Addition of nucleophiles to electron-deficient alkenes: structural studies on the incipient reaction and the zwitterionic intermediate
Bell, Paul C.; Wallis, John D.; Chemical Communications  (1999) 257–; doi:10.1039/a808488b

data_7110403
_publ_section_title
;
 Addition of nucleophiles to electron-deficient alkenes: structural
 studies on the incipient reaction and the zwitterionic intermediate
;
_journal_issue                   3
_journal_name_full               'Chemical Communications'
_journal_page_first              257
_journal_paper_doi               10.1039/a808488b
_journal_year                    1999
_chemical_formula_sum            'C16 H13 N3'
_chemical_formula_weight         247.29
_chemical_melting_point          430.0(10)
_chemical_name_systematic
; 
2-(8-dimethylamino)naphth-1-yl)ethene-1,1-dinitrile 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 103.38(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.606(10)
_cell_length_b                   9.042(5)
_cell_length_c                   11.073(10)
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.5
_cell_volume                     1325.3(17)
_computing_cell_refinement       'DENZO (Nonius, 1997b)'
_computing_data_collection       'KappaCCD (Nonius, 1997a)'
_computing_data_reduction        DENZO
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 9.09
_diffrn_measurement_device       kappaCCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6044
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        'not measured'
_diffrn_standards_interval_count 'not measured'
_diffrn_standards_interval_time  'not measured'
_diffrn_standards_number         'not measured'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.068
_refine_ls_goodness_of_fit_obs   1.124
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_restrained_S_obs      1.124
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_obs          0.0502
_refine_ls_shift/esd_max         -0.040
_refine_ls_shift/esd_mean        0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s^2^(Fo^2^)+( 0.0442P)^2^+0.3224P] where w=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1280
_refine_ls_wR_factor_obs         0.1144
_reflns_number_observed          2082
_reflns_number_total             2677
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            808488bsup1.cif
_cod_data_source_block           dc10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '429-431' was changed to '430.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0442P)^2^+0.3224P] where w=(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^)+( 0.0442P)^2^+0.3224P] where
w=(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      'P 21/a'
_cod_database_code               7110403