Enantioselective indium(i)-catalyzed [4 + 2] annulation of alkoxyallenes and β,γ-unsaturated α-keto esters
Li, Sujia; Lv, Jian; Luo, Sanzhong; Organic Chemistry Frontiers 5 (2018) 1787–; doi:10.1039/C8QO00319J

data_1554312
_publ_section_title
;
 Enantioselective indium(i)-catalyzed [4 + 2] annulation of alkoxyallenes
 and \b,\g-unsaturated \a-keto esters
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1787
_journal_paper_doi               10.1039/C8QO00319J
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 Br O4'
_chemical_formula_sum            'C16 H17 Br O4'
_chemical_formula_weight         353.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-01 deposited with the CCDC.
2018-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.216(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.573(4)
_cell_length_b                   7.311(2)
_cell_length_c                   11.350(4)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4719
_cell_measurement_theta_min      1.9833
_cell_volume                     793.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9096
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         1.983
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0270P)^2^+0.2297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3405
_reflns_number_total             3605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00319j2.cif
_cod_data_source_block           mx6831a
_cod_database_code               1554312
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.572
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C5(H5), C8(H8)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              34851
_shelx_hkl_checksum              93708
_olex2_submission_special_instructions 'No special instructions were received'