Copper-catalyzed direct synthesis of 3-methylene-2-arylisoindolin-1-ones with calcium carbide as a surrogate of gaseous acetylene
Wu, Jianglong; Ma, Yinfeng; Wang, Yan; Wang, Chenyu; Luo, Hui; Li, Dianjun; Yang, Jinhui; Green Chemistry 25 (2023) 3425–3430; doi:10.1039/D2GC03572C

data_7246413
_publ_section_title
;
 Copper-catalyzed direct synthesis of 3-methylene-2-arylisoindolin-1-ones
 with calcium carbide as a surrogate of gaseous acetylene
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3425
_journal_page_last               3430
_journal_paper_doi               10.1039/D2GC03572C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H10 I N O'
_chemical_formula_sum            'C15 H10 I N O'
_chemical_formula_weight         347.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-19 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.381(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0551(6)
_cell_length_b                   7.4021(3)
_cell_length_c                   13.9932(6)
_cell_measurement_reflns_used    7995
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.97
_cell_volume                     1325.65(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12688
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.578
_diffrn_reflns_theta_min         1.591
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1627 before and 0.0371 after correction.
The Ratio of minimum to maximum transmission is 0.8340.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+1.2726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2437
_reflns_number_total             2735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03572c2.cif
_cod_data_source_block           wjl-1
_cod_depositor_comments          'Adding full bibliography for 7246413.cif.'
_cod_database_code               7246413
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.658
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14)
2.b X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_shelx_res_checksum              66390
_olex2_submission_special_instructions 'No special instructions were received'