Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027533/rn6006sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027533/rn6006Isup2.hkl
Contains datablock I

CCDC reference: 232152

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 top

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) top
Crystal data top
C20H27NO4F(000) = 744
Mr = 345.43Dx = 1.3 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 8.3541 (10) Åθ = 3.0–26.3°
b = 13.6308 (10) ŵ = 0.09 mm1
c = 15.4932 (10) ÅT = 293 K
V = 1764.3 (3) Å3Prism, colourless
Z = 40.8 × 0.4 × 0.2 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
θmax = 26.3°, θmin = 3.0°
non–profiled ω/2θ scansh = 103
2065 measured reflectionsk = 016
2044 independent reflectionsl = 319
1719 reflections with I > 2σ(I)3 standard reflections every 120 min
Rint = 0.023 intensity decay: 7%
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1708P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042(Δ/σ)max = 0.001
wR(F2) = 0.117Δρmax = 0.28 e Å3
S = 1.06Δρmin = 0.19 e Å3
2044 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
236 parametersExtinction coefficient: 0.012 (3)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1.1596 (2)0.66133 (15)0.51212 (14)0.0377 (5)
O11.3169 (3)0.33543 (14)0.50577 (16)0.0640 (6)
O20.6916 (3)0.69376 (15)0.69990 (14)0.0556 (6)
O30.9138 (2)0.70606 (12)0.56882 (11)0.0410 (4)
O41.0201 (2)0.79302 (13)0.46459 (13)0.0475 (5)
C10.8572 (4)0.3457 (2)0.7547 (2)0.0554 (7)
H1A0.89010.28630.72510.066*
H1B0.93940.3620.79650.066*
C20.7012 (5)0.3267 (2)0.8015 (2)0.0668 (9)
H2A0.71440.27250.84150.08*
H2B0.61870.3090.76030.08*
C30.6512 (4)0.4180 (2)0.85040 (19)0.0616 (9)
H3A0.73190.43210.89370.074*
H3B0.55190.40410.88050.074*
C40.6269 (3)0.5107 (2)0.79465 (16)0.0465 (7)
C50.7768 (3)0.52408 (18)0.73498 (14)0.0360 (5)
H50.8630.54550.77350.043*
C60.7609 (3)0.60653 (18)0.66686 (15)0.0351 (5)
H60.69570.58270.61860.042*
C70.9284 (3)0.62962 (16)0.63418 (15)0.0330 (5)
H70.99260.65480.68220.04*
C81.0128 (3)0.54334 (16)0.59512 (14)0.0313 (5)
H80.95530.52490.54240.038*
C91.0154 (3)0.45386 (17)0.65499 (15)0.0373 (5)
H91.08040.47150.70530.045*
C100.8432 (3)0.42957 (18)0.68869 (15)0.0383 (6)
C111.0991 (4)0.36626 (19)0.6103 (2)0.0545 (8)
H11A1.1470.32410.65360.065*
H11B1.02060.32810.57870.065*
C121.2245 (3)0.40117 (19)0.55025 (18)0.0451 (6)
C131.2643 (3)0.49322 (18)0.52820 (17)0.0388 (6)
C141.1793 (3)0.57761 (16)0.56909 (16)0.0338 (5)
H141.23810.59820.62080.041*
C151.3904 (4)0.4861 (2)0.4659 (2)0.0544 (7)
H151.44390.53750.4390.065*
C161.4152 (4)0.3905 (2)0.4547 (3)0.0672 (9)
H161.49020.36440.41680.081*
C171.0343 (3)0.72305 (16)0.51284 (16)0.0343 (5)
C180.6135 (4)0.5962 (3)0.85819 (19)0.0644 (9)
H18A0.58710.65510.82730.097*
H18B0.71370.60480.88750.097*
H18C0.53110.58240.89960.097*
C190.4684 (3)0.5035 (3)0.7456 (2)0.0684 (10)
H19A0.46750.44470.71150.103*
H19B0.45690.55950.70850.103*
H19C0.38130.50190.7860.103*
C200.7361 (4)0.3951 (2)0.61347 (18)0.0516 (7)
H20A0.76420.32920.59790.077*
H20B0.75150.43750.56470.077*
H20C0.62590.39720.6310.077*
HN1.237 (5)0.680 (3)0.485 (2)0.062*
HO20.643 (5)0.719 (3)0.659 (2)0.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0218 (9)0.0359 (10)0.0554 (12)0.0017 (8)0.0032 (9)0.0059 (10)
O10.0610 (14)0.0403 (10)0.0905 (15)0.0105 (10)0.0160 (12)0.0132 (10)
O20.0545 (13)0.0554 (12)0.0568 (11)0.0216 (10)0.0165 (10)0.0112 (10)
O30.0305 (9)0.0396 (9)0.0530 (9)0.0081 (8)0.0085 (8)0.0144 (8)
O40.0330 (9)0.0420 (9)0.0675 (11)0.0012 (8)0.0083 (9)0.0209 (10)
C10.0572 (18)0.0501 (14)0.0589 (16)0.0016 (14)0.0042 (16)0.0218 (14)
C20.068 (2)0.0626 (19)0.0695 (18)0.0073 (17)0.0076 (18)0.0321 (17)
C30.0534 (17)0.079 (2)0.0525 (16)0.0002 (17)0.0064 (15)0.0291 (16)
C40.0356 (13)0.0653 (17)0.0388 (12)0.0016 (13)0.0010 (11)0.0153 (13)
C50.0297 (11)0.0465 (13)0.0320 (11)0.0012 (11)0.0053 (10)0.0056 (11)
C60.0285 (12)0.0409 (12)0.0360 (11)0.0021 (10)0.0008 (10)0.0060 (10)
C70.0293 (11)0.0330 (11)0.0366 (11)0.0034 (9)0.0026 (10)0.0050 (9)
C80.0252 (10)0.0330 (11)0.0358 (10)0.0006 (9)0.0029 (9)0.0017 (9)
C90.0354 (12)0.0345 (12)0.0419 (12)0.0023 (10)0.0036 (11)0.0045 (10)
C100.0369 (13)0.0393 (12)0.0386 (12)0.0025 (11)0.0019 (11)0.0084 (11)
C110.0578 (18)0.0345 (13)0.0712 (18)0.0081 (13)0.0107 (17)0.0067 (13)
C120.0413 (13)0.0375 (12)0.0565 (15)0.0076 (12)0.0007 (13)0.0051 (12)
C130.0284 (11)0.0387 (12)0.0493 (13)0.0030 (10)0.0020 (11)0.0043 (11)
C140.0261 (11)0.0307 (11)0.0445 (12)0.0021 (9)0.0062 (10)0.0013 (10)
C150.0401 (15)0.0490 (14)0.0740 (18)0.0021 (13)0.0139 (15)0.0068 (15)
C160.0562 (19)0.0558 (17)0.090 (2)0.0057 (16)0.0255 (19)0.0165 (17)
C170.0249 (11)0.0321 (11)0.0459 (12)0.0024 (9)0.0006 (10)0.0034 (11)
C180.0595 (19)0.089 (2)0.0445 (14)0.006 (2)0.0150 (15)0.0047 (16)
C190.0330 (16)0.109 (3)0.0630 (17)0.0064 (17)0.0024 (14)0.025 (2)
C200.0484 (16)0.0536 (15)0.0528 (15)0.0164 (14)0.0025 (14)0.0023 (13)
Geometric parameters (Å, º) top
N—C171.343 (3)C7—C81.499 (3)
N—C141.452 (3)C7—H70.98
N—HN0.81 (4)C8—C141.522 (3)
O1—C161.365 (4)C8—C91.532 (3)
O1—C121.369 (3)C8—H80.98
O2—C61.418 (3)C9—C111.547 (4)
O2—HO20.83 (4)C9—C101.566 (4)
O3—C171.349 (3)C9—H90.98
O3—C71.458 (3)C10—C201.543 (4)
O4—C171.217 (3)C11—C121.479 (4)
C1—C21.515 (5)C11—H11A0.97
C1—C101.538 (3)C11—H11B0.97
C1—H1A0.97C12—C131.342 (4)
C1—H1B0.97C13—C151.432 (4)
C2—C31.515 (5)C13—C141.493 (3)
C2—H2A0.97C14—H140.98
C2—H2B0.97C15—C161.330 (4)
C3—C41.544 (4)C15—H150.93
C3—H3A0.97C16—H160.93
C3—H3B0.97C18—H18A0.96
C4—C191.530 (4)C18—H18B0.96
C4—C181.530 (4)C18—H18C0.96
C4—C51.567 (3)C19—H19A0.96
C5—C61.547 (3)C19—H19B0.96
C5—C101.575 (3)C19—H19C0.96
C5—H50.98C20—H20A0.96
C6—C71.521 (3)C20—H20B0.96
C6—H60.98C20—H20C0.96
C17—N—C14125.2 (2)C11—C9—C10113.7 (2)
C17—N—HN116 (3)C8—C9—H9107.2
C14—N—HN118 (3)C11—C9—H9107.2
C16—O1—C12105.7 (2)C10—C9—H9107.2
C6—O2—HO2106 (2)C1—C10—C20108.6 (2)
C17—O3—C7120.45 (17)C1—C10—C9108.0 (2)
C2—C1—C10112.3 (3)C20—C10—C9110.2 (2)
C2—C1—H1A109.1C1—C10—C5109.4 (2)
C10—C1—H1A109.1C20—C10—C5112.9 (2)
C2—C1—H1B109.1C9—C10—C5107.62 (19)
C10—C1—H1B109.1C12—C11—C9110.7 (2)
H1A—C1—H1B107.9C12—C11—H11A109.5
C1—C2—C3109.7 (3)C9—C11—H11A109.5
C1—C2—H2A109.7C12—C11—H11B109.5
C3—C2—H2A109.7C9—C11—H11B109.5
C1—C2—H2B109.7H11A—C11—H11B108.1
C3—C2—H2B109.7C13—C12—O1110.1 (2)
H2A—C2—H2B108.2C13—C12—C11129.5 (2)
C2—C3—C4115.4 (2)O1—C12—C11120.4 (2)
C2—C3—H3A108.4C12—C13—C15106.9 (2)
C4—C3—H3A108.4C12—C13—C14119.6 (2)
C2—C3—H3B108.4C15—C13—C14133.5 (2)
C4—C3—H3B108.4N—C14—C13113.7 (2)
H3A—C3—H3B107.5N—C14—C8107.38 (18)
C19—C4—C18107.7 (3)C13—C14—C8108.10 (19)
C19—C4—C3109.9 (3)N—C14—H14109.2
C18—C4—C3105.9 (2)C13—C14—H14109.2
C19—C4—C5113.9 (2)C8—C14—H14109.2
C18—C4—C5110.4 (2)C16—C15—C13105.6 (3)
C3—C4—C5108.7 (2)C16—C15—H15127.2
C6—C5—C4114.7 (2)C13—C15—H15127.2
C6—C5—C10108.28 (17)C15—C16—O1111.7 (3)
C4—C5—C10117.0 (2)C15—C16—H16124.2
C6—C5—H5105.2O1—C16—H16124.2
C4—C5—H5105.2O4—C17—N124.2 (2)
C10—C5—H5105.2O4—C17—O3117.2 (2)
O2—C6—C7108.8 (2)N—C17—O3118.66 (19)
O2—C6—C5113.43 (19)C4—C18—H18A109.5
C7—C6—C5107.37 (18)C4—C18—H18B109.5
O2—C6—H6109H18A—C18—H18B109.5
C7—C6—H6109C4—C18—H18C109.5
C5—C6—H6109H18A—C18—H18C109.5
O3—C7—C8108.64 (17)H18B—C18—H18C109.5
O3—C7—C6107.59 (17)C4—C19—H19A109.5
C8—C7—C6113.89 (19)C4—C19—H19B109.5
O3—C7—H7108.9H19A—C19—H19B109.5
C8—C7—H7108.9C4—C19—H19C109.5
C6—C7—H7108.9H19A—C19—H19C109.5
C7—C8—C14107.24 (18)H19B—C19—H19C109.5
C7—C8—C9112.75 (18)C10—C20—H20A109.5
C14—C8—C9113.07 (19)C10—C20—H20B109.5
C7—C8—H8107.9H20A—C20—H20B109.5
C14—C8—H8107.9C10—C20—H20C109.5
C9—C8—H8107.9H20A—C20—H20C109.5
C8—C9—C11110.46 (19)H20B—C20—H20C109.5
C8—C9—C10110.9 (2)
C10—C1—C2—C360.6 (3)C8—C9—C10—C556.7 (2)
C1—C2—C3—C458.9 (4)C11—C9—C10—C5178.1 (2)
C2—C3—C4—C1975.9 (4)C6—C5—C10—C1178.9 (2)
C2—C3—C4—C18168.1 (3)C4—C5—C10—C147.4 (3)
C2—C3—C4—C549.4 (4)C6—C5—C10—C2057.9 (3)
C19—C4—C5—C649.7 (3)C4—C5—C10—C2073.7 (2)
C18—C4—C5—C671.7 (3)C6—C5—C10—C964.0 (2)
C3—C4—C5—C6172.6 (2)C4—C5—C10—C9164.46 (19)
C19—C4—C5—C1078.8 (3)C8—C9—C11—C1231.2 (3)
C18—C4—C5—C10159.8 (2)C10—C9—C11—C12156.6 (2)
C3—C4—C5—C1044.0 (3)C16—O1—C12—C130.4 (3)
C4—C5—C6—O243.1 (3)C16—O1—C12—C11177.9 (3)
C10—C5—C6—O2175.9 (2)C9—C11—C12—C134.0 (5)
C4—C5—C6—C7163.4 (2)C9—C11—C12—O1178.0 (3)
C10—C5—C6—C763.8 (2)O1—C12—C13—C150.2 (3)
C17—O3—C7—C838.6 (3)C11—C12—C13—C15178.3 (3)
C17—O3—C7—C6162.4 (2)O1—C12—C13—C14179.7 (2)
O2—C6—C7—O357.9 (2)C11—C12—C13—C142.1 (5)
C5—C6—C7—O3178.99 (17)C17—N—C14—C13146.7 (2)
O2—C6—C7—C8178.33 (19)C17—N—C14—C827.2 (3)
C5—C6—C7—C858.5 (2)C12—C13—C14—N146.3 (3)
O3—C7—C8—C1462.2 (2)C15—C13—C14—N34.3 (4)
C6—C7—C8—C14177.89 (18)C12—C13—C14—C827.2 (3)
O3—C7—C8—C9172.68 (18)C15—C13—C14—C8153.4 (3)
C6—C7—C8—C952.8 (3)C7—C8—C14—N55.7 (2)
C7—C8—C9—C11178.2 (2)C9—C8—C14—N179.35 (17)
C14—C8—C9—C1159.9 (3)C7—C8—C14—C13178.77 (19)
C7—C8—C9—C1051.2 (3)C9—C8—C14—C1356.3 (3)
C14—C8—C9—C10173.10 (19)C12—C13—C15—C160.7 (4)
C2—C1—C10—C2069.2 (3)C14—C13—C15—C16179.9 (3)
C2—C1—C10—C9171.2 (3)C13—C15—C16—O11.0 (4)
C2—C1—C10—C554.4 (3)C12—O1—C16—C150.9 (4)
C8—C9—C10—C1174.7 (2)C14—N—C17—O4179.9 (2)
C11—C9—C10—C160.1 (3)C14—N—C17—O31.8 (4)
C8—C9—C10—C2066.7 (3)C7—O3—C17—O4174.1 (2)
C11—C9—C10—C2058.5 (3)C7—O3—C17—N7.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—HN···O3i0.81 (4)2.30 (4)3.057 (3)155 (3)
N—HN···O4i0.81 (4)2.52 (4)3.096 (3)129 (3)
O2—HO2···O4ii0.83 (4)2.17 (4)2.929 (3)151 (3)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1/2, y+3/2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds