An organic molecule modulated chemoselective cyclization of alkynyl nitriles tethered to 2-alkyl substituted chromones with multireactive sites.
Huang, Liping; Liu, Yang; Xie, Fuchun; Hu, Youhong; Organic letters 14 (2012) 6122–6125; doi:10.1021/ol302964x

data_1508793
_publ_section_title
;
 An organic molecule modulated chemoselective cyclization of alkynyl
 nitriles tethered to 2-alkyl substituted chromones with multireactive
 sites.
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_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6122
_journal_page_last               6125
_journal_paper_doi               10.1021/ol302964x
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.956(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1820(8)
_cell_length_b                   10.6061(11)
_cell_length_c                   13.7522(14)
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.511
_cell_measurement_theta_min      4.850
_cell_volume                     1193.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6136
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48773
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.009(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   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1551
_reflns_number_total             2216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302964x_si_001.cif
_cod_data_source_block           cd201406
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1508793