Remote stereoselective deconjugation of α,β-unsaturated esters by simple amidation reactions
Vishe, Mahesh; Hrdina, Radim; Poblador-Bahamonde, Amalia I.; Besnard, Céline; Guénée, Laure; Bürgi, Thomas; Lacour, Jérôme; Chem. Sci. 6 (2015) 4923–; doi:10.1039/C5SC01118C

data_1519946
_publ_section_title
;
 Remote stereoselective deconjugation of \a,\b-unsaturated esters by
 simple amidation reactions
;
_journal_issue                   8
_journal_name_full               'Chem. Sci.'
_journal_page_first              4923
_journal_paper_doi               10.1039/C5SC01118C
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C32 H30 F12 N2 O8, H2 O'
_chemical_formula_sum            'C32 H32 F12 N2 O9'
_chemical_formula_weight         816.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-01
_audit_creation_method
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  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2014-11-19 deposited with the CCDC.
2015-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.787(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9175(4)
_cell_length_b                   19.0210(5)
_cell_length_c                   17.2260(6)
_cell_measurement_reflns_used    7290
_cell_measurement_temperature    119.9(3)
_cell_measurement_theta_max      28.1559
_cell_measurement_theta_min      3.2065
_cell_volume                     3696.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      119.9(3)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9734
_diffrn_measurement_details
;
  1 omega  -96.00  -70.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2297 -178.0000 -150.0000 26

  2 omega  -80.00  -30.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672    0.0000  150.0000 50

  3 omega   23.00  103.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672    0.0000  150.0000 80

  4 omega  -10.00   45.00   1.0000   75.0000
omega____ theta____ kappa____ phi______ frames
    -       12.1672   57.0000  -90.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0517431000
_diffrn_orient_matrix_UB_12      0.0004817000
_diffrn_orient_matrix_UB_13      0.0348747000
_diffrn_orient_matrix_UB_21      -0.0104853000
_diffrn_orient_matrix_UB_22      -0.0354461000
_diffrn_orient_matrix_UB_23      0.0085228000
_diffrn_orient_matrix_UB_31      0.0341137000
_diffrn_orient_matrix_UB_32      -0.0115616000
_diffrn_orient_matrix_UB_33      -0.0245450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17106
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7663
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+2.7422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                5916
_reflns_number_total             7663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc01118c2.cif
_cod_data_source_block           macrocycle_4a
_cod_depositor_comments
'Adding full bibliography for 1519944--1519947.cif.'
_cod_database_code               1519946
_chemical_oxdiff_formula         'C32 H30 F12 N2 O8'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97