The title compound, C
18H
17N
3O, crystallizes in a conformation where the phenyl group is almost orthogonal to the aromatic part of the tetrahydronaphthalene moiety. In the crystal structure, molecules form one-dimensional extended chains
via N—H
O hydrogen bonds.
Supporting information
CCDC reference: 238799
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.082
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 26.32
From the CIF: _reflns_number_total 1632
Count of symmetry unique reflns 1637
Completeness (_total/calc) 99.69%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: Xtal3.7 (Hall et al., 2000); program(s) used to solve structure: Xtal3.7; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
cis-3-phenyl-3,3a,4,5-tetrahydrobenzo[
g]indazole-2-carboxamide
top
Crystal data top
C18H17N3O | F(000) = 308 |
Mr = 291.35 | Dx = 1.303 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 7.902 (7) Å | θ = 7.3–18.3° |
b = 7.004 (5) Å | µ = 0.08 mm−1 |
c = 13.736 (12) Å | T = 123 K |
β = 102.38 (8)° | Prism, colourless |
V = 742.6 (11) Å3 | 0.38 × 0.23 × 0.13 mm |
Z = 2 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.016 |
Radiation source: fine-focus sealed tube | θmax = 26.3°, θmin = 2.6° |
Graphite monochromator | h = 0→9 |
ω scans | k = 0→8 |
1697 measured reflections | l = −17→16 |
1632 independent reflections | 3 standard reflections every 200 reflections |
1473 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.117P] where P = (Fo2 + 2Fc2)/3 |
1632 reflections | (Δ/σ)max = 0.003 |
199 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.22 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. For (III), the ω-scan width was (0.65 + 0.72 tanθ)° with a ω-scan rate of
0.69–3.35° min-1. The scan angle was extended 25% on each side of each
peak for background measurement. Refinement was by full-matrix least-squares
methods. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O13 | 0.56308 (17) | 0.5399 (2) | 0.52162 (9) | 0.0225 (3) | |
N1 | 0.62075 (19) | 0.5149 (3) | 0.78380 (11) | 0.0193 (4) | |
N2 | 0.6114 (2) | 0.4610 (3) | 0.68449 (12) | 0.0193 (4) | |
N12 | 0.5120 (3) | 0.7613 (3) | 0.63285 (13) | 0.0272 (4) | |
H12A | 0.4776 | 0.8480 | 0.5865 | 0.033* | |
H12B | 0.5136 | 0.7881 | 0.6956 | 0.033* | |
C3 | 0.6800 (2) | 0.2683 (3) | 0.67344 (14) | 0.0184 (4) | |
H3 | 0.5982 | 0.1965 | 0.6204 | 0.022* | |
C3A | 0.6747 (2) | 0.1849 (3) | 0.77746 (15) | 0.0201 (4) | |
H3A | 0.5652 | 0.1101 | 0.7715 | 0.024* | |
C4 | 0.8256 (3) | 0.0615 (3) | 0.83134 (15) | 0.0270 (5) | |
H4A | 0.9363 | 0.1311 | 0.8367 | 0.032* | |
H4B | 0.8314 | −0.0579 | 0.7936 | 0.032* | |
C5 | 0.7964 (3) | 0.0150 (4) | 0.93574 (17) | 0.0320 (5) | |
H5A | 0.6959 | −0.0721 | 0.9291 | 0.038* | |
H5B | 0.8994 | −0.0531 | 0.9737 | 0.038* | |
C5A | 0.7641 (3) | 0.1891 (4) | 0.99392 (15) | 0.0256 (5) | |
C6 | 0.7980 (3) | 0.1855 (4) | 1.09845 (17) | 0.0331 (5) | |
H6 | 0.8422 | 0.0718 | 1.1323 | 0.040* | |
C7 | 0.7691 (3) | 0.3418 (4) | 1.15314 (17) | 0.0358 (6) | |
H7 | 0.7955 | 0.3359 | 1.2239 | 0.043* | |
C8 | 0.7013 (3) | 0.5083 (4) | 1.10534 (15) | 0.0312 (6) | |
H8 | 0.6810 | 0.6161 | 1.1432 | 0.037* | |
C9 | 0.6632 (3) | 0.5168 (4) | 1.00174 (15) | 0.0251 (5) | |
H9 | 0.6160 | 0.6301 | 0.9687 | 0.030* | |
C9A | 0.6947 (3) | 0.3578 (3) | 0.94617 (15) | 0.0210 (4) | |
C10 | 0.6605 (2) | 0.3634 (3) | 0.83690 (14) | 0.0181 (4) | |
C11 | 0.5617 (2) | 0.5886 (3) | 0.60791 (14) | 0.0180 (4) | |
C14 | 0.8591 (2) | 0.2716 (3) | 0.65000 (13) | 0.0195 (4) | |
C15 | 0.9100 (3) | 0.1154 (3) | 0.60067 (15) | 0.0249 (5) | |
H15 | 0.8316 | 0.0127 | 0.5808 | 0.030* | |
C16 | 1.0752 (3) | 0.1084 (4) | 0.58027 (15) | 0.0298 (5) | |
H16 | 1.1092 | 0.0016 | 0.5464 | 0.036* | |
C17 | 1.1895 (3) | 0.2579 (4) | 0.60962 (16) | 0.0307 (5) | |
H17 | 1.3023 | 0.2534 | 0.5959 | 0.037* | |
C18 | 1.1402 (3) | 0.4132 (4) | 0.65865 (16) | 0.0301 (5) | |
H18 | 1.2194 | 0.5150 | 0.6789 | 0.036* | |
C19 | 0.9749 (2) | 0.4213 (3) | 0.67850 (14) | 0.0238 (5) | |
H19 | 0.9411 | 0.5292 | 0.7116 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O13 | 0.0289 (7) | 0.0243 (8) | 0.0134 (7) | −0.0011 (7) | 0.0021 (5) | −0.0009 (6) |
N1 | 0.0192 (8) | 0.0254 (10) | 0.0129 (7) | 0.0003 (8) | 0.0022 (6) | −0.0007 (8) |
N2 | 0.0220 (8) | 0.0219 (9) | 0.0137 (8) | 0.0031 (7) | 0.0031 (6) | −0.0010 (7) |
N12 | 0.0441 (11) | 0.0221 (9) | 0.0143 (8) | 0.0050 (9) | 0.0037 (7) | 0.0030 (8) |
C3 | 0.0193 (9) | 0.0185 (10) | 0.0160 (9) | 0.0018 (8) | 0.0008 (7) | 0.0001 (9) |
C3A | 0.0175 (9) | 0.0223 (10) | 0.0201 (10) | −0.0014 (9) | 0.0027 (7) | 0.0022 (8) |
C4 | 0.0267 (10) | 0.0285 (12) | 0.0240 (10) | 0.0080 (9) | 0.0018 (8) | 0.0054 (10) |
C5 | 0.0348 (12) | 0.0289 (12) | 0.0297 (11) | 0.0080 (11) | 0.0011 (9) | 0.0115 (11) |
C5A | 0.0222 (10) | 0.0325 (12) | 0.0206 (10) | −0.0049 (10) | 0.0010 (8) | 0.0064 (10) |
C6 | 0.0303 (11) | 0.0422 (14) | 0.0227 (11) | −0.0029 (11) | −0.0029 (9) | 0.0128 (11) |
C7 | 0.0309 (12) | 0.0576 (17) | 0.0165 (10) | −0.0116 (12) | 0.0001 (9) | 0.0066 (11) |
C8 | 0.0280 (11) | 0.0472 (16) | 0.0196 (10) | −0.0092 (11) | 0.0080 (8) | −0.0052 (11) |
C9 | 0.0248 (10) | 0.0315 (12) | 0.0194 (9) | −0.0048 (10) | 0.0059 (7) | 0.0018 (10) |
C9A | 0.0174 (9) | 0.0291 (11) | 0.0156 (9) | −0.0038 (9) | 0.0015 (7) | 0.0031 (9) |
C10 | 0.0150 (9) | 0.0220 (10) | 0.0170 (9) | −0.0010 (8) | 0.0027 (7) | 0.0015 (9) |
C11 | 0.0160 (8) | 0.0201 (10) | 0.0169 (9) | −0.0023 (8) | 0.0015 (7) | 0.0020 (8) |
C14 | 0.0178 (9) | 0.0263 (10) | 0.0131 (9) | 0.0014 (9) | 0.0004 (7) | 0.0000 (9) |
C15 | 0.0224 (10) | 0.0274 (11) | 0.0235 (10) | 0.0012 (9) | 0.0018 (8) | −0.0045 (10) |
C16 | 0.0281 (11) | 0.0381 (13) | 0.0235 (11) | 0.0076 (11) | 0.0061 (8) | −0.0067 (11) |
C17 | 0.0190 (10) | 0.0508 (15) | 0.0223 (10) | 0.0028 (11) | 0.0042 (8) | −0.0022 (11) |
C18 | 0.0219 (10) | 0.0404 (15) | 0.0265 (12) | −0.0076 (10) | 0.0021 (8) | −0.0059 (10) |
C19 | 0.0232 (10) | 0.0299 (12) | 0.0175 (10) | −0.0020 (9) | 0.0024 (8) | −0.0062 (9) |
Geometric parameters (Å, º) top
O13—C11 | 1.236 (3) | C5A—C9A | 1.405 (3) |
N1—C10 | 1.287 (3) | C6—C7 | 1.375 (4) |
N1—N2 | 1.402 (2) | C6—H6 | 0.9500 |
N2—C11 | 1.372 (3) | C7—C8 | 1.388 (4) |
N2—C3 | 1.474 (3) | C7—H7 | 0.9500 |
N12—C11 | 1.339 (3) | C8—C9 | 1.391 (3) |
N12—H12A | 0.8800 | C8—H8 | 0.9500 |
N12—H12B | 0.8800 | C9—C9A | 1.402 (3) |
C3—C14 | 1.517 (3) | C9—H9 | 0.9500 |
C3—C3A | 1.553 (3) | C9A—C10 | 1.468 (3) |
C3—H3 | 1.0000 | C14—C15 | 1.391 (3) |
C3A—C10 | 1.511 (3) | C14—C19 | 1.392 (3) |
C3A—C4 | 1.529 (3) | C15—C16 | 1.393 (3) |
C3A—H3A | 1.0000 | C15—H15 | 0.9500 |
C4—C5 | 1.536 (3) | C16—C17 | 1.385 (4) |
C4—H4A | 0.9900 | C16—H16 | 0.9500 |
C4—H4B | 0.9900 | C17—C18 | 1.379 (4) |
C5—C5A | 1.509 (4) | C17—H17 | 0.9500 |
C5—H5A | 0.9900 | C18—C19 | 1.392 (3) |
C5—H5B | 0.9900 | C18—H18 | 0.9500 |
C5A—C6 | 1.403 (3) | C19—H19 | 0.9500 |
| | | |
C10—N1—N2 | 106.56 (18) | C6—C7—C8 | 120.2 (2) |
C11—N2—N1 | 121.15 (18) | C6—C7—H7 | 119.9 |
C11—N2—C3 | 124.65 (17) | C8—C7—H7 | 119.9 |
N1—N2—C3 | 113.75 (16) | C7—C8—C9 | 119.8 (2) |
C11—N12—H12A | 120.0 | C7—C8—H8 | 120.1 |
C11—N12—H12B | 120.0 | C9—C8—H8 | 120.1 |
H12A—N12—H12B | 120.0 | C8—C9—C9A | 119.9 (2) |
N2—C3—C14 | 112.86 (18) | C8—C9—H9 | 120.1 |
N2—C3—C3A | 99.58 (16) | C9A—C9—H9 | 120.1 |
C14—C3—C3A | 114.30 (17) | C9—C9A—C5A | 120.73 (19) |
N2—C3—H3 | 109.9 | C9—C9A—C10 | 121.4 (2) |
C14—C3—H3 | 109.9 | C5A—C9A—C10 | 117.9 (2) |
C3A—C3—H3 | 109.9 | N1—C10—C9A | 124.79 (19) |
C10—C3A—C4 | 110.29 (18) | N1—C10—C3A | 114.41 (17) |
C10—C3A—C3 | 101.87 (18) | C9A—C10—C3A | 120.78 (19) |
C4—C3A—C3 | 119.07 (18) | O13—C11—N12 | 123.93 (19) |
C10—C3A—H3A | 108.4 | O13—C11—N2 | 119.71 (19) |
C4—C3A—H3A | 108.4 | N12—C11—N2 | 116.35 (18) |
C3—C3A—H3A | 108.4 | C15—C14—C19 | 119.20 (19) |
C3A—C4—C5 | 108.30 (18) | C15—C14—C3 | 118.2 (2) |
C3A—C4—H4A | 110.0 | C19—C14—C3 | 122.6 (2) |
C5—C4—H4A | 110.0 | C14—C15—C16 | 120.4 (2) |
C3A—C4—H4B | 110.0 | C14—C15—H15 | 119.8 |
C5—C4—H4B | 110.0 | C16—C15—H15 | 119.8 |
H4A—C4—H4B | 108.4 | C17—C16—C15 | 119.7 (2) |
C5A—C5—C4 | 113.5 (2) | C17—C16—H16 | 120.1 |
C5A—C5—H5A | 108.9 | C15—C16—H16 | 120.1 |
C4—C5—H5A | 108.9 | C18—C17—C16 | 120.25 (19) |
C5A—C5—H5B | 108.9 | C18—C17—H17 | 119.9 |
C4—C5—H5B | 108.9 | C16—C17—H17 | 119.9 |
H5A—C5—H5B | 107.7 | C17—C18—C19 | 120.2 (2) |
C6—C5A—C9A | 117.6 (2) | C17—C18—H18 | 119.9 |
C6—C5A—C5 | 120.7 (2) | C19—C18—H18 | 119.9 |
C9A—C5A—C5 | 121.72 (19) | C18—C19—C14 | 120.2 (2) |
C7—C6—C5A | 121.8 (2) | C18—C19—H19 | 119.9 |
C7—C6—H6 | 119.1 | C14—C19—H19 | 119.9 |
C5A—C6—H6 | 119.1 | | |
| | | |
C10—N1—N2—C11 | 176.31 (17) | N2—N1—C10—C9A | 175.84 (16) |
C10—N1—N2—C3 | −11.1 (2) | N2—N1—C10—C3A | −2.7 (2) |
C11—N2—C3—C14 | 69.4 (2) | C9—C9A—C10—N1 | 8.8 (3) |
N1—N2—C3—C14 | −102.94 (19) | C5A—C9A—C10—N1 | −169.69 (18) |
C11—N2—C3—C3A | −168.99 (17) | C9—C9A—C10—C3A | −172.70 (18) |
N1—N2—C3—C3A | 18.67 (19) | C5A—C9A—C10—C3A | 8.8 (3) |
N2—C3—C3A—C10 | −17.73 (17) | C4—C3A—C10—N1 | 141.32 (18) |
C14—C3—C3A—C10 | 102.8 (2) | C3—C3A—C10—N1 | 14.0 (2) |
N2—C3—C3A—C4 | −139.21 (19) | C4—C3A—C10—C9A | −37.3 (2) |
C14—C3—C3A—C4 | −18.6 (3) | C3—C3A—C10—C9A | −164.65 (16) |
C10—C3A—C4—C5 | 57.3 (2) | N1—N2—C11—O13 | 176.33 (16) |
C3—C3A—C4—C5 | 174.43 (19) | C3—N2—C11—O13 | 4.5 (3) |
C3A—C4—C5—C5A | −52.6 (3) | N1—N2—C11—N12 | −4.4 (3) |
C4—C5—C5A—C6 | −156.25 (19) | C3—N2—C11—N12 | −176.19 (17) |
C4—C5—C5A—C9A | 25.7 (3) | N2—C3—C14—C15 | −155.28 (18) |
C9A—C5A—C6—C7 | −1.6 (3) | C3A—C3—C14—C15 | 91.9 (2) |
C5—C5A—C6—C7 | −179.7 (2) | N2—C3—C14—C19 | 26.7 (3) |
C5A—C6—C7—C8 | 1.3 (4) | C3A—C3—C14—C19 | −86.2 (3) |
C6—C7—C8—C9 | −0.2 (3) | C19—C14—C15—C16 | 0.2 (3) |
C7—C8—C9—C9A | −0.5 (3) | C3—C14—C15—C16 | −177.89 (19) |
C8—C9—C9A—C5A | 0.2 (3) | C14—C15—C16—C17 | 0.2 (3) |
C8—C9—C9A—C10 | −178.32 (18) | C15—C16—C17—C18 | −0.1 (3) |
C6—C5A—C9A—C9 | 0.9 (3) | C16—C17—C18—C19 | −0.3 (3) |
C5—C5A—C9A—C9 | 178.96 (19) | C17—C18—C19—C14 | 0.7 (3) |
C6—C5A—C9A—C10 | 179.40 (18) | C15—C14—C19—C18 | −0.7 (3) |
C5—C5A—C9A—C10 | −2.5 (3) | C3—C14—C19—C18 | 177.34 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12B···N1 | 0.88 | 2.33 | 2.693 (3) | 105 |
N12—H12A···O13i | 0.88 | 1.98 | 2.850 (3) | 171 |
C3—H3···O13ii | 1.00 | 2.36 | 3.350 (4) | 171 |
C17—H17···O13iii | 0.95 | 2.59 | 3.304 (3) | 132 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y−1/2, −z+1. |