Engaging vinylene carbonate in ruthenium-catalyzed regioselective C-4 methylenation and C-8 formylmethylation of isoquinolinones.
Thalakottukara, Dolly David; Gandhi, Thirumanavelan; Chemical communications (Cambridge, England) 60 (2024) 10358–10361; doi:10.1039/d4cc03466j

data_7133582
_publ_section_title
;
 Engaging vinylene carbonate in ruthenium-catalyzed regioselective C-4
 methylenation and C-8 formylmethylation of isoquinolinones.
;
_journal_issue                   75
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10358
_journal_page_last               10361
_journal_paper_doi               10.1039/d4cc03466j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C35 H30 N2 O2'
_chemical_formula_sum            'C35 H30 N2 O2'
_chemical_formula_weight         510.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-04-27 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                66.245(2)
_cell_angle_beta                 74.285(2)
_cell_angle_gamma                70.005(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4851(5)
_cell_length_b                   11.5807(5)
_cell_length_c                   13.2811(7)
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.48
_cell_volume                     1370.34(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1295
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42356
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         1.992
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1001 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.7603.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0981P)^2^+0.2278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.2278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2495
_reflns_number_total             5817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03466j2.cif
_cod_data_source_block           mo_vs_ext_n_phen_ethyldimer_4_
_cod_depositor_comments
'Adding full bibliography for 7133581--7133582.cif.'
_cod_database_code               7133582
_shelx_shelxl_version_number     2019/1
_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. Restrained distances
 C1-C2 \\sim C1A-C2
 with sigma of 0.02
 C1-C35 \\sim C1A-C35A
 with sigma of 0.02
 C2-C35 \\sim C2-C35A
 with sigma of 0.04
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C14-C16 \\sim C14-C16A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim C16 \\sim C35 \\sim C15: within 2A with sigma of 0.0001 and sigma for
terminal atoms of 0.0002 within 2A
C1A \\sim C15A \\sim C16A \\sim C35A: within 2A with sigma of 0.0001 and sigma
for terminal atoms of 0.0002 within 2A
Uanis(C1) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C15)
\\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of 0.0002
Uanis(C1A) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C35A)
\\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of 0.0002
4. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C35A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(1)
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(2)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C15(H15A,H15B), C1A(H1AA,H1AB), C15A(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C12(H12), C13(H13), C19(H19), C20(H20),
 C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C35(H35A,H35B,H35C), C35A(H35D,H35E,H35F), C16A(H16D,
 H16E,H16F)
;
_shelx_res_checksum              72338
_shelx_hkl_checksum              1106
_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'