Investigation of the reaction of 2-bromo-1-naphthol with arylacetonitriles and LiTMP: facile synthesis of 3-arylmethyl-1-hydroxynaphthalene-2-carbonitriles
Tandel, Sagun; Wang, Anlai; Zhang, Hongming; Yousuf, Pervaiz; Biehl, Edward R.; Journal of the Chemical Society, Perkin Transactions 1  (2000) 3149–; doi:10.1039/b003935g

data_7213372
_publ_section_title
;
 Investigation of the reaction of 2-bromo-1-naphthol with
 arylacetonitriles and LiTMP: facile synthesis of
 3-arylmethyl-1-hydroxynaphthalene-2-carbonitriles
;
_journal_issue                   18
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3149
_journal_paper_doi               10.1039/b003935g
_journal_year                    2000
_chemical_formula_sum            'C16 H11 N O S'
_chemical_formula_weight         265.32
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.131(1)
_cell_length_b                   12.598(2)
_cell_length_c                   13.699(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1230.7(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      228(2)
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            903
_diffrn_reflns_theta_max         22.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        1.50
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   n/a
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plates
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(19)
_refine_ls_extinction_coef       0.0010(13)
_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   1.040
_refine_ls_goodness_of_fit_obs   1.048
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_restrained_S_obs      1.048
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_obs          0.0322
_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^)+(0.0395P)^2^+0.2499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0897
_refine_ls_wR_factor_obs         0.0769
_reflns_number_observed          787
_reflns_number_total             903
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b003935gsup1.cif
_cod_data_source_block           st-587
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.2499P] 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^)+(0.0395P)^2^+0.2499P] 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)2(1)2(1)
_cod_database_code               7213372