Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles.
Zhou, Wei; Zhang, Yicheng; Li, Pinhua; Wang, Lei; Organic & biomolecular chemistry 10 (2012) 7184–7196; doi:10.1039/c2ob25969a

data_7152578
_publ_section_title
;
 Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles
 and 3-cyanobenzofurans through the sequential reactions of phenols with
 propiolonitriles.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7184
_journal_page_last               7196
_journal_paper_doi               10.1039/c2ob25969a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C15 H8 N2 O3'
_chemical_formula_sum            'C15 H8 N2 O3'
_chemical_formula_weight         264.23
_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                 101.186(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6348(6)
_cell_length_b                   14.4760(6)
_cell_length_c                   10.0498(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1232.33(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w 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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6833
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.9623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0098(14)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0464P)^2^+0.1685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1690
_reflns_number_total             2255
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25969a.txt
_cod_data_source_block           111205_smm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1232.34(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7152578