Cu/Pd Cooperatively Catalyzed Tandem C-N and C-P Bonds Formation: Access to Phosphorated 2H-Indazoles
Wei, Weiwei; Li, Xuanyi; Gu, Meng; Yao, Hequan; Lin, Aijun; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02323E

data_7155884
_publ_section_title
;
 Cu/Pd Cooperatively Catalyzed Tandem C-N and C-P Bonds Formation: Access
 to Phosphorated 2H-Indazoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02323E
_journal_year                    2017
_chemical_formula_moiety         'C24 H24 Cl N2 O3 P'
_chemical_formula_sum            'C24 H24 Cl N2 O3 P'
_chemical_formula_weight         454.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     dual
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-31 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.125(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.918(2)
_cell_length_b                   14.453(3)
_cell_length_c                   14.576(3)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    205
_cell_measurement_theta_max      26.804
_cell_measurement_theta_min      2.344
_cell_volume                     2290.9(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      205
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25756
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.116
_diffrn_reflns_theta_min         1.988
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0782 before and 0.0634 after correction. The Ratio of minimum to maximum transmission is 0.8950. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0710P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2811
_reflns_number_total             5054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02323e2.cif
_cod_data_source_block           mo_2017328-www170503-4-cl_0m
_cod_original_cell_volume        2290.8(7)
_cod_database_code               7155884
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 C24-C23 \\sim C26-C25
 with sigma of 0.02
 O3-C23 \\sim O3-C25
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C26)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: C23(0.4) H23A(0.4) H23B(0.4) C24(0.4) H24A(0.4) H24B(0.4)
 H24C(0.4) C25(0.6) H25A(0.6) H25B(0.6) C26(0.6) H26A(0.6) H26B(0.6) H26C(0.6)
6.a Ternary CH refined with riding coordinates:
 C8(H8)
6.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'