Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028771/su6230sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028771/su6230Isup2.hkl |
CCDC reference: 287730
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.065
- wR factor = 0.140
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.73 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CG1 .. 2.92 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Crystals of compound (I) (obtained from Arvee Pharma, Mysore, India) were grown by evaporation of a hexane solution.
H atoms were located from the difference electron-density maps and were refined isotropically. Distance and angle restraints were applied to C12—H12B and C11—C12—H12B, respectively. The refined distances are in the ranges: Car—H = 0.87 (3)–0.99 (3) Å, methyl C—H = 0.95 (3)–1.00 (3) Å, and methylene C—H = 0.95 (3)–1.00 (3) Å.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C14H19ClO | F(000) = 256 |
Mr = 238.76 | Dx = 1.179 Mg m−3 |
Monoclinic, P21/m | Melting point: 321 K |
Hall symbol: -P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 8.247 (1) Å | Cell parameters from 1047 reflections |
b = 7.242 (1) Å | θ = 5–26° |
c = 11.414 (2) Å | µ = 0.26 mm−1 |
β = 99.548 (3)° | T = 293 K |
V = 672.3 (2) Å3 | Cube, colorless |
Z = 2 | 0.33 × 0.31 × 0.24 mm |
Bruker SMART CCD area-detector diffractometer | 1333 independent reflections |
Radiation source: fine-focus sealed tube | 948 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 25.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.90, Tmax = 0.94 | k = −8→8 |
3612 measured reflections | l = −13→11 |
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)] = 0.065 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.140 | All H-atom parameters refined |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.014P] where P = (Fo2 + 2Fc2)/3 |
1333 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.15 e Å−3 |
2 restraints | Δρmin = −0.24 e Å−3 |
C14H19ClO | V = 672.3 (2) Å3 |
Mr = 238.76 | Z = 2 |
Monoclinic, P21/m | Mo Kα radiation |
a = 8.247 (1) Å | µ = 0.26 mm−1 |
b = 7.242 (1) Å | T = 293 K |
c = 11.414 (2) Å | 0.33 × 0.31 × 0.24 mm |
β = 99.548 (3)° |
Bruker SMART CCD area-detector diffractometer | 1333 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 948 reflections with I > 2σ(I) |
Tmin = 0.90, Tmax = 0.94 | Rint = 0.031 |
3612 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 2 restraints |
wR(F2) = 0.140 | All H-atom parameters refined |
S = 1.16 | Δρmax = 0.15 e Å−3 |
1333 reflections | Δρmin = −0.24 e Å−3 |
137 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.32876 (14) | 0.2500 | 0.94524 (9) | 0.0775 (5) | |
O1 | 0.3410 (3) | 0.2500 | 0.4744 (2) | 0.0752 (9) | |
C1 | 0.4802 (5) | 0.2500 | 0.8498 (4) | 0.0623 (12) | |
C2 | 0.4065 (4) | 0.2500 | 0.7199 (3) | 0.0443 (9) | |
C3 | 0.5428 (5) | 0.2500 | 0.6461 (3) | 0.0472 (9) | |
C4 | 0.4865 (5) | 0.2500 | 0.5144 (3) | 0.0460 (9) | |
C5 | 0.6117 (4) | 0.2500 | 0.4339 (3) | 0.0375 (8) | |
C6 | 0.5605 (4) | 0.2500 | 0.3121 (3) | 0.0436 (9) | |
C7 | 0.6723 (4) | 0.2500 | 0.2347 (3) | 0.0434 (9) | |
C8 | 0.8414 (4) | 0.2500 | 0.2756 (3) | 0.0387 (8) | |
C9 | 0.8913 (5) | 0.2500 | 0.3979 (3) | 0.0524 (10) | |
C10 | 0.7794 (4) | 0.2500 | 0.4751 (3) | 0.0528 (11) | |
C11 | 0.9699 (4) | 0.2500 | 0.1929 (3) | 0.0444 (9) | |
C12 | 0.8920 (6) | 0.2500 | 0.0614 (3) | 0.0607 (12) | |
C13 | 1.0771 (4) | 0.0775 (5) | 0.2172 (3) | 0.0590 (8) | |
H1 | 0.539 (3) | 0.143 (4) | 0.875 (2) | 0.075 (9)* | |
H2 | 0.335 (3) | 0.139 (3) | 0.7025 (18) | 0.047 (6)* | |
H3 | 0.610 (3) | 0.145 (3) | 0.665 (2) | 0.056 (7)* | |
H6 | 0.441 (4) | 0.2500 | 0.281 (3) | 0.053 (10)* | |
H7 | 0.632 (4) | 0.2500 | 0.152 (3) | 0.048 (10)* | |
H9 | 1.009 (4) | 0.2500 | 0.429 (3) | 0.056 (10)* | |
H10 | 0.815 (4) | 0.2500 | 0.551 (3) | 0.038 (9)* | |
H12A | 0.820 (3) | 0.147 (4) | 0.041 (2) | 0.087 (10)* | |
H12B | 0.973 (2) | 0.2500 | 0.0113 (11) | 0.097 (15)* | |
H13A | 1.133 (3) | 0.071 (4) | 0.297 (3) | 0.073 (9)* | |
H13B | 1.156 (3) | 0.078 (4) | 0.164 (2) | 0.070 (8)* | |
H13C | 1.013 (3) | −0.040 (4) | 0.206 (2) | 0.060 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0746 (8) | 0.1051 (10) | 0.0590 (7) | 0.000 | 0.0293 (6) | 0.000 |
O1 | 0.0373 (16) | 0.136 (3) | 0.0518 (16) | 0.000 | 0.0053 (12) | 0.000 |
C1 | 0.054 (3) | 0.083 (4) | 0.053 (3) | 0.000 | 0.018 (2) | 0.000 |
C2 | 0.041 (2) | 0.048 (2) | 0.044 (2) | 0.000 | 0.0085 (17) | 0.000 |
C3 | 0.041 (2) | 0.054 (3) | 0.047 (2) | 0.000 | 0.0079 (18) | 0.000 |
C4 | 0.040 (2) | 0.049 (2) | 0.049 (2) | 0.000 | 0.0060 (17) | 0.000 |
C5 | 0.0351 (19) | 0.0373 (19) | 0.0403 (19) | 0.000 | 0.0071 (15) | 0.000 |
C6 | 0.034 (2) | 0.047 (2) | 0.047 (2) | 0.000 | −0.0019 (17) | 0.000 |
C7 | 0.046 (2) | 0.045 (2) | 0.037 (2) | 0.000 | −0.0003 (17) | 0.000 |
C8 | 0.0372 (19) | 0.0366 (19) | 0.0411 (19) | 0.000 | 0.0028 (15) | 0.000 |
C9 | 0.035 (2) | 0.079 (3) | 0.042 (2) | 0.000 | 0.0029 (17) | 0.000 |
C10 | 0.043 (2) | 0.081 (3) | 0.033 (2) | 0.000 | 0.0012 (18) | 0.000 |
C11 | 0.039 (2) | 0.053 (2) | 0.0406 (19) | 0.000 | 0.0045 (16) | 0.000 |
C12 | 0.053 (3) | 0.090 (4) | 0.039 (2) | 0.000 | 0.010 (2) | 0.000 |
C13 | 0.0541 (19) | 0.065 (2) | 0.059 (2) | 0.0112 (17) | 0.0118 (16) | −0.0029 (17) |
Cl1—C1 | 1.788 (4) | C7—H7 | 0.95 (3) |
O1—C4 | 1.210 (4) | C8—C9 | 1.389 (5) |
C1—C2 | 1.506 (5) | C8—C11 | 1.532 (4) |
C1—H1 | 0.93 (2) | C9—C10 | 1.377 (5) |
C2—C3 | 1.512 (5) | C9—H9 | 0.98 (3) |
C2—H2 | 1.00 (2) | C10—H10 | 0.87 (3) |
C3—C4 | 1.499 (5) | C11—C13i | 1.529 (3) |
C3—H3 | 0.94 (2) | C11—C13 | 1.529 (3) |
C4—C5 | 1.492 (4) | C11—C12 | 1.531 (5) |
C5—C6 | 1.384 (4) | C12—H12A | 0.96 (3) |
C5—C10 | 1.385 (5) | C12—H12B | 0.949 (10) |
C6—C7 | 1.379 (5) | C13—H13A | 0.95 (3) |
C6—H6 | 0.99 (3) | C13—H13B | 0.96 (3) |
C7—C8 | 1.395 (5) | C13—H13C | 1.00 (3) |
C2—C1—Cl1 | 113.0 (3) | C7—C8—C11 | 123.3 (3) |
C2—C1—H1 | 113.9 (17) | C10—C9—C8 | 121.6 (3) |
Cl1—C1—H1 | 101.2 (17) | C10—C9—H9 | 120.1 (19) |
C1—C2—C3 | 109.4 (3) | C8—C9—H9 | 118.3 (19) |
C1—C2—H2 | 108.9 (13) | C9—C10—C5 | 121.4 (3) |
C3—C2—H2 | 111.1 (12) | C9—C10—H10 | 119 (2) |
C4—C3—C2 | 115.1 (3) | C5—C10—H10 | 120 (2) |
C4—C3—H3 | 107.7 (14) | C13i—C11—C13 | 109.6 (3) |
C2—C3—H3 | 109.4 (15) | C13i—C11—C12 | 108.3 (2) |
O1—C4—C5 | 120.8 (3) | C13—C11—C12 | 108.3 (2) |
O1—C4—C3 | 120.0 (3) | C13i—C11—C8 | 109.1 (2) |
C5—C4—C3 | 119.2 (3) | C13—C11—C8 | 109.1 (2) |
C6—C5—C10 | 117.5 (3) | C12—C11—C8 | 112.5 (3) |
C6—C5—C4 | 119.4 (3) | C11—C12—H12A | 112.6 (17) |
C10—C5—C4 | 123.0 (3) | C11—C12—H12B | 111.6 (11) |
C7—C6—C5 | 121.2 (3) | H12A—C12—H12B | 108.9 (19) |
C7—C6—H6 | 120.3 (18) | C11—C13—H13A | 112.7 (17) |
C5—C6—H6 | 118.5 (18) | C11—C13—H13B | 108.4 (15) |
C6—C7—C8 | 121.6 (3) | H13A—C13—H13B | 109 (2) |
C6—C7—H7 | 118.5 (19) | C11—C13—H13C | 113.1 (13) |
C8—C7—H7 | 119.9 (19) | H13A—C13—H13C | 104 (2) |
C9—C8—C7 | 116.7 (3) | H13B—C13—H13C | 109 (2) |
C9—C8—C11 | 120.0 (3) | ||
Cl1—C1—C2—C3 | 180 | C6—C7—C8—C11 | 180.0 |
C1—C2—C3—C4 | 180 | C7—C8—C9—C10 | 0.0 |
C2—C3—C4—O1 | 0.0 | C11—C8—C9—C10 | 180.0 |
C2—C3—C4—C5 | 180.0 | C8—C9—C10—C5 | 0.0 |
O1—C4—C5—C6 | 0.0 | C6—C5—C10—C9 | 0.0 |
C3—C4—C5—C6 | 180.0 | C4—C5—C10—C9 | 180.0 |
O1—C4—C5—C10 | 180.0 | C9—C8—C11—C13i | −59.8 (2) |
C3—C4—C5—C10 | 0.0 | C7—C8—C11—C13i | 120.2 (2) |
C10—C5—C6—C7 | 0.0 | C9—C8—C11—C13 | 59.8 (2) |
C4—C5—C6—C7 | 180.0 | C7—C8—C11—C13 | −120.2 (2) |
C5—C6—C7—C8 | 0.0 | C9—C8—C11—C12 | 180.0 |
C6—C7—C8—C9 | 0.0 | C7—C8—C11—C12 | 0.0 |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg1ii | 1.00 (2) | 2.92 (2) | 3.837 (1) | 154 (2) |
Symmetry code: (ii) −x+1, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H19ClO |
Mr | 238.76 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 293 |
a, b, c (Å) | 8.247 (1), 7.242 (1), 11.414 (2) |
β (°) | 99.548 (3) |
V (Å3) | 672.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.33 × 0.31 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.90, 0.94 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3612, 1333, 948 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.140, 1.16 |
No. of reflections | 1333 |
No. of parameters | 137 |
No. of restraints | 2 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.15, −0.24 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg1i | 1.00 (2) | 2.92 (2) | 3.837 (1) | 154 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1. |
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The title compound, 4-tert-butyl-γ-chloro-butyrophenone (or 4'-tert-butyl-4-chlorobutyrophenone), (I), belongs to the chemical class of butyrophenones, which are used as tranquillizers and act as antipsychotics through their action as dopamine antagonists (Brea et al., 2003). As part of our continuing interest in the solid-state studies on molecules of pharmaceutical interest, in this report we discuss the structure and crystal packing of compound (I).
The molecular structure of compound (I) is illustrated in Fig. 1. The molecule possesses Cs symmetry, with atoms Cl1 and C1–C12 lying in the mirror plane.
In the crystal structure, symmetry-related molecules stack along the b axis and this arrangement is stabilized by C—H···π interactions (Fig. 2 and Table 1) with typical dimensions (Nishio et al., 1998). The rest of the packing is governed by van der Waals forces.