Cu(I)-catalyzed cycloguanidination of olefins.
Zhao, Baoguo; Du, Haifeng; Shi, Yian; Organic letters 10 (2008) 1087–1090; doi:10.1021/ol702974s

data_1504538
_publ_section_title
;
 Cu(I)-catalyzed cycloguanidination of olefins.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1087
_journal_page_last               1090
_journal_paper_doi               10.1021/ol702974s
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_sum            'C22 H28 N4'
_chemical_formula_weight         348.48
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_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_method           'Bruker SHELXTL'
_cell_angle_alpha                105.763(2)
_cell_angle_beta                 90.439(2)
_cell_angle_gamma                95.360(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8540(2)
_cell_length_b                   10.1088(3)
_cell_length_c                   11.9207(3)
_cell_measurement_reflns_used    4886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.18
_cell_measurement_theta_min      2.35
_cell_volume                     1021.72(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.1084
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19956
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, SHeldrick, 1997'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.0213(18)
_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   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         10819
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0405P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                4614
_reflns_number_total             10819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702974s-file001.cif
_cod_data_source_block           ys170r_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1504538