Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles.
Li, Zhenghua; Sharma, Nandini; Sharma, Upendra K.; Jacobs, Jeroen; Van Meervelt, Luc; Van der Eycken, Erik V.; Chemical communications (Cambridge, England) 52 (2016) 5516–5519; doi:10.1039/c6cc00784h

data_7118827
_publ_section_title
;
 Ligand-controlled product selectivity in palladium-catalyzed domino
 post-Ugi construction of (spiro)polyheterocycles.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5516
_journal_page_last               5519
_journal_paper_doi               10.1039/c6cc00784h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C29 H29 F N2 O3, C2 H3 N'
_chemical_formula_sum            'C31 H32 F N3 O3'
_chemical_formula_weight         513.60
_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             2015-11-06
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Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
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_audit_update_record
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2015-11-09 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.553(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0851(3)
_cell_length_b                   16.6480(5)
_cell_length_c                   17.5220(5)
_cell_measurement_reflns_used    6436
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.9150
_cell_measurement_theta_min      2.9530
_cell_volume                     2620.71(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -71.00  -11.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.0732  -19.0000 -120.0000 60

  2 omega   -3.00   88.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   57.0000    0.0000 91

  3 omega  -50.00   40.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -57.0000 -150.0000 90
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0618336000
_diffrn_orient_matrix_UB_12      0.0265754000
_diffrn_orient_matrix_UB_13      0.0045475000
_diffrn_orient_matrix_UB_21      0.0465203000
_diffrn_orient_matrix_UB_22      -0.0313662000
_diffrn_orient_matrix_UB_23      0.0169488000
_diffrn_orient_matrix_UB_31      0.0157936000
_diffrn_orient_matrix_UB_32      -0.0110870000
_diffrn_orient_matrix_UB_33      -0.0370070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12261
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         5353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+1.9718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                4678
_reflns_number_total             5353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00784h2.cif
_cod_data_source_block           wdh1055
_cod_depositor_comments
'Adding full bibliography for 7118825--7118827.cif.'
_cod_database_code               7118827
_chemical_oxdiff_formula         'C20 H31 O4'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_olex2_date_sample_data_collection 2015-04-24
_olex2_submission_special_instructions 'No special instructions were received'