In the title compound, C
12H
14F
3N
3O, 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.
Supporting information
CCDC reference: 642941
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.50 × 0.49 × 0.46 mm |
Data collection top
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 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0899P)2 + 0.0155P] where P = (Fo2 + 2Fc2)/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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 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. |