In the title compound, C
23H
32ClNO
3S, molecules are linked
via C—H
N/O interactions, forming two-dimensional sheets parallel to the (100) plane.
Supporting information
CCDC reference: 296626
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.120
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 26.00
From the CIF: _reflns_number_total 4179
Count of symmetry unique reflns 2417
Completeness (_total/calc) 172.90%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1762
Fraction of Friedel pairs measured 0.729
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was synthesized from (-)-sultam and cinnamic chloride (Huang et al., 1999). Crystals suitable for X-ray data collection were obtained by slow evaporation of a methylene chloride solution at 292 K.
All the H atoms were constrained to an ideal geometry, with C—H = 0.95–1.00 Å, and with Uiso(H)= 1.2Ueq(C) or 1.5Ueq(methyl C). The absolute configuration, determined based on the Flack (1983) parameter, is consistent with the known absolute configuration of (-)-camphor-2,10-sultam (Boiadjiev et al., 2001).
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: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
N-[(3RS)-3-(4-Chlorophenyl)heptoyl]bornane-10,2-sultam
top
Crystal data top
C23H32ClNO3S | F(000) = 468 |
Mr = 438.01 | Dx = 1.261 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1773 reflections |
a = 9.2278 (13) Å | θ = 2.2–21.7° |
b = 9.6269 (14) Å | µ = 0.28 mm−1 |
c = 13.1720 (19) Å | T = 292 K |
β = 99.736 (2)° | Block, colorless |
V = 1153.3 (3) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3478 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 2.2° |
ϕ and ω scans | h = −11→10 |
6334 measured reflections | k = −11→11 |
4179 independent reflections | l = −16→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0545P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4179 reflections | Δρmax = 0.18 e Å−3 |
265 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1762 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.08 (8) |
Crystal data top
C23H32ClNO3S | V = 1153.3 (3) Å3 |
Mr = 438.01 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.2278 (13) Å | µ = 0.28 mm−1 |
b = 9.6269 (14) Å | T = 292 K |
c = 13.1720 (19) Å | 0.30 × 0.20 × 0.10 mm |
β = 99.736 (2)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3478 reflections with I > 2σ(I) |
6334 measured reflections | Rint = 0.025 |
4179 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.120 | Δρmax = 0.18 e Å−3 |
S = 1.04 | Δρmin = −0.19 e Å−3 |
4179 reflections | Absolute structure: Flack (1983), 1762 Friedel pairs |
265 parameters | Absolute structure parameter: 0.08 (8) |
1 restraint | |
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 | |
C1 | 0.2483 (4) | 0.8851 (5) | 0.0375 (3) | 0.0788 (12) | |
H1A | 0.2050 | 0.9158 | 0.0949 | 0.118* | |
H1B | 0.1726 | 0.8714 | −0.0212 | 0.118* | |
H1C | 0.3164 | 0.9539 | 0.0217 | 0.118* | |
C2 | 0.3824 (4) | 0.6945 (7) | −0.0335 (3) | 0.0951 (14) | |
H2A | 0.4484 | 0.7611 | −0.0552 | 0.143* | |
H2B | 0.2990 | 0.6822 | −0.0872 | 0.143* | |
H2C | 0.4323 | 0.6074 | −0.0194 | 0.143* | |
C3 | 0.3301 (4) | 0.7475 (4) | 0.0650 (3) | 0.0581 (9) | |
C4 | 0.3622 (4) | 0.5208 (4) | 0.1407 (4) | 0.0715 (11) | |
H4A | 0.3679 | 0.4652 | 0.0801 | 0.086* | |
H4B | 0.3414 | 0.4608 | 0.1956 | 0.086* | |
C5 | 0.5053 (4) | 0.6058 (5) | 0.1746 (3) | 0.0761 (12) | |
H5A | 0.5461 | 0.5885 | 0.2463 | 0.091* | |
H5B | 0.5786 | 0.5837 | 0.1323 | 0.091* | |
C6 | 0.4530 (4) | 0.7564 (4) | 0.1583 (3) | 0.0623 (10) | |
H6 | 0.5314 | 0.8216 | 0.1493 | 0.075* | |
C7 | 0.3695 (3) | 0.7968 (4) | 0.2446 (3) | 0.0601 (9) | |
H7A | 0.3412 | 0.8940 | 0.2403 | 0.072* | |
H7B | 0.4271 | 0.7784 | 0.3119 | 0.072* | |
C8 | 0.2342 (3) | 0.7008 (4) | 0.2223 (2) | 0.0471 (7) | |
H8 | 0.2419 | 0.6279 | 0.2748 | 0.056* | |
C9 | 0.2476 (3) | 0.6359 (3) | 0.1173 (3) | 0.0485 (8) | |
C10 | 0.0958 (3) | 0.5911 (4) | 0.0643 (3) | 0.0604 (9) | |
H10A | 0.0810 | 0.4931 | 0.0761 | 0.073* | |
H10B | 0.0850 | 0.6068 | −0.0094 | 0.073* | |
C11 | 0.0484 (3) | 0.8367 (4) | 0.2951 (2) | 0.0489 (8) | |
C12 | −0.1083 (3) | 0.8888 (4) | 0.2821 (3) | 0.0598 (9) | |
H12A | −0.1742 | 0.8097 | 0.2767 | 0.072* | |
H12B | −0.1302 | 0.9406 | 0.2181 | 0.072* | |
C13 | −0.1377 (4) | 0.9815 (4) | 0.3704 (2) | 0.0540 (8) | |
H13 | −0.0594 | 1.0514 | 0.3814 | 0.065* | |
C14 | −0.2833 (4) | 1.0598 (5) | 0.3379 (3) | 0.0710 (11) | |
H14A | −0.2864 | 1.0957 | 0.2687 | 0.085* | |
H14B | −0.3640 | 0.9947 | 0.3358 | 0.085* | |
C15 | −0.3062 (5) | 1.1798 (6) | 0.4090 (3) | 0.0774 (11) | |
H15A | −0.3306 | 1.1418 | 0.4722 | 0.093* | |
H15B | −0.2143 | 1.2300 | 0.4267 | 0.093* | |
C16 | −0.4202 (6) | 1.2771 (6) | 0.3662 (4) | 0.0999 (16) | |
H16A | −0.5125 | 1.2271 | 0.3503 | 0.120* | |
H16B | −0.3972 | 1.3127 | 0.3019 | 0.120* | |
C17 | −0.4410 (6) | 1.3972 (5) | 0.4337 (3) | 0.0923 (14) | |
H17A | −0.4494 | 1.3641 | 0.5012 | 0.138* | |
H17B | −0.5290 | 1.4464 | 0.4050 | 0.138* | |
H17C | −0.3581 | 1.4585 | 0.4383 | 0.138* | |
C18 | −0.1329 (3) | 0.9057 (4) | 0.4709 (3) | 0.0501 (8) | |
C19 | −0.0511 (4) | 0.9582 (4) | 0.5612 (3) | 0.0644 (10) | |
H19 | 0.0021 | 1.0397 | 0.5586 | 0.077* | |
C20 | −0.0473 (5) | 0.8922 (5) | 0.6545 (3) | 0.0742 (11) | |
H20 | 0.0091 | 0.9284 | 0.7138 | 0.089* | |
C21 | −0.1260 (5) | 0.7740 (5) | 0.6594 (3) | 0.0683 (11) | |
C22 | −0.2047 (4) | 0.7178 (4) | 0.5726 (3) | 0.0692 (11) | |
H22 | −0.2558 | 0.6351 | 0.5760 | 0.083* | |
C23 | −0.2083 (4) | 0.7845 (4) | 0.4794 (3) | 0.0624 (9) | |
H23 | −0.2635 | 0.7461 | 0.4205 | 0.075* | |
Cl1 | −0.12319 (16) | 0.69322 (17) | 0.77858 (8) | 0.1100 (5) | |
N1 | 0.0880 (2) | 0.7672 (3) | 0.21134 (18) | 0.0446 (6) | |
O1 | −0.1025 (3) | 0.7958 (3) | 0.04964 (18) | 0.0694 (7) | |
O2 | −0.1295 (2) | 0.6051 (3) | 0.1631 (2) | 0.0637 (7) | |
O3 | 0.1381 (2) | 0.8544 (3) | 0.37085 (17) | 0.0699 (7) | |
S1 | −0.03484 (7) | 0.69304 (9) | 0.11799 (5) | 0.04449 (19) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.075 (2) | 0.081 (3) | 0.083 (3) | −0.006 (2) | 0.022 (2) | 0.032 (2) |
C2 | 0.083 (3) | 0.143 (4) | 0.067 (2) | 0.000 (4) | 0.034 (2) | −0.004 (4) |
C3 | 0.0535 (19) | 0.075 (3) | 0.0492 (18) | −0.0005 (17) | 0.0175 (15) | 0.0043 (16) |
C4 | 0.060 (2) | 0.057 (2) | 0.100 (3) | 0.0092 (19) | 0.020 (2) | −0.002 (2) |
C5 | 0.047 (2) | 0.100 (3) | 0.082 (3) | 0.019 (2) | 0.0126 (19) | 0.004 (3) |
C6 | 0.0403 (18) | 0.078 (3) | 0.070 (2) | −0.0116 (18) | 0.0147 (16) | −0.002 (2) |
C7 | 0.0434 (17) | 0.075 (3) | 0.061 (2) | −0.0107 (17) | 0.0064 (15) | −0.0119 (19) |
C8 | 0.0394 (14) | 0.0575 (19) | 0.0436 (15) | 0.0041 (18) | 0.0050 (12) | 0.0047 (18) |
C9 | 0.0401 (16) | 0.0507 (19) | 0.0545 (19) | 0.0034 (14) | 0.0070 (14) | −0.0064 (15) |
C10 | 0.0508 (19) | 0.061 (2) | 0.069 (2) | −0.0031 (17) | 0.0097 (17) | −0.0213 (19) |
C11 | 0.0481 (17) | 0.060 (2) | 0.0405 (17) | −0.0053 (16) | 0.0114 (14) | −0.0029 (15) |
C12 | 0.0504 (19) | 0.076 (3) | 0.054 (2) | 0.0059 (18) | 0.0096 (15) | −0.0089 (18) |
C13 | 0.0574 (19) | 0.054 (2) | 0.054 (2) | −0.0013 (16) | 0.0173 (16) | −0.0109 (17) |
C14 | 0.076 (3) | 0.080 (3) | 0.059 (2) | 0.020 (2) | 0.0159 (19) | 0.001 (2) |
C15 | 0.085 (2) | 0.081 (3) | 0.068 (2) | 0.022 (3) | 0.0179 (19) | 0.000 (3) |
C16 | 0.113 (4) | 0.096 (4) | 0.087 (3) | 0.034 (3) | 0.006 (3) | −0.009 (3) |
C17 | 0.119 (3) | 0.069 (3) | 0.087 (3) | 0.024 (3) | 0.009 (3) | −0.003 (2) |
C18 | 0.0442 (16) | 0.050 (2) | 0.058 (2) | 0.0073 (16) | 0.0138 (15) | −0.0114 (16) |
C19 | 0.073 (2) | 0.064 (2) | 0.058 (2) | −0.0098 (19) | 0.0163 (19) | −0.0172 (19) |
C20 | 0.085 (3) | 0.086 (3) | 0.050 (2) | 0.010 (3) | 0.0065 (19) | −0.021 (2) |
C21 | 0.084 (3) | 0.066 (3) | 0.059 (2) | 0.019 (2) | 0.023 (2) | −0.004 (2) |
C22 | 0.085 (2) | 0.054 (3) | 0.072 (2) | −0.004 (2) | 0.021 (2) | −0.001 (2) |
C23 | 0.066 (2) | 0.059 (2) | 0.059 (2) | 0.000 (2) | 0.0046 (17) | −0.0117 (19) |
Cl1 | 0.1659 (12) | 0.1015 (9) | 0.0667 (6) | 0.0293 (11) | 0.0313 (7) | 0.0185 (8) |
N1 | 0.0355 (12) | 0.0528 (16) | 0.0458 (14) | −0.0022 (12) | 0.0081 (10) | −0.0065 (12) |
O1 | 0.0736 (15) | 0.0746 (18) | 0.0527 (14) | 0.0116 (14) | −0.0101 (12) | 0.0034 (13) |
O2 | 0.0509 (13) | 0.0605 (16) | 0.0809 (17) | −0.0127 (12) | 0.0144 (12) | −0.0038 (13) |
O3 | 0.0533 (13) | 0.105 (2) | 0.0488 (14) | 0.0036 (14) | 0.0027 (11) | −0.0200 (14) |
S1 | 0.0395 (3) | 0.0468 (4) | 0.0455 (4) | −0.0012 (4) | 0.0024 (3) | −0.0053 (4) |
Geometric parameters (Å, º) top
C1—C3 | 1.537 (5) | C12—C13 | 1.526 (4) |
C1—H1A | 0.9600 | C12—H12A | 0.9700 |
C1—H1B | 0.9600 | C12—H12B | 0.9700 |
C1—H1C | 0.9600 | C13—C18 | 1.506 (5) |
C2—C3 | 1.546 (5) | C13—C14 | 1.537 (5) |
C2—H2A | 0.9600 | C13—H13 | 0.9800 |
C2—H2B | 0.9600 | C14—C15 | 1.525 (6) |
C2—H2C | 0.9600 | C14—H14A | 0.9700 |
C3—C6 | 1.527 (5) | C14—H14B | 0.9700 |
C3—C9 | 1.545 (5) | C15—C16 | 1.450 (6) |
C4—C9 | 1.527 (5) | C15—H15A | 0.9700 |
C4—C5 | 1.553 (5) | C15—H15B | 0.9700 |
C4—H4A | 0.9700 | C16—C17 | 1.490 (6) |
C4—H4B | 0.9700 | C16—H16A | 0.9700 |
C5—C6 | 1.531 (6) | C16—H16B | 0.9700 |
C5—H5A | 0.9700 | C17—H17A | 0.9600 |
C5—H5B | 0.9700 | C17—H17B | 0.9600 |
C6—C7 | 1.528 (5) | C17—H17C | 0.9600 |
C6—H6 | 0.9800 | C18—C23 | 1.372 (5) |
C7—C8 | 1.541 (5) | C18—C19 | 1.392 (5) |
C7—H7A | 0.9700 | C19—C20 | 1.378 (6) |
C7—H7B | 0.9700 | C19—H19 | 0.9300 |
C8—N1 | 1.477 (4) | C20—C21 | 1.357 (6) |
C8—C9 | 1.542 (4) | C20—H20 | 0.9300 |
C8—H8 | 0.9800 | C21—C22 | 1.359 (5) |
C9—C10 | 1.518 (4) | C21—Cl1 | 1.748 (4) |
C10—S1 | 1.791 (3) | C22—C23 | 1.382 (5) |
C10—H10A | 0.9700 | C22—H22 | 0.9300 |
C10—H10B | 0.9700 | C23—H23 | 0.9300 |
C11—O3 | 1.196 (3) | N1—S1 | 1.684 (2) |
C11—N1 | 1.391 (4) | O1—S1 | 1.411 (2) |
C11—C12 | 1.513 (4) | O2—S1 | 1.417 (2) |
| | | |
C3—C1—H1A | 109.5 | C11—C12—C13 | 113.4 (3) |
C3—C1—H1B | 109.5 | C11—C12—H12A | 108.9 |
H1A—C1—H1B | 109.5 | C13—C12—H12A | 108.9 |
C3—C1—H1C | 109.5 | C11—C12—H12B | 108.9 |
H1A—C1—H1C | 109.5 | C13—C12—H12B | 108.9 |
H1B—C1—H1C | 109.5 | H12A—C12—H12B | 107.7 |
C3—C2—H2A | 109.5 | C18—C13—C12 | 113.8 (3) |
C3—C2—H2B | 109.5 | C18—C13—C14 | 112.2 (3) |
H2A—C2—H2B | 109.5 | C12—C13—C14 | 109.5 (3) |
C3—C2—H2C | 109.5 | C18—C13—H13 | 107.0 |
H2A—C2—H2C | 109.5 | C12—C13—H13 | 107.0 |
H2B—C2—H2C | 109.5 | C14—C13—H13 | 107.0 |
C6—C3—C1 | 114.2 (3) | C15—C14—C13 | 113.9 (3) |
C6—C3—C9 | 92.0 (3) | C15—C14—H14A | 108.8 |
C1—C3—C9 | 116.4 (3) | C13—C14—H14A | 108.8 |
C6—C3—C2 | 113.5 (3) | C15—C14—H14B | 108.8 |
C1—C3—C2 | 107.3 (4) | C13—C14—H14B | 108.8 |
C9—C3—C2 | 113.1 (4) | H14A—C14—H14B | 107.7 |
C9—C4—C5 | 101.6 (3) | C16—C15—C14 | 114.7 (3) |
C9—C4—H4A | 111.4 | C16—C15—H15A | 108.6 |
C5—C4—H4A | 111.4 | C14—C15—H15A | 108.6 |
C9—C4—H4B | 111.4 | C16—C15—H15B | 108.6 |
C5—C4—H4B | 111.4 | C14—C15—H15B | 108.6 |
H4A—C4—H4B | 109.3 | H15A—C15—H15B | 107.6 |
C6—C5—C4 | 103.1 (3) | C15—C16—C17 | 115.3 (4) |
C6—C5—H5A | 111.1 | C15—C16—H16A | 108.4 |
C4—C5—H5A | 111.1 | C17—C16—H16A | 108.4 |
C6—C5—H5B | 111.1 | C15—C16—H16B | 108.4 |
C4—C5—H5B | 111.1 | C17—C16—H16B | 108.4 |
H5A—C5—H5B | 109.1 | H16A—C16—H16B | 107.5 |
C3—C6—C7 | 102.3 (3) | C16—C17—H17A | 109.5 |
C3—C6—C5 | 103.5 (3) | C16—C17—H17B | 109.5 |
C7—C6—C5 | 108.8 (4) | H17A—C17—H17B | 109.5 |
C3—C6—H6 | 113.7 | C16—C17—H17C | 109.5 |
C7—C6—H6 | 113.7 | H17A—C17—H17C | 109.5 |
C5—C6—H6 | 113.7 | H17B—C17—H17C | 109.5 |
C6—C7—C8 | 101.5 (3) | C23—C18—C19 | 116.6 (3) |
C6—C7—H7A | 111.5 | C23—C18—C13 | 122.9 (3) |
C8—C7—H7A | 111.5 | C19—C18—C13 | 120.5 (3) |
C6—C7—H7B | 111.5 | C20—C19—C18 | 121.5 (4) |
C8—C7—H7B | 111.5 | C20—C19—H19 | 119.2 |
H7A—C7—H7B | 109.3 | C18—C19—H19 | 119.2 |
N1—C8—C7 | 117.1 (3) | C21—C20—C19 | 119.7 (4) |
N1—C8—C9 | 107.4 (2) | C21—C20—H20 | 120.1 |
C7—C8—C9 | 103.2 (2) | C19—C20—H20 | 120.1 |
N1—C8—H8 | 109.6 | C20—C21—C22 | 120.6 (4) |
C7—C8—H8 | 109.6 | C20—C21—Cl1 | 119.3 (3) |
C9—C8—H8 | 109.6 | C22—C21—Cl1 | 120.2 (4) |
C10—C9—C4 | 116.1 (3) | C21—C22—C23 | 119.4 (4) |
C10—C9—C8 | 108.7 (2) | C21—C22—H22 | 120.3 |
C4—C9—C8 | 105.7 (3) | C23—C22—H22 | 120.3 |
C10—C9—C3 | 118.6 (3) | C18—C23—C22 | 122.1 (4) |
C4—C9—C3 | 102.6 (3) | C18—C23—H23 | 118.9 |
C8—C9—C3 | 103.8 (3) | C22—C23—H23 | 118.9 |
C9—C10—S1 | 107.0 (2) | C11—N1—C8 | 119.3 (2) |
C9—C10—H10A | 110.3 | C11—N1—S1 | 123.2 (2) |
S1—C10—H10A | 110.3 | C8—N1—S1 | 112.3 (2) |
C9—C10—H10B | 110.3 | O1—S1—O2 | 116.67 (16) |
S1—C10—H10B | 110.3 | O1—S1—N1 | 109.84 (15) |
H10A—C10—H10B | 108.6 | O2—S1—N1 | 109.53 (14) |
O3—C11—N1 | 119.6 (3) | O1—S1—C10 | 112.78 (17) |
O3—C11—C12 | 124.1 (3) | O2—S1—C10 | 110.01 (17) |
N1—C11—C12 | 116.4 (3) | N1—S1—C10 | 96.06 (14) |
| | | |
C9—C4—C5—C6 | −3.8 (4) | C11—C12—C13—C14 | 165.0 (3) |
C1—C3—C6—C7 | 61.8 (4) | C18—C13—C14—C15 | 66.4 (4) |
C9—C3—C6—C7 | −58.4 (3) | C12—C13—C14—C15 | −166.3 (3) |
C2—C3—C6—C7 | −174.8 (4) | C13—C14—C15—C16 | 164.1 (4) |
C1—C3—C6—C5 | 174.9 (3) | C14—C15—C16—C17 | −178.4 (4) |
C9—C3—C6—C5 | 54.7 (3) | C12—C13—C18—C23 | −49.7 (4) |
C2—C3—C6—C5 | −61.7 (5) | C14—C13—C18—C23 | 75.3 (4) |
C4—C5—C6—C3 | −33.2 (4) | C12—C13—C18—C19 | 131.1 (3) |
C4—C5—C6—C7 | 75.1 (4) | C14—C13—C18—C19 | −103.8 (4) |
C3—C6—C7—C8 | 43.2 (4) | C23—C18—C19—C20 | −0.5 (5) |
C5—C6—C7—C8 | −65.8 (3) | C13—C18—C19—C20 | 178.7 (3) |
C6—C7—C8—N1 | −126.1 (3) | C18—C19—C20—C21 | −0.8 (6) |
C6—C7—C8—C9 | −8.4 (3) | C19—C20—C21—C22 | 2.2 (6) |
C5—C4—C9—C10 | 170.1 (3) | C19—C20—C21—Cl1 | −178.7 (3) |
C5—C4—C9—C8 | −69.4 (3) | C20—C21—C22—C23 | −2.2 (6) |
C5—C4—C9—C3 | 39.1 (4) | Cl1—C21—C22—C23 | 178.7 (3) |
N1—C8—C9—C10 | −31.2 (4) | C19—C18—C23—C22 | 0.4 (5) |
C7—C8—C9—C10 | −155.6 (3) | C13—C18—C23—C22 | −178.7 (3) |
N1—C8—C9—C4 | −156.5 (3) | C21—C22—C23—C18 | 0.9 (6) |
C7—C8—C9—C4 | 79.1 (3) | O3—C11—N1—C8 | 7.9 (5) |
N1—C8—C9—C3 | 95.9 (3) | C12—C11—N1—C8 | −173.7 (3) |
C7—C8—C9—C3 | −28.4 (3) | O3—C11—N1—S1 | 160.3 (3) |
C6—C3—C9—C10 | 173.1 (3) | C12—C11—N1—S1 | −21.3 (4) |
C1—C3—C9—C10 | 54.7 (4) | C7—C8—N1—C11 | −63.3 (4) |
C2—C3—C9—C10 | −70.2 (4) | C9—C8—N1—C11 | −178.7 (3) |
C6—C3—C9—C4 | −57.5 (3) | C7—C8—N1—S1 | 141.5 (2) |
C1—C3—C9—C4 | −175.8 (3) | C9—C8—N1—S1 | 26.1 (3) |
C2—C3—C9—C4 | 59.2 (4) | C11—N1—S1—O1 | 77.9 (3) |
C6—C3—C9—C8 | 52.4 (3) | C8—N1—S1—O1 | −128.0 (2) |
C1—C3—C9—C8 | −65.9 (4) | C11—N1—S1—O2 | −51.4 (3) |
C2—C3—C9—C8 | 169.1 (3) | C8—N1—S1—O2 | 102.7 (2) |
C4—C9—C10—S1 | 142.2 (3) | C11—N1—S1—C10 | −165.2 (3) |
C8—C9—C10—S1 | 23.3 (4) | C8—N1—S1—C10 | −11.1 (3) |
C3—C9—C10—S1 | −94.8 (3) | C9—C10—S1—O1 | 106.8 (3) |
O3—C11—C12—C13 | 6.6 (5) | C9—C10—S1—O2 | −121.0 (3) |
N1—C11—C12—C13 | −171.7 (3) | C9—C10—S1—N1 | −7.7 (3) |
C11—C12—C13—C18 | −68.6 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O2 | 0.97 | 2.55 | 3.139 (5) | 119 |
C1—H1A···N1 | 0.96 | 2.47 | 3.141 (4) | 126 |
C20—H20···O2i | 0.93 | 2.48 | 3.363 (5) | 159 |
C10—H10A···O1ii | 0.97 | 2.55 | 3.220 (4) | 126 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z. |
Experimental details
Crystal data |
Chemical formula | C23H32ClNO3S |
Mr | 438.01 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 292 |
a, b, c (Å) | 9.2278 (13), 9.6269 (14), 13.1720 (19) |
β (°) | 99.736 (2) |
V (Å3) | 1153.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6334, 4179, 3478 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.120, 1.04 |
No. of reflections | 4179 |
No. of parameters | 265 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.19 |
Absolute structure | Flack (1983), 1762 Friedel pairs |
Absolute structure parameter | 0.08 (8) |
Selected geometric parameters (Å, º) topC8—N1 | 1.477 (4) | C21—Cl1 | 1.748 (4) |
C10—S1 | 1.791 (3) | N1—S1 | 1.684 (2) |
C11—O3 | 1.196 (3) | O1—S1 | 1.411 (2) |
C11—N1 | 1.391 (4) | O2—S1 | 1.417 (2) |
| | | |
C9—C10—S1 | 107.0 (2) | N1—S1—C10 | 96.06 (14) |
| | | |
C9—C4—C5—C6 | −3.8 (4) | C12—C13—C18—C23 | −49.7 (4) |
C6—C7—C8—C9 | −8.4 (3) | C14—C13—C18—C19 | −103.8 (4) |
N1—C8—C9—C10 | −31.2 (4) | C9—C8—N1—S1 | 26.1 (3) |
C8—C9—C10—S1 | 23.3 (4) | C8—N1—S1—C10 | −11.1 (3) |
C11—C12—C13—C14 | 165.0 (3) | C9—C10—S1—N1 | −7.7 (3) |
C14—C15—C16—C17 | −178.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O2 | 0.97 | 2.55 | 3.139 (5) | 119 |
C1—H1A···N1 | 0.96 | 2.47 | 3.141 (4) | 126 |
C20—H20···O2i | 0.93 | 2.48 | 3.363 (5) | 159 |
C10—H10A···O1ii | 0.97 | 2.55 | 3.220 (4) | 126 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z. |
The readily available enantiomers of bornane-10,2-sultam serve as efficient, versatile and practical chiral auxiliaries (Oppolzer, 1990), and we have focused our attention on this matter. In this paper, we present the X-ray crystallographic analysis of the title compound, (I).
In (I), the six-membered ring of sultam exhibits a boat form (Fig. 1). The C9/C4/C5/C6 and C6/C7/C8/C9 planes form a dihedral angle of 111.1 (1)°. The C3/C6/C9 plane forms almost equal dihedral angles with the above planes [124.1 (1) and 124.7 (1)°, respectively]. The molecules are linked via C—H···N/O interactions (Table 2) along the b and c axes, forming two-dimensional sheets parallel to the (100) plane (Fig. 2).