Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055183/bt2580sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055183/bt2580Isup2.hkl |
CCDC reference: 672867
Key indicators
- Single-crystal X-ray study
- T = 218 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.097
- Data-to-parameter ratio = 23.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.86 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl2 - P .. 6.78 su
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 0.863 Tmax scaled 0.811 Tmin scaled 0.712
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared by literature methods (Märkl & Alig, 1984) and a suitable crystal was grown by crystallization from hexane.
All H atoms were placed in calculated positions and refined using a riding model with C—H = 0.98 Å for methylene groups and C—H = 0.99 Å for tertiary H atoms and U(H)=1.2Ueq(C).
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms have been excluded for clarity. |
C12H22Cl2NP | F(000) = 600 |
Mr = 282.18 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4694 (8) Å | Cell parameters from 30 reflections |
b = 17.8264 (18) Å | θ = 5.5–12.5° |
c = 12.939 (2) Å | µ = 0.52 mm−1 |
β = 96.872 (10)° | T = 218 K |
V = 1481.5 (3) Å3 | Block, colourless |
Z = 4 | 0.60 × 0.60 × 0.40 mm |
Siemens P4 diffractometer | 3150 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.087 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
profile fitting of θ/2θ scans | h = −1→8 |
Absorption correction: ψ scan (PROGRAM?; REFERENCE?) | k = −1→23 |
Tmin = 0.825, Tmax = 0.940 | l = −16→16 |
4540 measured reflections | 3 standard reflections every 97 reflections |
3387 independent reflections | intensity decay: none |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0422P)2 + 0.5948P] where P = (Fo2 + 2Fc2)/3 |
3387 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C12H22Cl2NP | V = 1481.5 (3) Å3 |
Mr = 282.18 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.4694 (8) Å | µ = 0.52 mm−1 |
b = 17.8264 (18) Å | T = 218 K |
c = 12.939 (2) Å | 0.60 × 0.60 × 0.40 mm |
β = 96.872 (10)° |
Siemens P4 diffractometer | 3150 reflections with I > 2σ(I) |
Absorption correction: ψ scan (PROGRAM?; REFERENCE?) | Rint = 0.087 |
Tmin = 0.825, Tmax = 0.940 | 3 standard reflections every 97 reflections |
4540 measured reflections | intensity decay: none |
3387 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.42 e Å−3 |
3387 reflections | Δρmin = −0.44 e Å−3 |
145 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 | ||
P | 0.39761 (7) | 0.13232 (2) | 0.62770 (3) | 0.04246 (13) | |
Cl1 | 0.25915 (8) | 0.17300 (4) | 0.75460 (3) | 0.06987 (19) | |
Cl2 | 0.69212 (6) | 0.17705 (3) | 0.67608 (3) | 0.04867 (13) | |
N | 0.3064 (2) | 0.18837 (7) | 0.53336 (9) | 0.0338 (3) | |
C11 | 0.2174 (2) | 0.15378 (8) | 0.43283 (10) | 0.0304 (3) | |
H11 | 0.1720 | 0.1955 | 0.3849 | 0.036* | |
C12 | 0.3785 (3) | 0.10924 (11) | 0.38213 (13) | 0.0460 (4) | |
H12A | 0.4303 | 0.0679 | 0.4281 | 0.055* | |
H12B | 0.4966 | 0.1418 | 0.3722 | 0.055* | |
C13 | 0.2853 (3) | 0.07775 (12) | 0.27726 (15) | 0.0558 (5) | |
H13A | 0.2487 | 0.1192 | 0.2288 | 0.067* | |
H13B | 0.3892 | 0.0466 | 0.2484 | 0.067* | |
C14 | 0.0926 (3) | 0.03115 (10) | 0.28753 (14) | 0.0522 (4) | |
H14A | 0.0311 | 0.0148 | 0.2183 | 0.063* | |
H14B | 0.1321 | −0.0137 | 0.3291 | 0.063* | |
C15 | −0.0672 (3) | 0.07542 (10) | 0.33883 (14) | 0.0456 (4) | |
H15A | −0.1855 | 0.0429 | 0.3484 | 0.055* | |
H15B | −0.1189 | 0.1169 | 0.2932 | 0.055* | |
C16 | 0.0250 (2) | 0.10661 (9) | 0.44403 (12) | 0.0394 (3) | |
H16A | −0.0792 | 0.1375 | 0.4731 | 0.047* | |
H16B | 0.0627 | 0.0651 | 0.4923 | 0.047* | |
C21 | 0.3110 (2) | 0.27110 (7) | 0.54083 (10) | 0.0285 (3) | |
H21 | 0.3746 | 0.2839 | 0.6121 | 0.034* | |
C22 | 0.0923 (2) | 0.30448 (9) | 0.52723 (13) | 0.0393 (3) | |
H22A | 0.0125 | 0.2843 | 0.5807 | 0.047* | |
H22B | 0.0208 | 0.2903 | 0.4589 | 0.047* | |
C23 | 0.1021 (3) | 0.38991 (10) | 0.53599 (16) | 0.0507 (4) | |
H23A | −0.0390 | 0.4105 | 0.5225 | 0.061* | |
H23B | 0.1590 | 0.4039 | 0.6070 | 0.061* | |
C24 | 0.2366 (3) | 0.42339 (9) | 0.45938 (15) | 0.0508 (4) | |
H24A | 0.1733 | 0.4131 | 0.3881 | 0.061* | |
H24B | 0.2441 | 0.4779 | 0.4687 | 0.061* | |
C25 | 0.4545 (3) | 0.39077 (9) | 0.47516 (13) | 0.0424 (3) | |
H25A | 0.5223 | 0.4048 | 0.5443 | 0.051* | |
H25B | 0.5366 | 0.4117 | 0.4231 | 0.051* | |
C26 | 0.4490 (2) | 0.30532 (8) | 0.46541 (11) | 0.0333 (3) | |
H26A | 0.3954 | 0.2913 | 0.3940 | 0.040* | |
H26B | 0.5906 | 0.2854 | 0.4803 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P | 0.0523 (3) | 0.0380 (2) | 0.0340 (2) | −0.00576 (17) | −0.00762 (17) | 0.01147 (15) |
Cl1 | 0.0472 (2) | 0.1311 (5) | 0.0323 (2) | −0.0049 (3) | 0.00896 (17) | 0.0195 (2) |
Cl2 | 0.0336 (2) | 0.0675 (3) | 0.0429 (2) | 0.00425 (17) | −0.00350 (15) | 0.00985 (18) |
N | 0.0439 (7) | 0.0295 (6) | 0.0260 (5) | −0.0043 (5) | −0.0046 (5) | 0.0024 (4) |
C11 | 0.0345 (7) | 0.0303 (6) | 0.0254 (6) | −0.0021 (5) | 0.0000 (5) | 0.0000 (5) |
C12 | 0.0372 (8) | 0.0569 (10) | 0.0446 (9) | 0.0003 (7) | 0.0073 (6) | −0.0099 (7) |
C13 | 0.0584 (11) | 0.0672 (12) | 0.0441 (9) | 0.0000 (9) | 0.0160 (8) | −0.0195 (8) |
C14 | 0.0636 (11) | 0.0451 (9) | 0.0474 (9) | −0.0027 (8) | 0.0035 (8) | −0.0180 (7) |
C15 | 0.0420 (8) | 0.0460 (9) | 0.0475 (9) | −0.0091 (7) | 0.0002 (7) | −0.0118 (7) |
C16 | 0.0392 (7) | 0.0416 (8) | 0.0380 (8) | −0.0079 (6) | 0.0074 (6) | −0.0064 (6) |
C21 | 0.0298 (6) | 0.0292 (6) | 0.0258 (6) | −0.0010 (5) | 0.0004 (5) | −0.0003 (5) |
C22 | 0.0307 (7) | 0.0437 (8) | 0.0440 (8) | 0.0014 (6) | 0.0059 (6) | −0.0004 (6) |
C23 | 0.0454 (9) | 0.0454 (9) | 0.0608 (11) | 0.0131 (7) | 0.0039 (8) | −0.0111 (8) |
C24 | 0.0644 (11) | 0.0272 (7) | 0.0583 (11) | 0.0028 (7) | −0.0031 (8) | 0.0005 (7) |
C25 | 0.0487 (9) | 0.0338 (7) | 0.0443 (8) | −0.0109 (6) | 0.0034 (7) | 0.0015 (6) |
C26 | 0.0332 (7) | 0.0332 (7) | 0.0340 (7) | −0.0017 (5) | 0.0058 (5) | 0.0016 (5) |
P—N | 1.6322 (12) | C16—H16A | 0.9800 |
P—Cl2 | 2.0910 (6) | C16—H16B | 0.9800 |
P—Cl1 | 2.0920 (8) | C21—C22 | 1.5259 (19) |
N—C21 | 1.4780 (17) | C21—C26 | 1.5263 (18) |
N—C11 | 1.4915 (17) | C21—H21 | 0.9900 |
C11—C12 | 1.520 (2) | C22—C23 | 1.528 (2) |
C11—C16 | 1.523 (2) | C22—H22A | 0.9800 |
C11—H11 | 0.9900 | C22—H22B | 0.9800 |
C12—C13 | 1.525 (2) | C23—C24 | 1.518 (3) |
C12—H12A | 0.9800 | C23—H23A | 0.9800 |
C12—H12B | 0.9800 | C23—H23B | 0.9800 |
C13—C14 | 1.517 (3) | C24—C25 | 1.516 (3) |
C13—H13A | 0.9800 | C24—H24A | 0.9800 |
C13—H13B | 0.9800 | C24—H24B | 0.9800 |
C14—C15 | 1.516 (2) | C25—C26 | 1.529 (2) |
C14—H14A | 0.9800 | C25—H25A | 0.9800 |
C14—H14B | 0.9800 | C25—H25B | 0.9800 |
C15—C16 | 1.524 (2) | C26—H26A | 0.9800 |
C15—H15A | 0.9800 | C26—H26B | 0.9800 |
C15—H15B | 0.9800 | ||
N—P—Cl2 | 103.02 (5) | C11—C16—H16B | 109.5 |
N—P—Cl1 | 102.97 (5) | C15—C16—H16B | 109.5 |
Cl2—P—Cl1 | 95.35 (3) | H16A—C16—H16B | 108.1 |
C21—N—C11 | 118.18 (10) | N—C21—C22 | 111.74 (12) |
C21—N—P | 124.00 (9) | N—C21—C26 | 111.44 (11) |
C11—N—P | 117.80 (9) | C22—C21—C26 | 112.07 (11) |
N—C11—C12 | 112.28 (12) | N—C21—H21 | 107.1 |
N—C11—C16 | 112.33 (12) | C22—C21—H21 | 107.1 |
C12—C11—C16 | 111.28 (13) | C26—C21—H21 | 107.1 |
N—C11—H11 | 106.8 | C21—C22—C23 | 110.51 (13) |
C12—C11—H11 | 106.8 | C21—C22—H22A | 109.5 |
C16—C11—H11 | 106.8 | C23—C22—H22A | 109.5 |
C11—C12—C13 | 110.96 (14) | C21—C22—H22B | 109.5 |
C11—C12—H12A | 109.4 | C23—C22—H22B | 109.5 |
C13—C12—H12A | 109.4 | H22A—C22—H22B | 108.1 |
C11—C12—H12B | 109.4 | C24—C23—C22 | 111.44 (14) |
C13—C12—H12B | 109.4 | C24—C23—H23A | 109.3 |
H12A—C12—H12B | 108.0 | C22—C23—H23A | 109.3 |
C14—C13—C12 | 111.44 (15) | C24—C23—H23B | 109.3 |
C14—C13—H13A | 109.3 | C22—C23—H23B | 109.3 |
C12—C13—H13A | 109.3 | H23A—C23—H23B | 108.0 |
C14—C13—H13B | 109.3 | C25—C24—C23 | 110.97 (14) |
C12—C13—H13B | 109.3 | C25—C24—H24A | 109.4 |
H13A—C13—H13B | 108.0 | C23—C24—H24A | 109.4 |
C15—C14—C13 | 111.35 (14) | C25—C24—H24B | 109.4 |
C15—C14—H14A | 109.4 | C23—C24—H24B | 109.4 |
C13—C14—H14A | 109.4 | H24A—C24—H24B | 108.0 |
C15—C14—H14B | 109.4 | C24—C25—C26 | 111.05 (13) |
C13—C14—H14B | 109.4 | C24—C25—H25A | 109.4 |
H14A—C14—H14B | 108.0 | C26—C25—H25A | 109.4 |
C14—C15—C16 | 111.49 (14) | C24—C25—H25B | 109.4 |
C14—C15—H15A | 109.3 | C26—C25—H25B | 109.4 |
C16—C15—H15A | 109.3 | H25A—C25—H25B | 108.0 |
C14—C15—H15B | 109.3 | C21—C26—C25 | 110.79 (12) |
C16—C15—H15B | 109.3 | C21—C26—H26A | 109.5 |
H15A—C15—H15B | 108.0 | C25—C26—H26A | 109.5 |
C11—C16—C15 | 110.70 (13) | C21—C26—H26B | 109.5 |
C11—C16—H16A | 109.5 | C25—C26—H26B | 109.5 |
C15—C16—H16A | 109.5 | H26A—C26—H26B | 108.1 |
Cl2—P—N—C21 | −48.37 (12) | C12—C11—C16—C15 | −55.90 (18) |
Cl1—P—N—C21 | 50.35 (12) | C14—C15—C16—C11 | 55.61 (19) |
Cl2—P—N—C11 | 130.23 (10) | C11—N—C21—C22 | 63.11 (16) |
Cl1—P—N—C11 | −131.06 (10) | P—N—C21—C22 | −118.30 (13) |
C21—N—C11—C12 | 116.26 (14) | C11—N—C21—C26 | −63.14 (16) |
P—N—C11—C12 | −62.42 (16) | P—N—C21—C26 | 115.45 (12) |
C21—N—C11—C16 | −117.42 (14) | N—C21—C22—C23 | 179.66 (13) |
P—N—C11—C16 | 63.90 (15) | C26—C21—C22—C23 | −54.44 (17) |
N—C11—C12—C13 | −177.33 (14) | C21—C22—C23—C24 | 55.33 (19) |
C16—C11—C12—C13 | 55.79 (19) | C22—C23—C24—C25 | −57.0 (2) |
C11—C12—C13—C14 | −55.2 (2) | C23—C24—C25—C26 | 56.89 (19) |
C12—C13—C14—C15 | 55.1 (2) | N—C21—C26—C25 | −179.22 (12) |
C13—C14—C15—C16 | −55.3 (2) | C22—C21—C26—C25 | 54.72 (16) |
N—C11—C16—C15 | 177.25 (12) | C24—C25—C26—C21 | −55.55 (17) |
Experimental details
Crystal data | |
Chemical formula | C12H22Cl2NP |
Mr | 282.18 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 218 |
a, b, c (Å) | 6.4694 (8), 17.8264 (18), 12.939 (2) |
β (°) | 96.872 (10) |
V (Å3) | 1481.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.52 |
Crystal size (mm) | 0.60 × 0.60 × 0.40 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | ψ scan (PROGRAM?; REFERENCE?) |
Tmin, Tmax | 0.825, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4540, 3387, 3150 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.097, 1.05 |
No. of reflections | 3387 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.44 |
Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Siemens, 1996).
The title molecule, (I) (Fig. 1), adopts an approximate Cs symmetry with a plane bisecting the phosphorus and nitrogen atoms and each of the two cyclohexyl groups which are in chair conformations. The chlorides sit either side of this plane. The nitrogen is essentially planar (sum of angles = 359.98°). There are no intermolecular interactions.