N-[3-(Trifluoro­meth­yl)phen­yl]perhydro­pyridazine-1-carboxamide

In the title compound, C₁₂H₁₄F₃N₃O, the perhydro­pyridazine ring adopts a chair conformation. The amide group and the benzene ring are coplanar. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into a chain along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.173
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C12
PLAT431_ALERT_2_B Short Inter HL..A Contact  F2     ..  F2      ..       2.55 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.754     1.000
            Tmin(prime) and Tmax expected:      0.939     0.946
            RR(prime) =      0.760
            Please check that your absorption correction is appropriate.
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.126
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 .............       0.76
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         300 Deg.
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.946
            Tmax scaled      0.946 Tmin scaled      0.714
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
   2 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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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).

N-[3-(Trifluoromethyl)phenyl]perhydropyridazine-1-carboxamide

Crystal data

C12H14F3N3O	Z = 2
Mr = 273.26	F(000) = 284
Triclinic, P1	Dx = 1.409 Mg m^−3
Hall symbol: -P 1	Melting point: 381 K
a = 5.8360 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1649 (14) Å	Cell parameters from 1369 reflections
c = 12.2330 (18) Å	θ = 5.7–53.6°
α = 91.394 (3)°	µ = 0.12 mm^−1
β = 96.658 (3)°	T = 293 K
γ = 97.337 (3)°	Prism, colourless
V = 644.06 (17) Å^3	0.50 × 0.49 × 0.46 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2478 independent reflections
Radiation source: fine-focus sealed tube	1781 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.126
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.754, Tmax = 1.000	k = −10→11
3536 measured reflections	l = −14→11

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0899P)^2 + 0.0155P] where P = (Fo^2 + 2Fc^2)/3
2478 reflections	(Δ/σ)max = 0.008
208 parameters	Δρmax = 0.22 e Å^−3
43 restraints	Δρmin = −0.25 e Å^−3

Special details

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	0.4780 (18)	0.6446 (7)	0.9400 (6)	0.110 (3)	0.505 (12)
F2	0.535 (2)	0.8660 (7)	0.9929 (7)	0.132 (3)	0.505 (12)
F3	0.7935 (11)	0.7301 (18)	1.0228 (7)	0.155 (4)	0.505 (12)
F1'	0.7317 (19)	0.6380 (8)	0.9879 (5)	0.124 (3)	0.495 (12)
F2'	0.4155 (11)	0.7185 (16)	0.9448 (6)	0.128 (3)	0.495 (12)
F3'	0.704 (2)	0.8489 (8)	1.0326 (5)	0.123 (3)	0.495 (12)
O1	0.7066 (3)	0.8561 (2)	0.41509 (14)	0.0753 (6)
N1	0.4931 (4)	0.7834 (2)	0.55379 (16)	0.0623 (6)
N2	0.3313 (3)	0.7593 (2)	0.37506 (15)	0.0614 (6)
N3	0.1263 (3)	0.6986 (3)	0.41657 (16)	0.0639 (6)
C1	0.6514 (4)	0.8167 (2)	0.64803 (19)	0.0520 (5)
C2	0.5771 (4)	0.7759 (2)	0.74767 (18)	0.0557 (6)
H2	0.4268	0.7286	0.7491	0.067*
C3	0.7230 (4)	0.8045 (2)	0.84486 (19)	0.0588 (6)
C4	0.9467 (4)	0.8736 (3)	0.8442 (2)	0.0676 (7)
H4	1.0464	0.8920	0.9095	0.081*
C5	1.0199 (4)	0.9150 (3)	0.7451 (2)	0.0681 (7)
H5	1.1700	0.9630	0.7443	0.082*
C6	0.8775 (4)	0.8871 (2)	0.6480 (2)	0.0598 (6)
H6	0.9315	0.9151	0.5821	0.072*
C7	0.5232 (4)	0.8036 (2)	0.44614 (19)	0.0538 (6)
C8	0.3262 (4)	0.7679 (3)	0.25576 (18)	0.0643 (7)
H8A	0.4809	0.8023	0.2376	0.077*
H8B	0.2230	0.8375	0.2289	0.077*
C9	0.2435 (5)	0.6200 (3)	0.2018 (2)	0.0773 (8)
H9A	0.3608	0.5553	0.2188	0.093*
H9B	0.2213	0.6290	0.1225	0.093*
C10	0.0183 (6)	0.5538 (3)	0.2399 (2)	0.0878 (9)
H10A	−0.0226	0.4537	0.2099	0.105*
H10B	−0.1051	0.6101	0.2132	0.105*
C11	0.0412 (5)	0.5535 (3)	0.3644 (2)	0.0807 (8)
H11A	−0.1095	0.5193	0.3873	0.097*
H11B	0.1472	0.4847	0.3898	0.097*
C12	0.6382 (5)	0.7592 (3)	0.9511 (2)	0.0777 (8)
H1	0.362 (4)	0.745 (3)	0.561 (2)	0.064 (7)*
H3	0.035 (4)	0.763 (2)	0.402 (2)	0.085 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.156 (7)	0.093 (3)	0.074 (3)	−0.033 (3)	0.037 (4)	0.009 (2)
F2	0.182 (6)	0.141 (4)	0.093 (4)	0.057 (4)	0.069 (4)	0.009 (3)
F3	0.124 (4)	0.242 (9)	0.094 (5)	0.027 (5)	−0.018 (3)	0.077 (6)
F1'	0.208 (7)	0.098 (4)	0.072 (3)	0.032 (4)	0.017 (4)	0.032 (3)
F2'	0.078 (3)	0.227 (9)	0.073 (3)	−0.010 (5)	0.013 (2)	0.051 (5)
F3'	0.190 (7)	0.101 (4)	0.070 (3)	−0.031 (4)	0.041 (4)	−0.019 (3)
O1	0.0532 (10)	0.1073 (13)	0.0656 (11)	−0.0043 (8)	0.0216 (8)	0.0157 (9)
N1	0.0438 (10)	0.0910 (14)	0.0496 (11)	−0.0072 (9)	0.0115 (8)	0.0072 (9)
N2	0.0512 (11)	0.0903 (13)	0.0424 (10)	−0.0021 (9)	0.0160 (8)	0.0063 (9)
N3	0.0480 (11)	0.0972 (16)	0.0465 (10)	0.0002 (11)	0.0158 (9)	0.0011 (10)
C1	0.0442 (11)	0.0564 (12)	0.0552 (12)	0.0031 (9)	0.0088 (9)	0.0059 (9)
C2	0.0464 (12)	0.0647 (13)	0.0553 (13)	0.0012 (9)	0.0085 (10)	0.0082 (10)
C3	0.0565 (13)	0.0600 (13)	0.0586 (14)	0.0043 (10)	0.0038 (11)	0.0065 (10)
C4	0.0556 (14)	0.0724 (15)	0.0701 (16)	0.0030 (11)	−0.0062 (12)	0.0031 (12)
C5	0.0467 (12)	0.0720 (15)	0.0823 (18)	−0.0035 (10)	0.0067 (12)	0.0036 (12)
C6	0.0487 (12)	0.0661 (14)	0.0649 (14)	0.0013 (10)	0.0145 (11)	0.0055 (11)
C7	0.0457 (12)	0.0632 (13)	0.0561 (13)	0.0080 (9)	0.0185 (10)	0.0108 (10)
C8	0.0679 (15)	0.0809 (16)	0.0471 (13)	0.0096 (12)	0.0167 (11)	0.0156 (11)
C9	0.0889 (19)	0.0944 (19)	0.0520 (14)	0.0103 (14)	0.0254 (13)	0.0012 (12)
C10	0.096 (2)	0.102 (2)	0.0580 (16)	−0.0199 (16)	0.0159 (15)	−0.0052 (14)
C11	0.0784 (17)	0.100 (2)	0.0580 (15)	−0.0203 (14)	0.0163 (13)	0.0104 (13)
C12	0.0782 (19)	0.093 (2)	0.0562 (16)	−0.0027 (16)	−0.0023 (14)	0.0106 (14)

Geometric parameters (Å, º)

F1—C12	1.307 (7)	C3—C4	1.377 (3)
F2—C12	1.336 (6)	C3—C12	1.493 (4)
F3—C12	1.245 (6)	C4—C5	1.377 (4)
F1'—C12	1.362 (6)	C4—H4	0.93
F2'—C12	1.298 (7)	C5—C6	1.367 (3)
F3'—C12	1.269 (5)	C5—H5	0.93
O1—C7	1.222 (2)	C6—H6	0.93
N1—C7	1.362 (3)	C8—C9	1.490 (4)
N1—C1	1.393 (3)	C8—H8A	0.97
N1—H1	0.81 (2)	C8—H8B	0.97
N2—C7	1.348 (3)	C9—C10	1.505 (4)
N2—N3	1.408 (2)	C9—H9A	0.97
N2—C8	1.461 (3)	C9—H9B	0.97
N3—C11	1.463 (3)	C10—C11	1.513 (4)
N3—H3	0.855 (19)	C10—H10A	0.97
C1—C2	1.385 (3)	C10—H10B	0.97
C1—C6	1.393 (3)	C11—H11A	0.97
C2—C3	1.378 (3)	C11—H11B	0.97
C2—H2	0.93
C7—N1—C1	129.47 (19)	C9—C8—H8A	109.7
C7—N1—H1	112.1 (19)	N2—C8—H8B	109.7
C1—N1—H1	118.5 (19)	C9—C8—H8B	109.7
C7—N2—N3	119.04 (18)	H8A—C8—H8B	108.2
C7—N2—C8	123.10 (18)	C8—C9—C10	111.3 (2)
N3—N2—C8	117.84 (19)	C8—C9—H9A	109.4
N2—N3—C11	110.5 (2)	C10—C9—H9A	109.4
N2—N3—H3	102.7 (19)	C8—C9—H9B	109.4
C11—N3—H3	113.9 (19)	C10—C9—H9B	109.4
C2—C1—N1	117.17 (18)	H9A—C9—H9B	108.0
C2—C1—C6	118.5 (2)	C9—C10—C11	110.4 (2)
N1—C1—C6	124.3 (2)	C9—C10—H10A	109.6
C3—C2—C1	120.9 (2)	C11—C10—H10A	109.6
C3—C2—H2	119.6	C9—C10—H10B	109.6
C1—C2—H2	119.6	C11—C10—H10B	109.6
C4—C3—C2	120.3 (2)	H10A—C10—H10B	108.1
C4—C3—C12	120.0 (2)	N3—C11—C10	113.0 (2)
C2—C3—C12	119.7 (2)	N3—C11—H11A	109.0
C3—C4—C5	118.7 (2)	C10—C11—H11A	109.0
C3—C4—H4	120.6	N3—C11—H11B	109.0
C5—C4—H4	120.6	C10—C11—H11B	109.0
C6—C5—C4	121.6 (2)	H11A—C11—H11B	107.8
C6—C5—H5	119.2	F3'—C12—F2'	110.0 (5)
C4—C5—H5	119.2	F3—C12—F1	106.6 (6)
C5—C6—C1	119.9 (2)	F3—C12—F2	107.6 (6)
C5—C6—H6	120.0	F1—C12—F2	104.4 (5)
C1—C6—H6	120.0	F3'—C12—F1'	100.7 (5)
O1—C7—N2	122.1 (2)	F2'—C12—F1'	103.5 (5)
O1—C7—N1	123.9 (2)	F3—C12—C3	114.3 (4)
N2—C7—N1	114.00 (18)	F1—C12—C3	113.3 (4)
N2—C8—C9	109.90 (18)	F2—C12—C3	110.0 (3)
N2—C8—H8A	109.7
C7—N2—N3—C11	−125.3 (2)	C1—N1—C7—N2	−179.7 (2)
C8—N2—N3—C11	53.3 (3)	C7—N2—C8—C9	124.8 (2)
C7—N1—C1—C2	−176.2 (2)	N3—N2—C8—C9	−53.7 (3)
C7—N1—C1—C6	3.5 (4)	N2—C8—C9—C10	51.7 (3)
N1—C1—C2—C3	179.9 (2)	C8—C9—C10—C11	−53.0 (3)
C6—C1—C2—C3	0.2 (3)	N2—N3—C11—C10	−51.7 (3)
C1—C2—C3—C4	−0.5 (4)	C9—C10—C11—N3	53.2 (4)
C1—C2—C3—C12	−180.0 (2)	C4—C3—C12—F3	−28.9 (10)
C2—C3—C4—C5	0.9 (4)	C2—C3—C12—F3	150.6 (9)
C12—C3—C4—C5	−179.7 (2)	C4—C3—C12—F3'	39.1 (9)
C3—C4—C5—C6	−1.0 (4)	C2—C3—C12—F3'	−141.4 (8)
C4—C5—C6—C1	0.7 (4)	C4—C3—C12—F2'	168.7 (8)
C2—C1—C6—C5	−0.3 (3)	C2—C3—C12—F2'	−11.8 (9)
N1—C1—C6—C5	−180.0 (2)	C4—C3—C12—F1	−151.3 (6)
N3—N2—C7—O1	179.5 (2)	C2—C3—C12—F1	28.2 (7)
C8—N2—C7—O1	1.0 (4)	C4—C3—C12—F2	92.3 (7)
N3—N2—C7—N1	−0.1 (3)	C2—C3—C12—F2	−88.3 (7)
C8—N2—C7—N1	−178.7 (2)	C4—C3—C12—F1'	−74.6 (6)
C1—N1—C7—O1	0.7 (4)	C2—C3—C12—F1'	104.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3	0.81 (2)	2.11 (3)	2.585 (3)	117 (2)
N3—H3···O1^i	0.85 (2)	2.22 (2)	2.997 (3)	152 (3)
C6—H6···O1	0.93	2.31	2.902 (3)	121

Symmetry code: (i) x−1, y, z.