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_7156070
_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         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_chemical_melting_point          516.1(10)
_chemical_name_systematic        4-benzhydrylisoquinolin-1(2H)-one
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                94.198(3)
_cell_angle_beta                 102.080(2)
_cell_angle_gamma                102.439(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6454(2)
_cell_length_b                   8.8659(4)
_cell_length_c                   15.1694(5)
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.146
_cell_measurement_theta_min      2.370
_cell_volume                     846.86(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12644
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.593
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0850P)^2^+0.0260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2285
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02788e2.cif
_cod_data_source_block           cc_amr4_152_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '242-244 degree centigrade' was
changed to '516.1(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_original_cell_volume        846.86(5)
_cod_database_code               7156070
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
;
_shelx_res_checksum              92556
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'