Synthesis of Spiro Ketals, Orthoesters, and Orthocarbonates by CpRu-Catalyzed Decomposition of α-Diazo-β-ketoesters.
Tortoreto, Cecilia; Achard, Thierry; Egger, Léo; Guénée, Laure; Lacour, Jérôme; Organic letters 18 (2016) 240–243; doi:10.1021/acs.orglett.5b03380

data_1542381
_publ_section_title
;
 Synthesis of Spiro Ketals, Orthoesters, and Orthocarbonates by
 CpRu-Catalyzed Decomposition of \a-Diazo-\b-ketoesters.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              240
_journal_page_last               243
_journal_paper_doi               10.1021/acs.orglett.5b03380
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H20 O8'
_chemical_formula_sum            'C16 H20 O8'
_chemical_formula_weight         340.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.478(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.60173(18)
_cell_length_b                   12.9474(2)
_cell_length_c                   13.2032(3)
_cell_measurement_reflns_used    6379
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      73.0480
_cell_measurement_theta_min      4.7660
_cell_volume                     1627.43(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_Acta
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12682
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.32
_diffrn_reflns_theta_min         4.80
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3015
_exptl_crystal_size_mid          0.2292
_exptl_crystal_size_min          0.0623
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.3100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2834
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03380_si_002.cif
_cod_data_source_block           4nprime
_cod_original_cell_volume        1627.43(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1542381