Palladium-catalysed stereoselective synthesis of 4-(diarylmethylidene)-3,4-dihydroisoquinolin-1(2H)-ones: expedient access to 4-substituted isoquinolin-1(2H)-ones and isoquinolines.
Mondal, Amrita; Kundu, Priyanka; Jash, Moumita; Chowdhury, Chinmay; Organic & biomolecular chemistry 16 (2018) 963–980; doi:10.1039/c7ob02788e

data_7156068
_publ_section_title
;
 Palladium-catalysed stereoselective synthesis of
 4-(diarylmethylidene)-3,4-dihydroisoquinolin-1(2H)-ones: expedient access
 to 4-substituted isoquinolin-1(2H)-ones and isoquinolines.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              963
_journal_page_last               980
_journal_paper_doi               10.1039/c7ob02788e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C23 H21 N3 O3'
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_chemical_melting_point          460.1(10)
_chemical_name_systematic
(Z)-4-((2,4-dimethoxypyrimidin-5-yl)(phenyl)methylene)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-29 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.324(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.091(4)
_cell_length_b                   12.635(5)
_cell_length_c                   25.986(10)
_cell_measurement_reflns_used    3837
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.77
_cell_volume                     3967(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.697
_diffrn_reflns_theta_min         2.332
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8853.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0870P)^2^+0.2205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2202
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02788e2.cif
_cod_data_source_block           cc_amr4_31bp_0m_pl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '186-188 degree centigrade' was
changed to '460.1(10)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156068--7156071.cif.
;
_cod_database_code               7156068
_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.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00Z(H00Z), C010(H010), C011(H011), C014(H014), C015(H015), C019(H019),
 C01A(H01A), C01B(H01B), C01D(H01D), C01K(H01K)
2.c Idealised Me refined as rotating group:
 C01G(H01C,H01E,H01F), C01H(H01G,H01H,H01I), C01L(H01J,H01L,H01M)
;
_shelx_res_checksum              70044
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'