The Importance of Weak C−H···O Bonds and π···π Stacking Interactions in the Formation of Organic 1,8-Bis(dimethylamino)naphthalene Complexes withZ‘ > 1
Nichol, Gary S.; Clegg, William; Crystal Growth & Design 6 (2006) 451–; doi:10.1021/cg0503806

data_4504635
_publ_section_title
;
 The Importance of Weak C&#x2212;H&#x00B7;&#x00B7;&#x00B7;O Bonds and
 \p&#x00B7;&#x00B7;&#x00B7;\p Stacking Interactions in the Formation of
 Organic 1,8-Bis(dimethylamino)naphthalene Complexes withZ&#x2018; &gt; 1
;
_journal_issue                   2
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              451
_journal_paper_doi               10.1021/cg0503806
_journal_volume                  6
_journal_year                    2006
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H19 N2 +, C5 H3 N2 O4'
_chemical_formula_sum            'C19 H22 N4 O4'
_chemical_formula_weight         370.41
_chemical_name_systematic
;
1-dimethylammonium,8-dimethylaminonaphthalene ororate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.598(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   25.641(7)
_cell_length_b                   11.581(2)
_cell_length_c                   27.303(8)
_cell_measurement_reflns_used    28494
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.2
_cell_volume                     7770(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            56638
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         0.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_correction_T_min  0.8991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick 2003'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.32
_platon_squeeze_details
; ?
SQUEEZE used to remove what appeared to be either disordered solvent or 
disordered proton sponge.  This disorder could not be satisfactorily modelled
either as methanol or PS.  wR2 dropped by around 15% after SQUEEZE
;
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2001
_refine_ls_number_reflns         14444
_refine_ls_number_restraints     913
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0802
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+17.8674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2090
_refine_ls_wR_factor_ref         0.2212
_reflns_number_gt                10802
_reflns_number_total             14444
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cg0503806si20050804_115445.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4504635