Organocatalysis by bimacrocyclic NHCs: unexpected formation of a cyclic hemiacetal instead of a γ-butyrolactone
Winkelmann, Ole; Näther, Christian; Lüning, Ulrich; Organic & Biomolecular Chemistry 7 (2009) 553–556; doi:10.1039/b815828b

data_7150557
_publ_section_title
;
 Organocatalysis by bimacrocyclic NHCs: unexpected formation of a
 cyclic hemiacetal instead of a \g-butyrolactone
;
_journal_issue                   3
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              553
_journal_page_last               556
_journal_paper_doi               10.1039/b815828b
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C37 H53 Cl7 N2 O4'
_chemical_formula_weight         837.96
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 128.674(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.471(3)
_cell_length_b                   12.5614(7)
_cell_length_c                   16.7632(14)
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2.5
_cell_volume                     4351.7(9)
_computing_cell_refinement       'STOE IPDS-1 program package'
_computing_data_collection       'STOE IPDS-1 program package'
_computing_data_reduction        'STOE IPDS-1 program package'
_computing_molecular_graphics    'XP in SHELXTL-PC'
_computing_publication_material  'XCIF in SHELXTL-PC'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9095
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.82
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0628
_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^)+(0.1066P)^2^+0.0104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1870
_reflns_number_gt                2266
_reflns_number_total             3828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815828b.txt
_cod_data_source_block           luen25
_cod_original_cell_volume        4351.6(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7150557