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_4022857
_publ_section_title
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 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
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_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         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_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   mexed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5415(7)
_cell_length_b                   12.4658(8)
_cell_length_c                   13.8618(9)
_cell_measurement_reflns_used    5106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.07
_cell_measurement_theta_min      2.20
_cell_volume                     1821.6(2)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20481
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0576P)^2^+0.3438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                4198
_reflns_number_total             4362
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo062667vsi20061228_103806.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 
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_cod_database_code               4022857