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The electron density distribution of morphine hydrate has been determined from high-resolution single-crystal X-ray diffraction measurements at 25 K. A topological analysis was applied and, in order to analyze the submolecular transferability based on an experimental electron density, a partitioning of the molecule into atomic regions was carried out, making use of Bader's zero-flux surfaces to yield atomic volumes and charges. The properties obtained were compared with the theoretical calculations of smaller fragment molecules, from which the complete morphine molecule can be reconstructed, and with theoretical studies of another opiate, Oripavine PEO, reported in the literature.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810501637X/lc5024sup1.cif
Contains datablock MORPH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810501637X/lc5024sup2.hkl
Contains datablock MORPH

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup3.pdf
Linear plot of V_{001} values

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup4.pdf
Linear plot of N_{001} values

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S010876810501637X/lc5024sup5.pdf
Numerical data

CCDC reference: 280359

Computing details top

Data collection: SMART (Bruker, 1997-2001); cell refinement: SAINT (Bruker, 1997-2001); data reduction: SAINT (Bruker, 1997-2001); program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(MORPH) top
Crystal data top
C17H19NO3·H2OZ = 4
Mr = 303.35F(000) = 648
Orthorhombic, P212121Dx = 1.318 Mg m3
Hall symbol: P 2ac 2abMo Kα radiation, λ = 0.7107 Å
a = 7.431 (6) ŵ = 0.09 mm1
b = 13.769 (9) ÅT = 25 K
c = 14.944 (13) ÅPrism, colourless
V = 1529 (2) Å30.5 × 0.35 × 0.35 mm
Data collection top
Bruker SMART Apex CCD Detector on Huber four circle
diffractometer
Rint = 0.04
ϕ scansθmax = 54.6°
67606 measured reflectionsh = 1617
9984 independent reflectionsk = 2925
8069 reflections with I > 3 σ(I)l = 3332
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullOnly H-atom displacement parameters refined
R[F2 > 2σ(F2)] = 0.023 w1 = 1/[s2(Fo)]
wR(F2) = 0.020(Δ/σ)max = 0.000047
S = 0.65Δρmax = 0.22 e Å3
8069 reflectionsΔρmin = 0.20 e Å3
682 parameters
Crystal data top
C17H19NO3·H2OV = 1529 (2) Å3
Mr = 303.35Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.431 (6) ŵ = 0.09 mm1
b = 13.769 (9) ÅT = 25 K
c = 14.944 (13) Å0.5 × 0.35 × 0.35 mm
Data collection top
Bruker SMART Apex CCD Detector on Huber four circle
diffractometer
8069 reflections with I > 3 σ(I)
67606 measured reflectionsRint = 0.04
9984 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.020Only H-atom displacement parameters refined
S = 0.65Δρmax = 0.22 e Å3
8069 reflectionsΔρmin = 0.20 e Å3
682 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.61639 (7)0.89628 (3)0.26177 (4)0.0091 (1)
O20.71984 (7)0.65587 (4)0.47286 (3)0.0091 (1)
O30.87996 (7)0.76148 (3)0.33796 (3)0.0072 (1)
N11.18029 (6)0.49795 (3)0.12824 (3)0.0071 (1)
C10.69069 (7)0.71688 (3)0.07852 (3)0.0086 (1)
C20.63118 (7)0.80010 (3)0.12507 (3)0.0087 (1)
C30.69205 (6)0.82259 (3)0.21303 (3)0.0073 (1)
C40.82078 (6)0.75969 (3)0.24963 (3)0.0065 (1)
C50.95874 (6)0.66546 (3)0.35590 (3)0.0065 (1)
C60.82277 (6)0.60129 (3)0.40948 (3)0.0070 (1)
C70.69673 (6)0.54364 (3)0.34986 (3)0.0076 (1)
C80.75891 (6)0.49860 (3)0.27558 (3)0.0074 (1)
C90.98294 (6)0.49028 (3)0.14576 (3)0.0066 (1)
C100.86331 (7)0.55334 (3)0.08189 (3)0.0081 (1)
C110.81922 (6)0.65394 (3)0.11762 (3)0.0070 (1)
C120.88716 (6)0.68091 (3)0.20146 (3)0.0062 (1)
C131.00782 (6)0.62104 (3)0.26207 (3)0.0058 (1)
C140.95218 (6)0.51359 (3)0.24709 (3)0.0061 (1)
C151.20924 (6)0.63318 (3)0.23899 (3)0.0077 (1)
C161.25082 (6)0.59768 (3)0.14308 (3)0.0084 (1)
C171.23142 (7)0.46153 (4)0.03812 (3)0.0105 (1)
O40.44890 (8)0.77409 (4)0.40240 (4)0.0118 (1)
H10.636750.698820.013510.0230*
H20.525160.844570.097400.0160*
H51.076600.680800.395920.0140*
H60.908120.551650.446030.0120*
H70.558110.536460.370630.0110*
H80.670290.452540.237080.0110*
H90.950610.414310.137470.0150*
H10A0.760670.519500.072770.0100*
H10B0.911780.554520.024170.0150*
H110.702150.931570.298320.0220*
H141.030830.470300.280300.0110*
H15A1.288040.588710.283940.0110*
H15B1.248020.708630.243260.0150*
H16A1.391900.598330.125530.0190*
H16B1.196710.644910.092060.0150*
H17A1.164700.393540.023930.0140*
H17B1.375160.450180.036660.0110*
H17C1.197560.512040.014620.0130*
H210.799860.685540.516170.0210*
H410.540840.731780.426700.0160*
H420.490910.814350.353440.0110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0074 (1)0.0074 (1)0.0124 (2)0.0021 (1)0.0010 (1)0.0020 (1)
O20.0090 (1)0.0110 (1)0.0073 (1)0.0001 (1)0.0009 (1)0.0017 (1)
O30.0085 (1)0.0060 (1)0.0071 (1)0.0009 (1)0.0010 (1)0.0006 (1)
N10.0066 (1)0.0069 (1)0.0079 (1)0.0002 (1)0.0013 (1)0.0001 (1)
C10.0099 (1)0.0082 (1)0.0076 (1)0.0018 (1)0.0024 (1)0.0002 (1)
C20.0094 (1)0.0075 (1)0.0092 (1)0.0021 (1)0.0022 (1)0.0006 (1)
C30.0068 (1)0.0063 (1)0.0089 (1)0.0013 (1)0.0009 (1)0.0002 (1)
C40.0066 (1)0.0058 (1)0.0071 (1)0.0011 (1)0.0009 (1)0.0002 (1)
C50.0064 (1)0.0065 (1)0.0065 (1)0.0001 (1)0.0008 (1)0.0002 (1)
C60.0071 (1)0.0074 (1)0.0065 (1)0.0001 (1)0.0001 (1)0.0001 (1)
C70.0063 (1)0.0088 (1)0.0077 (1)0.0009 (1)0.0008 (1)0.0008 (1)
C80.0062 (1)0.0080 (1)0.0081 (1)0.0018 (1)0.0007 (1)0.0011 (1)
C90.0066 (1)0.0059 (1)0.0072 (1)0.0003 (1)0.0003 (1)0.0002 (1)
C100.0096 (1)0.0075 (1)0.0073 (1)0.0016 (1)0.0012 (1)0.0012 (1)
C110.0080 (1)0.0065 (1)0.0066 (1)0.0011 (1)0.0014 (1)0.0002 (1)
C120.0067 (1)0.0055 (1)0.0064 (1)0.0009 (1)0.0009 (1)0.0002 (1)
C130.0051 (1)0.0055 (1)0.0068 (1)0.0001 (1)0.0003 (1)0.0001 (1)
C140.0058 (1)0.0054 (1)0.0070 (1)0.0003 (1)0.0003 (1)0.0000 (1)
C150.0059 (1)0.0075 (1)0.0096 (1)0.0006 (1)0.0002 (1)0.0006 (1)
C160.0077 (1)0.0077 (1)0.0099 (1)0.0006 (1)0.0022 (1)0.0003 (1)
C170.0113 (2)0.0107 (2)0.0096 (2)0.0016 (1)0.0028 (1)0.0009 (1)
O40.0096 (2)0.0143 (2)0.0116 (2)0.0010 (1)0.0014 (1)0.0010 (2)
Geometric parameters (Å, º) top
O1—C31.3697 (7)C10—C111.5202 (8)
O2—C61.4307 (7)C11—C121.4009 (8)
O3—C41.3916 (7)C12—C131.5179 (8)
O3—C51.4706 (7)C13—C151.5451 (8)
O1—H110.9700C13—C141.5524 (8)
O2—H210.9700C15—C161.5456 (8)
O4—H410.9700C1—H11.0800
O4—H420.9700C2—H21.0800
N1—C161.4864 (8)C5—H51.0800
N1—C91.4935 (8)C6—H61.0800
N1—C171.4865 (8)C7—H71.0800
C1—C111.4159 (8)C8—H81.0800
C1—C21.4115 (8)C9—H91.0800
C2—C31.4242 (8)C10—H10A0.9000
C3—C41.4016 (8)C10—H10B0.9300
C4—C121.3922 (8)C14—H140.9700
C5—C61.5629 (8)C15—H15B1.0800
C5—C131.5727 (8)C15—H15A1.0800
C6—C71.5170 (8)C16—H16B1.0800
C7—C81.3529 (8)C16—H16A1.0800
C8—C141.5122 (8)C17—H17C1.0800
C9—C101.5669 (8)C17—H17A1.0800
C9—C141.5647 (8)C17—H17B1.0800
C4—O3—C5106.43 (4)C9—C14—C13107.23 (3)
C3—O1—H11114.00C13—C15—C16111.50 (4)
C6—O2—H21110.00N1—C16—C15111.10 (4)
H41—O4—H42114.00C11—C1—H1119.00
C9—N1—C17112.71 (4)C2—C1—H1121.00
C9—N1—C16112.67 (4)C1—C2—H2120.00
C16—N1—C17110.90 (4)C3—C2—H2118.00
C2—C1—C11120.32 (4)C6—C5—H5111.00
C1—C2—C3122.13 (4)C13—C5—H5112.00
O1—C3—C4122.03 (4)O3—C5—H5104.00
C2—C3—C4116.27 (4)C5—C6—H6104.00
O1—C3—C2121.43 (4)C7—C6—H6109.00
O3—C4—C3125.10 (4)O2—C6—H6108.00
C3—C4—C12121.43 (4)C8—C7—H7121.00
O3—C4—C12113.10 (4)C6—C7—H7118.00
C6—C5—C13112.76 (3)C14—C8—H8121.00
O3—C5—C13106.23 (4)C7—C8—H8120.00
O3—C5—C6110.14 (4)N1—C9—H9105.00
O2—C6—C5112.82 (4)C10—C9—H9110.00
O2—C6—C7109.49 (4)C14—C9—H9106.00
C5—C6—C7113.21 (4)C9—C10—H10A107.00
C6—C7—C8120.72 (4)C9—C10—H10B111.00
C7—C8—C14119.53 (4)C11—C10—H10B113.00
C10—C9—C14113.14 (3)H10A—C10—H10B101.00
N1—C9—C10114.28 (4)C11—C10—H10A110.00
N1—C9—C14107.37 (4)C8—C14—H14110.00
C9—C10—C11114.41 (4)C13—C14—H14111.00
C1—C11—C12116.74 (4)C9—C14—H14106.00
C1—C11—C10123.93 (4)C13—C15—H15A109.00
C10—C11—C12118.55 (4)C16—C15—H15A107.00
C11—C12—C13127.06 (4)C16—C15—H15B108.00
C4—C12—C11122.77 (4)H15A—C15—H15B111.00
C4—C12—C13108.90 (4)C13—C15—H15B110.00
C5—C13—C12100.59 (3)N1—C16—H16A108.00
C12—C13—C14105.91 (3)C15—C16—H16A115.00
C5—C13—C15112.44 (4)C15—C16—H16B113.00
C14—C13—C15109.20 (3)N1—C16—H16B109.00
C5—C13—C14115.94 (4)H16A—C16—H16B101.00
C12—C13—C15112.35 (4)N1—C17—H17B109.00
C8—C14—C13110.03 (3)N1—C17—H17C113.00
C8—C14—C9112.53 (4)N1—C17—H17A111.00
C5—O3—C4—C3159.65 (4)O2—C6—C7—C8169.23 (4)
C5—O3—C4—C1213.41 (5)C5—C6—C7—C842.41 (5)
C4—O3—C5—C6101.16 (4)C6—C7—C8—C145.71 (6)
C4—O3—C5—C1321.24 (5)C7—C8—C14—C9158.76 (4)
C17—N1—C16—C15176.12 (4)C7—C8—C14—C1339.26 (5)
C16—N1—C9—C1063.19 (5)C14—C9—C10—C1130.61 (5)
C16—N1—C9—C1463.17 (5)N1—C9—C10—C1192.69 (5)
C9—N1—C16—C1556.49 (5)C10—C9—C14—C858.61 (5)
C17—N1—C9—C14170.40 (4)N1—C9—C14—C8174.36 (3)
C17—N1—C9—C1063.24 (5)N1—C9—C14—C1364.53 (4)
C11—C1—C2—C32.03 (7)C10—C9—C14—C1362.50 (5)
C2—C1—C11—C122.50 (7)C9—C10—C11—C120.16 (6)
C2—C1—C11—C10167.21 (4)C9—C10—C11—C1169.37 (4)
C1—C2—C3—O1171.51 (5)C1—C11—C12—C46.50 (7)
C1—C2—C3—C42.69 (7)C10—C11—C12—C131.87 (7)
O1—C3—C4—C12175.36 (4)C1—C11—C12—C13172.16 (4)
C2—C3—C4—O3171.30 (4)C10—C11—C12—C4163.78 (4)
O1—C3—C4—O32.85 (7)C11—C12—C13—C5154.18 (4)
C2—C3—C4—C121.21 (6)C11—C12—C13—C1433.11 (6)
C3—C4—C12—C13173.95 (4)C11—C12—C13—C1586.04 (5)
O3—C4—C12—C130.61 (5)C4—C12—C13—C513.10 (4)
C3—C4—C12—C116.01 (7)C4—C12—C13—C14134.17 (4)
O3—C4—C12—C11167.33 (4)C4—C12—C13—C15106.68 (4)
O3—C5—C6—C788.80 (4)C5—C13—C14—C847.75 (5)
O3—C5—C13—C1220.58 (4)C5—C13—C14—C9170.44 (4)
C13—C5—C6—O2154.71 (4)C12—C13—C14—C862.81 (4)
C13—C5—C6—C729.67 (5)C5—C13—C15—C16174.72 (3)
O3—C5—C6—O236.25 (5)C12—C13—C15—C1662.08 (4)
C6—C5—C13—C1413.50 (5)C14—C13—C15—C1655.12 (5)
C6—C5—C13—C15140.13 (4)C15—C13—C14—C961.33 (4)
O3—C5—C13—C1599.15 (4)C12—C13—C14—C959.88 (4)
C6—C5—C13—C12100.15 (4)C15—C13—C14—C8175.98 (4)
O3—C5—C13—C14134.23 (4)C13—C15—C16—N151.52 (5)

Experimental details

Crystal data
Chemical formulaC17H19NO3·H2O
Mr303.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)25
a, b, c (Å)7.431 (6), 13.769 (9), 14.944 (13)
V3)1529 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.5 × 0.35 × 0.35
Data collection
DiffractometerBruker SMART Apex CCD Detector on Huber four circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 3 σ(I)] reflections
67606, 9984, 8069
Rint0.04
(sin θ/λ)max1)1.147
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.020, 0.65
No. of reflections8069
No. of parameters682
H-atom treatmentOnly H-atom displacement parameters refined
Δρmax, Δρmin (e Å3)0.22, 0.20

Computer programs: SMART (Bruker, 1997-2001), SAINT (Bruker, 1997-2001), Koritsanszky et al., (2003).

Selected geometric parameters (Å, º) top
O1—C31.3697 (7)N1—C161.4864 (8)
O2—C61.4307 (7)N1—C91.4935 (8)
O3—C41.3916 (7)N1—C171.4865 (8)
O3—C51.4706 (7)
C4—O3—C5106.43 (4)O3—C5—C13106.23 (4)
C9—N1—C17112.71 (4)O3—C5—C6110.14 (4)
C9—N1—C16112.67 (4)O2—C6—C5112.82 (4)
C16—N1—C17110.90 (4)O2—C6—C7109.49 (4)
O1—C3—C4122.03 (4)N1—C9—C10114.28 (4)
O1—C3—C2121.43 (4)N1—C9—C14107.37 (4)
O3—C4—C3125.10 (4)N1—C16—C15111.10 (4)
O3—C4—C12113.10 (4)
 

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