(−)-N-[(3R)-3-(4-Fluoro­phen­yl)penta­noyl]bornane-10,2-sultam

In the title compound, C₂₁H₂₈FNO₃S, six-membered ring of sultam shows a boat form. C—H...O inter­actions exist between mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.060
• wR factor = 0.182
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
SYMMS02_ALERT_1_B  The unit-cell lengths a and c should not be equal for a
            monoclinic cell
  Cell       7.8481   16.6590    7.8481
  Angles    90.0000   90.8400   90.0000

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18    ..  O1      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  O2      ..       2.70 Ang.

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           26.99
           From the CIF: _reflns_number_total               3902
           Count of symmetry unique reflns         2311
           Completeness (_total/calc)            168.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1591
           Fraction of Friedel pairs measured     0.688
           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 C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

(-)-N-[(3R)-3-(4-Fluorophenyl)-pentanoyl]bornane-10,2-sultam

Crystal data

C21H28FNO3S	F(000) = 420
Mr = 393.50	Dx = 1.274 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2728 reflections
a = 7.8481 (11) Å	θ = 2.6–24.9°
b = 16.659 (2) Å	µ = 0.19 mm^−1
c = 7.8481 (11) Å	T = 298 K
β = 90.84 (1)°	Block, colourless
V = 1026.0 (3) Å^3	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area detector diffractometer	3461 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 27.0°, θmin = 2.6°
φ and ω scans	h = −9→10
6306 measured reflections	k = −21→20
3902 independent reflections	l = −8→10

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)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.182	w = 1/[σ^2(Fo^2) + (0.1117P)^2 + 0.0834P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
3902 reflections	Δρmax = 0.36 e Å^−3
247 parameters	Δρmin = −0.22 e Å^−3
1 restraint	Absolute structure: Flack (1983); 1609 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (8)

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
C1	0.2937 (5)	0.9757 (2)	0.5302 (4)	0.0511 (8)
C2	0.1138 (6)	1.0098 (4)	0.5568 (7)	0.0797 (14)
H2A	0.0275	0.9748	0.5075	0.096*
H2B	0.0910	1.0172	0.6770	0.096*
C3	0.1194 (8)	1.0899 (4)	0.4640 (7)	0.0934 (17)
H3A	0.0848	1.1334	0.5381	0.112*
H3B	0.0457	1.0893	0.3637	0.112*
C4	0.3095 (7)	1.0989 (3)	0.4137 (6)	0.0733 (12)
H4	0.3478	1.1544	0.3979	0.088*
C5	0.3345 (5)	1.0439 (2)	0.2591 (5)	0.0571 (9)
H5A	0.4489	1.0485	0.2150	0.069*
H5B	0.2527	1.0558	0.1688	0.069*
C6	0.3033 (4)	0.9601 (2)	0.3363 (4)	0.0447 (7)
H6	0.1943	0.9387	0.2940	0.054*
C7	0.4051 (6)	1.0522 (2)	0.5559 (5)	0.0646 (11)
C8	0.3842 (10)	1.0895 (4)	0.7334 (6)	0.0996 (19)
H8A	0.4453	1.1394	0.7391	0.149*
H8B	0.4286	1.0534	0.8183	0.149*
H8C	0.2655	1.0991	0.7535	0.149*
C9	0.5958 (7)	1.0450 (3)	0.5254 (7)	0.0815 (15)
H9A	0.6144	1.0124	0.4266	0.122*
H9B	0.6501	1.0207	0.6228	0.122*
H9C	0.6429	1.0974	0.5074	0.122*
C10	0.3423 (7)	0.9002 (2)	0.6232 (5)	0.0655 (11)
H10A	0.2409	0.8703	0.6533	0.079*
H10B	0.4050	0.9131	0.7271	0.079*
C11	0.4719 (4)	0.8730 (2)	0.1480 (4)	0.0449 (7)
C12	0.6166 (5)	0.8160 (2)	0.1236 (6)	0.0615 (10)
H12A	0.5748	0.7681	0.0663	0.074*
H12B	0.6622	0.8001	0.2341	0.074*
C13	0.7569 (5)	0.8528 (3)	0.0202 (5)	0.0616 (10)
H13	0.7102	0.8636	−0.0940	0.074*
C14	0.8156 (6)	0.9324 (3)	0.0951 (7)	0.0732 (12)
H14A	0.7157	0.9652	0.1147	0.088*
H14B	0.8686	0.9219	0.2053	0.088*
C15	0.9362 (6)	0.9798 (4)	−0.0072 (8)	0.0864 (17)
H15A	1.0356	0.9481	−0.0294	0.130*
H15B	0.9688	1.0272	0.0545	0.130*
H15C	0.8825	0.9948	−0.1132	0.130*
C16	0.9076 (5)	0.7958 (3)	0.0003 (5)	0.0577 (9)
C17	0.9999 (6)	0.7672 (3)	0.1392 (6)	0.0678 (11)
H17	0.9671	0.7807	0.2490	0.081*
C18	1.1423 (6)	0.7181 (3)	0.1152 (7)	0.0809 (14)
H18	1.2035	0.6979	0.2081	0.097*
C19	1.1888 (6)	0.7007 (3)	−0.0436 (8)	0.0743 (13)
C20	1.1012 (6)	0.7285 (3)	−0.1828 (7)	0.0701 (12)
H20	1.1368	0.7154	−0.2918	0.084*
C21	0.9608 (5)	0.7756 (3)	−0.1613 (6)	0.0636 (10)
H21	0.9004	0.7943	−0.2562	0.076*
F1	1.3280 (4)	0.6527 (2)	−0.0662 (6)	0.1151 (13)
N1	0.4398 (3)	0.90035 (16)	0.3106 (3)	0.0418 (6)
O1	0.3970 (6)	0.76620 (18)	0.4578 (4)	0.0823 (10)
O2	0.6461 (5)	0.8440 (3)	0.5344 (4)	0.0966 (11)
O3	0.3933 (4)	0.9023 (2)	0.0306 (3)	0.0612 (7)
S1	0.47124 (13)	0.84194 (6)	0.48565 (10)	0.0560 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.070 (2)	0.050 (2)	0.0337 (15)	0.0024 (17)	0.0049 (14)	0.0008 (14)
C2	0.079 (3)	0.099 (4)	0.062 (3)	0.021 (3)	0.022 (2)	−0.008 (2)
C3	0.105 (4)	0.091 (4)	0.084 (3)	0.049 (3)	0.015 (3)	−0.005 (3)
C4	0.106 (4)	0.053 (2)	0.061 (2)	0.019 (2)	−0.002 (2)	0.005 (2)
C5	0.066 (2)	0.054 (2)	0.051 (2)	0.0090 (18)	−0.0006 (17)	0.0141 (16)
C6	0.0420 (16)	0.056 (2)	0.0356 (15)	0.0062 (14)	−0.0025 (12)	0.0005 (14)
C7	0.097 (3)	0.045 (2)	0.051 (2)	0.000 (2)	−0.005 (2)	−0.0047 (16)
C8	0.173 (6)	0.068 (3)	0.057 (3)	−0.009 (4)	−0.009 (3)	−0.017 (2)
C9	0.083 (3)	0.070 (3)	0.091 (4)	−0.015 (3)	−0.027 (3)	−0.007 (2)
C10	0.111 (3)	0.050 (2)	0.0356 (17)	0.002 (2)	0.0100 (19)	0.0011 (15)
C11	0.0451 (16)	0.0501 (18)	0.0395 (17)	−0.0055 (14)	0.0046 (13)	0.0048 (13)
C12	0.065 (2)	0.057 (2)	0.062 (2)	0.0009 (18)	0.0131 (18)	−0.0012 (17)
C13	0.0507 (18)	0.067 (3)	0.067 (2)	0.0063 (19)	0.0111 (16)	0.014 (2)
C14	0.066 (2)	0.062 (3)	0.092 (3)	0.002 (2)	0.013 (2)	−0.002 (2)
C15	0.055 (2)	0.079 (4)	0.125 (5)	−0.004 (2)	0.011 (3)	0.034 (3)
C16	0.0466 (19)	0.058 (2)	0.068 (2)	−0.0014 (17)	0.0005 (17)	0.0080 (18)
C17	0.069 (3)	0.066 (3)	0.068 (3)	0.009 (2)	0.002 (2)	0.006 (2)
C18	0.067 (3)	0.082 (3)	0.093 (4)	0.012 (3)	−0.019 (2)	0.011 (3)
C19	0.053 (2)	0.059 (3)	0.112 (4)	0.0029 (18)	0.000 (2)	−0.017 (3)
C20	0.067 (2)	0.063 (3)	0.080 (3)	−0.008 (2)	0.012 (2)	−0.018 (2)
C21	0.056 (2)	0.071 (3)	0.064 (2)	−0.008 (2)	0.0007 (18)	0.005 (2)
F1	0.0810 (19)	0.092 (2)	0.172 (4)	0.0365 (18)	0.006 (2)	−0.024 (2)
N1	0.0476 (13)	0.0449 (15)	0.0329 (12)	0.0021 (12)	−0.0032 (10)	0.0057 (10)
O1	0.145 (3)	0.0461 (17)	0.0562 (17)	0.0015 (19)	0.0155 (17)	0.0050 (13)
O2	0.096 (2)	0.123 (3)	0.0699 (19)	0.032 (2)	−0.0304 (16)	0.008 (2)
O3	0.0674 (15)	0.0811 (19)	0.0350 (12)	0.0095 (14)	0.0019 (11)	0.0020 (12)
S1	0.0834 (6)	0.0467 (5)	0.0376 (4)	0.0119 (5)	−0.0071 (4)	0.0074 (4)

Geometric parameters (Å, º)

C1—C10	1.502 (5)	C11—O3	1.205 (4)
C1—C2	1.539 (6)	C11—N1	1.381 (4)
C1—C6	1.547 (5)	C11—C12	1.496 (5)
C1—C7	1.557 (6)	C12—C13	1.507 (5)
C2—C3	1.522 (9)	C12—H12A	0.970
C2—H2A	0.970	C12—H12B	0.970
C2—H2B	0.970	C13—C14	1.520 (7)
C3—C4	1.556 (8)	C13—C16	1.527 (6)
C3—H3A	0.970	C13—H13	0.980
C3—H3B	0.970	C14—C15	1.479 (7)
C4—C5	1.536 (6)	C14—H14A	0.970
C4—C7	1.546 (6)	C14—H14B	0.970
C4—H4	0.980	C15—H15A	0.960
C5—C6	1.543 (5)	C15—H15B	0.960
C5—H5A	0.970	C15—H15C	0.960
C5—H5B	0.970	C16—C21	1.383 (6)
C6—N1	1.478 (4)	C16—C17	1.384 (6)
C6—H6	0.980	C17—C18	1.401 (7)
C7—C9	1.523 (7)	C17—H17	0.930
C7—C8	1.536 (6)	C18—C19	1.335 (8)
C8—H8A	0.960	C18—H18	0.930
C8—H8B	0.960	C19—C20	1.363 (7)
C8—H8C	0.960	C19—F1	1.368 (5)
C9—H9A	0.960	C20—C21	1.365 (6)
C9—H9B	0.960	C20—H20	0.930
C9—H9C	0.960	C21—H21	0.930
C10—S1	1.778 (4)	N1—S1	1.699 (3)
C10—H10A	0.970	O1—S1	1.405 (4)
C10—H10B	0.970	O2—S1	1.420 (4)
C10—C1—C2	118.0 (4)	C1—C10—H10B	110.2
C10—C1—C6	108.8 (3)	S1—C10—H10B	110.2
C2—C1—C6	104.7 (3)	H10A—C10—H10B	108.5
C10—C1—C7	119.0 (3)	O3—C11—N1	118.4 (3)
C2—C1—C7	101.3 (4)	O3—C11—C12	122.7 (3)
C6—C1—C7	103.3 (3)	N1—C11—C12	118.5 (3)
C3—C2—C1	103.0 (4)	C11—C12—C13	111.9 (3)
C3—C2—H2A	111.2	C11—C12—H12A	109.2
C1—C2—H2A	111.2	C13—C12—H12A	109.2
C3—C2—H2B	111.2	C11—C12—H12B	109.2
C1—C2—H2B	111.2	C13—C12—H12B	109.2
H2A—C2—H2B	109.1	H12A—C12—H12B	107.9
C2—C3—C4	103.9 (4)	C12—C13—C14	111.5 (4)
C2—C3—H3A	111.0	C12—C13—C16	112.0 (3)
C4—C3—H3A	111.0	C14—C13—C16	110.5 (3)
C2—C3—H3B	111.0	C12—C13—H13	107.5
C4—C3—H3B	111.0	C14—C13—H13	107.5
H3A—C3—H3B	109.0	C16—C13—H13	107.5
C5—C4—C7	101.7 (3)	C15—C14—C13	116.7 (5)
C5—C4—C3	106.1 (4)	C15—C14—H14A	108.1
C7—C4—C3	103.0 (4)	C13—C14—H14A	108.1
C5—C4—H4	114.8	C15—C14—H14B	108.1
C7—C4—H4	114.8	C13—C14—H14B	108.1
C3—C4—H4	114.8	H14A—C14—H14B	107.3
C4—C5—C6	102.0 (3)	C14—C15—H15A	109.5
C4—C5—H5A	111.4	C14—C15—H15B	109.5
C6—C5—H5A	111.4	H15A—C15—H15B	109.5
C4—C5—H5B	111.4	C14—C15—H15C	109.5
C6—C5—H5B	111.4	H15A—C15—H15C	109.5
H5A—C5—H5B	109.2	H15B—C15—H15C	109.5
N1—C6—C5	115.8 (3)	C21—C16—C17	118.5 (4)
N1—C6—C1	107.1 (3)	C21—C16—C13	119.3 (4)
C5—C6—C1	104.1 (3)	C17—C16—C13	122.0 (4)
N1—C6—H6	109.8	C16—C17—C18	120.2 (5)
C5—C6—H6	109.8	C16—C17—H17	119.9
C1—C6—H6	109.8	C18—C17—H17	119.9
C9—C7—C8	107.0 (4)	C19—C18—C17	118.8 (5)
C9—C7—C4	113.2 (4)	C19—C18—H18	120.6
C8—C7—C4	113.1 (4)	C17—C18—H18	120.6
C9—C7—C1	117.8 (3)	C18—C19—C20	122.2 (4)
C8—C7—C1	112.4 (4)	C18—C19—F1	118.5 (5)
C4—C7—C1	93.0 (3)	C20—C19—F1	119.3 (5)
C7—C8—H8A	109.5	C19—C20—C21	119.6 (4)
C7—C8—H8B	109.5	C19—C20—H20	120.2
H8A—C8—H8B	109.5	C21—C20—H20	120.2
C7—C8—H8C	109.5	C20—C21—C16	120.5 (4)
H8A—C8—H8C	109.5	C20—C21—H21	119.7
H8B—C8—H8C	109.5	C16—C21—H21	119.7
C7—C9—H9A	109.5	C11—N1—C6	119.3 (3)
C7—C9—H9B	109.5	C11—N1—S1	122.2 (2)
H9A—C9—H9B	109.5	C6—N1—S1	111.8 (2)
C7—C9—H9C	109.5	O1—S1—O2	117.4 (3)
H9A—C9—H9C	109.5	O1—S1—N1	109.49 (17)
H9B—C9—H9C	109.5	O2—S1—N1	109.4 (2)
C1—C10—S1	107.7 (2)	O1—S1—C10	110.2 (2)
C1—C10—H10A	110.2	O2—S1—C10	112.3 (2)
S1—C10—H10A	110.2	N1—S1—C10	95.84 (17)
C10—C1—C2—C3	172.9 (4)	C11—C12—C13—C14	53.5 (5)
C6—C1—C2—C3	−66.1 (5)	C11—C12—C13—C16	178.0 (3)
C7—C1—C2—C3	41.1 (5)	C12—C13—C14—C15	−172.0 (4)
C1—C2—C3—C4	−7.2 (5)	C16—C13—C14—C15	62.7 (5)
C2—C3—C4—C5	77.2 (5)	C12—C13—C16—C21	123.3 (4)
C2—C3—C4—C7	−29.3 (5)	C14—C13—C16—C21	−111.7 (5)
C7—C4—C5—C6	42.8 (4)	C12—C13—C16—C17	−60.6 (6)
C3—C4—C5—C6	−64.6 (4)	C14—C13—C16—C17	64.4 (5)
C4—C5—C6—N1	−126.2 (3)	C21—C16—C17—C18	−0.9 (7)
C4—C5—C6—C1	−9.0 (4)	C13—C16—C17—C18	−177.0 (4)
C10—C1—C6—N1	−31.6 (4)	C16—C17—C18—C19	1.2 (8)
C2—C1—C6—N1	−158.5 (3)	C17—C18—C19—C20	−0.7 (8)
C7—C1—C6—N1	95.8 (3)	C17—C18—C19—F1	180.0 (4)
C10—C1—C6—C5	−154.7 (3)	C18—C19—C20—C21	−0.1 (8)
C2—C1—C6—C5	78.3 (4)	F1—C19—C20—C21	179.2 (4)
C7—C1—C6—C5	−27.4 (4)	C19—C20—C21—C16	0.5 (7)
C5—C4—C7—C9	64.4 (5)	C17—C16—C21—C20	0.0 (7)
C3—C4—C7—C9	174.2 (4)	C13—C16—C21—C20	176.2 (4)
C5—C4—C7—C8	−173.6 (4)	O3—C11—N1—C6	4.1 (5)
C3—C4—C7—C8	−63.8 (6)	C12—C11—N1—C6	176.8 (3)
C5—C4—C7—C1	−57.6 (4)	O3—C11—N1—S1	153.1 (3)
C3—C4—C7—C1	52.2 (4)	C12—C11—N1—S1	−34.2 (4)
C10—C1—C7—C9	53.7 (5)	C5—C6—N1—C11	−66.7 (4)
C2—C1—C7—C9	−175.1 (4)	C1—C6—N1—C11	177.7 (3)
C6—C1—C7—C9	−66.9 (5)	C5—C6—N1—S1	141.3 (3)
C10—C1—C7—C8	−71.5 (5)	C1—C6—N1—S1	25.7 (3)
C2—C1—C7—C8	59.7 (5)	C11—N1—S1—O1	−47.8 (3)
C6—C1—C7—C8	167.9 (4)	C6—N1—S1—O1	103.3 (3)
C10—C1—C7—C4	171.9 (3)	C11—N1—S1—O2	82.2 (3)
C2—C1—C7—C4	−56.9 (4)	C6—N1—S1—O2	−126.7 (3)
C6—C1—C7—C4	51.3 (3)	C11—N1—S1—C10	−161.7 (3)
C2—C1—C10—S1	143.0 (4)	C6—N1—S1—C10	−10.5 (3)
C6—C1—C10—S1	24.1 (4)	C1—C10—S1—O1	−121.7 (3)
C7—C1—C10—S1	−93.7 (4)	C1—C10—S1—O2	105.3 (4)
O3—C11—C12—C13	58.5 (5)	C1—C10—S1—N1	−8.5 (3)
N1—C11—C12—C13	−113.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3^i	0.97	2.39	3.216 (4)	143
C18—H18···O1^ii	0.93	2.71	3.422 (5)	134
C21—H21···O2^iii	0.93	2.70	3.596 (4)	163

Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x, y, z−1.