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_4102828
_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         'C13 H20 Cl1 N3 O2'
_chemical_formula_sum            'C13 H20 Cl N3 O2'
_chemical_formula_weight         285.77
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Jul 07 09:31:00 2009'
_audit_creation_method           'PLATON <TABLE ACC> option'
_cell_angle_alpha                89.462(6)
_cell_angle_beta                 85.558(6)
_cell_angle_gamma                75.247(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4161(5)
_cell_length_b                   8.3883(6)
_cell_length_c                   12.2595(9)
_cell_measurement_reflns_used    9319
_cell_measurement_temperature    123
_cell_measurement_theta_max      66.4831
_cell_measurement_theta_min      3.6222
_cell_volume                     735.24(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega -101.00  -52.40   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6137  179.0000 -180.0000 27

  2 omega  -85.00  -34.60   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6137  150.0000  -59.0000 28

  3 omega -101.00  -56.00   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6137  179.0000  120.0000 25

  4 omega  -26.00   -0.80   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000  103.0000 -176.0000 14

  5 omega  -51.00   10.20   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  -69.0000  125.0000 34

  6 omega   11.00   52.40   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  -69.0000  125.0000 23

  7 omega   15.00   51.00   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000  -39.0000 20

  8 omega   12.00   40.80   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000 -100.0000 16

  9 omega   57.00   87.60   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000  -39.0000 17

 10 omega   74.00  110.00   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   77.0000  142.0000 20

 11 omega   16.00   52.00   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   79.0000   63.0000 20

 12 omega   14.00   46.40   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   77.0000  142.0000 18

 13 omega   54.00  122.40   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   79.0000   63.0000 38

 14 omega   18.00   63.00   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000 -174.0000 25

 15 omega   74.00  129.80   1.8000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000 -174.0000 31

 16 omega  -47.00  -16.40   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -52.0000  -82.0000 -116.0000 17

 17 omega   23.00   51.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  -14.0000 16

 18 omega  -59.00  -26.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000   30.0000 18

 19 omega  -61.00  -28.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -62.0000  -77.0000  -14.0000 18

 20 omega   30.00   57.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   79.0000  167.0000 15

 21 omega   36.00   66.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -160.0000 17

 22 omega  -77.00  -39.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -72.0000  -73.0000  -34.0000 21

 23 omega  -72.00  -43.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -73.0000   97.0000 16

 24 omega  -87.00  -42.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -71.0000   19.0000 25

 25 omega  -82.00  -46.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -60.0000   56.0000 20

 26 omega  -80.00  -44.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -69.0000  -75.0000 20

 27 omega  -73.00  -42.40   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -76.0000  -77.0000 -120.0000 17

 28 omega  -75.00  -48.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -68.0000 -123.0000 15

 29 omega  -83.00  -47.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -73.0000  159.0000 20

 30 omega -158.00 -105.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -77.0000   75.0000 29

 31 omega  -73.00  -46.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -77.0000   75.0000 15

 32 omega  -79.00  -50.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -80.0000  -69.0000   -5.0000 16

 33 omega  -82.00  -53.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -84.0000  -71.0000 -160.0000 16

 34 omega  -93.00  -60.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -66.0000 -124.0000 18

 35 omega -108.00  -63.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000   90.0000 25

 36 omega -117.00  -86.40   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -120.0000 17

 37 omega  -90.00  -57.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -69.0000  -84.0000 18

 38 omega -121.00  -58.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -69.0000  145.0000 35

 39 omega  -90.00  -57.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -71.0000 -174.0000 18

 40 omega -163.00 -132.40   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   60.0000 17

 41 omega  -94.00  -58.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000  -82.0000 20

 42 omega  -82.00  -56.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000 -120.0000 14

 43 omega  -90.00  -57.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000    0.0000 18

 44 omega -101.00  -59.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -73.0000  -49.0000 23

 45 omega  -91.00  -58.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -77.0000   60.0000 18

 46 omega   63.00   90.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 15

 47 omega   74.00  110.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 20

 48 omega   73.00  137.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 36

 49 omega   97.00  163.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 37

 50 omega   62.00   89.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 15

 51 omega  141.00  171.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 17

 52 omega   62.00   89.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 15

 53 omega  122.00  174.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 29

 54 omega   60.00   99.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 22

 55 omega   37.00  127.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -90.0000 50

 56 omega  124.00  163.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 22

 57 omega   60.00  103.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 24

 58 omega   60.00  171.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 62

 59 omega   98.00  171.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 41

 60 omega   53.00  126.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -82.0000   10.0000 41

 61 omega  113.00  152.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -150.0000 22

 62 omega   21.00   48.00   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -82.0000   10.0000 15

 63 omega   15.00  124.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  150.0000 61

 64 omega   60.00  169.80   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 61

 65 omega   71.00  105.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000   60.0000 19

 66 omega   60.00  171.60   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 62

 67 omega   92.00  171.20   1.8000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 44

;
_diffrn_measurement_device_type
'Goniometer Xcalibur, detector: Ruby (Gemini ultra Mo)'
_diffrn_measurement_method       '\w scans'
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12697
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.55
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         3.62
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    ref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0534P)^2^+0.1893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                2376
_reflns_number_total             2564
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja103756y_si_003.cif
_cod_data_source_block           ur-rk117-hcl
_cod_original_cell_volume        735.25(9)
_cod_original_formula_sum        'C13 H20 Cl1 N3 O2'
_cod_database_code               4102828