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_7029671
_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         'C39 H32 Cl N3 O P2 Ru S, 0.5(C2 H8 O2)'
_chemical_formula_sum            'C40 H36 Cl N3 O2 P2 Ru S'
_chemical_formula_weight         821.24
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.312(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3822(5)
_cell_length_b                   16.6752(6)
_cell_length_c                   15.1543(4)
_cell_measurement_reflns_used    7467
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0120
_cell_measurement_theta_min      3.8050
_cell_volume                     3612.4(2)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.4015
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Gemini A ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0222648000
_diffrn_orient_matrix_UB_12      -0.0241633000
_diffrn_orient_matrix_UB_13      0.0299627000
_diffrn_orient_matrix_UB_21      0.0338681000
_diffrn_orient_matrix_UB_22      -0.0304620000
_diffrn_orient_matrix_UB_23      -0.0032566000
_diffrn_orient_matrix_UB_31      0.0286100000
_diffrn_orient_matrix_UB_32      0.0172364000
_diffrn_orient_matrix_UB_33      0.0362028000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18987
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77532
_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    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         6367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0323P)^2^+3.0193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                5292
_reflns_number_total             6367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt00006d2.cif
_cod_data_source_block           pv3
_cod_depositor_comments
'Adding full bibliography for 7029671--7029673.cif.'
_cod_database_code               7029671
_chemical_oxdiff_formula         'Ru1 P2 O3 N2 C40 H40'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Sof(O5)=Sof(C1A)=1-FVAR(2)
 Sof(O1)=Sof(C1B)=FVAR(2)
3.a Rotating group:
 N3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30),
 C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C1D(H1DA,H1DB,H1DC)
;