Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.
Goldberg, Alexander F. G.; O'Connor, Nicholas R; Craig, 2nd, Robert A; Stoltz, Brian M.; Organic letters 14 (2012) 5314–5317; doi:10.1021/ol302494n

data_1508696
_publ_section_title
;
 Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor
 cyclopropanes with heterocumulenes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5314
_journal_page_last               5317
_journal_paper_doi               10.1021/ol302494n
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H29 N2 O4, Br, H2 O'
_chemical_formula_sum            'C20 H31 Br N2 O5'
_chemical_formula_weight         459.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2012-10-01
_audit_creation_method
; 
  Olex2 1.2 
  (compiled May  9 2012 12:37:22, GUI svn.r4230) 
  shelxl Beta test 2012/4 
  and manual edit 
;
_cell_angle_alpha                98.815(5)
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_cell_length_b                   15.1323(12)
_cell_length_c                   29.190(2)
_cell_measurement_reflns_used    9397
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.33
_cell_measurement_theta_min      2.62
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_computing_cell_refinement       'SAINT V8.18C (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2_2011.2-3 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.18C (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_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 beta test 2012/4 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
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_diffrn_measured_fraction_theta_full 0.997
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_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_l_min       -46
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_diffrn_reflns_point_group_measured_fraction_full 0.985
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_diffrn_reflns_theta_full        25.000
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_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0912 before and 0.0737 after correction. 
The Ratio of minimum to maximum transmission is 0.8047. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         3.054
_refine_diff_density_min         -1.324
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
; 
 Flack x determined using 18047 quotients [(I+)-I(-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0646(18)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         54469
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.641
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0565
_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^)] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1152
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_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                44418
_reflns_number_total             54469
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol302494n_si_002.cif
_cod_data_source_block           afg04
_cod_original_cell_volume        3388.9(5)
_cod_database_code               1508696
_diffrn_reflns_sigmai/neti       0.0781
_refine_ls_abs_structure_hooft   0.059(2)
_shelx_estimated_absorpt_t_max   0.744
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_shelx_hkl_checksum              4849
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_shelxl_version_number           2012-4