Efficient and versatile catalysis of N-alkylation of heterocyclic amines with alcohols and one-pot synthesis of 2-aryl substituted benzazoles with newly designed ruthenium(ii) complexes of PNS thiosemicarbazones.
Ramachandran, Rangasamy; Prakash, Govindan; Selvamurugan, Sellappan; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Ramkumar, Venkatachalam; Dalton transactions (Cambridge, England : 2003) 43 (2014) 7889–7902; doi:10.1039/c4dt00006d

data_7029673
_publ_section_title
;
 Efficient and versatile catalysis of N-alkylation of heterocyclic amines
 with alcohols and one-pot synthesis of 2-aryl substituted benzazoles with
 newly designed ruthenium(ii) complexes of PNS thiosemicarbazones.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7889
_journal_page_last               7902
_journal_paper_doi               10.1039/c4dt00006d
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C45 H36 As Cl N3 O P Ru S'
_chemical_formula_sum            'C45 H36 As Cl N3 O P Ru S'
_chemical_formula_weight         909.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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           SHELXL-97
_cell_angle_alpha                97.686(7)
_cell_angle_beta                 94.380(7)
_cell_angle_gamma                96.521(7)
_cell_formula_units_Z            2
_cell_length_a                   10.2991(8)
_cell_length_b                   13.1254(11)
_cell_length_c                   15.2952(13)
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    295.0(2)
_cell_measurement_theta_max      28.7030
_cell_measurement_theta_min      3.6270
_cell_volume                     2026.9(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295.0(2)
_diffrn_detector_area_resol_mean 10.4015
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Gemini A ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14624
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+1.7359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1218
_reflns_number_gt                5013
_reflns_number_total             7165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt00006d2.cif
_cod_data_source_block           ruasl3
_cod_depositor_comments
'Adding full bibliography for 7029671--7029673.cif.'
_cod_original_cell_volume        2027.0(3)
_cod_database_code               7029673
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C5(H5), C4(H4), C9(H9), C14(H14), C13(H13), C12(H12),
 C11(H11), C21(H21), C20(H20), C19(H19), C18(H18), C17(H17), C27(H27), C26(H26),
  C25(H25), C24(H24), C23(H23), C29(H29), C30(H30), C31(H31), C32(H32),
 C33(H33), C39(H39), C38(H38), C37(H37), C36(H36), C35(H35), C41(H41), C42(H42),
  C43(H43), C44(H44), C45(H45)
2.c Fitted hexagon refined as free rotating group:
 C3(C8,C7,C6,C5,C4), C15(C14,C13,C12,C11,C10), C16(C21,C20,C19,C18,C17),
 C22(C27,C26,C25,C24,C23), C28(C29,C30,C31,C32,C33), C34(C39,C38,C37,C36,C35),
 C40(C41,C42,C43,C44,C45)
;