1,8-Bis(dimethylethyleneguanidino)naphthalene: Tailoring the Basicity of Bisguanidine "Proton Sponges" by Experiment and Theory
Volker Raab; Klaus Harms; Jörg Sundermeyer; Borislav Kovačevič; Zvonimir B. Maksič; Journal of Organic Chemistry 68 (2003) 8790–8797; doi:10.1021/jo034906+

data_4022538
_publ_section_title
;
 1,8-Bis(dimethylethyleneguanidino)naphthalene: Tailoring the
 Basicity of Bisguanidine "Proton Sponges" by Experiment and Theory
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8790
_journal_page_last               8797
_journal_paper_doi               10.1021/jo034906+
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C20 H27 F6 N6 P'
_chemical_formula_weight         496.45
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.330(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7197(5)
_cell_length_b                   11.5542(5)
_cell_length_c                   22.8721(14)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.9
_cell_volume                     2273.9(2)
_computing_cell_refinement       'Stoe Cell'
_computing_data_collection       'Stoe Expose'
_computing_data_reduction        'Stoe Integrate'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDS'
_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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17693
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9242
_exptl_absorpt_correction_T_min  0.8942
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Nugget
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0004(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          1.608
_refine_ls_shift/su_mean         0.057
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.1026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                3113
_reflns_number_total             4416
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034906+si20030701_125252.cif
_cod_data_source_block           raab02
_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      'P 21/n'
_cod_database_code               4022538