	0.023 (4)	0.0280 (19)	0.0008 (19)	0.0081 (13)	−0.0067 (15)
O2	0.0546 (18)	0.023 (5)	0.029 (2)	0.006 (2)	0.0084 (13)	−0.0054 (15)
N1	0.047 (2)	0.028 (6)	0.049 (3)	−0.008 (4)	0.0061 (17)	−0.002 (3)
N2	0.046 (2)	0.031 (6)	0.038 (3)	−0.003 (3)	0.0111 (17)	0.000 (2)
N3	0.0379 (19)	0.025 (5)	0.034 (2)	0.003 (2)	−0.0045 (16)	−0.0011 (18)
N4	0.053 (2)	0.057 (7)	0.039 (3)	−0.013 (3)	0.0094 (19)	0.004 (2)
C1	0.022 (2)	0.025 (5)	0.024 (3)	0.000 (3)	−0.0014 (17)	0.0014 (19)
C2	0.022 (2)	0.024 (5)	0.028 (3)	0.004 (3)	0.0035 (17)	0.002 (2)
C3	0.022 (2)	0.021 (5)	0.025 (3)	0.006 (3)	0.0035 (16)	0.000 (2)
C4	0.027 (2)	0.027 (5)	0.029 (3)	0.004 (3)	0.0053 (18)	0.001 (2)
C5	0.0246 (19)	0.007 (5)	0.033 (3)	−0.003 (3)	0.0038 (17)	0.002 (2)
C6	0.025 (2)	0.020 (5)	0.024 (3)	0.003 (3)	0.0048 (17)	0.0024 (19)
C7	0.024 (2)	0.020 (6)	0.025 (3)	0.001 (4)	0.0018 (16)	0.001 (2)
C8	0.029 (2)	0.016 (6)	0.028 (3)	0.000 (3)	0.0043 (18)	−0.002 (2)
C9	0.040 (2)	0.030 (7)	0.031 (3)	0.009 (3)	0.0056 (19)	0.002 (2)
C10	0.034 (2)	0.039 (7)	0.021 (3)	0.002 (3)	0.0014 (17)	0.000 (2)
C11	0.035 (2)	0.035 (7)	0.027 (3)	0.003 (3)	0.0032 (18)	0.005 (2)
C12	0.042 (2)	0.044 (7)	0.030 (3)	0.003 (3)	0.009 (2)	−0.002 (2)
C13	0.051 (3)	0.039 (7)	0.026 (3)	0.009 (3)	−0.002 (2)	−0.002 (2)
C14	0.052 (3)	0.044 (9)	0.073 (4)	−0.008 (3)	−0.013 (2)	−0.005 (3)
C15	0.051 (3)	0.032 (7)	0.027 (3)	−0.007 (3)	0.011 (2)	0.006 (2)

Geometric parameters (Å, º)

Cl1—C5	1.709 (6)	C3—C8	1.444 (6)
Cl2—C6	1.716 (5)	C4—C5	1.459 (6)
O1—C1	1.257 (5)	C5—C6	1.347 (7)
O2—C4	1.250 (6)	C9—C10	1.356 (6)
N1—C7	1.151 (8)	C9—H9	0.9300
N2—C8	1.147 (5)	C10—C11	1.379 (5)
N3—C9	1.335 (5)	C10—H10	0.9300
N3—C13	1.341 (5)	C11—C12	1.388 (6)
N3—C14	1.479 (6)	C11—C15	1.431 (7)
N4—C15	1.153 (5)	C12—C13	1.350 (6)
C1—C6	1.454 (8)	C12—H12	0.9300
C1—C2	1.458 (6)	C13—H13	0.9300
C2—C3	1.396 (7)	C14—H14A	0.9600
C2—C7	1.417 (8)	C14—H14B	0.9600
C3—C4	1.428 (8)	C14—H14C	0.9600
C9—N3—C13	120.8 (4)	N3—C9—C10	121.1 (4)
C9—N3—C14	120.7 (4)	N3—C9—H9	119.5
C13—N3—C14	118.4 (4)	C10—C9—H9	119.5
O1—C1—C6	123.4 (4)	C9—C10—C11	119.0 (4)
O1—C1—C2	120.4 (6)	C9—C10—H10	120.5
C6—C1—C2	116.2 (4)	C11—C10—H10	120.5
C3—C2—C7	122.8 (4)	C10—C11—C12	119.1 (4)
C3—C2—C1	120.0 (6)	C10—C11—C15	121.3 (4)
C7—C2—C1	117.2 (4)	C12—C11—C15	119.6 (4)
C2—C3—C4	123.3 (4)	C13—C12—C11	119.5 (4)
C2—C3—C8	119.1 (6)	C13—C12—H12	120.2
C4—C3—C8	117.6 (4)	C11—C12—H12	120.2
O2—C4—C3	123.0 (4)	N3—C13—C12	120.5 (4)
O2—C4—C5	121.5 (6)	N3—C13—H13	119.7
C3—C4—C5	115.4 (4)	C12—C13—H13	119.7
C6—C5—C4	122.3 (6)	N3—C14—H14A	109.5
C6—C5—Cl1	121.4 (4)	N3—C14—H14B	109.5
C4—C5—Cl1	116.2 (4)	H14A—C14—H14B	109.5
C5—C6—C1	122.5 (4)	N3—C14—H14C	109.5
C5—C6—Cl2	122.2 (5)	H14A—C14—H14C	109.5
C1—C6—Cl2	115.3 (3)	H14B—C14—H14C	109.5
N1—C7—C2	179.5 (4)	N4—C15—C11	176.8 (5)
N2—C8—C3	177.7 (6)
O1—C1—C2—C3	−177.0 (4)	Cl1—C5—C6—C1	179.4 (3)
C6—C1—C2—C3	3.1 (5)	C4—C5—C6—Cl2	−178.8 (3)
O1—C1—C2—C7	5.9 (5)	Cl1—C5—C6—Cl2	1.4 (5)
C6—C1—C2—C7	−174.0 (4)	O1—C1—C6—C5	176.6 (3)
C7—C2—C3—C4	178.7 (4)	C2—C1—C6—C5	−3.5 (6)
C1—C2—C3—C4	1.8 (6)	O1—C1—C6—Cl2	−5.3 (5)
C7—C2—C3—C8	−1.3 (6)	C2—C1—C6—Cl2	174.5 (3)
C1—C2—C3—C8	−178.3 (3)	C13—N3—C9—C10	0.5 (8)
C2—C3—C4—O2	175.6 (4)	C14—N3—C9—C10	177.2 (6)
C8—C3—C4—O2	−4.4 (6)	N3—C9—C10—C11	0.3 (8)
C2—C3—C4—C5	−6.0 (6)	C9—C10—C11—C12	−0.8 (8)
C8—C3—C4—C5	174.1 (3)	C9—C10—C11—C15	−177.2 (6)
O2—C4—C5—C6	−176.0 (4)	C10—C11—C12—C13	0.4 (8)
C3—C4—C5—C6	5.5 (6)	C15—C11—C12—C13	176.9 (6)
O2—C4—C5—Cl1	3.8 (5)	C9—N3—C13—C12	−0.9 (8)
C3—C4—C5—Cl1	−174.7 (3)	C14—N3—C13—C12	−177.7 (6)
C4—C5—C6—C1	−0.9 (6)	C11—C12—C13—N3	0.4 (8)

(test3_0.86GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.710 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.6277 (4) Å	Cell parameters from 1833 reflections
b = 10.0050 (17) Å	θ = 2.0–26.4°
c = 20.3418 (16) Å	µ = 0.50 mm^−1
β = 94.609 (5)°	T = 293 K
V = 1344.5 (3) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1457 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.369 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.364, Tmax = 0.450	k = −8→8
6881 measured reflections	l = −23→23

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 1.4732P] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.002
1457 reflections	Δρmax = 0.27 e Å^−3
209 parameters	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.20949 (18)	0.11052 (19)	−0.00704 (6)	0.0330 (6)
Cl2	0.12077 (17)	0.28017 (18)	0.11832 (5)	0.0326 (6)
O1	0.1399 (4)	0.5688 (4)	0.09474 (15)	0.0304 (14)
O2	0.2954 (5)	0.2756 (5)	−0.11898 (15)	0.0346 (15)
N1	0.2959 (7)	0.8166 (8)	−0.0078 (2)	0.0377 (19)
N2	0.4178 (6)	0.5986 (6)	−0.1704 (2)	0.0375 (19)
N3	0.3154 (5)	0.9561 (6)	0.18186 (19)	0.0324 (16)
N4	1.0016 (7)	1.2095 (7)	0.2502 (2)	0.048 (2)
C1	0.1855 (6)	0.4984 (8)	0.0472 (2)	0.0236 (16)
C2	0.2496 (6)	0.5617 (8)	−0.0127 (2)	0.0248 (16)
C3	0.2922 (7)	0.4862 (8)	−0.0670 (2)	0.0226 (16)
C4	0.2693 (7)	0.3445 (8)	−0.0692 (2)	0.0252 (16)
C5	0.2185 (6)	0.2808 (7)	−0.0074 (2)	0.0209 (15)
C6	0.1773 (6)	0.3535 (7)	0.0459 (2)	0.0229 (15)
C7	0.2769 (8)	0.7020 (10)	−0.0106 (2)	0.0229 (18)
C8	0.3600 (6)	0.5507 (7)	−0.1244 (2)	0.0262 (19)
C9	0.3471 (7)	0.9996 (7)	0.2437 (2)	0.032 (2)
H9	0.252251	0.982063	0.273831	0.038*
C10	0.5175 (7)	1.0697 (7)	0.2629 (2)	0.033 (2)
H10	0.538829	1.101048	0.305912	0.040*
C11	0.6592 (7)	1.0939 (7)	0.2178 (2)	0.031 (2)
C12	0.6233 (7)	1.0460 (8)	0.1542 (2)	0.037 (2)
H12	0.716994	1.060206	0.123307	0.045*
C13	0.4506 (7)	0.9781 (8)	0.1376 (2)	0.039 (2)
H13	0.425231	0.946261	0.094757	0.047*
C14	0.1322 (8)	0.8774 (9)	0.1614 (3)	0.045 (2)
H14A	0.171221	0.790284	0.147202	0.068*
H14B	0.056244	0.922097	0.125705	0.068*
H14C	0.050192	0.868652	0.197965	0.068*
C15	0.8476 (8)	1.1602 (7)	0.2372 (2)	0.0295 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0443 (7)	0.022 (2)	0.0335 (9)	0.0000 (8)	0.0078 (5)	0.0005 (6)
Cl2	0.0444 (7)	0.0300 (19)	0.0246 (8)	−0.0025 (8)	0.0091 (5)	0.0059 (6)
O1	0.0391 (18)	0.027 (5)	0.026 (2)	0.002 (2)	0.0086 (14)	−0.0090 (17)
O2	0.053 (2)	0.028 (5)	0.024 (2)	0.006 (2)	0.0088 (15)	−0.0037 (16)
N1	0.044 (3)	0.030 (6)	0.040 (3)	0.004 (4)	0.0087 (19)	−0.002 (3)
N2	0.044 (2)	0.038 (7)	0.031 (3)	−0.004 (3)	0.0095 (19)	0.001 (2)
N3	0.034 (2)	0.030 (6)	0.032 (3)	0.005 (2)	−0.0023 (17)	−0.002 (2)
N4	0.052 (3)	0.057 (7)	0.036 (3)	−0.012 (3)	0.007 (2)	0.004 (2)
C1	0.020 (2)	0.027 (6)	0.024 (3)	0.001 (3)	0.0042 (19)	0.000 (2)
C2	0.025 (2)	0.028 (6)	0.023 (3)	0.007 (3)	0.0049 (19)	0.002 (2)
C3	0.024 (2)	0.021 (6)	0.023 (3)	0.000 (3)	0.0048 (19)	0.002 (2)
C4	0.027 (2)	0.028 (6)	0.021 (3)	0.003 (3)	0.0055 (19)	0.000 (2)
C5	0.020 (2)	0.016 (6)	0.026 (3)	−0.001 (3)	−0.0004 (18)	0.004 (2)
C6	0.023 (2)	0.024 (5)	0.022 (3)	0.000 (3)	0.0024 (18)	0.000 (2)
C7	0.025 (3)	0.022 (6)	0.023 (3)	0.013 (4)	0.0050 (18)	0.003 (3)
C8	0.030 (2)	0.023 (7)	0.026 (3)	−0.001 (3)	0.006 (2)	−0.003 (2)
C9	0.038 (3)	0.032 (8)	0.026 (3)	0.004 (3)	0.006 (2)	−0.001 (2)
C10	0.032 (2)	0.044 (7)	0.023 (3)	0.003 (3)	0.004 (2)	0.001 (2)
C11	0.036 (2)	0.029 (7)	0.027 (3)	0.005 (3)	0.006 (2)	0.001 (2)
C12	0.040 (3)	0.047 (8)	0.025 (3)	0.006 (3)	0.008 (2)	0.003 (3)
C13	0.047 (3)	0.046 (8)	0.025 (3)	0.008 (3)	0.001 (2)	−0.002 (2)
C14	0.051 (3)	0.017 (9)	0.065 (5)	−0.006 (3)	−0.010 (3)	−0.005 (3)
C15	0.044 (3)	0.021 (7)	0.025 (3)	−0.001 (3)	0.010 (2)	0.008 (2)

Geometric parameters (Å, º)

Cl1—C5	1.705 (7)	C3—C8	1.437 (7)
Cl2—C6	1.714 (5)	C4—C5	1.473 (7)
O1—C1	1.252 (6)	C5—C6	1.351 (8)
O2—C4	1.249 (6)	C9—C10	1.360 (7)
N1—C7	1.155 (8)	C9—H9	0.9300
N2—C8	1.145 (6)	C10—C11	1.385 (6)
N3—C9	1.331 (6)	C10—H10	0.9300
N3—C13	1.339 (6)	C11—C12	1.382 (7)
N3—C14	1.479 (7)	C11—C15	1.441 (8)
N4—C15	1.145 (6)	C12—C13	1.350 (8)
C1—C6	1.451 (9)	C12—H12	0.9300
C1—C2	1.467 (7)	C13—H13	0.9300
C2—C3	1.386 (8)	C14—H14A	0.9600
C2—C7	1.415 (10)	C14—H14B	0.9600
C3—C4	1.426 (9)	C14—H14C	0.9600
C9—N3—C13	121.2 (5)	N3—C9—C10	120.3 (4)
C9—N3—C14	120.3 (4)	N3—C9—H9	119.8
C13—N3—C14	118.5 (4)	C10—C9—H9	119.8
O1—C1—C6	124.5 (5)	C9—C10—C11	119.4 (5)
O1—C1—C2	120.2 (7)	C9—C10—H10	120.3
C6—C1—C2	115.4 (5)	C11—C10—H10	120.3
C3—C2—C7	122.1 (5)	C12—C11—C10	118.9 (5)
C3—C2—C1	121.2 (7)	C12—C11—C15	119.8 (4)
C7—C2—C1	116.6 (5)	C10—C11—C15	121.2 (4)
C2—C3—C4	122.6 (5)	C13—C12—C11	119.2 (4)
C2—C3—C8	119.9 (7)	C13—C12—H12	120.4
C4—C3—C8	117.5 (5)	C11—C12—H12	120.4
O2—C4—C3	123.5 (5)	N3—C13—C12	120.9 (5)
O2—C4—C5	120.6 (7)	N3—C13—H13	119.6
C3—C4—C5	115.8 (5)	C12—C13—H13	119.6
C6—C5—C4	121.8 (7)	N3—C14—H14A	109.5
C6—C5—Cl1	121.7 (4)	N3—C14—H14B	109.5
C4—C5—Cl1	116.5 (4)	H14A—C14—H14B	109.5
C5—C6—C1	122.9 (5)	N3—C14—H14C	109.5
C5—C6—Cl2	122.1 (6)	H14A—C14—H14C	109.5
C1—C6—Cl2	115.0 (4)	H14B—C14—H14C	109.5
N1—C7—C2	178.4 (5)	N4—C15—C11	176.6 (6)
N2—C8—C3	177.8 (7)
O1—C1—C2—C3	−177.1 (4)	Cl1—C5—C6—C1	179.4 (3)
C6—C1—C2—C3	2.0 (6)	C4—C5—C6—Cl2	−179.3 (3)
O1—C1—C2—C7	6.5 (6)	Cl1—C5—C6—Cl2	2.0 (6)
C6—C1—C2—C7	−174.4 (4)	O1—C1—C6—C5	176.8 (4)
C7—C2—C3—C4	178.6 (4)	C2—C1—C6—C5	−2.3 (7)
C1—C2—C3—C4	2.5 (7)	O1—C1—C6—Cl2	−5.6 (6)
C7—C2—C3—C8	−2.1 (7)	C2—C1—C6—Cl2	175.3 (3)
C1—C2—C3—C8	−178.3 (4)	C13—N3—C9—C10	1.0 (9)
C2—C3—C4—O2	175.6 (4)	C14—N3—C9—C10	178.6 (6)
C8—C3—C4—O2	−3.6 (7)	N3—C9—C10—C11	−0.8 (10)
C2—C3—C4—C5	−6.4 (7)	C9—C10—C11—C12	0.0 (9)
C8—C3—C4—C5	174.4 (4)	C9—C10—C11—C15	−176.0 (6)
O2—C4—C5—C6	−175.9 (4)	C10—C11—C12—C13	0.7 (9)
C3—C4—C5—C6	6.1 (6)	C15—C11—C12—C13	176.7 (7)
O2—C4—C5—Cl1	2.9 (6)	C9—N3—C13—C12	−0.4 (10)
C3—C4—C5—Cl1	−175.1 (3)	C14—N3—C13—C12	−178.0 (7)
C4—C5—C6—C1	−1.8 (7)	C11—C12—C13—N3	−0.5 (10)

(test3_1.42GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.760 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.5155 (3) Å	Cell parameters from 1909 reflections
b = 9.9444 (12) Å	θ = 2.0–26.6°
c = 20.2293 (11) Å	µ = 0.51 mm^−1
β = 94.662 (4)°	T = 293 K
V = 1306.37 (18) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1418 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	973 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.362 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.357, Tmax = 0.450	k = −8→8
6645 measured reflections	l = −22→23

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0478P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1418 reflections	Δρmax = 0.22 e Å^−3
209 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.21184 (14)	0.10945 (16)	−0.00673 (5)	0.0289 (5)
Cl2	0.12333 (14)	0.27986 (15)	0.11911 (4)	0.0289 (5)
O1	0.1412 (4)	0.5700 (4)	0.09518 (12)	0.0277 (12)
O2	0.2992 (4)	0.2740 (4)	−0.11938 (12)	0.0308 (13)
N1	0.2944 (6)	0.8189 (7)	−0.00801 (16)	0.0341 (17)
N2	0.4162 (5)	0.6004 (5)	−0.17266 (17)	0.0304 (16)
N3	0.3138 (4)	0.9577 (5)	0.18052 (15)	0.0276 (14)
N4	1.0101 (5)	1.2122 (5)	0.25165 (15)	0.0387 (16)
C1	0.1869 (5)	0.4986 (7)	0.04709 (18)	0.0204 (15)
C2	0.2515 (5)	0.5635 (7)	−0.01293 (18)	0.0217 (15)
C3	0.2942 (5)	0.4866 (6)	−0.06753 (18)	0.0189 (14)
C4	0.2722 (5)	0.3437 (7)	−0.06975 (19)	0.0216 (15)
C5	0.2196 (5)	0.2812 (7)	−0.00702 (17)	0.0190 (14)
C6	0.1812 (6)	0.3539 (6)	0.04593 (18)	0.0218 (14)
C7	0.2756 (6)	0.7041 (9)	−0.01089 (18)	0.0214 (17)
C8	0.3610 (5)	0.5514 (6)	−0.1256 (2)	0.0227 (17)
C9	0.3451 (6)	1.0022 (6)	0.24310 (19)	0.0269 (17)
H9	0.247038	0.985079	0.272963	0.032*
C10	0.5176 (5)	1.0715 (5)	0.26343 (18)	0.0249 (16)
H10	0.538978	1.102101	0.306892	0.030*
C11	0.6614 (5)	1.0960 (6)	0.21826 (19)	0.0238 (17)
C12	0.6281 (6)	1.0489 (6)	0.15377 (19)	0.0327 (18)
H12	0.724054	1.064546	0.123032	0.039*
C13	0.4526 (6)	0.9797 (6)	0.13644 (19)	0.0328 (17)
H13	0.428441	0.947115	0.093421	0.039*
C14	0.1280 (6)	0.8776 (7)	0.1596 (2)	0.046 (2)
H14A	0.045250	0.867195	0.196401	0.069*
H14B	0.168823	0.790662	0.144714	0.069*
H14C	0.049632	0.923028	0.124058	0.069*
C15	0.8530 (7)	1.1629 (6)	0.23809 (18)	0.0259 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0373 (6)	0.0203 (18)	0.0297 (8)	0.0005 (7)	0.0059 (4)	0.0003 (5)
Cl2	0.0367 (6)	0.0283 (17)	0.0224 (7)	−0.0033 (6)	0.0067 (4)	0.0057 (5)
O1	0.0388 (15)	0.022 (4)	0.0235 (18)	0.0025 (18)	0.0072 (12)	−0.0095 (14)
O2	0.0478 (17)	0.023 (5)	0.0231 (19)	0.0055 (18)	0.0089 (13)	−0.0049 (14)
N1	0.035 (2)	0.030 (6)	0.037 (3)	−0.005 (3)	0.0024 (15)	−0.001 (2)
N2	0.0363 (19)	0.028 (6)	0.028 (2)	−0.003 (2)	0.0062 (15)	0.0023 (18)
N3	0.0322 (18)	0.022 (5)	0.027 (2)	0.003 (2)	−0.0052 (14)	−0.0026 (17)
N4	0.044 (2)	0.039 (6)	0.034 (3)	−0.010 (3)	0.0073 (18)	0.0003 (19)
C1	0.0181 (18)	0.024 (5)	0.020 (2)	0.003 (3)	0.0054 (16)	0.0023 (19)
C2	0.018 (2)	0.025 (5)	0.022 (2)	0.003 (3)	0.0024 (16)	0.001 (2)
C3	0.0197 (19)	0.015 (5)	0.022 (3)	−0.001 (3)	0.0025 (16)	0.0019 (19)
C4	0.0182 (19)	0.023 (5)	0.024 (3)	0.004 (3)	0.0014 (16)	−0.001 (2)
C5	0.0216 (19)	0.011 (5)	0.024 (3)	0.000 (2)	0.0012 (16)	0.0017 (18)
C6	0.022 (2)	0.025 (5)	0.019 (2)	0.003 (3)	0.0039 (16)	0.0048 (18)
C7	0.020 (2)	0.022 (6)	0.023 (3)	−0.003 (4)	0.0027 (16)	0.002 (2)
C8	0.0207 (19)	0.020 (6)	0.027 (3)	−0.003 (2)	0.0023 (17)	−0.003 (2)
C9	0.030 (2)	0.025 (7)	0.026 (3)	0.003 (2)	0.0080 (17)	−0.001 (2)
C10	0.029 (2)	0.025 (6)	0.020 (3)	0.001 (2)	0.0014 (16)	−0.0005 (18)
C11	0.028 (2)	0.015 (6)	0.028 (3)	0.003 (2)	0.0046 (17)	0.0038 (19)
C12	0.039 (2)	0.041 (7)	0.019 (3)	0.001 (3)	0.0105 (18)	0.000 (2)
C13	0.043 (2)	0.033 (6)	0.022 (3)	0.010 (3)	0.0022 (18)	0.000 (2)
C14	0.042 (3)	0.043 (8)	0.051 (4)	−0.015 (3)	−0.014 (2)	−0.002 (3)
C15	0.040 (2)	0.015 (6)	0.024 (3)	0.001 (3)	0.0093 (19)	0.0049 (19)

Geometric parameters (Å, º)

Cl1—C5	1.709 (6)	C3—C8	1.438 (6)
Cl2—C6	1.722 (4)	C4—C5	1.478 (6)
O1—C1	1.259 (5)	C5—C6	1.333 (6)
O2—C4	1.244 (5)	C9—C10	1.354 (6)
N1—C7	1.149 (7)	C9—H9	0.9300
N2—C8	1.152 (5)	C10—C11	1.382 (5)
N3—C13	1.339 (5)	C10—H10	0.9300
N3—C9	1.341 (5)	C11—C12	1.386 (6)
N3—C14	1.482 (6)	C11—C15	1.442 (6)
N4—C15	1.148 (5)	C12—C13	1.356 (6)
C1—C6	1.439 (8)	C12—H12	0.9300
C1—C2	1.467 (6)	C13—H13	0.9300
C2—C3	1.390 (7)	C14—H14A	0.9600
C2—C7	1.407 (8)	C14—H14B	0.9600
C3—C4	1.429 (8)	C14—H14C	0.9600
C13—N3—C9	121.0 (4)	N3—C9—C10	120.9 (3)
C13—N3—C14	118.5 (3)	N3—C9—H9	119.5
C9—N3—C14	120.4 (3)	C10—C9—H9	119.5
O1—C1—C6	124.6 (4)	C9—C10—C11	118.6 (4)
O1—C1—C2	119.6 (6)	C9—C10—H10	120.7
C6—C1—C2	115.8 (4)	C11—C10—H10	120.7
C3—C2—C7	122.7 (4)	C10—C11—C12	120.0 (4)
C3—C2—C1	120.4 (6)	C10—C11—C15	121.0 (4)
C7—C2—C1	116.9 (4)	C12—C11—C15	118.9 (3)
C2—C3—C4	123.1 (4)	C13—C12—C11	118.6 (4)
C2—C3—C8	119.8 (6)	C13—C12—H12	120.7
C4—C3—C8	117.1 (4)	C11—C12—H12	120.7
O2—C4—C3	124.0 (4)	N3—C13—C12	120.8 (4)
O2—C4—C5	121.1 (6)	N3—C13—H13	119.6
C3—C4—C5	114.9 (4)	C12—C13—H13	119.6
C6—C5—C4	122.2 (6)	N3—C14—H14A	109.5
C6—C5—Cl1	122.1 (4)	N3—C14—H14B	109.5
C4—C5—Cl1	115.6 (4)	H14A—C14—H14B	109.5
C5—C6—C1	123.3 (4)	N3—C14—H14C	109.5
C5—C6—Cl2	121.8 (5)	H14A—C14—H14C	109.5
C1—C6—Cl2	114.9 (3)	H14B—C14—H14C	109.5
N1—C7—C2	178.7 (4)	N4—C15—C11	176.6 (5)
N2—C8—C3	178.4 (6)
O1—C1—C2—C3	−177.3 (4)	Cl1—C5—C6—C1	179.9 (3)
C6—C1—C2—C3	2.8 (5)	C4—C5—C6—Cl2	−179.1 (3)
O1—C1—C2—C7	5.3 (5)	Cl1—C5—C6—Cl2	0.7 (5)
C6—C1—C2—C7	−174.6 (4)	O1—C1—C6—C5	176.2 (3)
C7—C2—C3—C4	179.3 (4)	C2—C1—C6—C5	−3.8 (6)
C1—C2—C3—C4	2.1 (6)	O1—C1—C6—Cl2	−4.5 (5)
C7—C2—C3—C8	−1.6 (6)	C2—C1—C6—Cl2	175.4 (2)
C1—C2—C3—C8	−178.9 (3)	C13—N3—C9—C10	0.5 (7)
C2—C3—C4—O2	176.0 (3)	C14—N3—C9—C10	177.7 (5)
C8—C3—C4—O2	−3.0 (6)	N3—C9—C10—C11	0.1 (8)
C2—C3—C4—C5	−5.6 (5)	C9—C10—C11—C12	−0.4 (7)
C8—C3—C4—C5	175.3 (3)	C9—C10—C11—C15	−176.6 (5)
O2—C4—C5—C6	−177.0 (4)	C10—C11—C12—C13	0.2 (7)
C3—C4—C5—C6	4.6 (5)	C15—C11—C12—C13	176.5 (5)
O2—C4—C5—Cl1	3.1 (5)	C9—N3—C13—C12	−0.7 (8)
C3—C4—C5—Cl1	−175.2 (3)	C14—N3—C13—C12	−178.0 (5)
C4—C5—C6—C1	0.1 (6)	C11—C12—C13—N3	0.3 (8)

(test3_1.85GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.795 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.4387 (2) Å	Cell parameters from 1960 reflections
b = 9.9135 (11) Å	θ = 2.0–26.7°
c = 20.1349 (10) Å	µ = 0.52 mm^−1
β = 94.729 (3)°	T = 293 K
V = 1280.83 (16) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1390 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	982 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.372 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.368, Tmax = 0.449	k = −8→8
6531 measured reflections	l = −23→22

Refinement

Refinement on F^2	192 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 0.2085P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1390 reflections	Δρmax = 0.25 e Å^−3
209 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.21350 (15)	0.10860 (16)	−0.00654 (5)	0.0268 (5)
Cl2	0.12508 (14)	0.27982 (16)	0.11979 (5)	0.0273 (5)
O1	0.1434 (4)	0.5710 (4)	0.09558 (13)	0.0260 (12)
O2	0.3017 (4)	0.2726 (4)	−0.11992 (13)	0.0273 (13)
N1	0.2928 (6)	0.8197 (7)	−0.00807 (17)	0.0312 (17)
N2	0.4153 (5)	0.5997 (5)	−0.17377 (18)	0.0283 (16)
N3	0.3128 (5)	0.9582 (5)	0.18015 (16)	0.0249 (14)
N4	1.0157 (5)	1.2133 (6)	0.25263 (16)	0.0387 (17)
C1	0.1889 (6)	0.4985 (7)	0.04704 (19)	0.0181 (15)
C2	0.2522 (6)	0.5641 (7)	−0.01311 (19)	0.0197 (15)
C3	0.2950 (6)	0.4863 (7)	−0.06818 (19)	0.0200 (15)
C4	0.2730 (6)	0.3437 (7)	−0.0702 (2)	0.0206 (15)
C5	0.2210 (5)	0.2807 (7)	−0.00712 (18)	0.0167 (14)
C6	0.1830 (5)	0.3534 (7)	0.04636 (19)	0.0157 (14)
C7	0.2752 (7)	0.7045 (9)	−0.01127 (19)	0.0194 (18)
C8	0.3606 (6)	0.5516 (6)	−0.1268 (2)	0.0191 (17)
C9	0.3434 (6)	1.0026 (6)	0.24299 (19)	0.0241 (18)
H9	0.244183	0.984948	0.272884	0.029*
C10	0.5165 (6)	1.0727 (6)	0.26342 (19)	0.0265 (17)
H10	0.537111	1.103132	0.307159	0.032*
C11	0.6642 (6)	1.0990 (6)	0.2183 (2)	0.0251 (18)
C12	0.6307 (6)	1.0506 (6)	0.1540 (2)	0.0295 (18)
H12	0.728433	1.065702	0.123247	0.035*
C13	0.4534 (6)	0.9805 (6)	0.1360 (2)	0.0284 (17)
H13	0.429587	0.947894	0.092744	0.034*
C14	0.1251 (6)	0.8773 (8)	0.1588 (2)	0.044 (2)
H14A	0.047405	0.921901	0.122382	0.066*
H14B	0.039536	0.868205	0.195365	0.066*
H14C	0.166895	0.789589	0.144719	0.066*
C15	0.8550 (7)	1.1657 (6)	0.23876 (19)	0.0270 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0345 (6)	0.0173 (18)	0.0288 (8)	0.0011 (7)	0.0047 (4)	0.0005 (5)
Cl2	0.0342 (6)	0.0273 (17)	0.0209 (7)	−0.0026 (6)	0.0060 (4)	0.0050 (5)
O1	0.0323 (15)	0.022 (4)	0.0243 (19)	0.0028 (18)	0.0060 (12)	−0.0070 (15)
O2	0.0435 (17)	0.016 (5)	0.023 (2)	0.0046 (18)	0.0079 (13)	−0.0025 (14)
N1	0.033 (2)	0.025 (6)	0.035 (3)	0.001 (3)	0.0023 (15)	−0.001 (2)
N2	0.036 (2)	0.022 (6)	0.028 (3)	0.001 (2)	0.0056 (16)	0.0017 (19)
N3	0.0284 (18)	0.019 (5)	0.026 (2)	0.005 (2)	−0.0046 (15)	−0.0015 (17)
N4	0.039 (2)	0.045 (6)	0.032 (3)	−0.010 (3)	0.0052 (18)	0.000 (2)
C1	0.0162 (19)	0.019 (5)	0.019 (3)	0.004 (3)	0.0002 (16)	−0.0003 (19)
C2	0.018 (2)	0.016 (5)	0.026 (3)	0.003 (3)	0.0017 (17)	0.003 (2)
C3	0.0181 (19)	0.019 (5)	0.023 (3)	−0.001 (3)	0.0011 (16)	0.002 (2)
C4	0.017 (2)	0.022 (5)	0.023 (3)	0.002 (3)	0.0011 (17)	0.003 (2)
C5	0.0202 (19)	0.007 (5)	0.023 (3)	0.000 (2)	0.0023 (17)	−0.0002 (19)
C6	0.0169 (19)	0.009 (5)	0.021 (3)	0.002 (3)	0.0008 (16)	0.0026 (19)
C7	0.020 (2)	0.017 (6)	0.022 (3)	−0.001 (4)	0.0059 (16)	0.004 (3)
C8	0.021 (2)	0.012 (6)	0.025 (3)	0.001 (2)	0.0023 (17)	−0.002 (2)
C9	0.027 (2)	0.022 (7)	0.024 (3)	0.002 (2)	0.0022 (17)	0.001 (2)
C10	0.028 (2)	0.035 (6)	0.016 (3)	0.003 (3)	0.0011 (17)	0.000 (2)
C11	0.027 (2)	0.024 (7)	0.024 (3)	0.000 (2)	0.0033 (17)	0.003 (2)
C12	0.032 (2)	0.039 (7)	0.017 (3)	0.003 (3)	0.0055 (17)	0.002 (2)
C13	0.038 (2)	0.028 (6)	0.020 (3)	0.013 (3)	0.0006 (18)	0.000 (2)
C14	0.039 (3)	0.044 (9)	0.046 (4)	−0.011 (3)	−0.012 (2)	−0.002 (3)
C15	0.036 (2)	0.021 (7)	0.024 (3)	−0.002 (3)	0.0066 (19)	0.006 (2)

Geometric parameters (Å, º)

Cl1—C5	1.707 (6)	C3—C8	1.440 (6)
Cl2—C6	1.717 (5)	C4—C5	1.478 (6)
O1—C1	1.266 (6)	C5—C6	1.335 (7)
O2—C4	1.251 (6)	C9—C10	1.349 (6)
N1—C7	1.149 (7)	C9—H9	0.9300
N2—C8	1.141 (5)	C10—C11	1.393 (5)
N3—C13	1.338 (5)	C10—H10	0.9300
N3—C9	1.339 (5)	C11—C12	1.382 (6)
N3—C14	1.484 (6)	C11—C15	1.426 (6)
N4—C15	1.150 (5)	C12—C13	1.359 (7)
C1—C6	1.439 (8)	C12—H12	0.9300
C1—C2	1.462 (6)	C13—H13	0.9300
C2—C3	1.397 (7)	C14—H14A	0.9600
C2—C7	1.400 (8)	C14—H14B	0.9600
C3—C4	1.421 (8)	C14—H14C	0.9600
C13—N3—C9	121.2 (4)	N3—C9—C10	120.7 (4)
C13—N3—C14	118.4 (4)	N3—C9—H9	119.6
C9—N3—C14	120.3 (3)	C10—C9—H9	119.6
O1—C1—C6	124.5 (4)	C9—C10—C11	119.3 (4)
O1—C1—C2	119.0 (6)	C9—C10—H10	120.4
C6—C1—C2	116.5 (4)	C11—C10—H10	120.4
C3—C2—C7	122.9 (4)	C12—C11—C10	119.0 (4)
C3—C2—C1	119.9 (6)	C12—C11—C15	119.7 (3)
C7—C2—C1	117.1 (4)	C10—C11—C15	121.1 (4)
C2—C3—C4	123.1 (4)	C13—C12—C11	119.3 (4)
C2—C3—C8	119.5 (6)	C13—C12—H12	120.3
C4—C3—C8	117.4 (4)	C11—C12—H12	120.3
O2—C4—C3	124.2 (4)	N3—C13—C12	120.5 (4)
O2—C4—C5	120.6 (6)	N3—C13—H13	119.8
C3—C4—C5	115.2 (4)	C12—C13—H13	119.8
C6—C5—C4	122.3 (6)	N3—C14—H14A	109.5
C6—C5—Cl1	121.8 (4)	N3—C14—H14B	109.5
C4—C5—Cl1	115.9 (4)	H14A—C14—H14B	109.5
C5—C6—C1	122.7 (4)	N3—C14—H14C	109.5
C5—C6—Cl2	122.2 (5)	H14A—C14—H14C	109.5
C1—C6—Cl2	115.1 (3)	H14B—C14—H14C	109.5
N1—C7—C2	178.2 (4)	N4—C15—C11	175.3 (6)
N2—C8—C3	177.9 (6)
O1—C1—C2—C3	−177.4 (4)	Cl1—C5—C6—C1	179.9 (3)
C6—C1—C2—C3	2.5 (5)	C4—C5—C6—Cl2	−179.4 (3)
O1—C1—C2—C7	5.1 (5)	Cl1—C5—C6—Cl2	0.4 (5)
C6—C1—C2—C7	−174.9 (4)	O1—C1—C6—C5	176.2 (3)
C7—C2—C3—C4	179.7 (4)	C2—C1—C6—C5	−3.7 (6)
C1—C2—C3—C4	2.4 (6)	O1—C1—C6—Cl2	−4.3 (5)
C7—C2—C3—C8	−1.7 (6)	C2—C1—C6—Cl2	175.8 (2)
C1—C2—C3—C8	−178.9 (3)	C13—N3—C9—C10	0.7 (8)
C2—C3—C4—O2	176.8 (4)	C14—N3—C9—C10	178.0 (5)
C8—C3—C4—O2	−1.9 (6)	N3—C9—C10—C11	0.2 (8)
C2—C3—C4—C5	−5.8 (6)	C9—C10—C11—C12	−1.0 (8)
C8—C3—C4—C5	175.5 (3)	C9—C10—C11—C15	−176.2 (5)
O2—C4—C5—C6	−177.9 (4)	C10—C11—C12—C13	1.1 (7)
C3—C4—C5—C6	4.6 (5)	C15—C11—C12—C13	176.3 (6)
O2—C4—C5—Cl1	2.4 (5)	C9—N3—C13—C12	−0.7 (8)
C3—C4—C5—Cl1	−175.2 (3)	C14—N3—C13—C12	−178.0 (5)
C4—C5—C6—C1	0.1 (6)	C11—C12—C13—N3	−0.2 (8)

(test3_2.55GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.834 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.3580 (4) Å	Cell parameters from 1653 reflections
b = 9.895 (2) Å	θ = 2.0–26.9°
c = 20.0093 (18) Å	µ = 0.54 mm^−1
β = 95.314 (7)°	T = 293 K
V = 1253.5 (3) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1374 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.108
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.0°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.365 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.361, Tmax = 0.449	k = −8→8
6405 measured reflections	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.140	H-atom parameters constrained
wR(F^2) = 0.377	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.36	(Δ/σ)max < 0.001
1374 reflections	Δρmax = 1.50 e Å^−3
94 parameters	Δρmin = −1.60 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2234 (4)	0.1128 (4)	−0.00453 (13)	0.0313 (10)*
Cl2	0.1324 (4)	0.2836 (4)	0.12234 (13)	0.0295 (10)*
O1	0.1562 (11)	0.5751 (11)	0.0988 (4)	0.034 (2)*
O2	0.3144 (11)	0.2808 (11)	−0.1175 (4)	0.035 (2)*
N1	0.2818 (12)	0.8227 (19)	−0.0080 (4)	0.032 (2)*
N2	0.4095 (12)	0.6029 (13)	−0.1749 (5)	0.032 (2)*
N3	0.3067 (12)	0.9592 (13)	0.1800 (4)	0.030 (2)*
N4	1.0214 (12)	1.2149 (13)	0.2538 (4)	0.032 (2)*
C1	0.2043 (14)	0.5101 (18)	0.0484 (5)	0.028 (3)*
C2	0.2658 (13)	0.5671 (17)	−0.0100 (5)	0.025 (3)*
C3	0.3098 (14)	0.4941 (17)	−0.0667 (5)	0.026 (3)*
C4	0.2870 (13)	0.3532 (17)	−0.0679 (5)	0.024 (2)*
C5	0.2354 (13)	0.2894 (17)	−0.0058 (5)	0.024 (3)*
C6	0.1956 (14)	0.3635 (17)	0.0476 (5)	0.025 (2)*
C7	0.2754 (14)	0.706 (2)	−0.0105 (5)	0.026 (3)*
C8	0.3631 (13)	0.5566 (15)	−0.1261 (5)	0.018 (2)*
C9	0.3403 (14)	1.0026 (16)	0.2426 (5)	0.026 (3)*
H9	0.241867	0.982676	0.272777	0.031*
C10	0.5148 (15)	1.0756 (15)	0.2641 (6)	0.031 (3)*
H10	0.534528	1.108034	0.307890	0.038*
C11	0.6646 (13)	1.1006 (14)	0.2180 (5)	0.023 (2)*
C12	0.6309 (15)	1.0473 (16)	0.1538 (5)	0.028 (3)*
H12	0.731694	1.058484	0.123450	0.034*
C13	0.4518 (14)	0.9796 (16)	0.1359 (5)	0.029 (3)*
H13	0.427298	0.946223	0.092486	0.035*
C14	0.1202 (17)	0.884 (2)	0.1583 (7)	0.052 (4)*
H14A	0.159956	0.799005	0.139560	0.077*
H14B	0.035580	0.934151	0.124818	0.077*
H14C	0.040453	0.866910	0.195885	0.077*
C15	0.8584 (15)	1.1687 (17)	0.2391 (5)	0.031 (3)*

Geometric parameters (Å, º)

Cl1—C5	1.749 (17)	C3—C8	1.407 (16)
Cl2—C6	1.770 (12)	C4—C5	1.458 (16)
O1—C1	1.257 (15)	C5—C6	1.339 (17)
O2—C4	1.249 (15)	C9—C10	1.360 (16)
N1—C7	1.156 (18)	C9—H9	0.9300
N2—C8	1.142 (13)	C10—C11	1.408 (14)
N3—C9	1.323 (13)	C10—H10	0.9300
N3—C13	1.350 (12)	C11—C12	1.385 (15)
N3—C14	1.435 (16)	C11—C15	1.433 (15)
N4—C15	1.146 (13)	C12—C13	1.341 (16)
C1—C2	1.386 (16)	C12—H12	0.9300
C1—C6	1.45 (2)	C13—H13	0.9300
C2—C7	1.38 (2)	C14—H14A	0.9600
C2—C3	1.395 (17)	C14—H14B	0.9600
C3—C4	1.40 (2)	C14—H14C	0.9600
C9—N3—C13	120.6 (9)	N3—C9—C10	121.9 (9)
C9—N3—C14	120.9 (9)	N3—C9—H9	119.1
C13—N3—C14	118.4 (10)	C10—C9—H9	119.1
O1—C1—C2	125.2 (15)	C9—C10—C11	117.8 (10)
O1—C1—C6	120.5 (11)	C9—C10—H10	121.1
C2—C1—C6	114.3 (11)	C11—C10—H10	121.1
C7—C2—C1	115.4 (11)	C12—C11—C10	119.0 (10)
C7—C2—C3	119.9 (10)	C12—C11—C15	120.4 (8)
C1—C2—C3	124.7 (15)	C10—C11—C15	120.3 (9)
C2—C3—C4	120.0 (11)	C13—C12—C11	119.5 (9)
C2—C3—C8	122.8 (14)	C13—C12—H12	120.3
C4—C3—C8	117.1 (10)	C11—C12—H12	120.3
O2—C4—C3	124.1 (11)	C12—C13—N3	121.0 (10)
O2—C4—C5	119.2 (14)	C12—C13—H13	119.5
C3—C4—C5	116.6 (10)	N3—C13—H13	119.5
C6—C5—C4	121.1 (14)	N3—C14—H14A	109.5
C6—C5—Cl1	121.6 (10)	N3—C14—H14B	109.5
C4—C5—Cl1	117.3 (9)	H14A—C14—H14B	109.5
C5—C6—C1	123.1 (11)	N3—C14—H14C	109.5
C5—C6—Cl2	120.2 (12)	H14A—C14—H14C	109.5
C1—C6—Cl2	116.7 (8)	H14B—C14—H14C	109.5
N1—C7—C2	177.0 (10)	N4—C15—C11	174.6 (15)
N2—C8—C3	177.5 (14)
O1—C1—C2—C7	0.8 (14)	Cl1—C5—C6—C1	179.9 (7)
C6—C1—C2—C7	−180.0 (8)	C4—C5—C6—Cl2	179.8 (6)
O1—C1—C2—C3	−177.0 (9)	Cl1—C5—C6—Cl2	0.9 (12)
C6—C1—C2—C3	2.2 (14)	O1—C1—C6—C5	176.8 (9)
C7—C2—C3—C4	−175.9 (8)	C2—C1—C6—C5	−2.5 (14)
C1—C2—C3—C4	1.8 (15)	O1—C1—C6—Cl2	−4.2 (12)
C7—C2—C3—C8	−0.5 (14)	C2—C1—C6—Cl2	176.6 (7)
C1—C2—C3—C8	177.2 (8)	C13—N3—C9—C10	4 (2)
C2—C3—C4—O2	176.9 (9)	C14—N3—C9—C10	−179.3 (15)
C8—C3—C4—O2	1.3 (14)	N3—C9—C10—C11	−2 (2)
C2—C3—C4—C5	−5.4 (13)	C9—C10—C11—C12	−1.6 (19)
C8—C3—C4—C5	179.0 (8)	C9—C10—C11—C15	−175.6 (13)
O2—C4—C5—C6	−177.0 (9)	C10—C11—C12—C13	4 (2)
C3—C4—C5—C6	5.1 (13)	C15—C11—C12—C13	177.5 (14)
O2—C4—C5—Cl1	2.0 (12)	C11—C12—C13—N3	−2 (2)
C3—C4—C5—Cl1	−175.9 (7)	C9—N3—C13—C12	−2 (2)
C4—C5—C6—C1	−1.2 (14)	C14—N3—C13—C12	−178.7 (15)

(test3_3.09GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.887 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2590 (2) Å	Cell parameters from 1965 reflections
b = 9.8519 (12) Å	θ = 2.1–27.2°
c = 19.8571 (11) Å	µ = 0.55 mm^−1
β = 95.624 (4)°	T = 293 K
V = 1218.56 (17) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1312 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	969 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.1°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.373 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.368, Tmax = 0.449	k = −8→7
6137 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 4.2141P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1312 reflections	Δρmax = 0.56 e Å^−3
94 parameters	Δρmin = −0.72 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2320 (2)	0.1163 (2)	−0.00400 (7)	0.0230 (4)*
Cl2	0.1388 (2)	0.2862 (2)	0.12396 (7)	0.0223 (4)*
O1	0.1674 (6)	0.5777 (6)	0.1016 (2)	0.0236 (10)*
O2	0.3254 (6)	0.2821 (6)	−0.1171 (2)	0.0260 (11)*
N1	0.2653 (7)	0.8311 (9)	−0.0089 (2)	0.0241 (13)*
N2	0.4009 (7)	0.6046 (8)	−0.1773 (3)	0.0249 (13)*
N3	0.3035 (7)	0.9609 (7)	0.1792 (2)	0.0241 (12)*
N4	1.0260 (8)	1.2187 (8)	0.2553 (3)	0.0327 (14)*
C1	0.2132 (8)	0.5102 (9)	0.0517 (3)	0.0169 (13)*
C2	0.2712 (8)	0.5741 (9)	−0.0092 (3)	0.0156 (13)*
C3	0.3157 (8)	0.4961 (9)	−0.0652 (3)	0.0161 (13)*
C4	0.2979 (8)	0.3527 (9)	−0.0666 (3)	0.0176 (14)*
C5	0.2441 (8)	0.2892 (9)	−0.0034 (3)	0.0158 (13)*
C6	0.2070 (8)	0.3635 (9)	0.0509 (3)	0.0147 (13)*
C7	0.2702 (8)	0.7140 (11)	−0.0094 (3)	0.0140 (13)*
C8	0.3618 (8)	0.5620 (8)	−0.1269 (3)	0.0148 (13)*
C9	0.3369 (8)	1.0069 (9)	0.2431 (3)	0.0220 (14)*
H9	0.235065	0.989696	0.273149	0.026*
C10	0.5156 (8)	1.0778 (9)	0.2646 (3)	0.0231 (15)*
H10	0.537444	1.109611	0.308814	0.028*
C11	0.6658 (9)	1.1019 (9)	0.2190 (3)	0.0225 (14)*
C12	0.6321 (9)	1.0526 (9)	0.1540 (3)	0.0253 (15)*
H12	0.732286	1.068513	0.123320	0.030*
C13	0.4514 (9)	0.9803 (9)	0.1352 (3)	0.0269 (15)*
H13	0.429594	0.944119	0.091765	0.032*
C14	0.1129 (9)	0.8804 (11)	0.1572 (3)	0.0345 (17)*
H14A	0.025467	0.871021	0.194013	0.052*
H14B	0.156041	0.792192	0.143042	0.052*
H14C	0.032127	0.925177	0.120014	0.052*
C15	0.8638 (9)	1.1706 (9)	0.2398 (3)	0.0225 (15)*

Geometric parameters (Å, º)

Cl1—C5	1.705 (9)	C3—C8	1.440 (8)
Cl2—C6	1.728 (6)	C4—C5	1.471 (8)
O1—C1	1.249 (8)	C5—C6	1.342 (9)
O2—C4	1.246 (8)	C9—C10	1.351 (9)
N1—C7	1.154 (9)	C9—H9	0.9300
N2—C8	1.134 (7)	C10—C11	1.388 (8)
N3—C9	1.345 (8)	C10—H10	0.9300
N3—C13	1.348 (7)	C11—C12	1.374 (9)
N3—C14	1.463 (9)	C11—C15	1.437 (9)
N4—C15	1.135 (8)	C12—C13	1.358 (9)
C1—C2	1.441 (9)	C12—H12	0.9300
C1—C6	1.446 (10)	C13—H13	0.9300
C2—C7	1.378 (10)	C14—H14A	0.9600
C2—C3	1.403 (9)	C14—H14B	0.9600
C3—C4	1.417 (10)	C14—H14C	0.9600
C9—N3—C13	120.8 (6)	N3—C9—C10	121.3 (5)
C9—N3—C14	120.8 (5)	N3—C9—H9	119.4
C13—N3—C14	118.3 (5)	C10—C9—H9	119.4
O1—C1—C2	121.9 (7)	C9—C10—C11	118.4 (6)
O1—C1—C6	122.2 (6)	C9—C10—H10	120.8
C2—C1—C6	115.9 (5)	C11—C10—H10	120.8
C7—C2—C3	123.2 (6)	C12—C11—C10	120.0 (6)
C7—C2—C1	116.0 (5)	C12—C11—C15	119.0 (5)
C3—C2—C1	120.8 (7)	C10—C11—C15	120.8 (5)
C2—C3—C4	122.7 (5)	C13—C12—C11	119.4 (5)
C2—C3—C8	119.9 (7)	C13—C12—H12	120.3
C4—C3—C8	117.1 (5)	C11—C12—H12	120.3
O2—C4—C3	123.7 (6)	N3—C13—C12	120.1 (6)
O2—C4—C5	120.7 (7)	N3—C13—H13	119.9
C3—C4—C5	115.6 (5)	C12—C13—H13	119.9
C6—C5—C4	121.7 (7)	N3—C14—H14A	109.5
C6—C5—Cl1	122.7 (5)	N3—C14—H14B	109.5
C4—C5—Cl1	115.6 (5)	H14A—C14—H14B	109.5
C5—C6—C1	123.2 (6)	N3—C14—H14C	109.5
C5—C6—Cl2	120.6 (6)	H14A—C14—H14C	109.5
C1—C6—Cl2	116.1 (4)	H14B—C14—H14C	109.5
N1—C7—C2	178.5 (6)	N4—C15—C11	176.2 (8)
N2—C8—C3	174.9 (8)
O1—C1—C2—C7	−0.8 (7)	Cl1—C5—C6—C1	−178.9 (4)
C6—C1—C2—C7	177.9 (5)	C4—C5—C6—Cl2	178.7 (4)
O1—C1—C2—C3	−178.1 (5)	Cl1—C5—C6—Cl2	−1.3 (6)
C6—C1—C2—C3	0.7 (7)	O1—C1—C6—C5	176.2 (5)
C7—C2—C3—C4	−174.3 (5)	C2—C1—C6—C5	−2.5 (7)
C1—C2—C3—C4	2.8 (8)	O1—C1—C6—Cl2	−1.5 (7)
C7—C2—C3—C8	−0.4 (7)	C2—C1—C6—Cl2	179.7 (4)
C1—C2—C3—C8	176.6 (4)	C13—N3—C9—C10	2.2 (11)
C2—C3—C4—O2	176.0 (5)	C14—N3—C9—C10	178.0 (8)
C8—C3—C4—O2	2.0 (8)	N3—C9—C10—C11	−0.2 (12)
C2—C3—C4—C5	−4.2 (7)	C9—C10—C11—C12	−0.9 (11)
C8—C3—C4—C5	−178.2 (4)	C9—C10—C11—C15	−176.8 (8)
O2—C4—C5—C6	−177.9 (5)	C10—C11—C12—C13	0.0 (12)
C3—C4—C5—C6	2.3 (7)	C15—C11—C12—C13	176.0 (8)
O2—C4—C5—Cl1	2.1 (7)	C9—N3—C13—C12	−3.1 (11)
C3—C4—C5—Cl1	−177.7 (4)	C14—N3—C13—C12	−179.0 (8)
C4—C5—C6—C1	1.0 (8)	C11—C12—C13—N3	2.0 (12)

(test3_3.95GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.916 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2058 (3) Å	Cell parameters from 1972 reflections
b = 9.8299 (15) Å	θ = 2.1–27.3°
c = 19.7739 (13) Å	µ = 0.56 mm^−1
β = 95.781 (5)°	T = 293 K
V = 1200.1 (2) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1290 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.3°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.371 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.366, Tmax = 0.449	k = −8→8
6073 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 3.3338P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1290 reflections	Δρmax = 0.54 e Å^−3
94 parameters	Δρmin = −0.55 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.23248 (19)	0.1157 (2)	−0.00366 (6)	0.0213 (4)*
Cl2	0.13994 (19)	0.2863 (2)	0.12473 (6)	0.0211 (4)*
O1	0.1688 (5)	0.5782 (5)	0.10216 (19)	0.0228 (9)*
O2	0.3268 (6)	0.2814 (6)	−0.11688 (18)	0.0241 (10)*
N1	0.2655 (6)	0.8307 (9)	−0.0091 (2)	0.0213 (12)*
N2	0.3997 (7)	0.6038 (7)	−0.1785 (2)	0.0244 (12)*
N3	0.3044 (6)	0.9610 (7)	0.1788 (2)	0.0218 (11)*
N4	1.0292 (7)	1.2215 (7)	0.2561 (2)	0.0280 (13)*
C1	0.2139 (7)	0.5102 (8)	0.0523 (2)	0.0150 (12)*
C2	0.2706 (7)	0.5743 (8)	−0.0091 (2)	0.0130 (12)*
C3	0.3142 (7)	0.4967 (8)	−0.0656 (2)	0.0154 (12)*
C4	0.2990 (7)	0.3524 (8)	−0.0665 (3)	0.0173 (13)*
C5	0.2453 (7)	0.2881 (8)	−0.0032 (2)	0.0129 (12)*
C6	0.2071 (7)	0.3626 (8)	0.0515 (2)	0.0135 (12)*
C7	0.2700 (7)	0.7143 (10)	−0.0097 (2)	0.0121 (12)*
C8	0.3601 (7)	0.5608 (8)	−0.1273 (3)	0.0152 (12)*
C9	0.3339 (8)	1.0074 (8)	0.2426 (3)	0.0190 (13)*
H9	0.229928	0.990785	0.272320	0.023*
C10	0.5155 (8)	1.0788 (8)	0.2642 (3)	0.0218 (14)*
H10	0.537288	1.110509	0.308629	0.026*
C11	0.6672 (8)	1.1037 (8)	0.2191 (3)	0.0224 (14)*
C12	0.6324 (9)	1.0534 (9)	0.1534 (3)	0.0258 (14)*
H12	0.732628	1.069589	0.122355	0.031*
C13	0.4520 (8)	0.9809 (9)	0.1349 (3)	0.0259 (14)*
H13	0.429773	0.944452	0.091336	0.031*
C14	0.1107 (9)	0.8811 (10)	0.1562 (3)	0.0358 (17)*
H14A	0.025136	0.868753	0.193593	0.054*
H14B	0.153390	0.793869	0.140239	0.054*
H14C	0.026870	0.928272	0.120099	0.054*
C15	0.8665 (8)	1.1736 (8)	0.2408 (3)	0.0218 (14)*

Geometric parameters (Å, º)

Cl1—C5	1.697 (8)	C3—C8	1.428 (8)
Cl2—C6	1.720 (6)	C4—C5	1.469 (8)
O1—C1	1.245 (7)	C5—C6	1.347 (8)
O2—C4	1.243 (7)	C9—C10	1.359 (8)
N1—C7	1.144 (9)	C9—H9	0.9300
N2—C8	1.145 (7)	C10—C11	1.382 (7)
N3—C9	1.337 (7)	C10—H10	0.9300
N3—C13	1.338 (7)	C11—C12	1.388 (8)
N3—C14	1.467 (9)	C11—C15	1.441 (8)
N4—C15	1.128 (7)	C12—C13	1.346 (9)
C1—C2	1.443 (8)	C12—H12	0.9300
C1—C6	1.451 (9)	C13—H13	0.9300
C2—C7	1.376 (10)	C14—H14A	0.9600
C2—C3	1.402 (8)	C14—H14B	0.9600
C3—C4	1.421 (10)	C14—H14C	0.9600
C9—N3—C13	121.6 (5)	N3—C9—C10	120.2 (5)
C9—N3—C14	120.0 (4)	N3—C9—H9	119.9
C13—N3—C14	118.3 (5)	C10—C9—H9	119.9
O1—C1—C2	121.6 (7)	C9—C10—C11	119.1 (5)
O1—C1—C6	122.5 (5)	C9—C10—H10	120.4
C2—C1—C6	115.8 (5)	C11—C10—H10	120.4
C7—C2—C3	122.5 (5)	C10—C11—C12	119.3 (6)
C7—C2—C1	116.3 (5)	C10—C11—C15	120.8 (5)
C3—C2—C1	121.1 (7)	C12—C11—C15	119.8 (5)
C2—C3—C4	122.4 (5)	C13—C12—C11	119.3 (5)
C2—C3—C8	120.8 (7)	C13—C12—H12	120.3
C4—C3—C8	116.6 (5)	C11—C12—H12	120.3
O2—C4—C3	123.8 (5)	N3—C13—C12	120.4 (6)
O2—C4—C5	120.2 (7)	N3—C13—H13	119.8
C3—C4—C5	116.0 (5)	C12—C13—H13	119.8
C6—C5—C4	121.5 (7)	N3—C14—H14A	109.5
C6—C5—Cl1	122.4 (5)	N3—C14—H14B	109.5
C4—C5—Cl1	116.1 (4)	H14A—C14—H14B	109.5
C5—C6—C1	123.1 (5)	N3—C14—H14C	109.5
C5—C6—Cl2	121.1 (6)	H14A—C14—H14C	109.5
C1—C6—Cl2	115.8 (4)	H14B—C14—H14C	109.5
N1—C7—C2	178.2 (5)	N4—C15—C11	175.6 (8)
N2—C8—C3	175.4 (7)
O1—C1—C2—C7	−0.6 (7)	Cl1—C5—C6—C1	−179.0 (4)
C6—C1—C2—C7	177.8 (4)	C4—C5—C6—Cl2	178.9 (3)
O1—C1—C2—C3	−177.9 (4)	Cl1—C5—C6—Cl2	−0.6 (6)
C6—C1—C2—C3	0.4 (6)	O1—C1—C6—C5	176.7 (5)
C7—C2—C3—C4	−175.2 (4)	C2—C1—C6—C5	−1.6 (7)
C1—C2—C3—C4	1.9 (7)	O1—C1—C6—Cl2	−1.8 (6)
C7—C2—C3—C8	−0.1 (7)	C2—C1—C6—Cl2	179.9 (3)
C1—C2—C3—C8	177.0 (4)	C13—N3—C9—C10	1.1 (10)
C2—C3—C4—O2	176.5 (4)	C14—N3—C9—C10	178.5 (7)
C8—C3—C4—O2	1.2 (7)	N3—C9—C10—C11	0.6 (11)
C2—C3—C4—C5	−3.0 (7)	C9—C10—C11—C12	−1.0 (11)
C8—C3—C4—C5	−178.3 (4)	C9—C10—C11—C15	−177.1 (7)
O2—C4—C5—C6	−177.7 (5)	C10—C11—C12—C13	−0.3 (11)
C3—C4—C5—C6	1.8 (6)	C15—C11—C12—C13	175.9 (7)
O2—C4—C5—Cl1	1.8 (6)	C9—N3—C13—C12	−2.5 (11)
C3—C4—C5—Cl1	−178.7 (3)	C14—N3—C13—C12	−179.9 (7)
C4—C5—C6—C1	0.5 (7)	C11—C12—C13—N3	2.0 (11)

(test3_4.80GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 346.15	Dx = 1.965 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1216 (6) Å	Cell parameters from 781 reflections
b = 9.806 (4) Å	θ = 2.1–25.4°
c = 19.603 (3) Å	µ = 0.57 mm^−1
β = 96.013 (12)°	T = 293 K
V = 1170.2 (5) Å^3	Block, black
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1271 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	651 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.157
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.4°, θmin = 2.1°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.372 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.367, Tmax = 0.449	k = −8→7
5803 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.116	H-atom parameters constrained
wR(F^2) = 0.348	w = 1/[σ^2(Fo^2) + (0.1997P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1271 reflections	Δρmax = 0.85 e Å^−3
94 parameters	Δρmin = −0.61 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2330 (4)	0.1147 (5)	−0.00304 (14)	0.0317 (11)*
Cl2	0.1409 (5)	0.2868 (5)	0.12592 (14)	0.0322 (11)*
O1	0.1688 (13)	0.5779 (12)	0.1035 (4)	0.034 (2)*
O2	0.3290 (12)	0.2806 (13)	−0.1168 (4)	0.032 (2)*
N1	0.2663 (14)	0.833 (2)	−0.0083 (4)	0.031 (3)*
N2	0.4022 (17)	0.6025 (16)	−0.1796 (5)	0.041 (3)*
N3	0.3073 (14)	0.9631 (15)	0.1777 (5)	0.031 (3)*
N4	1.0364 (16)	1.2243 (16)	0.2584 (5)	0.041 (3)*
C1	0.2130 (16)	0.5100 (19)	0.0533 (5)	0.023 (3)*
C2	0.2692 (17)	0.572 (2)	−0.0081 (5)	0.028 (3)*
C3	0.3121 (15)	0.4940 (18)	−0.0668 (5)	0.021 (3)*
C4	0.2982 (16)	0.3484 (18)	−0.0677 (5)	0.020 (3)*
C5	0.2450 (15)	0.2834 (18)	−0.0027 (5)	0.019 (3)*
C6	0.2069 (15)	0.3638 (17)	0.0535 (5)	0.017 (3)*
C7	0.2670 (16)	0.717 (3)	−0.0095 (5)	0.022 (3)*
C8	0.3582 (18)	0.5587 (19)	−0.1276 (6)	0.029 (3)*
C9	0.3299 (18)	1.0085 (19)	0.2412 (6)	0.030 (3)*
H9	0.224263	0.988619	0.270565	0.036*
C10	0.5143 (19)	1.0869 (18)	0.2643 (6)	0.035 (3)*
H10	0.531026	1.124810	0.307983	0.041*
C11	0.6672 (18)	1.1050 (17)	0.2198 (6)	0.029 (3)*
C12	0.637 (2)	1.059 (2)	0.1534 (7)	0.039 (3)*
H12	0.737800	1.078936	0.122441	0.047*
C13	0.4545 (17)	0.9846 (19)	0.1348 (6)	0.035 (3)*
H13	0.433130	0.947909	0.090830	0.042*
C14	0.113 (2)	0.879 (2)	0.1549 (7)	0.041 (4)*
H14A	0.036888	0.855841	0.193785	0.061*
H14B	0.158911	0.797038	0.133790	0.061*
H14C	0.016239	0.929452	0.122408	0.061*
C15	0.8699 (19)	1.175 (2)	0.2423 (6)	0.036 (4)*

Geometric parameters (Å, º)

Cl1—C5	1.656 (17)	C3—C4	1.43 (2)
Cl2—C6	1.694 (12)	C4—C5	1.491 (16)
O1—C1	1.239 (16)	C5—C6	1.394 (18)
O2—C4	1.201 (15)	C9—C10	1.401 (19)
N1—C7	1.14 (2)	C9—H9	0.9300
N2—C8	1.163 (15)	C10—C11	1.356 (17)
N3—C13	1.313 (14)	C10—H10	0.9300
N3—C9	1.315 (15)	C11—C12	1.369 (18)
N3—C14	1.479 (18)	C11—C15	1.445 (19)
N4—C15	1.143 (15)	C12—C13	1.354 (19)
C1—C2	1.423 (18)	C12—H12	0.9300
C1—C6	1.43 (2)	C13—H13	0.9300
C2—C7	1.42 (2)	C14—H14A	0.9600
C2—C3	1.428 (19)	C14—H14B	0.9600
C3—C8	1.405 (18)	C14—H14C	0.9600
C13—N3—C9	122.8 (12)	N3—C9—C10	119.5 (11)
C13—N3—C14	118.7 (11)	N3—C9—H9	120.3
C9—N3—C14	118.4 (9)	C10—C9—H9	120.3
O1—C1—C2	122.2 (17)	C11—C10—C9	116.8 (12)
O1—C1—C6	121.8 (12)	C11—C10—H10	121.6
C2—C1—C6	115.9 (12)	C9—C10—H10	121.6
C7—C2—C1	116.2 (12)	C10—C11—C12	122.3 (12)
C7—C2—C3	121.5 (11)	C10—C11—C15	119.6 (11)
C1—C2—C3	122.3 (17)	C12—C11—C15	118.1 (10)
C8—C3—C2	120.8 (15)	C13—C12—C11	117.3 (12)
C8—C3—C4	117.2 (11)	C13—C12—H12	121.3
C2—C3—C4	121.9 (11)	C11—C12—H12	121.3
O2—C4—C3	123.3 (11)	N3—C13—C12	121.1 (12)
O2—C4—C5	121.0 (15)	N3—C13—H13	119.5
C3—C4—C5	115.7 (10)	C12—C13—H13	119.5
C6—C5—C4	120.2 (15)	N3—C14—H14A	109.5
C6—C5—Cl1	123.9 (10)	N3—C14—H14B	109.5
C4—C5—Cl1	115.9 (9)	H14A—C14—H14B	109.5
C5—C6—C1	123.9 (11)	N3—C14—H14C	109.5
C5—C6—Cl2	119.0 (13)	H14A—C14—H14C	109.5
C1—C6—Cl2	117.1 (8)	H14B—C14—H14C	109.5
N1—C7—C2	177.8 (11)	N4—C15—C11	176.1 (17)
N2—C8—C3	174.7 (17)
O1—C1—C2—C7	−1.4 (15)	Cl1—C5—C6—C1	−178.7 (8)
C6—C1—C2—C7	177.6 (10)	C4—C5—C6—Cl2	178.6 (7)
O1—C1—C2—C3	−177.6 (10)	Cl1—C5—C6—Cl2	−0.8 (12)
C6—C1—C2—C3	1.4 (14)	O1—C1—C6—C5	176.9 (10)
C7—C2—C3—C8	1.3 (15)	C2—C1—C6—C5	−2.2 (15)
C1—C2—C3—C8	177.3 (10)	O1—C1—C6—Cl2	−1.1 (14)
C7—C2—C3—C4	−175.2 (10)	C2—C1—C6—Cl2	179.9 (7)
C1—C2—C3—C4	0.9 (15)	C13—N3—C9—C10	2 (2)
C8—C3—C4—O2	1.8 (15)	C14—N3—C9—C10	179.2 (15)
C2—C3—C4—O2	178.4 (9)	N3—C9—C10—C11	−4 (2)
C8—C3—C4—C5	−178.9 (8)	C9—C10—C11—C12	5 (2)
C2—C3—C4—C5	−2.3 (14)	C9—C10—C11—C15	−174.7 (15)
O2—C4—C5—C6	−179.1 (10)	C10—C11—C12—C13	−5 (2)
C3—C4—C5—C6	1.6 (13)	C15—C11—C12—C13	174.8 (16)
O2—C4—C5—Cl1	0.3 (13)	C9—N3—C13—C12	−2 (2)
C3—C4—C5—Cl1	−179.0 (8)	C14—N3—C13—C12	−179.1 (16)
C4—C5—C6—C1	0.7 (15)	C11—C12—C13—N3	3 (2)

(test3_5.48GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 276.92	Dx = 1.989 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0779 (9) Å	Cell parameters from 654 reflections
b = 9.783 (6) Å	θ = 2.1–22.9°
c = 19.555 (4) Å	µ = 0.58 mm^−1
β = 96.225 (16)°	T = 293 K
V = 1155.9 (7) Å^3	Block, black
Z = 5	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1257 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.173
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.1°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.367 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.362, Tmax = 0.449	k = −7→7
5634 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.137	H-atom parameters constrained
wR(F^2) = 0.384	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1257 reflections	Δρmax = 0.90 e Å^−3
94 parameters	Δρmin = −0.79 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2345 (5)	0.1144 (6)	−0.00246 (16)	0.0315 (12)*
Cl2	0.1426 (5)	0.2870 (6)	0.12660 (17)	0.0339 (13)*
O1	0.1723 (14)	0.5776 (14)	0.1038 (5)	0.033 (3)*
O2	0.3309 (14)	0.2805 (16)	−0.1177 (4)	0.033 (3)*
N1	0.2624 (16)	0.835 (2)	−0.0086 (5)	0.031 (3)*
N2	0.398 (2)	0.604 (2)	−0.1807 (7)	0.046 (4)*
N3	0.3047 (16)	0.9615 (18)	0.1772 (5)	0.029 (3)*
N4	1.0406 (19)	1.2265 (19)	0.2604 (6)	0.044 (4)*
C1	0.2136 (19)	0.514 (2)	0.0532 (7)	0.026 (4)*
C2	0.2705 (18)	0.571 (2)	−0.0088 (6)	0.021 (4)*
C3	0.3133 (17)	0.493 (2)	−0.0679 (6)	0.020 (3)*
C4	0.3006 (18)	0.348 (2)	−0.0666 (6)	0.020 (3)*
C5	0.2456 (17)	0.284 (2)	−0.0031 (5)	0.016 (3)*
C6	0.2106 (19)	0.367 (2)	0.0551 (6)	0.022 (3)*
C7	0.2667 (17)	0.713 (3)	−0.0100 (5)	0.015 (3)*
C8	0.355 (2)	0.556 (2)	−0.1288 (7)	0.026 (4)*
C9	0.332 (2)	1.004 (2)	0.2412 (7)	0.029 (4)*
H9	0.232136	0.977841	0.271484	0.034*
C10	0.511 (2)	1.089 (2)	0.2645 (8)	0.038 (4)*
H10	0.521501	1.129864	0.307581	0.046*
C11	0.671 (2)	1.108 (2)	0.2200 (8)	0.038 (4)*
C12	0.643 (3)	1.060 (2)	0.1544 (8)	0.045 (4)*
H12	0.747641	1.078000	0.124113	0.054*
C13	0.458 (2)	0.985 (2)	0.1340 (7)	0.043 (4)*
H13	0.438308	0.949846	0.089612	0.051*
C14	0.112 (2)	0.884 (2)	0.1539 (8)	0.042 (4)*
H14A	0.036993	0.925753	0.113540	0.051*
H14B	0.014627	0.880639	0.189400	0.051*
H14C	0.154693	0.792402	0.143078	0.051*
C15	0.872 (2)	1.180 (2)	0.2438 (7)	0.037 (4)*

Geometric parameters (Å, º)

Cl1—C5	1.66 (2)	C3—C4	1.42 (2)
Cl2—C6	1.695 (15)	C4—C5	1.465 (19)
O1—C1	1.218 (18)	C5—C6	1.44 (2)
O2—C4	1.230 (18)	C9—C10	1.40 (2)
N1—C7	1.19 (2)	C9—H9	0.9300
N2—C8	1.170 (18)	C10—C11	1.39 (2)
N3—C9	1.312 (17)	C10—H10	0.9300
N3—C13	1.346 (17)	C11—C12	1.36 (2)
N3—C14	1.43 (2)	C11—C15	1.44 (2)
N4—C15	1.135 (18)	C12—C13	1.36 (2)
C1—C2	1.41 (2)	C12—H12	0.9300
C1—C6	1.43 (3)	C13—H13	0.9300
C2—C7	1.39 (2)	C14—H14A	0.9600
C2—C3	1.43 (2)	C14—H14B	0.9600
C3—C8	1.39 (2)	C14—H14C	0.9600
C9—N3—C13	121.2 (13)	N3—C9—C10	120.8 (13)
C9—N3—C14	119.3 (11)	N3—C9—H9	119.6
C13—N3—C14	119.5 (13)	C10—C9—H9	119.6
O1—C1—C2	126 (2)	C11—C10—C9	116.6 (15)
O1—C1—C6	119.0 (14)	C11—C10—H10	121.7
C2—C1—C6	115.0 (14)	C9—C10—H10	121.7
C7—C2—C1	113.8 (14)	C12—C11—C10	121.5 (16)
C7—C2—C3	121.6 (13)	C12—C11—C15	119.1 (13)
C1—C2—C3	124.4 (19)	C10—C11—C15	119.3 (14)
C8—C3—C4	118.4 (13)	C11—C12—C13	118.3 (15)
C8—C3—C2	121.3 (18)	C11—C12—H12	120.8
C4—C3—C2	120.2 (13)	C13—C12—H12	120.8
O2—C4—C3	120.7 (13)	N3—C13—C12	121.0 (15)
O2—C4—C5	121.5 (17)	N3—C13—H13	119.5
C3—C4—C5	117.8 (12)	C12—C13—H13	119.5
C6—C5—C4	119.4 (17)	N3—C14—H14A	109.5
C6—C5—Cl1	123.7 (11)	N3—C14—H14B	109.5
C4—C5—Cl1	116.9 (11)	H14A—C14—H14B	109.5
C1—C6—C5	123.2 (13)	N3—C14—H14C	109.5
C1—C6—Cl2	119.4 (10)	H14A—C14—H14C	109.5
C5—C6—Cl2	117.3 (15)	H14B—C14—H14C	109.5
N1—C7—C2	177.7 (11)	N4—C15—C11	174 (2)
N2—C8—C3	176.6 (19)
O1—C1—C2—C7	−2.9 (18)	C2—C1—C6—C5	−4.6 (17)
C6—C1—C2—C7	178.4 (11)	O1—C1—C6—Cl2	1.7 (16)
O1—C1—C2—C3	−178.5 (12)	C2—C1—C6—Cl2	−179.5 (9)
C6—C1—C2—C3	2.8 (17)	C4—C5—C6—C1	3.8 (17)
C7—C2—C3—C8	0.7 (17)	Cl1—C5—C6—C1	−178.0 (9)
C1—C2—C3—C8	176.0 (12)	C4—C5—C6—Cl2	178.9 (8)
C7—C2—C3—C4	−175.5 (11)	Cl1—C5—C6—Cl2	−2.9 (14)
C1—C2—C3—C4	−0.2 (17)	C13—N3—C9—C10	7 (3)
C8—C3—C4—O2	1.6 (17)	C14—N3—C9—C10	−175.4 (18)
C2—C3—C4—O2	177.9 (10)	N3—C9—C10—C11	−9 (3)
C8—C3—C4—C5	−177.1 (10)	C9—C10—C11—C12	8 (3)
C2—C3—C4—C5	−0.7 (16)	C9—C10—C11—C15	−172.6 (19)
O2—C4—C5—C6	−179.6 (11)	C10—C11—C12—C13	−4 (3)
C3—C4—C5—C6	−1.0 (15)	C15—C11—C12—C13	176 (2)
O2—C4—C5—Cl1	2.0 (15)	C9—N3—C13—C12	−3 (3)
C3—C4—C5—Cl1	−179.3 (8)	C14—N3—C13—C12	179.4 (19)
O1—C1—C6—C5	176.6 (11)	C11—C12—C13—N3	2 (3)

(test3_6.00GPa)

Crystal data

C8Cl2N2O2·C7H7N2	F(000) = 700
Mr = 276.92	Dx = 2.017 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0307 (11) Å	Cell parameters from 616 reflections
b = 9.769 (6) Å	θ = 2.1–25.7°
c = 19.465 (5) Å	µ = 0.59 mm^−1
β = 96.336 (18)°	T = 293 K
V = 1139.8 (8) Å^3	Block, black
Z = 5	0.25 × 0.10 × 0.05 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	1226 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.171
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.3°, θmin = 2.1°
Absorption correction: gaussian Gaussian integration over a grid of 16 x 16 x 16 points = 4096 total grid points Based upon method of Burnham (1966) Data corrected for diamond-anvil cell absorption Note that exptl_absorpt_correction_tmin and _tmax the total correction factors applied to the intensities The individual factors are: range of dac transmission factors (min-max) 0.376 0.454 range of gasket transmission (min-max) 1.000 1.000 range of P media transmission (min-max) 1.000 1.000 thickness of diamond anvil 1: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 1: 0.000 mm, mu = 0.0000 mm-1 thickness of diamond anvil 2: 1.950 mm, mu = 0.2020 mm-1 thickness of platten 2: 0.000 mm, mu = 0.0000 mm-1 Gasket shadowing corrections were made based upon Gasket thickness = 100.0 microns, radius = 150.0 microns Gasket absorption coeff = 0.00 mm-1 REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00 Non-absorbing pressure medium	h = −7→7
Tmin = 0.371, Tmax = 0.449	k = −7→7
5596 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.141	H-atom parameters constrained
wR(F^2) = 0.399	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1226 reflections	Δρmax = 0.99 e Å^−3
94 parameters	Δρmin = −0.85 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2338 (6)	0.1131 (6)	−0.00176 (18)	0.0342 (13)*
Cl2	0.1432 (6)	0.2879 (7)	0.12747 (18)	0.0359 (14)*
O1	0.1716 (16)	0.5766 (16)	0.1044 (5)	0.039 (3)*
O2	0.3299 (15)	0.2801 (17)	−0.1176 (5)	0.035 (3)*
N1	0.2674 (19)	0.838 (3)	−0.0094 (6)	0.038 (4)*
N2	0.398 (2)	0.605 (2)	−0.1823 (7)	0.048 (4)*
N3	0.3007 (18)	0.966 (2)	0.1760 (6)	0.035 (3)*
N4	1.040 (2)	1.227 (2)	0.2611 (7)	0.050 (4)*
C1	0.217 (2)	0.512 (2)	0.0532 (7)	0.026 (4)*
C2	0.268 (2)	0.574 (3)	−0.0092 (7)	0.030 (4)*
C3	0.312 (2)	0.497 (2)	−0.0680 (7)	0.027 (4)*
C4	0.294 (2)	0.352 (2)	−0.0667 (7)	0.030 (4)*
C5	0.2516 (19)	0.285 (2)	−0.0028 (6)	0.025 (4)*
C6	0.2075 (18)	0.365 (2)	0.0543 (6)	0.015 (3)*
C7	0.2644 (19)	0.722 (3)	−0.0105 (6)	0.016 (4)*
C8	0.355 (2)	0.558 (3)	−0.1295 (8)	0.033 (4)*
C9	0.328 (2)	1.007 (2)	0.2407 (7)	0.028 (4)*
H9	0.227026	0.981082	0.271044	0.033*
C10	0.511 (2)	1.092 (2)	0.2639 (8)	0.036 (4)*
H10	0.524249	1.132805	0.307301	0.043*
C11	0.667 (2)	1.110 (2)	0.2198 (8)	0.037 (5)*
C12	0.643 (2)	1.065 (2)	0.1533 (8)	0.033 (4)*
H12	0.744876	1.086646	0.122563	0.040*
C13	0.462 (2)	0.988 (2)	0.1347 (8)	0.041 (5)*
H13	0.447855	0.947057	0.091224	0.049*
C14	0.110 (3)	0.883 (3)	0.1514 (8)	0.045 (5)*
H14A	0.159668	0.793884	0.139371	0.067*
H14B	0.031882	0.925702	0.111317	0.067*
H14C	0.012970	0.875539	0.186951	0.067*
C15	0.873 (2)	1.180 (2)	0.2436 (7)	0.035 (4)*

Geometric parameters (Å, º)

Cl1—C5	1.69 (2)	C3—C4	1.42 (3)
Cl2—C6	1.694 (15)	C4—C5	1.45 (2)
O1—C1	1.234 (19)	C5—C6	1.41 (2)
O2—C4	1.25 (2)	C9—C10	1.41 (2)
N1—C7	1.14 (2)	C9—H9	0.9300
N2—C8	1.180 (19)	C10—C11	1.35 (2)
N3—C9	1.317 (18)	C10—H10	0.9300
N3—C13	1.345 (18)	C11—C12	1.36 (2)
N3—C14	1.44 (2)	C11—C15	1.45 (2)
N4—C15	1.123 (19)	C12—C13	1.34 (2)
C1—C2	1.42 (2)	C12—H12	0.9300
C1—C6	1.44 (3)	C13—H13	0.9300
C2—C3	1.42 (2)	C14—H14A	0.9600
C2—C7	1.44 (3)	C14—H14B	0.9600
C3—C8	1.39 (2)	C14—H14C	0.9600
C9—N3—C13	120.0 (14)	N3—C9—C10	119.8 (13)
C9—N3—C14	120.1 (12)	N3—C9—H9	120.1
C13—N3—C14	119.5 (14)	C10—C9—H9	120.1
O1—C1—C2	124 (2)	C11—C10—C9	116.6 (16)
O1—C1—C6	119.1 (15)	C11—C10—H10	121.7
C2—C1—C6	116.7 (14)	C9—C10—H10	121.7
C3—C2—C1	123 (2)	C10—C11—C12	123.5 (16)
C3—C2—C7	121.3 (15)	C10—C11—C15	119.3 (15)
C1—C2—C7	115.7 (14)	C12—C11—C15	117.1 (13)
C8—C3—C2	123 (2)	C13—C12—C11	116.0 (14)
C8—C3—C4	117.6 (14)	C13—C12—H12	122.0
C2—C3—C4	119.4 (15)	C11—C12—H12	122.0
O2—C4—C3	121.6 (15)	C12—C13—N3	123.2 (16)
O2—C4—C5	119 (2)	C12—C13—H13	118.4
C3—C4—C5	118.9 (14)	N3—C13—H13	118.4
C6—C5—C4	119.7 (19)	N3—C14—H14A	109.5
C6—C5—Cl1	121.8 (13)	N3—C14—H14B	109.5
C4—C5—Cl1	118.4 (13)	H14A—C14—H14B	109.5
C5—C6—C1	122.1 (14)	N3—C14—H14C	109.5
C5—C6—Cl2	119.9 (16)	H14A—C14—H14C	109.5
C1—C6—Cl2	118.0 (10)	H14B—C14—H14C	109.5
N1—C7—C2	177.4 (14)	N4—C15—C11	176 (2)
N2—C8—C3	177 (2)
O1—C1—C2—C3	−177.7 (13)	Cl1—C5—C6—C1	−178.4 (10)
C6—C1—C2—C3	−0.7 (18)	C4—C5—C6—Cl2	176.6 (9)
O1—C1—C2—C7	−0.3 (19)	Cl1—C5—C6—Cl2	2.1 (15)
C6—C1—C2—C7	176.6 (12)	O1—C1—C6—C5	178.4 (12)
C1—C2—C3—C8	177.9 (13)	C2—C1—C6—C5	1.3 (18)
C7—C2—C3—C8	0.6 (19)	O1—C1—C6—Cl2	−2.1 (17)
C1—C2—C3—C4	3 (2)	C2—C1—C6—Cl2	−179.2 (9)
C7—C2—C3—C4	−174.3 (12)	C13—N3—C9—C10	9 (3)
C8—C3—C4—O2	4 (2)	C14—N3—C9—C10	−177.9 (19)
C2—C3—C4—O2	179.5 (12)	N3—C9—C10—C11	−9 (3)
C8—C3—C4—C5	179.4 (11)	C9—C10—C11—C12	7 (3)
C2—C3—C4—C5	−5.4 (19)	C9—C10—C11—C15	−171.7 (19)
O2—C4—C5—C6	−178.8 (12)	C10—C11—C12—C13	−6 (3)
C3—C4—C5—C6	5.9 (18)	C15—C11—C12—C13	173 (2)
O2—C4—C5—Cl1	−4.2 (17)	C11—C12—C13—N3	7 (3)
C3—C4—C5—Cl1	−179.4 (10)	C9—N3—C13—C12	−8 (3)
C4—C5—C6—C1	−3.9 (18)	C14—N3—C13—C12	179 (2)