Experimental and theoretical study of the [3 + 2] cycloaddition of carbonyl ylides with alkynes.
Bentabed-Ababsa, Ghenia; Hamza-Reguig, Samira; Derdour, Aïcha; Domingo, Luis R.; Sáez, José A; Roisnel, Thierry; Dorcet, Vincent; Nassar, Ekhlass; Mongin, Florence; Organic & biomolecular chemistry 10 (2012) 8434–8444; doi:10.1039/c2ob26442k

data_7152704
_publ_section_title
;
 Experimental and theoretical study of the [3 + 2] cycloaddition of
 carbonyl ylides with alkynes.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8434
_journal_page_last               8444
_journal_paper_doi               10.1039/c2ob26442k
_journal_volume                  10
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_sum            'C18 H11 Cl N2 O'
_chemical_formula_weight         306.74
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2010-03-30T15:45:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.615(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0917(5)
_cell_length_b                   17.5158(6)
_cell_length_c                   16.2080(6)
_cell_measurement_reflns_used    8736
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.67
_cell_measurement_wavelength     0.71073
_cell_volume                     2966.2(2)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20379
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0835P)^2^+0.9906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.131
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                6009
_reflns_number_total             6660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26442k.txt
_cod_data_source_block           3b
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7152704