Rhodium-catalyzed enantioselective cyclopropanation of electron deficient alkenes.
Wang, Hengbin; Guptill, David M.; Alvarez, Adrian Varela; Musaev, Djamaladdin G.; Davies, Huw M. L.; Chemical science (Royal Society of Chemistry : 2010) 4 (2013) 2844–2850; doi:10.1039/C3SC50425E

data_1514513
_publ_section_title
;
 Rhodium-catalyzed enantioselective cyclopropanation of electron deficient
 alkenes.
;
_journal_issue                   7
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              2844
_journal_page_last               2850
_journal_paper_doi               10.1039/C3SC50425E
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H21 Br O4'
_chemical_formula_sum            'C21 H21 Br O4'
_chemical_formula_weight         417.29
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2012-11-01
_audit_creation_method
;
Olex2 1.2-beta
(compiled Aug 15 2012 15:59:22, GUI svn.r4314)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0402(2)
_cell_length_b                   15.4144(4)
_cell_length_c                   20.7290(8)
_cell_measurement_reflns_used    5848
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.831
_cell_measurement_theta_min      2.368
_cell_volume                     1930.00(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21661
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.990
_diffrn_reflns_theta_min         1.646
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.152
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.7173.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.451
_exptl_crystal_size_min          0.346
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
Flack x determined using 1585 quotients [(I+)-I(-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.019(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         6098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0145P)^2^]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4554
_reflns_number_total             6098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3sc50425e.txt
_cod_data_source_block           hwxviii046
_cod_database_code               1514513
_diffrn_reflns_sigmai/neti       0.0721
_shelx_estimated_absorpt_t_max   0.523
_shelx_estimated_absorpt_t_min   0.430
_shelx_hkl_checksum              76791
_shelx_res_checksum              37203
_shelxl_version_number           2012-4