Double Smiles rearrangement of Passerini adducts towards benzoxazinones
E. Martinand-Lurin; A. Dos Santos; L. El Kaim; L. Grimaud; P. Retailleaub; Chem.Commun. 50 (2014) 2214–; doi:10.1039/c3cc49022j

data_7111982
_publ_section_title
;
 Double Smiles rearrangement of Passerini adducts towards benzoxazinones
;
_journal_name_full               Chem.Commun.
_journal_page_first              2214
_journal_paper_doi               10.1039/c3cc49022j
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C17 H20 Cl N O2'
_chemical_formula_sum            'C17 H20 Cl N O2'
_chemical_formula_weight         305.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                77.537(2)
_cell_angle_beta                 85.432(3)
_cell_angle_gamma                77.725(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8800(10)
_cell_length_b                   9.120(2)
_cell_length_c                   14.895(2)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     761.6(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6531
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.338
_diffrn_reflns_theta_min         3.548
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       'squared plate'
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.2838P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2393
_reflns_number_total             3038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc49022j.txt
_cod_data_source_block           compound_2b
_cod_database_code               7111982
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.975
_shelxl_version_number           2012-9
_shelx_res_checksum              39846