2-α-Hydroxyalkyl- and 2,7-Di(α-hydroxyalkyl) -1,8-bis(dimethylamino)naphthalenes: Stabilization of Nonconventional In/Out Conformers of "Proton Sponges" via N···H-O Intramolecular Hydrogen Bonding. A Remarkable Kind of Tandem Nitrogen Inversion
Alexander F. Pozharskii; Alexander V. Degtyarev; Oksana V. Ryabtsova; Valery A. Ozeryanskii; Mikhail E. Kletskii; Zoya A. Starikova; Lucjan Sobczyk; Alexander Filarowski; Journal of Organic Chemistry 72 (2007) 3006–3019; doi:10.1021/jo062667v

data_4022858
_publ_section_title
;
 2-\a-Hydroxyalkyl- and 2,7-Di(\a-hydroxyalkyl)
 -1,8-bis(dimethylamino)naphthalenes: Stabilization
 of Nonconventional In/Out Conformers of "Proton Sponges"
 via N&#x00B7;&#x00B7;&#x00B7;H-O Intramolecular Hydrogen Bonding.
 A Remarkable Kind of Tandem Nitrogen Inversion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3006
_journal_page_last               3019
_journal_paper_doi               10.1021/jo062667v
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C28 H30 N2 O2, 0.5(C2 H3 N)'
_chemical_formula_sum            'C29 H31.5 N2.5 O2'
_chemical_formula_weight         447.07
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.8420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   26.1078(17)
_cell_length_b                   8.7845(6)
_cell_length_c                   44.836(3)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.63
_cell_measurement_theta_min      2.46
_cell_volume                     9892.4(11)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.1356
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            54507
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3824
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         11911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1534
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0153P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                5681
_reflns_number_total             11911
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo062667vsi20061228_103824.cif
_cod_data_source_block           final
_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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C29 H31.50 N2.50 O2'
_cod_database_code               4022858