6α-Hydro­xy-17β-aza­vouacapane-17,7β-carbolactone

The title compound, C₂₀H₂₇NO₄, is an intermediate of nitro­genated vouacapan derivatives. The crystal structure has intermolecular hydrogen bonds that establish a regular arrangement in the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           26.26
           From the CIF: _reflns_number_total               2044
           Count of symmetry unique reflns         2044
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   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
   0 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

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997)and Mercury (CCDC, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C20H27NO4	F(000) = 744
Mr = 345.43	Dx = 1.3 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 8.3541 (10) Å	θ = 3.0–26.3°
b = 13.6308 (10) Å	µ = 0.09 mm^−1
c = 15.4932 (10) Å	T = 293 K
V = 1764.3 (3) Å^3	Prism, colourless
Z = 4	0.8 × 0.4 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 26.3°, θmin = 3.0°
non–profiled ω/2θ scans	h = −10→3
2065 measured reflections	k = 0→16
2044 independent reflections	l = −3→19
1719 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.023	intensity decay: 7%

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0775P)^2 + 0.1708P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max = 0.001
wR(F^2) = 0.117	Δρmax = 0.28 e Å^−3
S = 1.06	Δρmin = −0.19 e Å^−3
2044 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
236 parameters	Extinction coefficient: 0.012 (3)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N	1.1596 (2)	0.66133 (15)	0.51212 (14)	0.0377 (5)
O1	1.3169 (3)	0.33543 (14)	0.50577 (16)	0.0640 (6)
O2	0.6916 (3)	0.69376 (15)	0.69990 (14)	0.0556 (6)
O3	0.9138 (2)	0.70606 (12)	0.56882 (11)	0.0410 (4)
O4	1.0201 (2)	0.79302 (13)	0.46459 (13)	0.0475 (5)
C1	0.8572 (4)	0.3457 (2)	0.7547 (2)	0.0554 (7)
H1A	0.8901	0.2863	0.7251	0.066*
H1B	0.9394	0.362	0.7965	0.066*
C2	0.7012 (5)	0.3267 (2)	0.8015 (2)	0.0668 (9)
H2A	0.7144	0.2725	0.8415	0.08*
H2B	0.6187	0.309	0.7603	0.08*
C3	0.6512 (4)	0.4180 (2)	0.85040 (19)	0.0616 (9)
H3A	0.7319	0.4321	0.8937	0.074*
H3B	0.5519	0.4041	0.8805	0.074*
C4	0.6269 (3)	0.5107 (2)	0.79465 (16)	0.0465 (7)
C5	0.7768 (3)	0.52408 (18)	0.73498 (14)	0.0360 (5)
H5	0.863	0.5455	0.7735	0.043*
C6	0.7609 (3)	0.60653 (18)	0.66686 (15)	0.0351 (5)
H6	0.6957	0.5827	0.6186	0.042*
C7	0.9284 (3)	0.62962 (16)	0.63418 (15)	0.0330 (5)
H7	0.9926	0.6548	0.6822	0.04*
C8	1.0128 (3)	0.54334 (16)	0.59512 (14)	0.0313 (5)
H8	0.9553	0.5249	0.5424	0.038*
C9	1.0154 (3)	0.45386 (17)	0.65499 (15)	0.0373 (5)
H9	1.0804	0.4715	0.7053	0.045*
C10	0.8432 (3)	0.42957 (18)	0.68869 (15)	0.0383 (6)
C11	1.0991 (4)	0.36626 (19)	0.6103 (2)	0.0545 (8)
H11A	1.147	0.3241	0.6536	0.065*
H11B	1.0206	0.3281	0.5787	0.065*
C12	1.2245 (3)	0.40117 (19)	0.55025 (18)	0.0451 (6)
C13	1.2643 (3)	0.49322 (18)	0.52820 (17)	0.0388 (6)
C14	1.1793 (3)	0.57761 (16)	0.56909 (16)	0.0338 (5)
H14	1.2381	0.5982	0.6208	0.041*
C15	1.3904 (4)	0.4861 (2)	0.4659 (2)	0.0544 (7)
H15	1.4439	0.5375	0.439	0.065*
C16	1.4152 (4)	0.3905 (2)	0.4547 (3)	0.0672 (9)
H16	1.4902	0.3644	0.4168	0.081*
C17	1.0343 (3)	0.72305 (16)	0.51284 (16)	0.0343 (5)
C18	0.6135 (4)	0.5962 (3)	0.85819 (19)	0.0644 (9)
H18A	0.5871	0.6551	0.8273	0.097*
H18B	0.7137	0.6048	0.8875	0.097*
H18C	0.5311	0.5824	0.8996	0.097*
C19	0.4684 (3)	0.5035 (3)	0.7456 (2)	0.0684 (10)
H19A	0.4675	0.4447	0.7115	0.103*
H19B	0.4569	0.5595	0.7085	0.103*
H19C	0.3813	0.5019	0.786	0.103*
C20	0.7361 (4)	0.3951 (2)	0.61347 (18)	0.0516 (7)
H20A	0.7642	0.3292	0.5979	0.077*
H20B	0.7515	0.4375	0.5647	0.077*
H20C	0.6259	0.3972	0.631	0.077*
HN	1.237 (5)	0.680 (3)	0.485 (2)	0.062*
HO2	0.643 (5)	0.719 (3)	0.659 (2)	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0218 (9)	0.0359 (10)	0.0554 (12)	−0.0017 (8)	0.0032 (9)	0.0059 (10)
O1	0.0610 (14)	0.0403 (10)	0.0905 (15)	0.0105 (10)	0.0160 (12)	−0.0132 (10)
O2	0.0545 (13)	0.0554 (12)	0.0568 (11)	0.0216 (10)	0.0165 (10)	0.0112 (10)
O3	0.0305 (9)	0.0396 (9)	0.0530 (9)	0.0081 (8)	0.0085 (8)	0.0144 (8)
O4	0.0330 (9)	0.0420 (9)	0.0675 (11)	0.0012 (8)	0.0083 (9)	0.0209 (10)
C1	0.0572 (18)	0.0501 (14)	0.0589 (16)	0.0016 (14)	0.0042 (16)	0.0218 (14)
C2	0.068 (2)	0.0626 (19)	0.0695 (18)	−0.0073 (17)	0.0076 (18)	0.0321 (17)
C3	0.0534 (17)	0.079 (2)	0.0525 (16)	−0.0002 (17)	0.0064 (15)	0.0291 (16)
C4	0.0356 (13)	0.0653 (17)	0.0388 (12)	−0.0016 (13)	0.0010 (11)	0.0153 (13)
C5	0.0297 (11)	0.0465 (13)	0.0320 (11)	−0.0012 (11)	−0.0053 (10)	0.0056 (11)
C6	0.0285 (12)	0.0409 (12)	0.0360 (11)	0.0021 (10)	0.0008 (10)	0.0060 (10)
C7	0.0293 (11)	0.0330 (11)	0.0366 (11)	0.0034 (9)	−0.0026 (10)	0.0050 (9)
C8	0.0252 (10)	0.0330 (11)	0.0358 (10)	0.0006 (9)	−0.0029 (9)	0.0017 (9)
C9	0.0354 (12)	0.0345 (12)	0.0419 (12)	0.0023 (10)	−0.0036 (11)	0.0045 (10)
C10	0.0369 (13)	0.0393 (12)	0.0386 (12)	−0.0025 (11)	−0.0019 (11)	0.0084 (11)
C11	0.0578 (18)	0.0345 (13)	0.0712 (18)	0.0081 (13)	0.0107 (17)	0.0067 (13)
C12	0.0413 (13)	0.0375 (12)	0.0565 (15)	0.0076 (12)	0.0007 (13)	−0.0051 (12)
C13	0.0284 (11)	0.0387 (12)	0.0493 (13)	0.0030 (10)	−0.0020 (11)	−0.0043 (11)
C14	0.0261 (11)	0.0307 (11)	0.0445 (12)	0.0021 (9)	−0.0062 (10)	−0.0013 (10)
C15	0.0401 (15)	0.0490 (14)	0.0740 (18)	0.0021 (13)	0.0139 (15)	−0.0068 (15)
C16	0.0562 (19)	0.0558 (17)	0.090 (2)	0.0057 (16)	0.0255 (19)	−0.0165 (17)
C17	0.0249 (11)	0.0321 (11)	0.0459 (12)	−0.0024 (9)	0.0006 (10)	0.0034 (11)
C18	0.0595 (19)	0.089 (2)	0.0445 (14)	0.006 (2)	0.0150 (15)	0.0047 (16)
C19	0.0330 (16)	0.109 (3)	0.0630 (17)	−0.0064 (17)	−0.0024 (14)	0.025 (2)
C20	0.0484 (16)	0.0536 (15)	0.0528 (15)	−0.0164 (14)	−0.0025 (14)	−0.0023 (13)

Geometric parameters (Å, º)

N—C17	1.343 (3)	C7—C8	1.499 (3)
N—C14	1.452 (3)	C7—H7	0.98
N—HN	0.81 (4)	C8—C14	1.522 (3)
O1—C16	1.365 (4)	C8—C9	1.532 (3)
O1—C12	1.369 (3)	C8—H8	0.98
O2—C6	1.418 (3)	C9—C11	1.547 (4)
O2—HO2	0.83 (4)	C9—C10	1.566 (4)
O3—C17	1.349 (3)	C9—H9	0.98
O3—C7	1.458 (3)	C10—C20	1.543 (4)
O4—C17	1.217 (3)	C11—C12	1.479 (4)
C1—C2	1.515 (5)	C11—H11A	0.97
C1—C10	1.538 (3)	C11—H11B	0.97
C1—H1A	0.97	C12—C13	1.342 (4)
C1—H1B	0.97	C13—C15	1.432 (4)
C2—C3	1.515 (5)	C13—C14	1.493 (3)
C2—H2A	0.97	C14—H14	0.98
C2—H2B	0.97	C15—C16	1.330 (4)
C3—C4	1.544 (4)	C15—H15	0.93
C3—H3A	0.97	C16—H16	0.93
C3—H3B	0.97	C18—H18A	0.96
C4—C19	1.530 (4)	C18—H18B	0.96
C4—C18	1.530 (4)	C18—H18C	0.96
C4—C5	1.567 (3)	C19—H19A	0.96
C5—C6	1.547 (3)	C19—H19B	0.96
C5—C10	1.575 (3)	C19—H19C	0.96
C5—H5	0.98	C20—H20A	0.96
C6—C7	1.521 (3)	C20—H20B	0.96
C6—H6	0.98	C20—H20C	0.96
C17—N—C14	125.2 (2)	C11—C9—C10	113.7 (2)
C17—N—HN	116 (3)	C8—C9—H9	107.2
C14—N—HN	118 (3)	C11—C9—H9	107.2
C16—O1—C12	105.7 (2)	C10—C9—H9	107.2
C6—O2—HO2	106 (2)	C1—C10—C20	108.6 (2)
C17—O3—C7	120.45 (17)	C1—C10—C9	108.0 (2)
C2—C1—C10	112.3 (3)	C20—C10—C9	110.2 (2)
C2—C1—H1A	109.1	C1—C10—C5	109.4 (2)
C10—C1—H1A	109.1	C20—C10—C5	112.9 (2)
C2—C1—H1B	109.1	C9—C10—C5	107.62 (19)
C10—C1—H1B	109.1	C12—C11—C9	110.7 (2)
H1A—C1—H1B	107.9	C12—C11—H11A	109.5
C1—C2—C3	109.7 (3)	C9—C11—H11A	109.5
C1—C2—H2A	109.7	C12—C11—H11B	109.5
C3—C2—H2A	109.7	C9—C11—H11B	109.5
C1—C2—H2B	109.7	H11A—C11—H11B	108.1
C3—C2—H2B	109.7	C13—C12—O1	110.1 (2)
H2A—C2—H2B	108.2	C13—C12—C11	129.5 (2)
C2—C3—C4	115.4 (2)	O1—C12—C11	120.4 (2)
C2—C3—H3A	108.4	C12—C13—C15	106.9 (2)
C4—C3—H3A	108.4	C12—C13—C14	119.6 (2)
C2—C3—H3B	108.4	C15—C13—C14	133.5 (2)
C4—C3—H3B	108.4	N—C14—C13	113.7 (2)
H3A—C3—H3B	107.5	N—C14—C8	107.38 (18)
C19—C4—C18	107.7 (3)	C13—C14—C8	108.10 (19)
C19—C4—C3	109.9 (3)	N—C14—H14	109.2
C18—C4—C3	105.9 (2)	C13—C14—H14	109.2
C19—C4—C5	113.9 (2)	C8—C14—H14	109.2
C18—C4—C5	110.4 (2)	C16—C15—C13	105.6 (3)
C3—C4—C5	108.7 (2)	C16—C15—H15	127.2
C6—C5—C4	114.7 (2)	C13—C15—H15	127.2
C6—C5—C10	108.28 (17)	C15—C16—O1	111.7 (3)
C4—C5—C10	117.0 (2)	C15—C16—H16	124.2
C6—C5—H5	105.2	O1—C16—H16	124.2
C4—C5—H5	105.2	O4—C17—N	124.2 (2)
C10—C5—H5	105.2	O4—C17—O3	117.2 (2)
O2—C6—C7	108.8 (2)	N—C17—O3	118.66 (19)
O2—C6—C5	113.43 (19)	C4—C18—H18A	109.5
C7—C6—C5	107.37 (18)	C4—C18—H18B	109.5
O2—C6—H6	109	H18A—C18—H18B	109.5
C7—C6—H6	109	C4—C18—H18C	109.5
C5—C6—H6	109	H18A—C18—H18C	109.5
O3—C7—C8	108.64 (17)	H18B—C18—H18C	109.5
O3—C7—C6	107.59 (17)	C4—C19—H19A	109.5
C8—C7—C6	113.89 (19)	C4—C19—H19B	109.5
O3—C7—H7	108.9	H19A—C19—H19B	109.5
C8—C7—H7	108.9	C4—C19—H19C	109.5
C6—C7—H7	108.9	H19A—C19—H19C	109.5
C7—C8—C14	107.24 (18)	H19B—C19—H19C	109.5
C7—C8—C9	112.75 (18)	C10—C20—H20A	109.5
C14—C8—C9	113.07 (19)	C10—C20—H20B	109.5
C7—C8—H8	107.9	H20A—C20—H20B	109.5
C14—C8—H8	107.9	C10—C20—H20C	109.5
C9—C8—H8	107.9	H20A—C20—H20C	109.5
C8—C9—C11	110.46 (19)	H20B—C20—H20C	109.5
C8—C9—C10	110.9 (2)
C10—C1—C2—C3	−60.6 (3)	C8—C9—C10—C5	−56.7 (2)
C1—C2—C3—C4	58.9 (4)	C11—C9—C10—C5	178.1 (2)
C2—C3—C4—C19	75.9 (4)	C6—C5—C10—C1	−178.9 (2)
C2—C3—C4—C18	−168.1 (3)	C4—C5—C10—C1	−47.4 (3)
C2—C3—C4—C5	−49.4 (4)	C6—C5—C10—C20	−57.9 (3)
C19—C4—C5—C6	49.7 (3)	C4—C5—C10—C20	73.7 (2)
C18—C4—C5—C6	−71.7 (3)	C6—C5—C10—C9	64.0 (2)
C3—C4—C5—C6	172.6 (2)	C4—C5—C10—C9	−164.46 (19)
C19—C4—C5—C10	−78.8 (3)	C8—C9—C11—C12	31.2 (3)
C18—C4—C5—C10	159.8 (2)	C10—C9—C11—C12	156.6 (2)
C3—C4—C5—C10	44.0 (3)	C16—O1—C12—C13	−0.4 (3)
C4—C5—C6—O2	43.1 (3)	C16—O1—C12—C11	177.9 (3)
C10—C5—C6—O2	175.9 (2)	C9—C11—C12—C13	−4.0 (5)
C4—C5—C6—C7	163.4 (2)	C9—C11—C12—O1	178.0 (3)
C10—C5—C6—C7	−63.8 (2)	O1—C12—C13—C15	−0.2 (3)
C17—O3—C7—C8	−38.6 (3)	C11—C12—C13—C15	−178.3 (3)
C17—O3—C7—C6	−162.4 (2)	O1—C12—C13—C14	−179.7 (2)
O2—C6—C7—O3	−57.9 (2)	C11—C12—C13—C14	2.1 (5)
C5—C6—C7—O3	178.99 (17)	C17—N—C14—C13	146.7 (2)
O2—C6—C7—C8	−178.33 (19)	C17—N—C14—C8	27.2 (3)
C5—C6—C7—C8	58.5 (2)	C12—C13—C14—N	−146.3 (3)
O3—C7—C8—C14	62.2 (2)	C15—C13—C14—N	34.3 (4)
C6—C7—C8—C14	−177.89 (18)	C12—C13—C14—C8	−27.2 (3)
O3—C7—C8—C9	−172.68 (18)	C15—C13—C14—C8	153.4 (3)
C6—C7—C8—C9	−52.8 (3)	C7—C8—C14—N	−55.7 (2)
C7—C8—C9—C11	178.2 (2)	C9—C8—C14—N	179.35 (17)
C14—C8—C9—C11	−59.9 (3)	C7—C8—C14—C13	−178.77 (19)
C7—C8—C9—C10	51.2 (3)	C9—C8—C14—C13	56.3 (3)
C14—C8—C9—C10	173.10 (19)	C12—C13—C15—C16	0.7 (4)
C2—C1—C10—C20	−69.2 (3)	C14—C13—C15—C16	−179.9 (3)
C2—C1—C10—C9	171.2 (3)	C13—C15—C16—O1	−1.0 (4)
C2—C1—C10—C5	54.4 (3)	C12—O1—C16—C15	0.9 (4)
C8—C9—C10—C1	−174.7 (2)	C14—N—C17—O4	179.9 (2)
C11—C9—C10—C1	60.1 (3)	C14—N—C17—O3	−1.8 (4)
C8—C9—C10—C20	66.7 (3)	C7—O3—C17—O4	−174.1 (2)
C11—C9—C10—C20	−58.5 (3)	C7—O3—C17—N	7.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—HN···O3^i	0.81 (4)	2.30 (4)	3.057 (3)	155 (3)
N—HN···O4^i	0.81 (4)	2.52 (4)	3.096 (3)	129 (3)
O2—HO2···O4^ii	0.83 (4)	2.17 (4)	2.929 (3)	151 (3)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1/2, −y+3/2, −z+1.