Enantio- and Diastereoselective Cyclopropanation of β,γ-Unsaturated α-Ketoester by a Chiral Phosphate/Indium(III) Complex.
Zhong, Xingren; Lv, Jian; Luo, Sanzhong; Organic letters 19 (2017) 3331–3334; doi:10.1021/acs.orglett.7b01577

data_1556061
_publ_section_title
;
 Enantio- and Diastereoselective Cyclopropanation of \b,\g-Unsaturated
 \a-Ketoester by a Chiral Phosphate/Indium(III) Complex.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3331
_journal_page_last               3334
_journal_paper_doi               10.1021/acs.orglett.7b01577
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 Br2 O5'
_chemical_formula_sum            'C21 H18 Br2 O5'
_chemical_formula_weight         510.17
_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             2016-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.272(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1616(19)
_cell_length_b                   8.0804(16)
_cell_length_c                   12.874(2)
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4832
_cell_measurement_theta_min      1.5984
_cell_volume                     1046.1(3)
_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, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9464
	          2theta: -19.8881
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9464
	          2theta: -19.8881
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9464
	          2theta: -19.8881
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9464
	          2theta: -19.8881
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0332
_diffrn_orient_matrix_UB_12      0.1189
_diffrn_orient_matrix_UB_13      -0.0089
_diffrn_orient_matrix_UB_21      0.0854
_diffrn_orient_matrix_UB_22      0.0272
_diffrn_orient_matrix_UB_23      0.0430
_diffrn_orient_matrix_UB_31      0.0241
_diffrn_orient_matrix_UB_32      0.0011
_diffrn_orient_matrix_UB_33      -0.0747
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15264
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    3.903
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       Plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0394P)^2^+0.1174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                4601
_reflns_number_total             4725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01577_si_002.cif
_cod_data_source_block           a
_cod_database_code               1556061
_diffrn_number_total             4733
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              78785
_shelx_hkl_checksum              86856
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'