The synthesis of 2-arylmethyl-6-hydroxybenzenecarbonitriles from the base-mediated aryne reaction of bromophenols with arylacetonitriles
Tandel, Sagun; Zhang, Hongming; Qadri, Nabil; Ford, George P.; Biehl, Edward R.; Journal of the Chemical Society, Perkin Transactions 1  (2000) 587–; doi:10.1039/a907980g

data_7203917
_publ_section_title
;
 The synthesis of 2-arylmethyl-6-hydroxybenzenecarbonitriles from the
 base-mediated aryne reaction of bromophenols with arylacetonitriles
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              587
_journal_paper_doi               10.1039/a907980g
_journal_year                    2000
_chemical_compound_source
'recrystallized from hexane/ethyl acetate mixed solvents'
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_weight         209.24
_chemical_name_common            benzonitrile
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.53(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.496(1)
_cell_length_b                   11.407(1)
_cell_length_c                   18.715(1)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     2239.9(3)
_computing_cell_refinement       'Broker AXS P4 XSCANS'
_computing_data_collection       'Broker AXS P4 XSCANS'
_computing_data_reduction        'Broker AXS P4 XSCANS'
_computing_molecular_graphics    'SHELXL-plus (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      228(2)
_diffrn_measurement_device       'Broker AXS P4 diffractometer'
_diffrn_measurement_method       '\w/2\q scan'
_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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4180
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        8.27
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   n/a
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       plates
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0054(8)
_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_all   1.014
_refine_ls_goodness_of_fit_obs   1.093
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_restrained_S_obs      1.093
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_obs          0.0468
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1385
_refine_ls_wR_factor_obs         0.1108
_reflns_number_observed          2506
_reflns_number_total             3949
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            a907980g.txt
_cod_data_source_block           st-1097
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.2188P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7203917