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The chiral title compound, C16H24N2O3S, has been synthesized as a ligand for the asymmetric transfer hydrogenation process. The compound forms a layered structure with mol­ecules bonded in sheets via inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009701/si2003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009701/si2003Isup2.hkl
Contains datablock I

CCDC reference: 643093

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.060
  • wR factor = 0.183
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.151 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.15 PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.72 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT318_ALERT_2_C Check Hybridisation of N1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1' .. S1 .. 2.92 Ang.
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.72 From the CIF: _reflns_number_total 3483 From the CIF: _diffrn_reflns_limit_ max hkl 9. 12. 30. From the CIF: _diffrn_reflns_limit_ min hkl -9. -12. -30. TEST1: Expected hkl limits for theta max Calculated maximum hkl 9. 12. 32. Calculated minimum hkl -9. -12. -32. 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 27.72 From the CIF: _reflns_number_total 3483 Count of symmetry unique reflns 2231 Completeness (_total/calc) 156.12% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1252 Fraction of Friedel pairs measured 0.561 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2001); software used to prepare material for publication: SHELXL97.

N-(2-Aminophenyl)-1-[(1S,2R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept- 1-yl]methanesulfonamide top
Crystal data top
C16H24N2O3SF(000) = 696
Mr = 324.43Dx = 1.316 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 56 reflections
a = 6.9780 (14) Åθ = 5.5–10.4°
b = 9.5840 (19) ŵ = 0.21 mm1
c = 24.478 (5) ÅT = 295 K
V = 1637.0 (6) Å3Paralellepiped, colourless
Z = 41.0 × 0.6 × 0.4 mm
Data collection top
Kuma KM-4 κ-axis
diffractometer
Rint = 0.151
Radiation source: fine-focus sealed tubeθmax = 27.7°, θmin = 1.7°
Graphite monochromatorh = 99
separate ω–2θ scans for individual reflectionsk = 1212
4055 measured reflectionsl = 3030
3483 independent reflections3 standard reflections every 200 reflections
2482 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.060 w = 1/[σ2(Fo2) + (0.1164P)2 + 0.6351P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.183(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.69 e Å3
3483 reflectionsΔρmin = 0.46 e Å3
206 parametersExtinction correction: mixed
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (14)
Secondary atom site location: difference Fourier map
Special details top

Experimental. The crystal taken for the data collection exceeded dimensions of an uniformity area of the X-ray beam. Cutting the crystal would, however, disintegrate the crystal during the cutting procedure, and other crystals in the batch were too tiny for a measurement.

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
xyzUiso*/Ueq
S10.55230 (12)0.09221 (9)0.78541 (4)0.0354 (2)
O10.5398 (8)0.2390 (3)0.91663 (16)0.0742 (12)
H1'0.55880.26120.88470.12 (3)*
O20.4092 (4)0.1862 (3)0.80638 (13)0.0492 (8)
O30.4922 (5)0.0431 (3)0.76673 (13)0.0524 (8)
N10.6493 (5)0.1735 (3)0.73478 (14)0.0408 (8)
H10.61360.25760.72790.16 (4)*
N21.0406 (7)0.2478 (4)0.74437 (19)0.0602 (10)
H2B1.15990.26860.74780.08 (2)*
H2A0.95580.29190.76310.063 (16)*
C10.6664 (6)0.0048 (3)0.88845 (16)0.0351 (8)
C20.5160 (7)0.0891 (5)0.9202 (2)0.0576 (11)
H20.38720.06310.90790.069*
C30.5454 (11)0.0421 (7)0.9798 (2)0.0834 (19)
H3A0.59250.11821.00220.100*
H3B0.42710.00690.99540.100*
C40.6935 (7)0.0726 (5)0.9747 (2)0.0569 (12)
H40.75590.09771.00920.068*
C50.5978 (9)0.1958 (6)0.9451 (3)0.0711 (16)
H5A0.47240.21560.96030.069 (17)*
H5B0.67640.27910.94720.11 (3)*
C60.5820 (7)0.1430 (4)0.8856 (2)0.0496 (10)
H6A0.65520.20150.86090.060*
H6B0.44950.14080.87360.060*
C70.8314 (7)0.0159 (4)0.93076 (18)0.0436 (10)
C80.9857 (7)0.1193 (5)0.9132 (2)0.0595 (13)
H8A0.92660.20520.90210.089*
H8B1.07070.13670.94330.089*
H8C1.05690.08110.88320.089*
C90.9336 (9)0.1181 (5)0.9477 (3)0.0699 (16)
H9A1.04480.09530.96900.105*
H9B0.84830.17460.96910.105*
H9C0.97190.16880.91570.105*
C100.7346 (5)0.0682 (4)0.83507 (17)0.0360 (8)
H10A0.83300.00840.81970.043*
H10B0.79290.15790.84280.043*
C110.7919 (5)0.1112 (4)0.70105 (16)0.0379 (8)
C120.9856 (6)0.1441 (4)0.70897 (19)0.0423 (9)
C131.1195 (7)0.0718 (5)0.6785 (2)0.0501 (11)
H131.24920.08880.68420.060*
C141.0652 (8)0.0246 (4)0.6400 (2)0.0538 (11)
H141.15830.07150.61990.065*
C150.8758 (8)0.0522 (5)0.6308 (2)0.0610 (14)
H150.83980.11580.60410.073*
C160.7385 (7)0.0149 (4)0.66157 (19)0.0473 (10)
H160.60940.00440.65580.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0410 (4)0.0230 (4)0.0420 (5)0.0005 (4)0.0004 (4)0.0010 (4)
O10.124 (3)0.0391 (17)0.060 (2)0.035 (2)0.000 (2)0.0106 (16)
O20.0442 (16)0.0475 (16)0.0559 (18)0.0152 (12)0.0065 (13)0.0012 (14)
O30.074 (2)0.0284 (13)0.0547 (19)0.0209 (13)0.0073 (15)0.0014 (12)
N10.0588 (19)0.0196 (14)0.0440 (19)0.0078 (14)0.0068 (16)0.0080 (13)
N20.053 (2)0.053 (2)0.074 (3)0.0096 (19)0.003 (2)0.017 (2)
C10.0450 (19)0.0225 (15)0.038 (2)0.0007 (14)0.0022 (17)0.0020 (15)
C20.070 (3)0.045 (2)0.058 (3)0.018 (2)0.007 (2)0.003 (2)
C30.107 (5)0.088 (4)0.055 (3)0.046 (4)0.022 (3)0.013 (3)
C40.069 (3)0.053 (3)0.048 (3)0.009 (2)0.002 (2)0.017 (2)
C50.085 (4)0.054 (3)0.075 (4)0.016 (3)0.006 (3)0.027 (3)
C60.060 (3)0.0304 (17)0.059 (3)0.0054 (18)0.001 (2)0.0080 (18)
C70.053 (2)0.0297 (18)0.048 (2)0.0051 (17)0.007 (2)0.0009 (17)
C80.058 (3)0.049 (3)0.071 (3)0.017 (2)0.008 (2)0.006 (2)
C90.089 (4)0.037 (2)0.083 (4)0.005 (2)0.039 (3)0.002 (2)
C100.0373 (17)0.0264 (17)0.044 (2)0.0011 (13)0.0007 (15)0.0019 (15)
C110.049 (2)0.0200 (15)0.045 (2)0.0018 (14)0.0023 (16)0.0034 (15)
C120.053 (2)0.0270 (15)0.047 (2)0.0029 (15)0.0014 (18)0.0050 (16)
C130.052 (2)0.041 (2)0.057 (3)0.0047 (18)0.009 (2)0.015 (2)
C140.067 (3)0.033 (2)0.062 (3)0.005 (2)0.019 (2)0.0021 (19)
C150.076 (3)0.036 (2)0.071 (3)0.004 (2)0.018 (3)0.016 (2)
C160.058 (2)0.038 (2)0.045 (2)0.0065 (19)0.003 (2)0.0034 (18)
Geometric parameters (Å, º) top
S1—O31.437 (3)C5—H5A0.9700
S1—O21.439 (3)C5—H5B0.9700
S1—N11.613 (3)C6—H6A0.9700
S1—C101.774 (4)C6—H6B0.9700
O1—C21.449 (6)C7—C81.525 (6)
O1—H1'0.8200C7—C91.527 (6)
N1—C111.424 (5)C8—H8A0.9600
N1—H10.8600C8—H8B0.9600
N2—C121.373 (6)C8—H8C0.9600
N2—H2B0.8600C9—H9A0.9600
N2—H2A0.8600C9—H9B0.9600
C1—C101.518 (5)C9—H9C0.9600
C1—C61.535 (5)C10—H10A0.9700
C1—C21.535 (6)C10—H10B0.9700
C1—C71.561 (6)C11—C161.387 (6)
C2—C31.540 (7)C11—C121.401 (5)
C2—H20.9800C12—C131.382 (6)
C3—C41.514 (7)C13—C141.373 (7)
C3—H3A0.9700C13—H130.9300
C3—H3B0.9700C14—C151.367 (8)
C4—C51.538 (8)C14—H140.9300
C4—C71.542 (7)C15—C161.377 (7)
C4—H40.9800C15—H150.9300
C5—C61.546 (8)C16—H160.9300
O3—S1—O2118.4 (2)C1—C6—H6B111.1
O3—S1—N1108.29 (19)C5—C6—H6B111.1
O2—S1—N1105.24 (18)H6A—C6—H6B109.0
O3—S1—C10108.05 (18)C8—C7—C9107.1 (4)
O2—S1—C10109.53 (19)C8—C7—C4114.1 (4)
N1—S1—C10106.75 (18)C9—C7—C4113.5 (4)
C2—O1—H1'109.5C8—C7—C1114.6 (4)
C11—N1—S1122.4 (2)C9—C7—C1114.7 (3)
C11—N1—H1118.8C4—C7—C192.7 (3)
S1—N1—H1118.8C7—C8—H8A109.5
C12—N2—H2B120.0C7—C8—H8B109.5
C12—N2—H2A120.0H8A—C8—H8B109.5
H2B—N2—H2A120.0C7—C8—H8C109.5
C10—C1—C6116.8 (3)H8A—C8—H8C109.5
C10—C1—C2116.1 (3)H8B—C8—H8C109.5
C6—C1—C2104.3 (4)C7—C9—H9A109.5
C10—C1—C7113.0 (3)C7—C9—H9B109.5
C6—C1—C7101.3 (3)H9A—C9—H9B109.5
C2—C1—C7103.6 (3)C7—C9—H9C109.5
O1—C2—C1114.4 (4)H9A—C9—H9C109.5
O1—C2—C3109.4 (5)H9B—C9—H9C109.5
C1—C2—C3103.5 (4)C1—C10—S1114.6 (3)
O1—C2—H2109.8C1—C10—H10A108.6
C1—C2—H2109.8S1—C10—H10A108.6
C3—C2—H2109.8C1—C10—H10B108.6
C4—C3—C2103.0 (4)S1—C10—H10B108.6
C4—C3—H3A111.2H10A—C10—H10B107.6
C2—C3—H3A111.2C16—C11—C12120.3 (4)
C4—C3—H3B111.2C16—C11—N1119.7 (4)
C2—C3—H3B111.2C12—C11—N1120.0 (4)
H3A—C3—H3B109.1N2—C12—C13121.0 (4)
C3—C4—C5107.4 (5)N2—C12—C11121.3 (4)
C3—C4—C7103.1 (4)C13—C12—C11117.7 (4)
C5—C4—C7102.3 (4)C14—C13—C12121.4 (4)
C3—C4—H4114.2C14—C13—H13119.3
C5—C4—H4114.2C12—C13—H13119.3
C7—C4—H4114.2C15—C14—C13120.6 (4)
C4—C5—C6102.9 (4)C15—C14—H14119.7
C4—C5—H5A111.2C13—C14—H14119.7
C6—C5—H5A111.2C14—C15—C16119.5 (5)
C4—C5—H5B111.2C14—C15—H15120.2
C6—C5—H5B111.2C16—C15—H15120.2
H5A—C5—H5B109.1C15—C16—C11120.3 (5)
C1—C6—C5103.4 (4)C15—C16—H16119.9
C1—C6—H6A111.1C11—C16—H16119.9
C5—C6—H6A111.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.302.893 (5)130
O1—H1···S10.822.923.508 (4)130
N1—H1···O3i0.862.052.890 (4)165
N2—H2B···O2ii0.862.393.044 (6)133
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+1, y, z.
 

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