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The crystal structure of morphine 3-(1-naphthoate), (or 7,8-dide­hydro-4,5-epoxy-17-methyl­morphinan-6-yl naphthalene-1-carboxyl­ate), C28H25NO4, was determined at 123 K. An intramolecular hydrogen bond exists between the secondary alcohol and the naphthoate group. Within the crystal structure, there is no significant π–π stacking, but there are significant intermolecular C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025121/lh6134sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025121/lh6134Isup2.hkl
Contains datablock I

CCDC reference: 227879

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.082
  • Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
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 28.28 From the CIF: _reflns_number_total 2909 Count of symmetry unique reflns 2953 Completeness (_total/calc) 98.51% 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

7,8-didehydro-4,5-epoxy-17-methylmorphinan-6-(naphthalene-1-carboxylate) top
Crystal data top
C28H25NO4F(000) = 464
Mr = 439.49Dx = 1.325 Mg m3
Monoclinic, P21Melting point = 443–445 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.7421 (2) ÅCell parameters from 14873 reflections
b = 7.1908 (1) Åθ = 2.8–28.3°
c = 12.9536 (3) ŵ = 0.09 mm1
β = 111.900 (1)°T = 123 K
V = 1101.23 (4) Å3Acicular, colourless
Z = 20.24 × 0.20 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
2423 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Horizonally mounted graphite crystal monochromatorθmax = 28.3°, θmin = 2.8°
Detector resolution: 9 pixels mm-1h = 1616
CCD rotation images, thick slices scansk = 99
14873 measured reflectionsl = 1717
2909 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0416P)2 + 0.1452P]
where P = (Fo2 + 2Fc2)/3
2909 reflections(Δ/σ)max = 0.002
300 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.20 e Å3
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.

The absolute structure cannot be reliably determined therefore Friedel pairs have been merged.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.97625 (15)0.5834 (3)0.80473 (14)0.0197 (4)
C20.95002 (15)0.6995 (3)0.87606 (15)0.0217 (4)
C31.03452 (17)0.7424 (3)0.97782 (15)0.0246 (4)
H31.01700.81781.02940.030*
C41.14411 (16)0.6770 (3)1.00531 (15)0.0243 (4)
H41.20130.71281.07380.029*
C51.17139 (15)0.5579 (3)0.93257 (15)0.0213 (4)
C61.08361 (15)0.5091 (3)0.83582 (14)0.0180 (4)
C71.09088 (15)0.3931 (3)0.74229 (14)0.0196 (4)
C80.98416 (16)0.4608 (3)0.64533 (15)0.0215 (4)
H80.94690.35280.59690.026*
C91.00760 (16)0.6150 (3)0.57366 (14)0.0243 (4)
H91.01980.55010.51080.029*
C101.11380 (16)0.7231 (3)0.63347 (15)0.0258 (4)
H101.11500.85260.61960.031*
C111.20582 (17)0.6431 (3)0.70494 (16)0.0269 (4)
H111.27290.71430.73810.032*
C121.20539 (16)0.4407 (3)0.73428 (16)0.0238 (4)
H121.21500.36390.67400.029*
C131.29713 (16)0.3860 (3)0.84632 (17)0.0261 (4)
H131.37180.41610.84150.031*
C141.28953 (16)0.4995 (3)0.94609 (16)0.0274 (4)
H14A1.32170.42351.01450.033*
H14B1.33690.61230.95660.033*
C151.08588 (17)0.1840 (3)0.76422 (16)0.0255 (4)
H15A1.01530.15640.77660.031*
H15B1.08390.11370.69780.031*
C161.18642 (18)0.1202 (3)0.86447 (17)0.0300 (5)
H16A1.18050.17120.93310.036*
H16B1.18610.01720.86920.036*
C171.39082 (19)0.1051 (4)0.94437 (18)0.0410 (6)
H17A1.38740.03100.94080.061*
H17B1.39170.14661.01680.061*
H17C1.45970.14770.93490.061*
C180.79496 (15)0.8781 (3)0.75925 (15)0.0224 (4)
C190.67468 (16)0.9225 (3)0.73928 (15)0.0235 (4)
C200.61200 (17)0.7891 (3)0.76669 (17)0.0306 (5)
H200.64700.67650.80070.037*
C210.49613 (19)0.8184 (4)0.7446 (2)0.0398 (6)
H210.45330.72500.76290.048*
C220.44587 (18)0.9796 (4)0.69729 (19)0.0386 (6)
H220.36790.99790.68340.046*
C230.50686 (17)1.1216 (4)0.66800 (16)0.0304 (5)
C240.45392 (19)1.2879 (4)0.61676 (19)0.0372 (5)
H240.37581.30560.60220.045*
C250.51224 (19)1.4235 (4)0.58763 (18)0.0391 (6)
H250.47501.53400.55250.047*
C260.62925 (19)1.3980 (4)0.61029 (18)0.0363 (5)
H260.67051.49300.59100.044*
C270.68311 (17)1.2393 (3)0.65931 (17)0.0294 (5)
H270.76151.22560.67410.035*
C280.62430 (16)1.0943 (3)0.68863 (16)0.0251 (4)
N11.29231 (14)0.1822 (3)0.85621 (14)0.0296 (4)
O10.90821 (10)0.5354 (2)0.69825 (10)0.0220 (3)
O20.91084 (12)0.7307 (2)0.52420 (11)0.0329 (4)
H20.89020.77330.57400.049*
O30.83989 (11)0.7679 (2)0.85129 (11)0.0253 (3)
O40.84723 (11)0.9268 (2)0.70298 (11)0.0284 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0219 (9)0.0190 (10)0.0191 (9)0.0015 (8)0.0087 (8)0.0027 (8)
C20.0228 (9)0.0206 (9)0.0244 (9)0.0033 (8)0.0118 (8)0.0033 (8)
C30.0346 (10)0.0212 (10)0.0219 (9)0.0034 (9)0.0150 (8)0.0008 (8)
C40.0289 (10)0.0227 (10)0.0190 (9)0.0006 (9)0.0062 (8)0.0012 (8)
C50.0242 (9)0.0186 (9)0.0208 (9)0.0014 (8)0.0079 (8)0.0021 (8)
C60.0223 (9)0.0148 (9)0.0189 (8)0.0018 (8)0.0099 (7)0.0013 (7)
C70.0231 (9)0.0181 (9)0.0187 (8)0.0006 (8)0.0091 (7)0.0019 (8)
C80.0252 (9)0.0202 (9)0.0208 (8)0.0005 (8)0.0106 (7)0.0037 (8)
C90.0284 (10)0.0274 (10)0.0180 (8)0.0034 (9)0.0097 (8)0.0014 (8)
C100.0320 (10)0.0228 (10)0.0269 (10)0.0030 (9)0.0161 (9)0.0001 (9)
C110.0250 (10)0.0286 (11)0.0300 (10)0.0039 (9)0.0136 (9)0.0027 (9)
C120.0247 (10)0.0247 (10)0.0257 (9)0.0031 (9)0.0137 (8)0.0013 (9)
C130.0216 (9)0.0288 (11)0.0294 (10)0.0040 (9)0.0112 (8)0.0009 (9)
C140.0198 (9)0.0293 (11)0.0283 (10)0.0013 (9)0.0033 (8)0.0019 (9)
C150.0314 (11)0.0185 (10)0.0270 (10)0.0008 (9)0.0115 (8)0.0008 (9)
C160.0406 (12)0.0207 (10)0.0296 (10)0.0054 (10)0.0141 (9)0.0018 (9)
C170.0423 (13)0.0388 (13)0.0369 (12)0.0179 (12)0.0089 (10)0.0018 (11)
C180.0240 (9)0.0194 (9)0.0238 (9)0.0001 (8)0.0091 (8)0.0026 (8)
C190.0232 (9)0.0247 (10)0.0242 (9)0.0003 (9)0.0108 (8)0.0027 (9)
C200.0282 (10)0.0320 (11)0.0341 (11)0.0004 (10)0.0147 (9)0.0012 (10)
C210.0296 (11)0.0466 (15)0.0495 (13)0.0026 (11)0.0218 (10)0.0056 (12)
C220.0227 (10)0.0537 (16)0.0424 (12)0.0035 (11)0.0156 (10)0.0030 (12)
C230.0265 (10)0.0385 (12)0.0273 (10)0.0039 (10)0.0112 (8)0.0025 (10)
C240.0299 (11)0.0462 (14)0.0357 (11)0.0108 (11)0.0123 (9)0.0008 (11)
C250.0409 (13)0.0368 (13)0.0356 (12)0.0140 (12)0.0098 (10)0.0035 (11)
C260.0364 (12)0.0328 (12)0.0372 (12)0.0015 (11)0.0107 (10)0.0032 (11)
C270.0259 (10)0.0272 (11)0.0322 (10)0.0006 (9)0.0075 (9)0.0010 (9)
C280.0225 (9)0.0289 (11)0.0229 (9)0.0020 (9)0.0074 (8)0.0031 (9)
N10.0299 (9)0.0277 (9)0.0306 (9)0.0111 (8)0.0108 (7)0.0028 (8)
O10.0196 (6)0.0252 (7)0.0212 (6)0.0011 (6)0.0074 (5)0.0025 (6)
O20.0333 (8)0.0370 (9)0.0267 (7)0.0083 (7)0.0093 (6)0.0097 (7)
O30.0243 (7)0.0276 (8)0.0276 (7)0.0060 (6)0.0136 (6)0.0031 (6)
O40.0275 (7)0.0277 (8)0.0346 (7)0.0019 (7)0.0170 (6)0.0051 (7)
Geometric parameters (Å, º) top
C1—O11.372 (2)C15—C161.516 (3)
C1—C21.376 (3)C15—H15A0.9900
C1—C61.381 (2)C15—H15B0.9900
C2—C31.390 (3)C16—N11.462 (3)
C2—O31.406 (2)C16—H16A0.9900
C3—C41.388 (3)C16—H16B0.9900
C3—H30.9500C17—N11.455 (3)
C4—C51.410 (3)C17—H17A0.9800
C4—H40.9500C17—H17B0.9800
C5—C61.378 (3)C17—H17C0.9800
C5—C141.509 (3)C18—O41.208 (2)
C6—C71.502 (2)C18—O31.367 (2)
C7—C151.536 (3)C18—C191.491 (3)
C7—C121.540 (3)C19—C201.377 (3)
C7—C81.546 (3)C19—C281.433 (3)
C8—O11.480 (2)C20—C211.411 (3)
C8—C91.545 (3)C20—H200.9500
C8—H81.0000C21—C221.355 (4)
C9—O21.426 (2)C21—H210.9500
C9—C101.501 (3)C22—C231.418 (3)
C9—H91.0000C22—H220.9500
C10—C111.324 (3)C23—C241.411 (4)
C10—H100.9500C23—C281.432 (3)
C11—C121.504 (3)C24—C251.362 (4)
C11—H110.9500C24—H240.9500
C12—C131.537 (3)C25—C261.420 (3)
C12—H121.0000C25—H250.9500
C13—N11.474 (3)C26—C271.360 (3)
C13—C141.562 (3)C26—H260.9500
C13—H131.0000C27—C281.416 (3)
C14—H14A0.9900C27—H270.9500
C14—H14B0.9900O2—H20.8400
O1—C1—C2127.39 (16)H14A—C14—H14B107.6
O1—C1—C6112.44 (15)C16—C15—C7112.01 (17)
C2—C1—C6120.07 (16)C16—C15—H15A109.2
C1—C2—C3118.37 (17)C7—C15—H15A109.2
C1—C2—O3122.05 (16)C16—C15—H15B109.2
C3—C2—O3119.51 (16)C7—C15—H15B109.2
C4—C3—C2121.14 (17)H15A—C15—H15B107.9
C4—C3—H3119.4N1—C16—C15110.68 (16)
C2—C3—H3119.4N1—C16—H16A109.5
C3—C4—C5120.65 (17)C15—C16—H16A109.5
C3—C4—H4119.7N1—C16—H16B109.5
C5—C4—H4119.7C15—C16—H16B109.5
C6—C5—C4116.33 (17)H16A—C16—H16B108.1
C6—C5—C14118.11 (17)N1—C17—H17A109.5
C4—C5—C14125.14 (17)N1—C17—H17B109.5
C5—C6—C1123.13 (17)H17A—C17—H17B109.5
C5—C6—C7126.97 (17)N1—C17—H17C109.5
C1—C6—C7109.39 (15)H17A—C17—H17C109.5
C6—C7—C15112.05 (15)H17B—C17—H17C109.5
C6—C7—C12106.01 (15)O4—C18—O3123.25 (16)
C15—C7—C12109.64 (16)O4—C18—C19126.59 (17)
C6—C7—C8100.37 (15)O3—C18—C19110.15 (15)
C15—C7—C8111.98 (16)C20—C19—C28120.98 (18)
C12—C7—C8116.34 (15)C20—C19—C18117.65 (19)
O1—C8—C9108.95 (16)C28—C19—C18121.31 (17)
O1—C8—C7105.49 (13)C19—C20—C21120.5 (2)
C9—C8—C7113.94 (15)C19—C20—H20119.8
O1—C8—H8109.4C21—C20—H20119.8
C9—C8—H8109.4C22—C21—C20120.1 (2)
C7—C8—H8109.4C22—C21—H21119.9
O2—C9—C10113.09 (17)C20—C21—H21119.9
O2—C9—C8111.10 (15)C21—C22—C23121.5 (2)
C10—C9—C8113.60 (15)C21—C22—H22119.2
O2—C9—H9106.1C23—C22—H22119.2
C10—C9—H9106.1C24—C23—C22121.50 (19)
C8—C9—H9106.1C24—C23—C28119.1 (2)
C11—C10—C9121.94 (19)C22—C23—C28119.4 (2)
C11—C10—H10119.0C25—C24—C23121.5 (2)
C9—C10—H10119.0C25—C24—H24119.2
C10—C11—C12120.73 (19)C23—C24—H24119.2
C10—C11—H11119.6C24—C25—C26119.3 (2)
C12—C11—H11119.6C24—C25—H25120.3
C11—C12—C13114.39 (18)C26—C25—H25120.3
C11—C12—C7108.97 (17)C27—C26—C25120.9 (2)
C13—C12—C7106.59 (15)C27—C26—H26119.6
C11—C12—H12108.9C25—C26—H26119.6
C13—C12—H12108.9C26—C27—C28121.17 (19)
C7—C12—H12108.9C26—C27—H27119.4
N1—C13—C12107.15 (17)C28—C27—H27119.4
N1—C13—C14115.47 (18)C27—C28—C23118.00 (19)
C12—C13—C14112.80 (16)C27—C28—C19124.48 (17)
N1—C13—H13107.0C23—C28—C19117.51 (18)
C12—C13—H13107.0C17—N1—C16112.07 (18)
C14—C13—H13107.0C17—N1—C13113.29 (19)
C5—C14—C13114.61 (16)C16—N1—C13112.27 (16)
C5—C14—H14A108.6C1—O1—C8106.24 (13)
C13—C14—H14A108.6C9—O2—H2109.5
C5—C14—H14B108.6C18—O3—C2117.36 (14)
C13—C14—H14B108.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O40.842.233.067 (2)171
C3—H3···Cg1i0.952.703.577 (2)154
C16—H16b···Cg1ii0.993.144.004 (2)146
C14—H14a···Cg2iii0.993.244.068 (2)143
C25—H25···Cg3iv0.952.843.643 (3)143
Symmetry codes: (i) x, y+1/2, z; (ii) x, y1, z; (iii) x, y1/2, z; (iv) x+1, y+1/2, z+1.
 

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