Models for incomplete nucleophilic attack on a protonated carbonyl group and electron-deficient alkenes: salts and zwitterions from 1-dimethylamino-naphthalene-8-carbaldehyde.
Lari, Alberth; Pitak, Matuesz B.; Coles, Simon J.; Rees, Gregory J.; Day, Stephen P.; Smith, Mark E.; Hanna, John V.; Wallis, John D.; Organic & biomolecular chemistry 10 (2012) 7763–7779; doi:10.1039/c2ob25929j

data_7152630
_publ_section_title
;
 Models for incomplete nucleophilic attack on a protonated carbonyl group
 and electron-deficient alkenes: salts and zwitterions from
 1-dimethylamino-naphthalene-8-carbaldehyde.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7763
_journal_page_last               7779
_journal_paper_doi               10.1039/c2ob25929j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C19 H19 N3 O3'
_chemical_formula_sum            'C19 H19 N3 O3'
_chemical_formula_weight         337.37
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.456(3)
_cell_angle_beta                 85.190(2)
_cell_angle_gamma                65.248(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3360(4)
_cell_length_b                   8.7036(3)
_cell_length_c                   12.1220(6)
_cell_measurement_reflns_used    19881
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     795.56(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16118
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0736P)^2^+0.1386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                2967
_reflns_number_total             3656
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25929j.txt
_cod_data_source_block           compound_12
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152630