On the Regiochemical Differences between Pd-Catalyzed Heterocyclization-Allylation and -Arylation Reactions of Alkynylbenzamides: Preparation of 4-Allyl-isochromen-1-imines and Computational Study
Alvarez, Rosana; Vilar, Unai; Madich, Youssef; Aurrecoechea, Jose M.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02117H

data_7155888
_publ_section_title
;
 On the Regiochemical Differences between Pd-Catalyzed
 Heterocyclization-Allylation and -Arylation Reactions of
 Alkynylbenzamides: Preparation of 4-Allyl-isochromen-1-imines and
 Computational Study
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02117H
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H23 N O'
_chemical_formula_sum            'C22 H23 N O'
_chemical_formula_weight         317.41
_chemical_melting_point          338.0(10)
_chemical_name_systematic
(Z)-4-Allyl-N-butyl-3-phenyl-1H-isochromen-1-imine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-11-16T13:12:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-04-21 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.82820(10)
_cell_length_b                   12.0180(2)
_cell_length_c                   24.9007(3)
_cell_measurement_reflns_used    9618
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      76.27
_cell_measurement_theta_min      3.531
_cell_measurement_wavelength     1.54184
_cell_volume                     1744.13(5)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
  1 omega  -97.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  125.0000  -60.0000 94

  2 omega  -82.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -57.0000  120.0000 58

  3 omega   53.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   37.0000 -150.0000 43

  4 omega  -55.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000    0.0000 37

  5 omega   35.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 32

  6 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 25

  7 omega   39.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 27

  8 omega  127.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 25

  9 omega   43.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 25

 10 omega   44.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -60.0000 64

 11 omega   45.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  150.0000 61

 12 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 25

 13 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 25

 14 omega   40.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 36

 15 omega   81.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 25

 16 omega   30.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 46

 17 omega   35.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 31

 18 omega   89.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 27

 19 omega   34.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -180.0000 26

 20 omega   41.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25

 21 omega  -76.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -57.0000 -180.0000 65

 22 omega   41.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506   37.0000   90.0000 72

 23 omega  -34.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000    0.0000 26

 24 omega  -65.00  -39.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000    0.0000 26

 25 omega -158.00 -127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -111.0000  -60.0000 31

 26 omega  123.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 35

 27 omega   39.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 26

 28 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 25

 29 omega   45.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -90.0000 62

 30 omega   56.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  120.0000 53

 31 omega   44.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   30.0000 55

 32 omega  104.00  150.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 46

 33 omega  127.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

 34 omega   48.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 35

 35 omega   84.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 27

 36 omega   83.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 42

 37 omega   87.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 29

 38 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 34
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2294566
_diffrn_orient_matrix_UB_12      0.0591045
_diffrn_orient_matrix_UB_13      0.0113953
_diffrn_orient_matrix_UB_21      0.1203853
_diffrn_orient_matrix_UB_22      -0.1137319
_diffrn_orient_matrix_UB_23      0.004646
_diffrn_orient_matrix_UB_31      0.0523611
_diffrn_orient_matrix_UB_32      0.0024216
_diffrn_orient_matrix_UB_33      -0.060622
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15316
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.833
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.2012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.087
_reflns_number_gt                3304
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02117h2.cif
_cod_data_source_block           a20150418_uvb151614
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '337-339' was changed to '338.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1744.11(4)
_cod_database_code               7155888