(3S)-4-[(1S)-1-(Dibenzyl­amino)-2-phenyl­ethyl]-1,3,2-dioxathiane

The title compound, C₂₅H₂₇NO₃S, was obtained as the major product from the reaction of (3S,4S)-4-(dibenzyl­amino)-5-phenyl­pentane-1,3-diol and sulfuryl dichloride. The mol­ecular packing in the crystal is stabilized by weak inter­molecular inter­actions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.072
• wR factor = 0.215
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          4
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O1      ..       5.90 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17    -   C18     ..       5.90 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C6     -C11           1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT731_ALERT_1_C Bond    Calc   1.327(17), Rep    1.326(8) ......       2.12 su-Rat
              C15  -C16     1.555   1.555

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           25.00
           From the CIF: _reflns_number_total               4004
           Count of symmetry unique reflns         2284
           Completeness (_total/calc)            175.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1720
           Fraction of Friedel pairs measured     0.753
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  14 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

---

Computing details

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: ORTEP-3 (Farrugia, 1997) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

(3S)-4-[(1S)-1-(Dibenzylamino)-2-phenylethyl]-1,3,2-dioxathiane

Crystal data

C25H27NO3S	F(000) = 896
Mr = 421.54	Dx = 1.231 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5908 reflections
a = 10.855 (2) Å	θ = 2.2–22.0°
b = 11.643 (2) Å	µ = 0.17 mm^−1
c = 18.002 (4) Å	T = 273 K
V = 2275.1 (8) Å^3	Chunk, colourless
Z = 4	0.48 × 0.36 × 0.28 mm

Data collection

Bruker APEX area-detector diffractometer	4004 independent reflections
Radiation source: fine-focus sealed tube	3426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.924, Tmax = 0.955	k = −13→13
16447 measured reflections	l = −20→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.072	H-atom parameters constrained
wR(F^2) = 0.215	w = 1/[σ^2(Fo^2) + (0.1146P)^2 + 0.7614P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.003
4004 reflections	Δρmax = 0.42 e Å^−3
251 parameters	Δρmin = −0.22 e Å^−3
6 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48723 (18)	0.53385 (15)	0.78589 (7)	0.1173 (6)
C3	0.5506 (3)	0.5394 (3)	0.64627 (18)	0.0607 (8)
H3A	0.4647	0.5562	0.6335	0.073*
N1	0.7358 (2)	0.4422 (3)	0.59713 (17)	0.0641 (7)
C4	0.6054 (3)	0.4657 (3)	0.58551 (19)	0.0586 (7)
H4A	0.6019	0.5130	0.5405	0.070*
C6	0.4020 (3)	0.3908 (3)	0.5380 (2)	0.0675 (9)
O3	0.5527 (3)	0.4756 (2)	0.71562 (14)	0.0855 (8)
C5	0.5258 (3)	0.3591 (3)	0.5682 (2)	0.0681 (9)
H5A	0.5684	0.3113	0.5324	0.082*
H5B	0.5150	0.3146	0.6133	0.082*
C11	0.2971 (4)	0.3741 (5)	0.5780 (2)	0.0879 (13)
H11A	0.3022	0.3431	0.6256	0.105*
C2	0.6164 (4)	0.6501 (3)	0.6591 (3)	0.0771 (10)
H2A	0.6126	0.6963	0.6143	0.093*
H2B	0.7024	0.6346	0.6698	0.093*
O1	0.5614 (4)	0.6499 (4)	0.7888 (2)	0.1169 (12)
C13	0.8031 (4)	0.5445 (5)	0.4854 (3)	0.0988 (15)
C8	0.2764 (4)	0.4638 (6)	0.4406 (3)	0.1009 (15)
H8A	0.2704	0.4938	0.3928	0.121*
C7	0.3892 (4)	0.4356 (5)	0.4687 (2)	0.0860 (12)
H7A	0.4590	0.4473	0.4397	0.103*
C19	0.7609 (4)	0.3435 (4)	0.6447 (3)	0.0820 (11)
H19A	0.7565	0.2740	0.6151	0.098*
H19B	0.6978	0.3388	0.6827	0.098*
C12	0.8043 (4)	0.4342 (4)	0.5274 (3)	0.0814 (11)
H12A	0.7685	0.3743	0.4968	0.098*
H12B	0.8889	0.4129	0.5380	0.098*
O2	0.3653 (4)	0.5599 (5)	0.7643 (3)	0.1398 (17)
C24	1.0633 (6)	0.2606 (6)	0.7311 (4)	0.134 (2)
H24A	1.1075	0.1932	0.7387	0.161*
C25	0.9547 (6)	0.2560 (5)	0.6935 (4)	0.122 (2)
H25A	0.9274	0.1856	0.6754	0.146*
C10	0.1831 (4)	0.4026 (7)	0.5492 (3)	0.1113 (19)
H10A	0.1124	0.3896	0.5771	0.134*
C9	0.1738 (4)	0.4487 (6)	0.4814 (3)	0.1032 (16)
H9A	0.0973	0.4701	0.4627	0.124*
C1	0.5603 (5)	0.7167 (4)	0.7230 (3)	0.1021 (16)
H1A	0.6067	0.7868	0.7309	0.123*
H1B	0.4762	0.7376	0.7108	0.123*
C23	1.1065 (5)	0.3560 (6)	0.7564 (4)	0.123 (2)
H23A	1.1762	0.3571	0.7864	0.147*
C21	0.9366 (5)	0.4490 (5)	0.7022 (5)	0.140 (3)
H21A	0.8957	0.5174	0.6919	0.168*
C17	0.8487 (8)	0.7488 (7)	0.4761 (6)	0.189 (5)
H17A	0.8862	0.8160	0.4925	0.227*
C22	1.0492 (6)	0.4523 (6)	0.7386 (5)	0.159 (3)
H22A	1.0846	0.5227	0.7505	0.191*
C18	0.8566 (6)	0.6418 (5)	0.5134 (4)	0.135 (2)
H18A	0.8993	0.6376	0.5581	0.162*
C14	0.7416 (6)	0.5548 (6)	0.4189 (4)	0.132 (2)*
H14A	0.7063	0.4882	0.3999	0.158*
C15	0.7269 (10)	0.6532 (8)	0.3778 (6)	0.187 (4)*
H15A	0.6866	0.6578	0.3323	0.224*
C16	0.7792 (10)	0.7408 (12)	0.4129 (7)	0.201 (4)*
H16A	0.7658	0.8111	0.3898	0.241*
C20	0.8860 (4)	0.3497 (4)	0.6817 (2)	0.0774 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1519 (15)	0.1211 (11)	0.0790 (8)	−0.0150 (10)	0.0270 (8)	−0.0237 (7)
C3	0.0493 (16)	0.0667 (19)	0.0660 (18)	−0.0009 (15)	−0.0011 (14)	−0.0010 (16)
N1	0.0483 (14)	0.0675 (16)	0.0766 (17)	0.0015 (12)	0.0031 (12)	−0.0095 (14)
C4	0.0462 (15)	0.0653 (18)	0.0644 (18)	−0.0042 (14)	−0.0002 (13)	−0.0031 (15)
C6	0.0579 (18)	0.078 (2)	0.066 (2)	−0.0118 (17)	−0.0060 (16)	−0.0200 (18)
O3	0.110 (2)	0.0792 (17)	0.0674 (15)	−0.0072 (16)	0.0054 (14)	−0.0065 (13)
C5	0.0603 (19)	0.075 (2)	0.069 (2)	−0.0034 (17)	0.0001 (16)	−0.0138 (17)
C11	0.064 (2)	0.133 (4)	0.067 (2)	−0.016 (2)	0.0008 (18)	0.004 (2)
C2	0.063 (2)	0.065 (2)	0.103 (3)	−0.0045 (17)	0.006 (2)	−0.009 (2)
O1	0.131 (3)	0.127 (3)	0.092 (2)	0.008 (2)	−0.002 (2)	−0.041 (2)
C13	0.065 (2)	0.133 (4)	0.098 (3)	0.001 (3)	0.034 (2)	−0.009 (3)
C8	0.078 (3)	0.152 (4)	0.073 (2)	−0.020 (3)	−0.019 (2)	0.003 (3)
C7	0.067 (2)	0.129 (4)	0.062 (2)	−0.019 (2)	0.0025 (17)	−0.005 (2)
C19	0.059 (2)	0.090 (3)	0.097 (3)	0.0036 (19)	−0.012 (2)	0.002 (2)
C12	0.060 (2)	0.094 (3)	0.090 (3)	0.0056 (19)	0.0105 (19)	−0.022 (2)
O2	0.128 (3)	0.167 (4)	0.124 (3)	−0.036 (3)	0.045 (3)	−0.042 (3)
C24	0.145 (5)	0.099 (4)	0.158 (6)	0.034 (4)	−0.076 (5)	−0.002 (4)
C25	0.124 (4)	0.082 (3)	0.159 (5)	0.010 (3)	−0.064 (4)	0.010 (3)
C10	0.061 (2)	0.185 (6)	0.088 (3)	−0.011 (3)	0.007 (2)	−0.005 (3)
C9	0.064 (2)	0.149 (5)	0.097 (3)	−0.003 (3)	−0.020 (2)	−0.015 (3)
C1	0.089 (3)	0.075 (3)	0.143 (5)	−0.008 (2)	0.006 (3)	−0.043 (3)
C23	0.089 (3)	0.139 (5)	0.140 (5)	0.031 (3)	−0.052 (3)	−0.029 (4)
C21	0.107 (4)	0.105 (4)	0.208 (7)	0.049 (3)	−0.071 (5)	−0.058 (4)
C17	0.184 (8)	0.128 (6)	0.256 (11)	−0.058 (6)	0.133 (9)	−0.037 (7)
C22	0.113 (4)	0.134 (5)	0.230 (8)	0.039 (4)	−0.089 (5)	−0.085 (5)
C18	0.134 (5)	0.119 (5)	0.151 (6)	−0.042 (4)	0.056 (4)	−0.011 (4)

Geometric parameters (Å, º)

S1—O2	1.412 (6)	C19—C20	1.513 (6)
S1—O1	1.574 (5)	C19—H19A	0.9700
S1—O3	1.602 (3)	C19—H19B	0.9700
C3—O3	1.453 (4)	C12—H12A	0.9700
C3—C2	1.492 (5)	C12—H12B	0.9700
C3—C4	1.513 (5)	C24—C23	1.289 (8)
C3—H3A	0.9800	C24—C25	1.360 (8)
N1—C4	1.456 (4)	C24—H24A	0.9300
N1—C19	1.459 (5)	C25—C20	1.339 (7)
N1—C12	1.462 (5)	C25—H25A	0.9300
C4—C5	1.544 (5)	C10—C9	1.336 (8)
C4—H4A	0.9800	C10—H10A	0.9300
C6—C7	1.359 (6)	C9—H9A	0.9300
C6—C11	1.362 (6)	C1—H1A	0.9700
C6—C5	1.496 (5)	C1—H1B	0.9700
C5—H5A	0.9700	C23—C22	1.322 (9)
C5—H5B	0.9700	C23—H23A	0.9300
C11—C10	1.382 (7)	C21—C20	1.332 (7)
C11—H11A	0.9300	C21—C22	1.387 (8)
C2—C1	1.515 (6)	C21—H21A	0.9300
C2—H2A	0.9700	C17—C16	1.369 (8)
C2—H2B	0.9700	C17—C18	1.418 (8)
O1—C1	1.417 (7)	C17—H17A	0.9300
C13—C18	1.369 (7)	C22—H22A	0.9300
C13—C14	1.376 (7)	C18—H18A	0.9300
C13—C12	1.490 (8)	C14—C15	1.374 (8)
C8—C9	1.346 (7)	C14—H14A	0.9300
C8—C7	1.365 (6)	C15—C16	1.326 (8)
C8—H8A	0.9300	C15—H15A	0.9300
C7—H7A	0.9300	C16—H16A	0.9300
O2—S1—O1	107.7 (3)	H19A—C19—H19B	107.8
O2—S1—O3	106.8 (2)	N1—C12—C13	112.1 (3)
O1—S1—O3	99.41 (19)	N1—C12—H12A	109.2
O3—C3—C2	107.6 (3)	C13—C12—H12A	109.2
O3—C3—C4	109.0 (3)	N1—C12—H12B	109.2
C2—C3—C4	114.4 (3)	C13—C12—H12B	109.2
O3—C3—H3A	108.6	H12A—C12—H12B	107.9
C2—C3—H3A	108.6	C23—C24—C25	121.7 (5)
C4—C3—H3A	108.6	C23—C24—H24A	119.2
C4—N1—C19	114.5 (3)	C25—C24—H24A	119.2
C4—N1—C12	112.5 (3)	C20—C25—C24	122.0 (6)
C19—N1—C12	111.0 (3)	C20—C25—H25A	119.0
N1—C4—C3	112.7 (3)	C24—C25—H25A	119.0
N1—C4—C5	115.0 (3)	C9—C10—C11	120.5 (4)
C3—C4—C5	112.4 (3)	C9—C10—H10A	119.8
N1—C4—H4A	105.2	C11—C10—H10A	119.8
C3—C4—H4A	105.2	C10—C9—C8	119.2 (5)
C5—C4—H4A	105.2	C10—C9—H9A	120.4
C7—C6—C11	117.1 (4)	C8—C9—H9A	120.4
C7—C6—C5	121.4 (3)	O1—C1—C2	110.6 (4)
C11—C6—C5	121.5 (4)	O1—C1—H1A	109.5
C3—O3—S1	117.1 (2)	C2—C1—H1A	109.5
C6—C5—C4	112.3 (3)	O1—C1—H1B	109.5
C6—C5—H5A	109.2	C2—C1—H1B	109.5
C4—C5—H5A	109.2	H1A—C1—H1B	108.1
C6—C5—H5B	109.2	C24—C23—C22	118.3 (5)
C4—C5—H5B	109.2	C24—C23—H23A	120.9
H5A—C5—H5B	107.9	C22—C23—H23A	120.9
C6—C11—C10	121.0 (4)	C20—C21—C22	121.2 (5)
C6—C11—H11A	119.5	C20—C21—H21A	119.4
C10—C11—H11A	119.5	C22—C21—H21A	119.4
C3—C2—C1	111.5 (3)	C16—C17—C18	111.5 (9)
C3—C2—H2A	109.3	C16—C17—H17A	124.3
C1—C2—H2A	109.3	C18—C17—H17A	124.3
C3—C2—H2B	109.3	C23—C22—C21	120.4 (6)
C1—C2—H2B	109.3	C23—C22—H22A	119.8
H2A—C2—H2B	108.0	C21—C22—H22A	119.8
C1—O1—S1	116.0 (3)	C13—C18—C17	121.8 (8)
C18—C13—C14	117.0 (7)	C13—C18—H18A	119.1
C18—C13—C12	121.5 (5)	C17—C18—H18A	119.1
C14—C13—C12	121.4 (5)	C15—C14—C13	126.7 (8)
C9—C8—C7	120.5 (5)	C15—C14—H14A	116.7
C9—C8—H8A	119.7	C13—C14—H14A	116.7
C7—C8—H8A	119.7	C16—C15—C14	109.6 (11)
C6—C7—C8	121.6 (4)	C16—C15—H15A	125.2
C6—C7—H7A	119.2	C14—C15—H15A	125.2
C8—C7—H7A	119.2	C15—C16—C17	133.2 (12)
N1—C19—C20	112.8 (3)	C15—C16—H16A	113.4
N1—C19—H19A	109.0	C17—C16—H16A	113.4
C20—C19—H19A	109.0	C21—C20—C25	115.7 (4)
N1—C19—H19B	109.0	C21—C20—C19	122.3 (4)
C20—C19—H19B	109.0	C25—C20—C19	122.0 (4)