organic compounds
N-[3a-(4-Bromophenyl)-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-yl]formamide monohydrate
aCristallographie, Résonance Magnétique et Modélisations (CRM2), UMR CNRS-UHP 7036, Institut Jean Barriol, Université de Lorraine, BP 70239, Bd des Aiguillettes, 54506 Vandoeuvre-les-Nancy, France, and bTherapeutic Innovation Laboratory (UMR7200), Department of Medicinal Chemistry, Faculté de Pharmacie, CNRS Université de Strasbourg, 74 Route du Rhin, BP 60024, 67401 Illkirch, France
*Correspondence e-mail: emmanuel.aubert@crm2.uhp-nancy.fr
In the title compound, C26H24BrNO5·H2O, a synthetic analogue of natural flavagline, the cyclopentane ring adopts an (the flap atom bearing the phenyl group) and the vicinal phenyl and bromophenyl groups are slightly shifted relative to each other [CPh—C—C—CPhBr = 36.3 (2)°]. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds form S(5) motifs. In the crystal, the organic and the water molecules are linked by an O—H⋯O hydrogen bond. Pairs of organic and water molecules, located about inversion centers, interact through O—H⋯O hydrogen bonds, forming R44(20) and R44(26) motifs, which together lead to C22(9) motifs. The crystal packing is also characterized by N—H⋯O and C—H⋯O hydrogen bonds between neighbouring organic molecules, forming R22(10) and R22(18) motifs, respectively.
Related literature
For flavaglines and their anticancer, neuro- and cardioprotective activities, see: Ribeiro et al. (2012a,b); Bernard et al. (2011); Thuaud et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049641/bx2432sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049641/bx2432Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049641/bx2432Isup3.cml
Suitable crystals of the title compound were obtained by slow evaporation from acetone at room temperature.
H(—C) hydrogen atoms were postioned geometrically and were treated as riding on their parent C atoms. The torsion angles of the two methyl groups were obtained by
The hydrogen atom of the hydroxyl group was treated as riding on his parent O atom, while the torsion angle of the associated group was refined. Hydrogen atoms of the water molecule and of the formamide groupwere restrained to O—H=0.82 (1) Å and to N—H=0.87 (2) Å, respectively.For flavaglines and their anticancer, neuro- and cardioprotective activities, see: Ribeiro et al. (2012a,b); Bernard et al. (2011); Thuaud et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. View of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. |
C26H24BrNO5·H2O | Z = 2 |
Mr = 528.39 | F(000) = 544 |
Triclinic, P1 | Dx = 1.504 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.5941 (2) Å | Cell parameters from 17225 reflections |
b = 12.1107 (4) Å | θ = 3.8–76.4° |
c = 12.6642 (3) Å | µ = 2.77 mm−1 |
α = 70.537 (2)° | T = 110 K |
β = 73.495 (2)° | Plate, colourless |
γ = 73.898 (2)° | 0.34 × 0.26 × 0.07 mm |
V = 1166.98 (5) Å3 |
Agilent SuperNova diffractometer | 4860 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4814 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.4508 pixels mm-1 | θmax = 76.6°, θmin = 3.8° |
ω scans | h = −10→10 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived from Clark & Reid (1995)] | k = −15→12 |
Tmin = 0.551, Tmax = 0.868 | l = −15→15 |
24473 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0341P)2 + 1.1295P] where P = (Fo2 + 2Fc2)/3 |
4860 reflections | (Δ/σ)max = 0.002 |
322 parameters | Δρmax = 0.38 e Å−3 |
3 restraints | Δρmin = −0.59 e Å−3 |
C26H24BrNO5·H2O | γ = 73.898 (2)° |
Mr = 528.39 | V = 1166.98 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5941 (2) Å | Cu Kα radiation |
b = 12.1107 (4) Å | µ = 2.77 mm−1 |
c = 12.6642 (3) Å | T = 110 K |
α = 70.537 (2)° | 0.34 × 0.26 × 0.07 mm |
β = 73.495 (2)° |
Agilent SuperNova diffractometer | 4860 independent reflections |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived from Clark & Reid (1995)] | 4814 reflections with I > 2σ(I) |
Tmin = 0.551, Tmax = 0.868 | Rint = 0.021 |
24473 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 3 restraints |
wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.38 e Å−3 |
4860 reflections | Δρmin = −0.59 e Å−3 |
322 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.05195 (2) | 0.900096 (15) | 0.704006 (16) | 0.02799 (7) | |
O17 | 0.51357 (13) | 0.41085 (9) | 0.92476 (9) | 0.0149 (2) | |
H17 | 0.4752 | 0.3496 | 0.9649 | 0.022* | |
O1 | 0.60153 (14) | 0.39338 (9) | 0.65437 (9) | 0.0142 (2) | |
O13 | 0.62790 (15) | −0.02946 (10) | 0.73217 (10) | 0.0197 (2) | |
O15 | 0.73519 (15) | 0.13138 (10) | 0.99384 (9) | 0.0182 (2) | |
O33 | 0.32657 (16) | 0.26192 (11) | 1.08263 (11) | 0.0241 (3) | |
N18 | 0.79574 (19) | 0.41272 (13) | 0.96990 (11) | 0.0197 (3) | |
O20 | 1.05986 (18) | 0.32592 (16) | 0.98704 (13) | 0.0426 (4) | |
C21 | 0.82221 (18) | 0.59920 (14) | 0.55426 (13) | 0.0143 (3) | |
C11 | 0.81098 (18) | 0.49342 (13) | 0.65978 (12) | 0.0128 (3) | |
H11 | 0.8828 | 0.4215 | 0.6361 | 0.015* | |
C2 | 0.62613 (18) | 0.27675 (13) | 0.71823 (13) | 0.0133 (3) | |
C6 | 0.69272 (19) | 0.14421 (14) | 0.89379 (13) | 0.0145 (3) | |
C7 | 0.66121 (18) | 0.26081 (13) | 0.82267 (12) | 0.0131 (3) | |
C30 | 0.2423 (2) | 0.77447 (14) | 0.69946 (14) | 0.0190 (3) | |
C29 | 0.3489 (2) | 0.75174 (14) | 0.77164 (14) | 0.0182 (3) | |
H29 | 0.3348 | 0.8038 | 0.8171 | 0.022* | |
C10 | 0.86995 (19) | 0.50048 (14) | 0.75986 (12) | 0.0141 (3) | |
H10A | 0.8169 | 0.5772 | 0.7788 | 0.017* | |
H10B | 0.9918 | 0.4923 | 0.7419 | 0.017* | |
C28 | 0.47664 (19) | 0.65176 (14) | 0.77651 (13) | 0.0153 (3) | |
H28 | 0.5502 | 0.6353 | 0.8259 | 0.018* | |
C9 | 0.81604 (19) | 0.39483 (14) | 0.85875 (12) | 0.0143 (3) | |
H9 | 0.9024 | 0.3211 | 0.8529 | 0.017* | |
C27 | 0.49841 (18) | 0.57505 (13) | 0.70987 (12) | 0.0125 (3) | |
C14 | 0.5949 (2) | −0.01482 (16) | 0.62326 (15) | 0.0249 (4) | |
H14B | 0.4881 | 0.0400 | 0.6158 | 0.037* | |
H14C | 0.5910 | −0.0926 | 0.6173 | 0.037* | |
H14A | 0.6829 | 0.0182 | 0.5621 | 0.037* | |
C26 | 0.78129 (19) | 0.59676 (16) | 0.45604 (13) | 0.0190 (3) | |
H26 | 0.7440 | 0.5295 | 0.4570 | 0.023* | |
C22 | 0.8773 (2) | 0.69841 (15) | 0.55031 (14) | 0.0211 (3) | |
H22 | 0.9035 | 0.7025 | 0.6167 | 0.025* | |
C8 | 0.65169 (18) | 0.37999 (13) | 0.83925 (12) | 0.0119 (3) | |
C31 | 0.2653 (2) | 0.70372 (16) | 0.62875 (14) | 0.0213 (3) | |
H31 | 0.1942 | 0.7225 | 0.5772 | 0.026* | |
C4 | 0.64028 (19) | 0.07103 (14) | 0.75429 (13) | 0.0155 (3) | |
C12 | 0.63521 (18) | 0.46509 (13) | 0.71503 (12) | 0.0117 (3) | |
C25 | 0.7943 (2) | 0.69131 (17) | 0.35686 (14) | 0.0239 (4) | |
H25 | 0.7630 | 0.6894 | 0.2914 | 0.029* | |
C32 | 0.3941 (2) | 0.60461 (15) | 0.63388 (13) | 0.0181 (3) | |
H32 | 0.4115 | 0.5559 | 0.5846 | 0.022* | |
C3 | 0.61409 (19) | 0.18505 (14) | 0.67967 (13) | 0.0151 (3) | |
H3 | 0.5896 | 0.1995 | 0.6071 | 0.018* | |
C5 | 0.68119 (19) | 0.04909 (14) | 0.86002 (13) | 0.0166 (3) | |
H5 | 0.7009 | −0.0302 | 0.9083 | 0.020* | |
C16 | 0.7727 (2) | 0.01173 (15) | 1.06525 (14) | 0.0226 (3) | |
H16A | 0.6723 | −0.0219 | 1.0945 | 0.034* | |
H16C | 0.8136 | 0.0127 | 1.1297 | 0.034* | |
H16B | 0.8579 | −0.0374 | 1.0204 | 0.034* | |
C19 | 0.9206 (3) | 0.37794 (19) | 1.02350 (15) | 0.0300 (4) | |
H19 | 0.9008 | 0.3945 | 1.0950 | 0.036* | |
C23 | 0.8944 (3) | 0.79191 (16) | 0.45014 (16) | 0.0289 (4) | |
H23 | 0.9348 | 0.8582 | 0.4481 | 0.035* | |
C24 | 0.8529 (2) | 0.78850 (16) | 0.35359 (15) | 0.0279 (4) | |
H24 | 0.8644 | 0.8524 | 0.2854 | 0.033* | |
H33A | 0.338 (3) | 0.1995 (14) | 1.1318 (16) | 0.037 (7)* | |
H33B | 0.244 (2) | 0.273 (2) | 1.058 (2) | 0.045 (7)* | |
H18 | 0.704 (2) | 0.447 (2) | 0.9998 (19) | 0.031 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02195 (10) | 0.01868 (10) | 0.03460 (12) | 0.00392 (7) | −0.00600 (8) | −0.00272 (8) |
O17 | 0.0187 (5) | 0.0133 (5) | 0.0112 (5) | −0.0043 (4) | 0.0008 (4) | −0.0039 (4) |
O1 | 0.0223 (5) | 0.0122 (5) | 0.0114 (5) | −0.0053 (4) | −0.0063 (4) | −0.0035 (4) |
O13 | 0.0288 (6) | 0.0137 (5) | 0.0201 (6) | −0.0040 (5) | −0.0077 (5) | −0.0074 (4) |
O15 | 0.0281 (6) | 0.0134 (5) | 0.0139 (5) | −0.0020 (4) | −0.0102 (4) | −0.0017 (4) |
O33 | 0.0224 (6) | 0.0228 (6) | 0.0261 (6) | −0.0097 (5) | −0.0116 (5) | 0.0040 (5) |
N18 | 0.0255 (7) | 0.0251 (7) | 0.0121 (6) | −0.0115 (6) | −0.0061 (5) | −0.0028 (5) |
O20 | 0.0302 (8) | 0.0681 (11) | 0.0305 (7) | −0.0182 (7) | −0.0182 (6) | 0.0016 (7) |
C21 | 0.0110 (6) | 0.0166 (7) | 0.0120 (7) | −0.0010 (5) | −0.0001 (5) | −0.0029 (6) |
C11 | 0.0126 (7) | 0.0144 (7) | 0.0105 (6) | −0.0026 (5) | −0.0016 (5) | −0.0033 (5) |
C2 | 0.0130 (7) | 0.0124 (7) | 0.0135 (7) | −0.0023 (5) | −0.0017 (5) | −0.0036 (5) |
C6 | 0.0153 (7) | 0.0149 (7) | 0.0128 (7) | −0.0024 (6) | −0.0027 (5) | −0.0040 (6) |
C7 | 0.0135 (7) | 0.0136 (7) | 0.0129 (7) | −0.0028 (5) | −0.0024 (5) | −0.0049 (5) |
C30 | 0.0154 (7) | 0.0152 (7) | 0.0184 (7) | 0.0008 (6) | −0.0012 (6) | 0.0004 (6) |
C29 | 0.0196 (8) | 0.0149 (7) | 0.0178 (7) | −0.0021 (6) | −0.0021 (6) | −0.0043 (6) |
C10 | 0.0146 (7) | 0.0162 (7) | 0.0121 (7) | −0.0048 (6) | −0.0035 (5) | −0.0028 (6) |
C28 | 0.0165 (7) | 0.0157 (7) | 0.0140 (7) | −0.0035 (6) | −0.0039 (5) | −0.0037 (6) |
C9 | 0.0161 (7) | 0.0160 (7) | 0.0122 (7) | −0.0043 (6) | −0.0057 (5) | −0.0027 (6) |
C27 | 0.0122 (7) | 0.0135 (7) | 0.0104 (6) | −0.0049 (5) | −0.0010 (5) | −0.0009 (5) |
C14 | 0.0386 (10) | 0.0212 (8) | 0.0214 (8) | −0.0075 (7) | −0.0091 (7) | −0.0107 (7) |
C26 | 0.0159 (7) | 0.0253 (8) | 0.0150 (7) | −0.0049 (6) | −0.0029 (6) | −0.0041 (6) |
C22 | 0.0267 (8) | 0.0179 (8) | 0.0169 (7) | −0.0052 (6) | −0.0034 (6) | −0.0030 (6) |
C8 | 0.0136 (7) | 0.0125 (7) | 0.0093 (6) | −0.0027 (5) | −0.0020 (5) | −0.0027 (5) |
C31 | 0.0171 (7) | 0.0267 (9) | 0.0178 (7) | −0.0013 (6) | −0.0071 (6) | −0.0030 (6) |
C4 | 0.0150 (7) | 0.0145 (7) | 0.0183 (7) | −0.0026 (6) | −0.0013 (6) | −0.0086 (6) |
C12 | 0.0148 (7) | 0.0130 (7) | 0.0098 (6) | −0.0042 (5) | −0.0037 (5) | −0.0043 (5) |
C25 | 0.0169 (8) | 0.0335 (10) | 0.0138 (7) | 0.0015 (7) | −0.0043 (6) | −0.0013 (7) |
C32 | 0.0178 (7) | 0.0221 (8) | 0.0158 (7) | −0.0035 (6) | −0.0054 (6) | −0.0060 (6) |
C3 | 0.0162 (7) | 0.0168 (7) | 0.0141 (7) | −0.0034 (6) | −0.0030 (5) | −0.0067 (6) |
C5 | 0.0189 (7) | 0.0130 (7) | 0.0168 (7) | −0.0017 (6) | −0.0041 (6) | −0.0038 (6) |
C16 | 0.0334 (9) | 0.0146 (8) | 0.0174 (7) | −0.0015 (7) | −0.0107 (7) | 0.0005 (6) |
C19 | 0.0378 (11) | 0.0429 (11) | 0.0155 (8) | −0.0274 (9) | −0.0119 (7) | 0.0050 (7) |
C23 | 0.0388 (10) | 0.0170 (8) | 0.0252 (9) | −0.0075 (7) | −0.0039 (8) | 0.0005 (7) |
C24 | 0.0293 (9) | 0.0210 (8) | 0.0193 (8) | 0.0017 (7) | −0.0030 (7) | 0.0048 (7) |
Br1—C30 | 1.9023 (16) | C10—H10B | 0.9900 |
O17—C8 | 1.4194 (17) | C28—C27 | 1.395 (2) |
O17—H17 | 0.8400 | C28—H28 | 0.9500 |
O1—C2 | 1.3653 (18) | C9—C8 | 1.567 (2) |
O1—C12 | 1.4623 (16) | C9—H9 | 1.0000 |
O13—C4 | 1.3737 (18) | C27—C32 | 1.393 (2) |
O13—C14 | 1.4304 (19) | C27—C12 | 1.509 (2) |
O15—C6 | 1.3649 (18) | C14—H14B | 0.9800 |
O15—C16 | 1.4335 (19) | C14—H14C | 0.9800 |
O33—H33A | 0.805 (10) | C14—H14A | 0.9800 |
O33—H33B | 0.808 (10) | C26—C25 | 1.391 (2) |
N18—C19 | 1.328 (2) | C26—H26 | 0.9500 |
N18—C9 | 1.4497 (19) | C22—C23 | 1.394 (2) |
N18—H18 | 0.830 (16) | C22—H22 | 0.9500 |
O20—C19 | 1.226 (3) | C8—C12 | 1.5882 (19) |
C21—C22 | 1.390 (2) | C31—C32 | 1.386 (2) |
C21—C26 | 1.397 (2) | C31—H31 | 0.9500 |
C21—C11 | 1.514 (2) | C4—C3 | 1.389 (2) |
C11—C10 | 1.5270 (19) | C4—C5 | 1.402 (2) |
C11—C12 | 1.554 (2) | C25—C24 | 1.387 (3) |
C11—H11 | 1.0000 | C25—H25 | 0.9500 |
C2—C7 | 1.379 (2) | C32—H32 | 0.9500 |
C2—C3 | 1.391 (2) | C3—H3 | 0.9500 |
C6—C5 | 1.391 (2) | C5—H5 | 0.9500 |
C6—C7 | 1.399 (2) | C16—H16A | 0.9800 |
C7—C8 | 1.5035 (19) | C16—H16C | 0.9800 |
C30—C31 | 1.375 (2) | C16—H16B | 0.9800 |
C30—C29 | 1.385 (2) | C19—H19 | 0.9500 |
C29—C28 | 1.388 (2) | C23—C24 | 1.384 (3) |
C29—H29 | 0.9500 | C23—H23 | 0.9500 |
C10—C9 | 1.533 (2) | C24—H24 | 0.9500 |
C10—H10A | 0.9900 | ||
C8—O17—H17 | 109.5 | H14B—C14—H14A | 109.5 |
C2—O1—C12 | 108.14 (11) | H14C—C14—H14A | 109.5 |
C4—O13—C14 | 117.21 (13) | C25—C26—C21 | 121.01 (16) |
C6—O15—C16 | 116.71 (12) | C25—C26—H26 | 119.5 |
H33A—O33—H33B | 112 (3) | C21—C26—H26 | 119.5 |
C19—N18—C9 | 121.62 (16) | C21—C22—C23 | 120.81 (16) |
C19—N18—H18 | 119.6 (16) | C21—C22—H22 | 119.6 |
C9—N18—H18 | 118.7 (17) | C23—C22—H22 | 119.6 |
C22—C21—C26 | 118.30 (14) | O17—C8—C7 | 112.92 (12) |
C22—C21—C11 | 122.00 (14) | O17—C8—C9 | 111.29 (11) |
C26—C21—C11 | 119.67 (14) | C7—C8—C9 | 114.22 (12) |
C21—C11—C10 | 115.85 (12) | O17—C8—C12 | 111.92 (11) |
C21—C11—C12 | 115.75 (12) | C7—C8—C12 | 100.43 (11) |
C10—C11—C12 | 103.66 (11) | C9—C8—C12 | 105.31 (11) |
C21—C11—H11 | 107.0 | C30—C31—C32 | 118.93 (15) |
C10—C11—H11 | 107.0 | C30—C31—H31 | 120.5 |
C12—C11—H11 | 107.0 | C32—C31—H31 | 120.5 |
O1—C2—C7 | 113.50 (13) | O13—C4—C3 | 123.59 (14) |
O1—C2—C3 | 121.92 (13) | O13—C4—C5 | 114.11 (14) |
C7—C2—C3 | 124.57 (14) | C3—C4—C5 | 122.30 (14) |
O15—C6—C5 | 123.77 (14) | O1—C12—C27 | 107.13 (11) |
O15—C6—C7 | 116.53 (13) | O1—C12—C11 | 109.18 (11) |
C5—C6—C7 | 119.69 (14) | C27—C12—C11 | 113.61 (12) |
C2—C7—C6 | 118.19 (13) | O1—C12—C8 | 106.45 (11) |
C2—C7—C8 | 110.01 (13) | C27—C12—C8 | 116.28 (11) |
C6—C7—C8 | 131.76 (13) | C11—C12—C8 | 103.86 (11) |
C31—C30—C29 | 121.48 (15) | C24—C25—C26 | 119.93 (16) |
C31—C30—Br1 | 118.73 (12) | C24—C25—H25 | 120.0 |
C29—C30—Br1 | 119.69 (12) | C26—C25—H25 | 120.0 |
C30—C29—C28 | 118.95 (15) | C31—C32—C27 | 121.27 (15) |
C30—C29—H29 | 120.5 | C31—C32—H32 | 119.4 |
C28—C29—H29 | 120.5 | C27—C32—H32 | 119.4 |
C11—C10—C9 | 103.86 (12) | C4—C3—C2 | 115.59 (14) |
C11—C10—H10A | 111.0 | C4—C3—H3 | 122.2 |
C9—C10—H10A | 111.0 | C2—C3—H3 | 122.2 |
C11—C10—H10B | 111.0 | C6—C5—C4 | 119.58 (14) |
C9—C10—H10B | 111.0 | C6—C5—H5 | 120.2 |
H10A—C10—H10B | 109.0 | C4—C5—H5 | 120.2 |
C29—C28—C27 | 120.88 (14) | O15—C16—H16A | 109.5 |
C29—C28—H28 | 119.6 | O15—C16—H16C | 109.5 |
C27—C28—H28 | 119.6 | H16A—C16—H16C | 109.5 |
N18—C9—C10 | 112.30 (12) | O15—C16—H16B | 109.5 |
N18—C9—C8 | 112.54 (12) | H16A—C16—H16B | 109.5 |
C10—C9—C8 | 105.93 (11) | H16C—C16—H16B | 109.5 |
N18—C9—H9 | 108.6 | O20—C19—N18 | 124.46 (18) |
C10—C9—H9 | 108.6 | O20—C19—H19 | 117.8 |
C8—C9—H9 | 108.6 | N18—C19—H19 | 117.8 |
C32—C27—C28 | 118.33 (14) | C24—C23—C22 | 120.25 (17) |
C32—C27—C12 | 119.93 (13) | C24—C23—H23 | 119.9 |
C28—C27—C12 | 121.69 (13) | C22—C23—H23 | 119.9 |
O13—C14—H14B | 109.5 | C23—C24—C25 | 119.66 (16) |
O13—C14—H14C | 109.5 | C23—C24—H24 | 120.2 |
H14B—C14—H14C | 109.5 | C25—C24—H24 | 120.2 |
O13—C14—H14A | 109.5 | ||
C22—C21—C11—C10 | −2.2 (2) | Br1—C30—C31—C32 | −173.36 (12) |
C26—C21—C11—C10 | 175.78 (13) | C14—O13—C4—C3 | 3.5 (2) |
C22—C21—C11—C12 | 119.46 (16) | C14—O13—C4—C5 | −176.88 (14) |
C26—C21—C11—C12 | −62.55 (18) | C2—O1—C12—C27 | −135.71 (12) |
C12—O1—C2—C7 | 4.89 (16) | C2—O1—C12—C11 | 100.86 (13) |
C12—O1—C2—C3 | −175.84 (13) | C2—O1—C12—C8 | −10.68 (14) |
C16—O15—C6—C5 | 1.3 (2) | C32—C27—C12—O1 | −14.13 (18) |
C16—O15—C6—C7 | −178.07 (14) | C28—C27—C12—O1 | 168.42 (13) |
O1—C2—C7—C6 | −178.42 (13) | C32—C27—C12—C11 | 106.53 (15) |
C3—C2—C7—C6 | 2.3 (2) | C28—C27—C12—C11 | −70.93 (17) |
O1—C2—C7—C8 | 3.52 (18) | C32—C27—C12—C8 | −132.98 (14) |
C3—C2—C7—C8 | −175.74 (14) | C28—C27—C12—C8 | 49.56 (19) |
O15—C6—C7—C2 | 176.78 (13) | C21—C11—C12—O1 | 83.18 (15) |
C5—C6—C7—C2 | −2.7 (2) | C10—C11—C12—O1 | −148.84 (11) |
O15—C6—C7—C8 | −5.7 (2) | C21—C11—C12—C27 | −36.31 (17) |
C5—C6—C7—C8 | 174.89 (15) | C10—C11—C12—C27 | 91.67 (14) |
C31—C30—C29—C28 | −3.3 (2) | C21—C11—C12—C8 | −163.58 (12) |
Br1—C30—C29—C28 | 172.89 (12) | C10—C11—C12—C8 | −35.60 (14) |
C21—C11—C10—C9 | 170.38 (12) | O17—C8—C12—O1 | −108.19 (12) |
C12—C11—C10—C9 | 42.46 (14) | C7—C8—C12—O1 | 11.87 (14) |
C30—C29—C28—C27 | 0.1 (2) | C9—C8—C12—O1 | 130.74 (12) |
C19—N18—C9—C10 | −89.55 (18) | O17—C8—C12—C27 | 11.03 (17) |
C19—N18—C9—C8 | 151.02 (15) | C7—C8—C12—C27 | 131.09 (12) |
C11—C10—C9—N18 | −155.59 (13) | C9—C8—C12—C27 | −110.03 (13) |
C11—C10—C9—C8 | −32.37 (15) | O17—C8—C12—C11 | 136.61 (12) |
C29—C28—C27—C32 | 3.3 (2) | C7—C8—C12—C11 | −103.33 (12) |
C29—C28—C27—C12 | −179.23 (14) | C9—C8—C12—C11 | 15.55 (14) |
C22—C21—C26—C25 | −0.3 (2) | C21—C26—C25—C24 | 1.8 (3) |
C11—C21—C26—C25 | −178.41 (14) | C30—C31—C32—C27 | 0.7 (2) |
C26—C21—C22—C23 | −1.3 (2) | C28—C27—C32—C31 | −3.7 (2) |
C11—C21—C22—C23 | 176.71 (16) | C12—C27—C32—C31 | 178.72 (14) |
C2—C7—C8—O17 | 109.96 (14) | O13—C4—C3—C2 | 177.76 (14) |
C6—C7—C8—O17 | −67.8 (2) | C5—C4—C3—C2 | −1.9 (2) |
C2—C7—C8—C9 | −121.54 (14) | O1—C2—C3—C4 | −179.26 (13) |
C6—C7—C8—C9 | 60.7 (2) | C7—C2—C3—C4 | −0.1 (2) |
C2—C7—C8—C12 | −9.38 (15) | O15—C6—C5—C4 | −178.54 (14) |
C6—C7—C8—C12 | 172.91 (16) | C7—C6—C5—C4 | 0.9 (2) |
N18—C9—C8—O17 | 11.60 (17) | O13—C4—C5—C6 | −178.16 (14) |
C10—C9—C8—O17 | −111.47 (13) | C3—C4—C5—C6 | 1.5 (2) |
N18—C9—C8—C7 | −117.72 (14) | C9—N18—C19—O20 | −2.1 (3) |
C10—C9—C8—C7 | 119.21 (13) | C21—C22—C23—C24 | 1.6 (3) |
N18—C9—C8—C12 | 133.08 (13) | C22—C23—C24—C25 | −0.1 (3) |
C10—C9—C8—C12 | 10.01 (15) | C26—C25—C24—C23 | −1.5 (3) |
C29—C30—C31—C32 | 2.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H18···O17 | 0.83 | 2.31 | 2.652 (2) | 106 |
C32—H32···O1 | 0.95 | 2.28 | 2.661 (2) | 103 |
O17—H17···O33 | 0.84 | 1.90 | 2.686 (2) | 156 |
N18—H18···O17i | 0.83 | 2.38 | 3.185 (2) | 163 |
C28—H28···O33i | 0.95 | 2.53 | 3.328 (2) | 142 |
C29—H29···O15i | 0.95 | 2.62 | 3.516 (2) | 157 |
O33—H33A···O13ii | 0.81 | 2.21 | 3.015 (2) | 179 |
O33—H33B···O20iii | 0.81 | 1.90 | 2.699 (2) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C26H24BrNO5·H2O |
Mr | 528.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 110 |
a, b, c (Å) | 8.5941 (2), 12.1107 (4), 12.6642 (3) |
α, β, γ (°) | 70.537 (2), 73.495 (2), 73.898 (2) |
V (Å3) | 1166.98 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.77 |
Crystal size (mm) | 0.34 × 0.26 × 0.07 |
Data collection | |
Diffractometer | Agilent SuperNova |
Absorption correction | Analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived from Clark & Reid (1995)] |
Tmin, Tmax | 0.551, 0.868 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24473, 4860, 4814 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.631 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.074, 1.05 |
No. of reflections | 4860 |
No. of parameters | 322 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.59 |
Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N18—H18···O17 | 0.83 | 2.31 | 2.652 (2) | 106 |
C32—H32···O1 | 0.95 | 2.28 | 2.661 (2) | 103 |
O17—H17···O33 | 0.84 | 1.90 | 2.686 (2) | 156 |
N18—H18···O17i | 0.83 | 2.38 | 3.185 (2) | 163 |
C28—H28···O33i | 0.95 | 2.53 | 3.328 (2) | 142 |
C29—H29···O15i | 0.95 | 2.62 | 3.516 (2) | 157 |
O33—H33A···O13ii | 0.81 | 2.21 | 3.015 (2) | 179 |
O33—H33B···O20iii | 0.81 | 1.90 | 2.699 (2) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+2; (iii) x−1, y, z. |
Acknowledgements
The Service Commun de Diffraction X of the Université de Lorraine is thanked for providing access to crystallographic facilities. Generous financial support for this work was provided to LD by the Association pour la Recherche sur le Cancer (ARC, grant Nos. 3940 and SFI20111204054) and the Fondation pour la Recherche Médicale. We also thank the ARC (NR) and MNESR (FT) for fellowships.
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