Copper-catalyzed arylation of biguanide derivatives via C-N cross-coupling reactions.
Zhang, Chen; Huang, Bo; Bao, Ai-Qing; Li, Xiao; Guo, Shunna; Zhang, Jin-Quan; Xu, Jun-Zhi; Zhang, Rihao; Cui, Dong-Mei; Organic & biomolecular chemistry 13 (2015) 11432–11437; doi:10.1039/c5ob01258a

data_7154728
_publ_section_title
;
 Copper-catalyzed arylation of biguanide derivatives via C-N
 cross-coupling reactions.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11432
_journal_page_last               11437
_journal_paper_doi               10.1039/c5ob01258a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         ' C10 H16 N5, Br'
_chemical_formula_sum            'C10 H16 Br N5'
_chemical_formula_weight         286.19
_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_block_doi                 10.5517/cc1j7sg0
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-19 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.995(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2189(10)
_cell_length_b                   5.8949(4)
_cell_length_c                   18.2917(13)
_cell_measurement_reflns_used    6973
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1266.53(16)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9373
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    3.229
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.3463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless'
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.544
_refine_diff_density_min         -1.379
_refine_diff_density_rms         0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.711
_refine_ls_R_factor_all          0.1608
_refine_ls_R_factor_gt           0.1344
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4046
_refine_ls_wR_factor_ref         0.4318
_reflns_number_gt                1504
_reflns_number_total             2224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01258a2.cif
_cod_data_source_block           lx-0203
_cod_depositor_comments
'Adding full bibliography for 7154728--7154729.cif.'
_cod_database_code               7154728