Stereoselective synthesis of epsilon-lactones or spiro-heterocycles through NHC-catalyzed annulation: divergent reactivity by catalyst control
Min Wang; Zi-Qiang Rong; Yu Zhao; Chem.Commun. 50 (2014) 15309–; doi:10.1039/C4cc07788A

data_7116049
_publ_section_title
;
 Stereoselective synthesis of epsilon-lactones or spiro-heterocycles
 through NHC-catalyzed annulation: divergent reactivity by catalyst
 control
;
_journal_name_full               Chem.Commun.
_journal_page_first              15309
_journal_paper_doi               10.1039/C4cc07788A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C27 H24 Br N O3'
_chemical_formula_weight         490.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.518(4)
_cell_length_b                   10.893(4)
_cell_length_c                   19.602(7)
_cell_measurement_reflns_used    923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.69
_cell_volume                     2245.9(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.078
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
; 
 Flack x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.024(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0340P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4574
_reflns_number_total             5157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07788a2.cif
_cod_data_source_block           E233A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2245.8(14)
_cod_database_code               7116049
_shelx_estimated_absorpt_t_min   0.422
_shelx_estimated_absorpt_t_max   0.755
_shelxl_version_number           2013-4
_shelx_res_checksum              90936