2-Acetyl-N-[3-(trifluoro­meth­yl)phen­yl]perhydro­pyridazine-1-carboxamide

In the title compound, C₁₄H₁₆F₃N₃O₂, the perhydro­pyridazine ring adopts a chair conformation. The amide plane is twisted away from the attached benzene ring by 17.6 (2)°. In the crystalline state, mol­ecules exist as centrosymmetric dimers, connected by inter­molecular N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.052
• wR factor = 0.141
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C12

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.753     1.000
            Tmin(prime) and Tmax expected:      0.950     0.972
            RR(prime) =      0.770
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.128
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.30 oblat
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.61 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C13     ..       3.00 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2-Acetyl-N-[3-(trifluoromethyl)phenyl]perhydropyridazine-1-carboxamide

Crystal data

C14H16F3N3O2	F(000) = 656
Mr = 315.30	Dx = 1.380 Mg m^−3
Monoclinic, P21/c	Melting point: 473 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.6680 (17) Å	Cell parameters from 1660 reflections
b = 11.634 (2) Å	θ = 5.7–43.1°
c = 14.246 (3) Å	µ = 0.12 mm^−1
β = 108.696 (3)°	T = 293 K
V = 1517.8 (5) Å^3	Prism, colourless
Z = 4	0.43 × 0.40 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	1720 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.129
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
Tmin = 0.753, Tmax = 1.000	k = −13→14
7716 measured reflections	l = −13→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0631P)^2] where P = (Fo^2 + 2Fc^2)/3
2821 reflections	(Δ/σ)max = 0.003
232 parameters	Δρmax = 0.19 e Å^−3
42 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. remaining

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.5835 (8)	0.6297 (11)	0.1256 (7)	0.107 (4)	0.422 (12)
F2	0.4267 (17)	0.4986 (7)	0.0787 (7)	0.116 (4)	0.422 (12)
F3	0.3650 (13)	0.6699 (12)	0.0618 (7)	0.138 (4)	0.422 (12)
F1'	0.5318 (12)	0.6865 (7)	0.1066 (5)	0.133 (3)	0.578 (12)
F2'	0.5455 (11)	0.5067 (7)	0.1206 (5)	0.128 (3)	0.578 (12)
F3'	0.3459 (5)	0.5874 (10)	0.0500 (4)	0.108 (3)	0.578 (12)
N1	0.2125 (2)	0.45322 (16)	0.35396 (15)	0.0443 (5)
N2	0.0329 (2)	0.31358 (15)	0.32883 (14)	0.0443 (5)
N3	0.0224 (2)	0.34179 (16)	0.42135 (14)	0.0461 (5)
O1	0.1773 (2)	0.31923 (14)	0.23157 (13)	0.0586 (5)
O2	−0.1182 (2)	0.40643 (16)	0.50732 (16)	0.0756 (7)
C1	0.3132 (2)	0.52570 (18)	0.33055 (17)	0.0394 (5)
C2	0.3431 (2)	0.5219 (2)	0.24258 (17)	0.0436 (6)
H2	0.3013	0.4650	0.1964	0.052*
C3	0.4352 (3)	0.6024 (2)	0.22245 (19)	0.0493 (7)
C4	0.4999 (3)	0.6857 (2)	0.2899 (2)	0.0660 (8)
H4	0.5627	0.7390	0.2764	0.079*
C5	0.4706 (3)	0.6894 (3)	0.3782 (2)	0.0709 (9)
H5	0.5134	0.7461	0.4243	0.085*
C6	0.3794 (3)	0.6107 (2)	0.3992 (2)	0.0565 (7)
H6	0.3614	0.6141	0.4595	0.068*
C7	0.1462 (3)	0.35920 (19)	0.30057 (17)	0.0418 (6)
C8	−0.0199 (3)	0.1979 (2)	0.2960 (2)	0.0597 (8)
H8A	−0.0042	0.1814	0.2335	0.072*
H8B	−0.1240	0.1937	0.2856	0.072*
C9	0.0588 (3)	0.1094 (2)	0.3723 (2)	0.0691 (8)
H9A	0.1600	0.1044	0.3745	0.083*
H9B	0.0141	0.0346	0.3534	0.083*
C10	0.0526 (3)	0.1410 (2)	0.4740 (2)	0.0693 (8)
H10A	0.1137	0.0887	0.5229	0.083*
H10B	−0.0469	0.1331	0.4749	0.083*
C11	0.1042 (3)	0.2640 (2)	0.50117 (19)	0.0572 (7)
H11A	0.0885	0.2855	0.5628	0.069*
H11B	0.2078	0.2697	0.5104	0.069*
C12	0.4605 (4)	0.5979 (3)	0.1252 (2)	0.0725 (9)
C13	−0.0964 (3)	0.3999 (2)	0.4277 (2)	0.0568 (7)
C14	−0.1919 (3)	0.4540 (3)	0.3344 (3)	0.0869 (10)
H14A	−0.2386	0.3951	0.2879	0.130*
H14B	−0.1336	0.5014	0.3065	0.130*
H14C	−0.2647	0.5004	0.3488	0.130*
H1	0.190 (2)	0.4737 (18)	0.4043 (16)	0.036 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.066 (4)	0.177 (9)	0.109 (5)	−0.025 (4)	0.071 (4)	−0.005 (5)
F2	0.173 (9)	0.114 (5)	0.099 (5)	−0.042 (5)	0.098 (6)	−0.024 (4)
F3	0.159 (8)	0.169 (7)	0.093 (5)	0.041 (6)	0.051 (5)	0.063 (5)
F1'	0.173 (7)	0.144 (5)	0.103 (4)	−0.068 (4)	0.075 (4)	0.021 (3)
F2'	0.163 (6)	0.156 (5)	0.098 (4)	0.067 (5)	0.088 (4)	0.016 (3)
F3'	0.075 (3)	0.191 (7)	0.061 (2)	−0.018 (4)	0.026 (2)	0.000 (4)
N1	0.0525 (13)	0.0446 (11)	0.0469 (13)	−0.0089 (10)	0.0314 (11)	−0.0095 (10)
N2	0.0535 (13)	0.0406 (10)	0.0475 (12)	−0.0123 (9)	0.0282 (10)	−0.0076 (9)
N3	0.0528 (13)	0.0429 (11)	0.0524 (13)	−0.0092 (10)	0.0306 (10)	−0.0085 (9)
O1	0.0751 (13)	0.0547 (10)	0.0626 (12)	−0.0140 (9)	0.0454 (10)	−0.0166 (9)
O2	0.0912 (15)	0.0677 (13)	0.0978 (16)	−0.0233 (11)	0.0721 (13)	−0.0279 (11)
C1	0.0368 (13)	0.0399 (12)	0.0475 (14)	0.0018 (10)	0.0219 (11)	0.0016 (11)
C2	0.0417 (14)	0.0455 (13)	0.0477 (14)	0.0009 (11)	0.0202 (11)	−0.0002 (11)
C3	0.0421 (14)	0.0544 (15)	0.0593 (16)	0.0020 (12)	0.0274 (12)	0.0096 (13)
C4	0.0585 (18)	0.0672 (18)	0.086 (2)	−0.0198 (15)	0.0418 (16)	−0.0050 (16)
C5	0.0642 (19)	0.0728 (19)	0.087 (2)	−0.0303 (15)	0.0403 (17)	−0.0236 (16)
C6	0.0549 (17)	0.0658 (16)	0.0597 (17)	−0.0147 (14)	0.0336 (14)	−0.0128 (13)
C7	0.0505 (15)	0.0400 (13)	0.0414 (14)	−0.0002 (11)	0.0240 (12)	−0.0005 (11)
C8	0.0655 (18)	0.0551 (15)	0.0681 (18)	−0.0228 (14)	0.0349 (15)	−0.0197 (14)
C9	0.077 (2)	0.0438 (15)	0.093 (2)	−0.0039 (14)	0.0365 (17)	−0.0069 (15)
C10	0.084 (2)	0.0494 (16)	0.075 (2)	−0.0012 (15)	0.0261 (17)	0.0125 (14)
C11	0.0630 (17)	0.0577 (16)	0.0522 (16)	−0.0093 (14)	0.0201 (13)	−0.0015 (13)
C12	0.072 (2)	0.084 (2)	0.071 (2)	−0.012 (2)	0.037 (2)	0.0099 (19)
C13	0.0559 (17)	0.0449 (14)	0.082 (2)	−0.0135 (13)	0.0394 (16)	−0.0137 (14)
C14	0.072 (2)	0.074 (2)	0.115 (3)	0.0139 (18)	0.030 (2)	0.0076 (19)

Geometric parameters (Å, º)

F1—C12	1.244 (7)	C3—C12	1.482 (4)
F2—C12	1.320 (7)	C4—C5	1.375 (3)
F3—C12	1.355 (8)	C4—H4	0.93
F1'—C12	1.314 (6)	C5—C6	1.368 (3)
F2'—C12	1.357 (5)	C5—H5	0.93
F3'—C12	1.276 (5)	C6—H6	0.93
N1—C7	1.368 (3)	C8—C9	1.514 (4)
N1—C1	1.407 (3)	C8—H8A	0.97
N1—H1	0.85 (2)	C8—H8B	0.97
N2—C7	1.388 (3)	C9—C10	1.515 (4)
N2—N3	1.393 (2)	C9—H9A	0.97
N2—C8	1.462 (3)	C9—H9B	0.97
N3—C13	1.360 (3)	C10—C11	1.523 (4)
N3—C11	1.470 (3)	C10—H10A	0.97
O1—C7	1.209 (2)	C10—H10B	0.97
O2—C13	1.221 (3)	C11—H11A	0.97
C1—C2	1.374 (3)	C11—H11B	0.97
C1—C6	1.394 (3)	C13—C14	1.493 (4)
C2—C3	1.384 (3)	C14—H14A	0.96
C2—H2	0.93	C14—H14B	0.96
C3—C4	1.367 (4)	C14—H14C	0.96
C7—N1—C1	125.7 (2)	C8—C9—C10	110.9 (2)
C7—N1—H1	119.4 (14)	C8—C9—H9A	109.5
C1—N1—H1	114.8 (14)	C10—C9—H9A	109.5
C7—N2—N3	119.21 (18)	C8—C9—H9B	109.5
C7—N2—C8	119.11 (19)	C10—C9—H9B	109.5
N3—N2—C8	113.28 (17)	H9A—C9—H9B	108.1
C13—N3—N2	119.9 (2)	C9—C10—C11	111.2 (2)
C13—N3—C11	120.7 (2)	C9—C10—H10A	109.4
N2—N3—C11	113.73 (19)	C11—C10—H10A	109.4
C2—C1—C6	118.6 (2)	C9—C10—H10B	109.4
C2—C1—N1	124.1 (2)	C11—C10—H10B	109.4
C6—C1—N1	117.2 (2)	H10A—C10—H10B	108.0
C1—C2—C3	120.3 (2)	N3—C11—C10	109.3 (2)
C1—C2—H2	119.8	N3—C11—H11A	109.8
C3—C2—H2	119.8	C10—C11—H11A	109.8
C4—C3—C2	120.9 (2)	N3—C11—H11B	109.8
C4—C3—C12	120.4 (2)	C10—C11—H11B	109.8
C2—C3—C12	118.6 (2)	H11A—C11—H11B	108.3
C3—C4—C5	118.9 (2)	F3'—C12—F1'	106.0 (5)
C3—C4—H4	120.6	F1—C12—F2	110.1 (6)
C5—C4—H4	120.6	F1—C12—F3	105.4 (6)
C6—C5—C4	121.0 (2)	F2—C12—F3	101.6 (6)
C6—C5—H5	119.5	F3'—C12—F2'	105.1 (5)
C4—C5—H5	119.5	F1'—C12—F2'	103.8 (5)
C5—C6—C1	120.3 (2)	F1—C12—C3	115.4 (5)
C5—C6—H6	119.9	F2—C12—C3	114.3 (3)
C1—C6—H6	119.9	F3—C12—C3	108.7 (5)
O1—C7—N1	124.4 (2)	O2—C13—N3	119.6 (3)
O1—C7—N2	120.9 (2)	O2—C13—C14	124.0 (3)
N1—C7—N2	114.62 (19)	N3—C13—C14	116.4 (2)
N2—C8—C9	110.7 (2)	C13—C14—H14A	109.5
N2—C8—H8A	109.5	C13—C14—H14B	109.5
C9—C8—H8A	109.5	H14A—C14—H14B	109.5
N2—C8—H8B	109.5	C13—C14—H14C	109.5
C9—C8—H8B	109.5	H14A—C14—H14C	109.5
H8A—C8—H8B	108.1	H14B—C14—H14C	109.5
C7—N2—N3—C13	117.4 (2)	N3—N2—C8—C9	−55.5 (3)
C8—N2—N3—C13	−94.7 (3)	N2—C8—C9—C10	52.0 (3)
C7—N2—N3—C11	−88.9 (2)	C8—C9—C10—C11	−52.0 (3)
C8—N2—N3—C11	59.0 (3)	C13—N3—C11—C10	97.1 (3)
C7—N1—C1—C2	10.0 (4)	N2—N3—C11—C10	−56.5 (3)
C7—N1—C1—C6	−174.0 (2)	C9—C10—C11—N3	52.8 (3)
C6—C1—C2—C3	−1.1 (3)	C4—C3—C12—F1	33.0 (8)
N1—C1—C2—C3	174.9 (2)	C2—C3—C12—F1	−148.0 (7)
C1—C2—C3—C4	1.1 (4)	C4—C3—C12—F3'	−131.8 (7)
C1—C2—C3—C12	−177.8 (2)	C2—C3—C12—F3'	47.2 (7)
C2—C3—C4—C5	−0.9 (4)	C4—C3—C12—F1'	−8.3 (7)
C12—C3—C4—C5	178.1 (3)	C2—C3—C12—F1'	170.7 (6)
C3—C4—C5—C6	0.6 (4)	C4—C3—C12—F2	162.3 (8)
C4—C5—C6—C1	−0.6 (4)	C2—C3—C12—F2	−18.7 (9)
C2—C1—C6—C5	0.8 (4)	C4—C3—C12—F3	−85.0 (8)
N1—C1—C6—C5	−175.4 (2)	C2—C3—C12—F3	93.9 (8)
C1—N1—C7—O1	8.0 (4)	C4—C3—C12—F2'	108.8 (6)
C1—N1—C7—N2	−169.3 (2)	C2—C3—C12—F2'	−72.2 (6)
N3—N2—C7—O1	164.4 (2)	N2—N3—C13—O2	166.9 (2)
C8—N2—C7—O1	18.4 (4)	C11—N3—C13—O2	15.0 (3)
N3—N2—C7—N1	−18.1 (3)	N2—N3—C13—C14	−14.1 (3)
C8—N2—C7—N1	−164.1 (2)	C11—N3—C13—C14	−166.0 (2)
C7—N2—C8—C9	92.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.85 (2)	2.14 (2)	2.925 (3)	154 (2)
C2—H2···O1	0.93	2.22	2.827 (3)	122
C6—H6···O2^i	0.93	2.55	3.217 (4)	129
C8—H8B···Cg1^ii	0.97	2.83	3.716 (3)	152

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2.