Visible light mediated sp(3) C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction.
Chen, Yunyun; Feng, Gaofeng; Organic & biomolecular chemistry 13 (2015) 4260–4265; doi:10.1039/c5ob00201j

data_7154347
_publ_section_title
;
 Visible light mediated sp(3) C-H bond functionalization of
 N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component
 reaction.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4260
_journal_page_last               4265
_journal_paper_doi               10.1039/c5ob00201j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C29 H31 N3 O3'
_chemical_formula_weight         469.57
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-26 deposited with the CCDC.
2015-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.938(6)
_cell_length_b                   11.193(2)
_cell_length_c                   16.370(3)
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.085
_cell_volume                     5039.3(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      299.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32801
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc and Hexane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0812P)^2^+1.3974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                3418
_reflns_number_total             4946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00201j2.cif
_cod_data_source_block           cdc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '298-300' was changed to
'299.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7154347--7154348.cif.
;
_cod_original_cell_volume        5039.1(17)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7154347