Facile and Atom-Efficient Amidolithium-Catalyzed C‒C and C‒N Formation for the Construction of Substituted Guanidines and Propiolamidines
Ong, Tiow-Gan; O'Brien, Julie S.; Korobkov, Ilia; Richeson, Darrin S.; Organometallics 25 (2006) 4728–4730; doi:10.1021/om060539r

data_4082252
_publ_section_title
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 Facile and Atom-Efficient Amidolithium-Catalyzed C--C and C--N
 Formation for the Construction of Substituted Guanidines and
 Propiolamidines
;
_journal_coden_ASTM              ORGND7
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              4728
_journal_page_last               4730
_journal_paper_doi               10.1021/om060539r
_journal_volume                  25
_journal_year                    2006
_chemical_formula_sum            'C28 H44 Li2 N6 O2'
_chemical_formula_weight         510.57
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 116.908(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   38.889(6)
_cell_length_b                   10.2786(13)
_cell_length_c                   35.177(4)
_cell_measurement_reflns_used    303
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      20.81
_cell_measurement_theta_min      1.30
_cell_volume                     12539(3)
_computing_cell_refinement       'SMART, Bruker (2000)'
_computing_data_collection       'SMART, Bruker (2000)'
_computing_data_reduction        'XPREP, Bruker (2000)'
_computing_molecular_graphics    'SHELXTL, Bruker (2000)'
_computing_publication_material  'SHELXTL, Bruker (2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  '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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26740
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.288
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         6257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+24.4971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                4382
_reflns_number_total             6257
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4074306
_cod_data_source_file            om060539rsup1.cif
_cod_data_source_block           dr33
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' 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      C2/c
_cod_database_code               4082252