Racemic and diastereoselective construction of indole alkaloids under solvent- and catalyst-free microwave-assisted Pictet–Spengler condensation
Jida, Mouhamad; Soueidan, Olivier-Mohamad; Deprez, Benoit; Laconde, Guillaume; Deprez-Poulain, Rebecca; Green Chemistry 14 (2012) 909–; doi:10.1039/c2gc16596a

data_7207696
_publ_section_title
;
 Racemic and diastereoselective construction of indole alkaloids under
 solvent- and catalyst-free microwave-assisted Pictet--Spengler
 condensation
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              909
_journal_paper_doi               10.1039/c2gc16596a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C16 H18 N2 O1'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.303(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.715(4)
_cell_length_b                   11.090(4)
_cell_length_c                   13.771(7)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    293
_cell_measurement_theta_max      22
_cell_measurement_theta_min      2
_cell_volume                     1330.9(10)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31806
_diffrn_reflns_theta_full        28.296
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_min         2.337
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0510
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.0001383
_refine_ls_shift/su_mean         0.0000265
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.338 0.389 0.155
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1143
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0447
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2128
_reflns_number_total             3310
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.36
_oxford_diffrn_Wilson_scale      39.88
_oxford_refine_ls_r_factor_ref   0.0470
_oxford_refine_ls_scale          0.2000(6)
_oxford_reflns_number_all        3299
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c2gc16596a.txt
_cod_data_source_block           moj246-12-ok
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C16 H18 N2 O1'
_cod_database_code               7207696