In the crystal structure of the title compound, C
18H
22NO
2PS, molecules are linked by N—H
O hydrogen bonds, creating a chain of hydrogen-bonded molecules in the
a-axis direction.
Supporting information
CCDC reference: 642975
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.116
- Data-to-parameter ratio = 19.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C12 .. 7.20 su
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.600
From the CIF: _refine_ls_abs_structure_Flack_su 0.100
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.60
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C18 .. 5.74 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 27.49
From the CIF: _reflns_number_total 4102
Count of symmetry unique reflns 2384
Completeness (_total/calc) 172.06%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1718
Fraction of Friedel pairs measured 0.721
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P1 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem
1 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
5 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
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 166
analysis calculated for C~18~H~22~NO2~PS: C 62.45, H 6.44, P 8.63%;
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
2-Benzylamino-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphinane-2-thione
top
Crystal data top
C18H22NO2PS | Dx = 1.277 Mg m−3 |
Mr = 347.40 | Melting point: 420 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2389 reflections |
a = 6.6955 (6) Å | θ = 2.7–19.6° |
b = 15.2156 (13) Å | µ = 0.28 mm−1 |
c = 17.7423 (15) Å | T = 292 K |
V = 1807.5 (3) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.20 × 0.10 mm |
F(000) = 736 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4102 independent reflections |
Radiation source: fine-focus sealed tube | 2602 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
φ and ω scans | h = −7→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −19→17 |
Tmin = 0.947, Tmax = 0.973 | l = −16→23 |
10076 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max < 0.001 |
S = 0.96 | Δρmax = 0.26 e Å−3 |
4102 reflections | Δρmin = −0.15 e Å−3 |
210 parameters | Absolute structure: Flack (1983), 1718 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.6 (1) |
Secondary atom site location: difference Fourier map | |
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 | |
P1 | 0.88566 (13) | 0.84817 (5) | 0.07689 (4) | 0.0618 (2) | |
S1 | 0.79334 (17) | 0.77954 (5) | 0.16047 (5) | 0.0848 (3) | |
N1 | 0.8137 (5) | 0.81274 (15) | −0.00444 (13) | 0.0788 (8) | |
H1 | 0.7283 | 0.7705 | −0.0044 | 0.095* | |
O1 | 0.8232 (3) | 0.94851 (10) | 0.07744 (10) | 0.0502 (4) | |
O2 | 1.1217 (3) | 0.85530 (13) | 0.06953 (12) | 0.0803 (6) | |
C1 | 0.8180 (4) | 1.09561 (16) | 0.12247 (13) | 0.0471 (6) | |
C2 | 0.7508 (4) | 1.12421 (17) | 0.05297 (15) | 0.0561 (7) | |
H2 | 0.7687 | 1.0888 | 0.0108 | 0.067* | |
C3 | 0.6572 (5) | 1.20471 (19) | 0.04527 (19) | 0.0733 (9) | |
H3 | 0.6119 | 1.2228 | −0.0018 | 0.088* | |
C4 | 0.6313 (7) | 1.2575 (2) | 0.1064 (2) | 0.0910 (11) | |
H4 | 0.5681 | 1.3116 | 0.1012 | 0.109* | |
C5 | 0.6989 (6) | 1.2307 (2) | 0.1759 (2) | 0.0860 (11) | |
H5 | 0.6824 | 1.2672 | 0.2175 | 0.103* | |
C6 | 0.7915 (5) | 1.14967 (19) | 0.18430 (15) | 0.0648 (8) | |
H6 | 0.8358 | 1.1317 | 0.2315 | 0.078* | |
C7 | 0.9191 (4) | 1.00778 (14) | 0.13122 (12) | 0.0452 (6) | |
H7 | 0.8918 | 0.9860 | 0.1822 | 0.054* | |
C8 | 1.1465 (4) | 1.00658 (18) | 0.11896 (15) | 0.0554 (7) | |
C9 | 1.2191 (5) | 0.9125 (2) | 0.1242 (2) | 0.0767 (9) | |
H9A | 1.3623 | 0.9112 | 0.1158 | 0.092* | |
H9B | 1.1938 | 0.8904 | 0.1745 | 0.092* | |
C10 | 1.2492 (5) | 1.0583 (2) | 0.18298 (17) | 0.0785 (10) | |
H10A | 1.2034 | 1.0367 | 0.2308 | 0.118* | |
H10B | 1.2167 | 1.1195 | 0.1785 | 0.118* | |
H10C | 1.3912 | 1.0508 | 0.1794 | 0.118* | |
C11 | 1.2041 (5) | 1.0453 (2) | 0.04306 (16) | 0.0730 (9) | |
H11A | 1.3450 | 1.0379 | 0.0351 | 0.110* | |
H11B | 1.1720 | 1.1068 | 0.0423 | 0.110* | |
H11C | 1.1319 | 1.0158 | 0.0038 | 0.110* | |
C12 | 0.8780 (6) | 0.8446 (2) | −0.07733 (17) | 0.0903 (11) | |
H12A | 0.8521 | 0.7989 | −0.1142 | 0.108* | |
H12B | 1.0214 | 0.8532 | −0.0755 | 0.108* | |
C13 | 0.7846 (5) | 0.9280 (2) | −0.10531 (14) | 0.0600 (8) | |
C14 | 0.5875 (6) | 0.9480 (2) | −0.09257 (16) | 0.0722 (9) | |
H14 | 0.5083 | 0.9100 | −0.0644 | 0.087* | |
C15 | 0.5060 (6) | 1.0248 (3) | −0.12164 (18) | 0.0876 (11) | |
H15 | 0.3729 | 1.0385 | −0.1122 | 0.105* | |
C16 | 0.6198 (8) | 1.0801 (3) | −0.16376 (18) | 0.0933 (12) | |
H16 | 0.5647 | 1.1316 | −0.1828 | 0.112* | |
C17 | 0.8128 (8) | 1.0604 (3) | −0.17807 (18) | 0.0901 (12) | |
H17 | 0.8903 | 1.0977 | −0.2076 | 0.108* | |
C18 | 0.8936 (6) | 0.9847 (2) | −0.14854 (16) | 0.0770 (9) | |
H18 | 1.0269 | 0.9718 | −0.1583 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0753 (6) | 0.0444 (4) | 0.0657 (4) | 0.0013 (4) | −0.0058 (4) | −0.0077 (3) |
S1 | 0.1240 (9) | 0.0559 (4) | 0.0744 (5) | −0.0201 (5) | −0.0162 (5) | 0.0058 (4) |
N1 | 0.118 (3) | 0.0540 (13) | 0.0640 (14) | −0.0100 (15) | −0.0020 (15) | −0.0114 (12) |
O1 | 0.0496 (11) | 0.0415 (9) | 0.0595 (9) | −0.0053 (7) | −0.0054 (9) | −0.0067 (8) |
O2 | 0.0705 (15) | 0.0665 (12) | 0.1039 (15) | 0.0121 (12) | 0.0027 (13) | −0.0208 (12) |
C1 | 0.0479 (17) | 0.0423 (13) | 0.0511 (14) | −0.0112 (12) | 0.0048 (12) | −0.0040 (11) |
C2 | 0.060 (2) | 0.0483 (15) | 0.0596 (16) | −0.0042 (13) | −0.0022 (13) | −0.0037 (12) |
C3 | 0.083 (3) | 0.0521 (17) | 0.085 (2) | 0.0044 (16) | −0.0059 (18) | 0.0067 (16) |
C4 | 0.104 (3) | 0.0501 (18) | 0.119 (3) | 0.009 (2) | 0.010 (2) | 0.0002 (19) |
C5 | 0.113 (3) | 0.0548 (19) | 0.090 (2) | −0.0025 (19) | 0.018 (2) | −0.0237 (17) |
C6 | 0.080 (2) | 0.0543 (16) | 0.0605 (16) | −0.0096 (17) | 0.0071 (14) | −0.0078 (14) |
C7 | 0.0457 (17) | 0.0480 (14) | 0.0420 (12) | −0.0080 (12) | −0.0023 (11) | −0.0002 (11) |
C8 | 0.0414 (17) | 0.0665 (17) | 0.0585 (15) | −0.0063 (13) | −0.0012 (13) | −0.0009 (13) |
C9 | 0.055 (2) | 0.080 (2) | 0.095 (2) | 0.0087 (17) | −0.0111 (18) | −0.0044 (19) |
C10 | 0.055 (2) | 0.102 (3) | 0.078 (2) | −0.0190 (18) | −0.0138 (16) | −0.0028 (18) |
C11 | 0.058 (2) | 0.094 (2) | 0.0669 (17) | −0.0137 (17) | 0.0139 (16) | −0.0001 (17) |
C12 | 0.116 (3) | 0.082 (2) | 0.073 (2) | 0.017 (2) | 0.005 (2) | −0.0277 (19) |
C13 | 0.066 (2) | 0.0720 (19) | 0.0417 (14) | −0.0128 (16) | 0.0071 (14) | −0.0134 (13) |
C14 | 0.070 (2) | 0.089 (2) | 0.0578 (18) | −0.0157 (19) | 0.0119 (16) | 0.0006 (16) |
C15 | 0.069 (2) | 0.133 (3) | 0.0617 (19) | 0.019 (2) | 0.0016 (19) | −0.006 (2) |
C16 | 0.130 (4) | 0.100 (3) | 0.0503 (17) | 0.007 (3) | −0.004 (2) | 0.0035 (18) |
C17 | 0.109 (4) | 0.103 (3) | 0.0587 (19) | −0.042 (3) | −0.005 (2) | 0.0080 (19) |
C18 | 0.064 (2) | 0.111 (3) | 0.0562 (17) | −0.020 (2) | 0.0015 (16) | −0.0106 (18) |
Geometric parameters (Å, º) top
P1—O1 | 1.5829 (17) | C8—C10 | 1.544 (4) |
P1—O2 | 1.589 (2) | C9—H9A | 0.9700 |
P1—N1 | 1.614 (2) | C9—H9B | 0.9700 |
P1—S1 | 1.9162 (12) | C10—H10A | 0.9600 |
N1—C12 | 1.447 (4) | C10—H10B | 0.9600 |
N1—H1 | 0.8600 | C10—H10C | 0.9600 |
O1—C7 | 1.462 (3) | C11—H11A | 0.9600 |
O2—C9 | 1.457 (4) | C11—H11B | 0.9600 |
C1—C6 | 1.383 (3) | C11—H11C | 0.9600 |
C1—C2 | 1.383 (3) | C12—C13 | 1.500 (4) |
C1—C7 | 1.506 (3) | C12—H12A | 0.9700 |
C2—C3 | 1.383 (4) | C12—H12B | 0.9700 |
C2—H2 | 0.9300 | C13—C18 | 1.366 (4) |
C3—C4 | 1.362 (4) | C13—C14 | 1.373 (5) |
C3—H3 | 0.9300 | C14—C15 | 1.389 (5) |
C4—C5 | 1.374 (5) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.359 (5) |
C5—C6 | 1.389 (4) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—C17 | 1.350 (6) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—C8 | 1.538 (4) | C17—C18 | 1.376 (5) |
C7—H7 | 0.9800 | C17—H17 | 0.9300 |
C8—C9 | 1.515 (4) | C18—H18 | 0.9300 |
C8—C11 | 1.520 (4) | | |
| | | |
O1—P1—O2 | 101.38 (11) | O2—C9—H9A | 109.1 |
O1—P1—N1 | 104.41 (12) | C8—C9—H9A | 109.1 |
O2—P1—N1 | 104.25 (15) | O2—C9—H9B | 109.1 |
O1—P1—S1 | 115.83 (8) | C8—C9—H9B | 109.1 |
O2—P1—S1 | 114.93 (10) | H9A—C9—H9B | 107.9 |
N1—P1—S1 | 114.43 (11) | C8—C10—H10A | 109.5 |
C12—N1—P1 | 126.8 (2) | C8—C10—H10B | 109.5 |
C12—N1—H1 | 116.6 | H10A—C10—H10B | 109.5 |
P1—N1—H1 | 116.6 | C8—C10—H10C | 109.5 |
C7—O1—P1 | 118.89 (15) | H10A—C10—H10C | 109.5 |
C9—O2—P1 | 115.56 (19) | H10B—C10—H10C | 109.5 |
C6—C1—C2 | 118.6 (2) | C8—C11—H11A | 109.5 |
C6—C1—C7 | 120.3 (2) | C8—C11—H11B | 109.5 |
C2—C1—C7 | 121.2 (2) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 121.0 (3) | C8—C11—H11C | 109.5 |
C3—C2—H2 | 119.5 | H11A—C11—H11C | 109.5 |
C1—C2—H2 | 119.5 | H11B—C11—H11C | 109.5 |
C4—C3—C2 | 120.1 (3) | N1—C12—C13 | 117.1 (3) |
C4—C3—H3 | 119.9 | N1—C12—H12A | 108.0 |
C2—C3—H3 | 119.9 | C13—C12—H12A | 108.0 |
C3—C4—C5 | 119.9 (3) | N1—C12—H12B | 108.0 |
C3—C4—H4 | 120.1 | C13—C12—H12B | 108.0 |
C5—C4—H4 | 120.1 | H12A—C12—H12B | 107.3 |
C4—C5—C6 | 120.4 (3) | C18—C13—C14 | 117.8 (3) |
C4—C5—H5 | 119.8 | C18—C13—C12 | 119.9 (3) |
C6—C5—H5 | 119.8 | C14—C13—C12 | 122.2 (3) |
C1—C6—C5 | 120.0 (3) | C13—C14—C15 | 120.2 (3) |
C1—C6—H6 | 120.0 | C13—C14—H14 | 119.9 |
C5—C6—H6 | 120.0 | C15—C14—H14 | 119.9 |
O1—C7—C1 | 106.44 (19) | C16—C15—C14 | 120.3 (4) |
O1—C7—C8 | 109.6 (2) | C16—C15—H15 | 119.9 |
C1—C7—C8 | 116.2 (2) | C14—C15—H15 | 119.9 |
O1—C7—H7 | 108.1 | C17—C16—C15 | 120.2 (4) |
C1—C7—H7 | 108.1 | C17—C16—H16 | 119.9 |
C8—C7—H7 | 108.1 | C15—C16—H16 | 119.9 |
C9—C8—C11 | 109.8 (3) | C16—C17—C18 | 119.4 (4) |
C9—C8—C7 | 108.7 (2) | C16—C17—H17 | 120.3 |
C11—C8—C7 | 111.9 (2) | C18—C17—H17 | 120.3 |
C9—C8—C10 | 107.1 (2) | C13—C18—C17 | 122.1 (4) |
C11—C8—C10 | 109.9 (2) | C13—C18—H18 | 118.9 |
C7—C8—C10 | 109.3 (2) | C17—C18—H18 | 118.9 |
O2—C9—C8 | 112.3 (2) | | |
| | | |
O1—P1—N1—C12 | 60.0 (3) | C2—C1—C7—C8 | 87.9 (3) |
O2—P1—N1—C12 | −46.0 (3) | O1—C7—C8—C9 | −55.2 (3) |
S1—P1—N1—C12 | −172.4 (3) | C1—C7—C8—C9 | −175.8 (2) |
O2—P1—O1—C7 | −52.7 (2) | O1—C7—C8—C11 | 66.2 (3) |
N1—P1—O1—C7 | −160.78 (19) | C1—C7—C8—C11 | −54.4 (3) |
S1—P1—O1—C7 | 72.45 (18) | O1—C7—C8—C10 | −171.7 (2) |
O1—P1—O2—C9 | 51.8 (2) | C1—C7—C8—C10 | 67.6 (3) |
N1—P1—O2—C9 | 160.0 (2) | P1—O2—C9—C8 | −60.3 (3) |
S1—P1—O2—C9 | −73.9 (2) | C11—C8—C9—O2 | −64.6 (3) |
C6—C1—C2—C3 | −0.6 (4) | C7—C8—C9—O2 | 58.0 (3) |
C7—C1—C2—C3 | 179.7 (3) | C10—C8—C9—O2 | 176.0 (3) |
C1—C2—C3—C4 | 0.5 (5) | P1—N1—C12—C13 | −79.1 (4) |
C2—C3—C4—C5 | 0.2 (6) | N1—C12—C13—C18 | 146.8 (3) |
C3—C4—C5—C6 | −0.7 (6) | N1—C12—C13—C14 | −36.9 (4) |
C2—C1—C6—C5 | 0.1 (4) | C18—C13—C14—C15 | −1.6 (4) |
C7—C1—C6—C5 | 179.8 (3) | C12—C13—C14—C15 | −178.0 (3) |
C4—C5—C6—C1 | 0.6 (5) | C13—C14—C15—C16 | 1.0 (5) |
P1—O1—C7—C1 | −175.54 (16) | C14—C15—C16—C17 | 0.4 (5) |
P1—O1—C7—C8 | 58.1 (2) | C15—C16—C17—C18 | −1.1 (5) |
C6—C1—C7—O1 | 145.9 (2) | C14—C13—C18—C17 | 0.9 (4) |
C2—C1—C7—O1 | −34.4 (3) | C12—C13—C18—C17 | 177.4 (3) |
C6—C1—C7—C8 | −91.8 (3) | C16—C17—C18—C13 | 0.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.35 | 3.086 (3) | 144 |
Symmetry code: (i) x−1/2, −y+3/2, −z. |