Palladium catalyzed domino reaction of 1,4-disubstituted 1,2,3-triazoles via double C–H functionalization: one-pot synthesis of triazolo[1,5-f]phenanthridines
Kumar, Avnish; Shinde, Sundar S.; Tiwari, Dharmendra Kumar; Sridhar, Balasubramanian; Likhar, Pravin R.; RSC Advances 6 (2016) 43638–; doi:10.1039/C6RA06755G

data_7236213
_publ_section_title
;
 Palladium catalyzed domino reaction of 1,4-disubstituted 1,2,3-triazoles
 via double C--H functionalization: one-pot synthesis of
 triazolo[1,5-f]phenanthridines
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              43638
_journal_paper_doi               10.1039/C6RA06755G
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C24 H26 N6'
_chemical_formula_sum            'C24 H26 N6'
_chemical_formula_weight         398.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2015-06-25 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                75.952(5)
_cell_angle_beta                 79.091(5)
_cell_angle_gamma                71.433(5)
_cell_formula_units_Z            2
_cell_length_a                   7.619(2)
_cell_length_b                   9.692(3)
_cell_length_c                   15.884(5)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1070.6(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9893
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.261
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         9893
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1925P)^2^+0.3475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.2933
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6630
_reflns_number_total             9893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra06755g2.cif
_cod_data_source_block           ay
_cod_database_code               7236213
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.084) H3(0.091) H4(0.085) H5(0.079) H9(0.079) H10(0.086)
 H11(0.079) H15A(0.087) H15B(0.087) H16A(0.099) H16B(0.099) H17A(0.132)
 H17B(0.132) H18A(0.246) H18B(0.246) H18C(0.246) H19(0.081) H21A(0.123)
 H21B(0.123) H22A(0.155) H22B(0.155) H23A(0.142) H23B(0.142) H24A(0.228)
 H24B(0.228) H24C(0.228) H21C(0.091) H21D(0.091) H22C(0.129) H22D(0.129)
 H23C(0.195) H23D(0.195) H24D(0.356) H24E(0.356) H24F(0.356)
 Fixed X: H2(0.7219) H3(0.742) H4(0.7848) H5(0.7965) H9(0.7331) H10(0.7972)
 H11(0.7991) H15A(0.6807) H15B(0.8957) H16A(0.6305) H16B(0.8468) H17A(0.6668)
 H17B(0.8821) H18A(0.8306) H18B(0.7529) H18C(0.616) H19(0.4278) H21A(0.5255)
 H21B(0.4678) H22A(0.2081) H22B(0.2626) H23A(0.0268) H23B(0.1) H24A(0.1218)
 H24B(0.3225) H24C(0.2489) H21C(0.3125) H21D(0.4627) H22C(0.243) H22D(0.4176)
 H23C(0.241) H23D(0.065) H24D(0.1333) H24E(0.1598) H24F(0.3341)
 Fixed Y: H2(0.7294) H3(0.7393) H4(0.5233) H5(0.3042) H9(-0.099) H10(-0.1053)
 H11(0.11) H15A(0.2825) H15B(0.2606) H16A(0.4966) H16B(0.4722) H17A(0.2709)
 H17B(0.2475) H18A(0.4496) H18B(0.3252) H18C(0.4665) H19(0.2396) H21A(0.0643)
 H21B(0.2363) H22A(0.2148) H22B(0.0466) H23A(0.151) H23B(0.2875) H24A(0.1467)
 H24B(0.1454) H24C(0.0082) H21C(0.2769) H21D(0.2207) H22C(0.055) H22D(-0.0232)
 H23C(0.0096) H23D(0.0931) H24D(0.2614) H24E(0.3118) H24F(0.2291)
 Fixed Z: H2(0.3495) H3(0.2021) H4(0.1524) H5(0.2477) H9(0.4624) H10(0.5989)
 H11(0.6351) H15A(0.7223) H15B(0.7098) H16A(0.7769) H16B(0.7655) H17A(0.8781)
 H17B(0.867) H18A(0.9304) H18B(0.9938) H18C(0.9444) H19(0.3106) H21A(0.1074)
 H21B(0.1016) H22A(0.2051) H22B(0.2017) H23A(0.1203) H23B(0.0752) H24A(-0.0232)
 H24B(-0.0122) H24C(0.0332) H21C(0.1648) H21D(0.0881) H22C(0.2072) H22D(0.1488)
 H23C(0.0459) H23D(0.1039) H24D(-0.0249) H24E(0.0573) H24F(-0.0001)
;
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.986
_shelx_res_checksum              28490
_shelx_shelxl_version_number     2014/7