Silver-Free Palladium-Catalyzed sp(3) and sp(2) C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group.
Ye, Xiaohan; Xu, Chang; Wojtas, Lukasz; Akhmedov, Novruz G.; Chen, Hao; Shi, Xiaodong; Organic letters 18 (2016) 2970–2973; doi:10.1021/acs.orglett.6b01319

data_1543409
_publ_section_title
;
 Silver-Free Palladium-Catalyzed sp(3) and sp(2) C-H Alkynylation Promoted
 by a 1,2,3-Triazole Amine Directing Group.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2970
_journal_page_last               2973
_journal_paper_doi               10.1021/acs.orglett.6b01319
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 N6 O3 Pd'
_chemical_formula_sum            'C24 H22 N6 O3 Pd'
_chemical_formula_weight         548.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.190(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2220(3)
_cell_length_b                   20.4529(6)
_cell_length_c                   11.0286(3)
_cell_measurement_reflns_used    9637
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.91
_cell_measurement_theta_min      4.10
_cell_volume                     2253.76(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34308
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.077
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.979
_exptl_absorpt_correction_T_max  0.5878
_exptl_absorpt_correction_T_min  0.4395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1072 before and 0.0835 after correction.
The Ratio of minimum to maximum transmission is 0.7477.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 3679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         9183
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0107P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0597
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                8443
_reflns_number_total             9183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01319_si_002.cif
_cod_data_source_block           yxh_100_0m
_cod_depositor_comments          'Adding full bibliography for 1543409.cif.'
_cod_database_code               1543409
_shelx_estimated_absorpt_t_max   0.664
_shelx_estimated_absorpt_t_min   0.439
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C59(H59)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C60(H60A,H60B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C24(H24), C25(H25),
 C26(H26), C27(H27), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51),
  C64(H64), C65(H65), C66(H66), C67(H67)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C34(H34A,H34B,H34C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C74(H74A,H74B,H74C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'