Tandem reactions of 1,2-allenic ketones leading to substituted benzenes and α,β-unsaturated nitriles.
Zhang, Xinying; Jia, Xuefei; Fang, Liangliang; Liu, Nan; Wang, Jianji; Fan, Xuesen; Organic letters 13 (2011) 5024–5027; doi:10.1021/ol201789z

data_1502399
_publ_section_title
;
 Tandem reactions of 1,2-allenic ketones leading to substituted benzenes
 and \a,\b-unsaturated nitriles.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5024
_journal_page_last               5027
_journal_paper_doi               10.1021/ol201789z
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C13 H12 Cl N O'
_chemical_formula_weight         233.69
_space_group_IT_number           19
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.140(5)
_cell_length_b                   11.896(7)
_cell_length_c                   12.943(7)
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.96
_cell_volume                     1253.3(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9235
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.9326
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.231
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.1678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                1856
_reflns_number_total             2333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201789z_si_003.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1253.4(12)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502399