Conformations, Conformational Preferences, and Conformational Exchange of N'-Substituted N-Acylguanidines: Intermolecular Interactions Hold the Key
Roland Kleinmaier; Max Keller; Patrick Igel; Armin Buschauer; Ruth M. Gschwind; Journal of the American Chemical Society 132 (2010) 11223–11233; doi:10.1021/ja103756y

data_4102827
_publ_contact_author_address
;
                Institut fuer Organische Chemie
                Universitaet Regensburg
                Universitaetsstr.31
                93053 Regensburg
                Deutschland   
;
_publ_contact_author_email       ruth.gschwind@chemie.uni-regensburg.de
_publ_contact_author_fax         '+49 941 943 4617'
_publ_contact_author_name
;
                Ruth M. Gschwind
;
_publ_contact_author_phone       '+49 941 943 4625'
_publ_section_title
;
 Conformations, Conformational Preferences, and Conformational Exchange of
 N'-Substituted N-Acylguanidines: Intermolecular Interactions Hold the Key
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11223
_journal_page_last               11233
_journal_paper_doi               10.1021/ja103756y
_journal_volume                  132
_journal_year                    2010
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C14 H19 N3 O'
_chemical_formula_sum            'C14 H19 N3 O'
_chemical_formula_weight         245.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Sep 08 15:44:00 2008'
_audit_creation_method           'PLATON <TABLE ACC> option'
_cell_angle_alpha                90
_cell_angle_beta                 110.779(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9884(3)
_cell_length_b                   10.6312(3)
_cell_length_c                   11.4497(3)
_cell_measurement_reflns_used    4217
_cell_measurement_temperature    123
_cell_measurement_theta_max      66.3923
_cell_measurement_theta_min      3.9392
_cell_volume                     1364.36(7)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.5431
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -16.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.6137   45.0000  150.0000    0.0000    0.0000 53

  2 omega   35.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.6137 -130.0000  251.0000    0.0000    0.0000 37

  3 omega  -16.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.6137   45.0000    0.0000    0.0000    0.0000 53

  4 omega    7.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       11.6137 -140.0000   42.0000    0.0000    0.0000 37

  5 omega -129.00  -91.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -90.0000 -130.0000  251.0000    0.0000    0.0000 38

  6 omega -164.00 -122.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -90.0000 -140.0000   42.0000    0.0000    0.0000 42

  7 omega   15.00   73.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000  -77.0000  210.0000    0.0000    0.0000 58

  8 omega   19.00   72.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000  -44.0000  305.0000    0.0000    0.0000 53

  9 omega   66.00  119.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   45.0000  330.0000    0.0000    0.0000 53

 10 omega  114.00  172.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   77.0000  270.0000    0.0000    0.0000 58

 11 omega   66.00  119.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   45.0000  210.0000    0.0000    0.0000 53

 12 omega  115.00  168.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   45.0000   60.0000    0.0000    0.0000 53

 13 omega   60.00  118.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   77.0000   90.0000    0.0000    0.0000 58

 14 omega   66.00  119.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       93.5000   45.0000  300.0000    0.0000    0.0000 53

 15 omega -178.00   -1.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -90.0000    0.0000  300.0000    0.0000    0.0000 177

 16 omega -178.00  -13.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -90.0000    0.0000  120.0000    0.0000    0.0000 165

;
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8138
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.56
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0625P)^2^+0.1563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                1929
_reflns_number_total             2348
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja103756y_si_002.cif
_cod_data_source_block           ur-rk81fb
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4102827