A donor-acceptor cyclopropene as a dipole source for a silver(I) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
Xinfang Xu; Peter J. Zavalij; Michael P. Doyle; Chem.Commun. 49 (2013) 10287–; doi:10.1039/c3cc46415f

data_7109975
_publ_section_title
;
 A donor-acceptor cyclopropene as a dipole source for a silver(I)
 catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
;
_journal_name_full               Chem.Commun.
_journal_page_first              10287
_journal_paper_doi               10.1039/c3cc46415f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H25 Br Cl N O4'
_chemical_formula_sum            'C27 H25 Br Cl N O4'
_chemical_formula_weight         542.84
_chemical_name_common            XXU-33-BrCl
_chemical_name_systematic
;
Organics
;
_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_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2012 & ZCIF'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7782(6)
_cell_length_b                   10.1868(6)
_cell_length_c                   25.4096(14)
_cell_measurement_reflns_used    17359
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.2
_cell_volume                     2531.0(3)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  'Apex2, SHELXL-2012'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'ShelXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex II diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0981629
_diffrn_orient_matrix_UB_12      0.0126306
_diffrn_orient_matrix_UB_13      0.0098057
_diffrn_orient_matrix_UB_21      -0.0189035
_diffrn_orient_matrix_UB_22      -0.0940710
_diffrn_orient_matrix_UB_23      -0.0085552
_diffrn_orient_matrix_UB_31      0.0215570
_diffrn_orient_matrix_UB_32      -0.0250310
_diffrn_orient_matrix_UB_33      0.0371401
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.154
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_T_max  0.494
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
Refined as an inversion twin yielding the 2nd component
near 0 within s.u. Thus the measured crystal was enantiopure.
;
_refine_ls_abs_structure_Flack   -0.001(5)
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         7377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0110P)^2^+1.0680P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0498
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6754
_reflns_number_total             7377
_reflns_threshold_expression     'I > 2\s(I)'
_iucr_refine_instructions_details 'available per request'
_cod_data_source_file            c3cc46415f.txt
_cod_data_source_block           2483
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7109975
_shelx_estimated_absorpt_t_min   0.479
_shelx_estimated_absorpt_t_max   0.539
_iucr_refine_reflections_details 'available per request'