6a-Meth­yl-7-phenyl­sulfon­yl-6-phenyl­sulfonyl­meth­yl-7,7a-dihydro-6aH-cyclo­propa[d][1,2,3]triazolo[4,3-b]pyridazine acetone hemisolvate

Katrusiak, A.; Katrusiak, A.

doi:10.1107/S1600536805018106

6a-Methyl-7-phenylsulfonyl-6-phenylsulfonylmethyl-7,7a-dihydro-6aH-cyclopropa[d][1,2,3]triazolo[4,3-b]pyridazine acetone hemisolvate

In the title inclusion structure, C₂₀H₁₈N₄O₄S₂·0.5C₃H₆O, the phenyl groups form hydrophobic channels along [001], hosting acetone molecules. The phenylsulfonyl substituent group and the methyl group on the cyclopropane ring are syn with respect to each other, and the two phenylsulfonyl groups are positioned on the same side of the triazolopyridazine ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018106/lh6417sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018106/lh6417Isup2.hkl Contains datablock I

CCDC reference: 277711

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.011 Å
R factor = 0.058
wR factor = 0.121
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.92 Ratio

Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.158
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.16
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.32 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         11

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C32
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.01
PLAT751_ALERT_4_C Bond    Calc     0.96000, Rep    0.959(8) ......  Senseless su
              C31  -H31A    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.96000, Rep    0.958(9) ......  Senseless su
              C31  -H31B    1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     0.96000, Rep    0.963(9) ......  Senseless su
              C31  -H31C    1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.00, Rep    109.5(7) ......  Senseless su
              C32  -C31  -H31A    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.00, Rep    109.5(8) ......  Senseless su
              C32  -C31  -H31B    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      110.00, Rep    109.8(8) ......  Senseless su
              H31A -C31  -H31B    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      109.00, Rep    109.2(8) ......  Senseless su
              C32  -C31  -H31C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      109.00, Rep    109.4(9) ......  Senseless su
              H31A -C31  -H31C    1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      109.00, Rep    109.4(8) ......  Senseless su
              H31B -C31  -H31C    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H6 O

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C21.5 H21 N4 O4.5 S2
            Atom count from _chemical_formula_moiety:C20 H18 N4 O4 S2

   1 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

6a-Methyl-7-phenylsulfonyl-6-phenylsulfonylmethyl-7,7a-dihydro-6aH– cyclopropa[d][1,2,3]triazolo[4,3-b]pyridazine:acetone solvate 2:1 top

Crystal data top

C₂₀H₁₈N₄O₄S₂·0.5C₃H₆O	F(000) = 1968
M_r = 471.54	D_x = 1.385 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1368 reflections
a = 28.242 (6) Å	θ = 2.4–28.1°
b = 9.5962 (19) Å	µ = 0.27 mm⁻¹
c = 21.108 (4) Å	T = 293 K
β = 127.74 (3)°	Plate, colourless
V = 4524 (2) Å³	0.22 × 0.13 × 0.05 mm
Z = 8

Data collection top

Kuma KM-4 CCD diffractometer	1569 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.158
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
ω scans	h = −33→32
16780 measured reflections	k = −8→11
3985 independent reflections	l = −24→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²)]
3985 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.3223 (2)	0.6313 (5)	0.0841 (3)	0.0464 (14)
N2	0.2701 (3)	0.5526 (5)	0.0283 (3)	0.0513 (14)
C3	0.2337 (3)	0.5754 (7)	0.0456 (4)	0.0457 (19)
H3	0.199 (2)	0.535 (4)	0.018 (3)	0.024 (16)*
N4	0.2575 (2)	0.6628 (4)	0.1073 (3)	0.0324 (12)
N5	0.23116 (19)	0.7049 (4)	0.1419 (3)	0.0316 (12)
C6	0.2610 (3)	0.7943 (5)	0.1995 (3)	0.0279 (14)
C7	0.3221 (2)	0.8477 (5)	0.2338 (3)	0.0268 (14)
C8	0.3489 (2)	0.7937 (6)	0.1937 (3)	0.0339 (15)
H8A	0.3924	0.7801	0.2280	0.041*
C9	0.3126 (3)	0.6944 (6)	0.1299 (3)	0.0320 (15)
C10	0.3632 (2)	0.8757 (5)	0.3246 (3)	0.0395 (16)
H101	0.4024	0.8847	0.3387	0.051*
H102	0.3622	0.7963	0.3514	0.051*
H103	0.3538	0.9583	0.3407	0.051*
C11	0.2297 (2)	0.8435 (5)	0.2329 (3)	0.0338 (15)
H111	0.2590	0.8798	0.2865	0.041*
H112	0.2096	0.7653	0.2364	0.041*
S12	0.17616 (7)	0.97576 (15)	0.17108 (9)	0.0407 (5)
O13	0.15302 (16)	1.0249 (3)	0.2117 (2)	0.0530 (12)
O14	0.20384 (16)	1.0737 (3)	0.1514 (2)	0.0512 (11)
C15	0.1180 (3)	0.8916 (6)	0.0819 (3)	0.0430 (17)
C16	0.1196 (3)	0.8810 (6)	0.0190 (4)	0.0488 (17)
H16A	0.1508	0.9222	0.0222	0.059*
C17	0.0758 (3)	0.8105 (7)	−0.0491 (4)	0.065 (2)
H17A	0.0773	0.8035	−0.0918	0.078*
C18	0.0299 (3)	0.7505 (9)	−0.0533 (5)	0.109 (3)
H18A	−0.0004	0.7035	−0.0995	0.131*
C19	0.0284 (3)	0.7595 (9)	0.0093 (5)	0.118 (3)
H19A	−0.0030	0.7177	0.0054	0.142*
C20	0.0720 (3)	0.8287 (8)	0.0789 (4)	0.081 (2)
H20A	0.0709	0.8332	0.1220	0.097*
C21	0.3267 (2)	0.9409 (5)	0.1795 (3)	0.0285 (14)
H21A	0.2887	0.9584	0.1266	0.034*
S22	0.37809 (8)	1.08033 (16)	0.21937 (9)	0.0393 (5)
O23	0.35305 (18)	1.1943 (4)	0.2346 (2)	0.0605 (13)
O24	0.43637 (17)	1.0294 (4)	0.2835 (2)	0.0535 (12)
C25	0.3794 (3)	1.1288 (6)	0.1399 (3)	0.0343 (15)
C26	0.4209 (3)	1.0718 (6)	0.1334 (3)	0.0504 (17)
H26A	0.4475	1.0042	0.1694	0.060*
C27	0.4223 (3)	1.1168 (8)	0.0722 (4)	0.069 (2)
H27A	0.4503	1.0799	0.0671	0.083*
C28	0.3827 (3)	1.2154 (7)	0.0195 (4)	0.065 (2)
H28A	0.3842	1.2459	−0.0210	0.078*
C29	0.3405 (3)	1.2705 (6)	0.0251 (4)	0.058 (2)
H29A	0.3133	1.3367	−0.0116	0.070*
C30	0.3390 (3)	1.2267 (6)	0.0854 (4)	0.0490 (18)
H30A	0.3106	1.2631	0.0897	0.059*
O32	0.0000	0.8250 (8)	−0.2500	0.089 (3)
C32	0.0000	0.9497 (13)	−0.2500	0.070 (3)
C31	0.0323 (4)	1.0308 (9)	−0.2723 (5)	0.122 (3)
H31A	0.0464	0.9693	−0.2932	0.183*
H31B	0.0654	1.0782	−0.2261	0.183*
H31C	0.0054	1.0981	−0.3127	0.183*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.054 (4)	0.053 (4)	0.039 (3)	0.001 (3)	0.033 (3)	−0.006 (3)
N2	0.066 (4)	0.052 (4)	0.049 (4)	0.007 (3)	0.042 (4)	−0.009 (3)
C3	0.044 (5)	0.037 (5)	0.041 (5)	−0.012 (4)	0.018 (4)	−0.012 (4)
N4	0.033 (3)	0.033 (3)	0.029 (3)	−0.003 (3)	0.018 (3)	−0.006 (2)
N5	0.035 (3)	0.035 (3)	0.032 (3)	−0.003 (3)	0.024 (3)	−0.005 (2)
C6	0.034 (4)	0.029 (4)	0.029 (4)	0.009 (3)	0.023 (3)	0.012 (3)
C7	0.027 (4)	0.028 (3)	0.025 (3)	−0.004 (3)	0.015 (3)	0.003 (3)
C8	0.030 (4)	0.047 (4)	0.040 (4)	0.001 (3)	0.029 (4)	0.001 (3)
C9	0.036 (4)	0.037 (4)	0.024 (4)	0.002 (3)	0.019 (4)	0.001 (3)
C10	0.036 (4)	0.053 (4)	0.023 (4)	−0.006 (3)	0.015 (3)	0.003 (3)
C11	0.030 (4)	0.046 (4)	0.031 (4)	−0.008 (3)	0.022 (3)	−0.003 (3)
S12	0.0483 (12)	0.0394 (10)	0.0492 (11)	−0.0012 (9)	0.0374 (10)	−0.0035 (9)
O13	0.066 (3)	0.048 (3)	0.070 (3)	−0.002 (2)	0.055 (3)	−0.015 (2)
O14	0.068 (3)	0.036 (2)	0.065 (3)	−0.015 (2)	0.049 (3)	−0.002 (2)
C15	0.043 (5)	0.050 (4)	0.029 (4)	−0.003 (3)	0.019 (4)	0.003 (3)
C16	0.048 (5)	0.057 (4)	0.055 (5)	−0.005 (4)	0.038 (4)	0.005 (4)
C17	0.047 (5)	0.108 (6)	0.028 (5)	−0.011 (5)	0.018 (4)	−0.012 (4)
C18	0.067 (6)	0.203 (10)	0.046 (6)	−0.066 (6)	0.028 (5)	−0.037 (6)
C19	0.065 (7)	0.223 (10)	0.075 (7)	−0.072 (6)	0.047 (6)	−0.036 (7)
C20	0.064 (6)	0.140 (7)	0.052 (5)	−0.036 (5)	0.042 (5)	−0.010 (5)
C21	0.022 (3)	0.047 (4)	0.020 (3)	−0.008 (3)	0.014 (3)	−0.005 (3)
S22	0.0418 (12)	0.0493 (11)	0.0387 (11)	−0.0137 (10)	0.0307 (10)	−0.0094 (9)
O23	0.088 (4)	0.050 (3)	0.090 (4)	−0.017 (2)	0.078 (3)	−0.029 (2)
O24	0.037 (3)	0.086 (3)	0.026 (2)	−0.020 (2)	0.013 (2)	0.001 (2)
C25	0.038 (4)	0.038 (4)	0.034 (4)	−0.003 (3)	0.025 (4)	−0.002 (3)
C26	0.040 (4)	0.076 (5)	0.049 (4)	0.015 (4)	0.034 (4)	0.008 (4)
C27	0.060 (5)	0.114 (7)	0.060 (5)	0.015 (5)	0.051 (5)	0.012 (5)
C28	0.083 (6)	0.085 (6)	0.053 (5)	−0.001 (5)	0.055 (5)	0.016 (4)
C29	0.067 (6)	0.048 (5)	0.066 (6)	0.009 (4)	0.044 (5)	0.013 (4)
C30	0.061 (5)	0.050 (5)	0.060 (5)	−0.001 (4)	0.049 (5)	0.002 (4)
O32	0.117 (7)	0.064 (5)	0.053 (5)	0.000	0.035 (5)	0.000
C32	0.060 (8)	0.086 (10)	0.049 (7)	0.000	0.025 (6)	0.000
C31	0.116 (8)	0.119 (7)	0.151 (9)	−0.019 (6)	0.092 (7)	−0.002 (6)

Geometric parameters (Å, º) top

N1—C9	1.305 (6)	C17—C18	1.372 (8)
N1—N2	1.416 (6)	C17—H17A	0.9300
N2—C3	1.303 (7)	C18—C19	1.351 (9)
C3—N4	1.334 (7)	C18—H18A	0.9300
C3—H3	0.88 (4)	C19—C20	1.379 (9)
N4—C9	1.354 (6)	C19—H19A	0.9300
N4—N5	1.383 (5)	C20—H20A	0.9300
N5—C6	1.294 (6)	C21—S22	1.764 (5)
C6—C7	1.495 (6)	C21—H21A	0.9800
C6—C11	1.505 (6)	S22—O24	1.433 (4)
C7—C21	1.518 (6)	S22—O23	1.441 (3)
C7—C8	1.529 (6)	S22—C25	1.764 (5)
C7—C10	1.540 (6)	C25—C26	1.373 (6)
C8—C9	1.443 (7)	C25—C30	1.379 (7)
C8—C21	1.500 (6)	C26—C27	1.386 (7)
C8—H8A	0.9800	C26—H26A	0.9300
C10—H101	0.9600	C27—C28	1.365 (8)
C10—H102	0.9600	C27—H27A	0.9300
C10—H103	0.9600	C28—C29	1.373 (7)
C11—S12	1.784 (5)	C28—H28A	0.9300
C11—H111	0.9700	C29—C30	1.364 (7)
C11—H112	0.9700	C29—H29A	0.9300
S12—O14	1.438 (3)	C30—H30A	0.9300
S12—O13	1.439 (3)	O32—C32	1.197 (10)
S12—C15	1.763 (6)	C32—C31ⁱ	1.478 (8)
C15—C16	1.360 (7)	C32—C31	1.478 (8)
C15—C20	1.397 (7)	C31—H31A	0.959 (8)
C16—C17	1.369 (7)	C31—H31B	0.958 (9)
C16—H16A	0.9300	C31—H31C	0.963 (9)

C9—N1—N2	106.2 (5)	C16—C17—C18	119.1 (7)
C3—N2—N1	106.0 (5)	C16—C17—H17A	120.4
N2—C3—N4	111.5 (6)	C18—C17—H17A	120.4
N2—C3—H3	121 (3)	C19—C18—C17	120.3 (7)
N4—C3—H3	128 (3)	C19—C18—H18A	119.9
C3—N4—C9	105.6 (5)	C17—C18—H18A	119.9
C3—N4—N5	125.9 (5)	C18—C19—C20	122.0 (7)
C9—N4—N5	128.4 (5)	C18—C19—H19A	119.0
C6—N5—N4	116.0 (4)	C20—C19—H19A	119.0
N5—C6—C7	125.2 (5)	C19—C20—C15	117.2 (7)
N5—C6—C11	114.6 (5)	C19—C20—H20A	121.4
C7—C6—C11	120.2 (5)	C15—C20—H20A	121.4
C6—C7—C21	116.3 (4)	C8—C21—C7	60.9 (3)
C6—C7—C8	115.6 (4)	C8—C21—S22	119.8 (4)
C21—C7—C8	59.0 (3)	C7—C21—S22	120.8 (4)
C6—C7—C10	115.3 (4)	C8—C21—H21A	114.9
C21—C7—C10	119.3 (4)	C7—C21—H21A	114.9
C8—C7—C10	119.9 (5)	S22—C21—H21A	114.9
C9—C8—C21	117.7 (5)	O24—S22—O23	119.0 (3)
C9—C8—C7	115.5 (5)	O24—S22—C25	107.9 (3)
C21—C8—C7	60.1 (3)	O23—S22—C25	108.1 (3)
C9—C8—H8A	117.1	O24—S22—C21	109.0 (2)
C21—C8—H8A	117.1	O23—S22—C21	108.0 (2)
C7—C8—H8A	117.1	C25—S22—C21	103.7 (2)
N1—C9—N4	110.7 (5)	C26—C25—C30	120.6 (5)
N1—C9—C8	130.2 (6)	C26—C25—S22	120.4 (5)
N4—C9—C8	119.0 (5)	C30—C25—S22	119.0 (5)
C7—C10—H101	104.3	C25—C26—C27	118.9 (6)
C7—C10—H102	108.9	C25—C26—H26A	120.6
H101—C10—H102	109.5	C27—C26—H26A	120.6
C7—C10—H103	115.1	C28—C27—C26	119.9 (6)
H101—C10—H103	109.5	C28—C27—H27A	120.1
H102—C10—H103	109.5	C26—C27—H27A	120.1
C6—C11—S12	111.0 (4)	C27—C28—C29	121.3 (6)
C6—C11—H111	109.4	C27—C28—H28A	119.4
S12—C11—H111	109.4	C29—C28—H28A	119.4
C6—C11—H112	109.4	C30—C29—C28	119.0 (6)
S12—C11—H112	109.4	C30—C29—H29A	120.5
H111—C11—H112	108.0	C28—C29—H29A	120.5
O14—S12—O13	118.9 (2)	C29—C30—C25	120.4 (6)
O14—S12—C15	107.9 (3)	C29—C30—H30A	119.8
O13—S12—C15	108.7 (3)	C25—C30—H30A	119.8
O14—S12—C11	108.0 (2)	O32—C32—C31ⁱ	121.8 (5)
O13—S12—C11	106.8 (2)	O32—C32—C31	121.8 (5)
C15—S12—C11	105.9 (3)	C31ⁱ—C32—C31	116.4 (11)
C16—C15—C20	120.5 (6)	C32—C31—H31A	109.5 (7)
C16—C15—S12	120.7 (5)	C32—C31—H31B	109.5 (8)
C20—C15—S12	118.7 (5)	H31A—C31—H31B	109.8 (8)
C15—C16—C17	120.9 (6)	C32—C31—H31C	109.2 (8)
C15—C16—H16A	119.6	H31A—C31—H31C	109.4 (9)
C17—C16—H16A	119.6	H31B—C31—H31C	109.4 (8)

C9—N1—N2—C3	−0.1 (6)	O13—S12—C15—C20	−28.3 (6)
N1—N2—C3—N4	0.5 (7)	C11—S12—C15—C20	86.1 (6)
N2—C3—N4—C9	−0.7 (7)	C20—C15—C16—C17	1.1 (9)
N2—C3—N4—N5	−178.0 (5)	S12—C15—C16—C17	177.2 (5)
C3—N4—N5—C6	−177.6 (5)	C15—C16—C17—C18	0.2 (10)
C9—N4—N5—C6	5.7 (7)	C16—C17—C18—C19	−0.9 (13)
N4—N5—C6—C7	−3.7 (7)	C17—C18—C19—C20	0.3 (15)
N4—N5—C6—C11	177.0 (4)	C18—C19—C20—C15	0.9 (13)
N5—C6—C7—C21	68.7 (7)	C16—C15—C20—C19	−1.6 (11)
C11—C6—C7—C21	−112.0 (5)	S12—C15—C20—C19	−177.7 (6)
N5—C6—C7—C8	2.3 (7)	C9—C8—C21—C7	105.0 (5)
C11—C6—C7—C8	−178.4 (4)	C9—C8—C21—S22	−144.1 (4)
N5—C6—C7—C10	−144.5 (5)	C7—C8—C21—S22	110.9 (4)
C11—C6—C7—C10	34.8 (6)	C6—C7—C21—C8	−105.4 (5)
C6—C7—C8—C9	−2.1 (7)	C10—C7—C21—C8	109.2 (5)
C21—C7—C8—C9	−108.6 (5)	C6—C7—C21—S22	145.3 (4)
C10—C7—C8—C9	143.1 (5)	C8—C7—C21—S22	−109.3 (5)
C6—C7—C8—C21	106.5 (5)	C10—C7—C21—S22	−0.1 (7)
C10—C7—C8—C21	−108.2 (5)	C8—C21—S22—O24	−20.0 (4)
N2—N1—C9—N4	−0.4 (6)	C7—C21—S22—O24	51.8 (5)
N2—N1—C9—C8	−176.1 (5)	C8—C21—S22—O23	−150.7 (4)
C3—N4—C9—N1	0.7 (6)	C7—C21—S22—O23	−78.8 (5)
N5—N4—C9—N1	177.8 (4)	C8—C21—S22—C25	94.7 (4)
C3—N4—C9—C8	177.0 (5)	C7—C21—S22—C25	166.6 (4)
N5—N4—C9—C8	−5.9 (8)	O24—S22—C25—C26	23.3 (5)
C21—C8—C9—N1	111.0 (6)	O23—S22—C25—C26	153.2 (4)
C7—C8—C9—N1	179.1 (5)	C21—S22—C25—C26	−92.3 (5)
C21—C8—C9—N4	−64.4 (6)	O24—S22—C25—C30	−155.5 (4)
C7—C8—C9—N4	3.7 (7)	O23—S22—C25—C30	−25.5 (5)
N5—C6—C11—S12	−80.7 (5)	C21—S22—C25—C30	89.0 (5)
C7—C6—C11—S12	100.0 (5)	C30—C25—C26—C27	1.5 (9)
C6—C11—S12—O14	−45.5 (4)	S22—C25—C26—C27	−177.2 (5)
C6—C11—S12—O13	−174.5 (4)	C25—C26—C27—C28	−0.5 (10)
C6—C11—S12—C15	69.8 (5)	C26—C27—C28—C29	−0.8 (11)
O14—S12—C15—C16	25.4 (6)	C27—C28—C29—C30	0.9 (10)
O13—S12—C15—C16	155.6 (5)	C28—C29—C30—C25	0.2 (9)
C11—S12—C15—C16	−90.1 (5)	C26—C25—C30—C29	−1.4 (9)
O14—S12—C15—C20	−158.5 (5)	S22—C25—C30—C29	177.3 (5)

Symmetry code: (i) −x, y, −z−1/2.

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6a-Meth­yl-7-phenyl­sulfon­yl-6-phenyl­sulfonyl­meth­yl-7,7a-dihydro-6aH-cyclo­propa[d][1,2,3]triazolo[4,3-b]pyridazine acetone hemisolvate

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6a-Methyl-7-phenylsulfonyl-6-phenylsulfonylmethyl-7,7a-dihydro-6aH-cyclopropa[d][1,2,3]triazolo[4,3-b]pyridazine acetone hemisolvate