Room temperature C-O bond cleavage of vinyl cyclic synthons <i>via</i> a metallaphotoredox approach.
Keshri, Santosh Kumar; Kapur, Manmohan; Chemical communications (Cambridge, England) 60 (2024) 11164–11167; doi:10.1039/d4cc02815e

data_7133708
_publ_section_title
;
 Room temperature C-O bond cleavage of vinyl cyclic synthons <i>via</i> a
 metallaphotoredox approach.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11164
_journal_page_last               11167
_journal_paper_doi               10.1039/d4cc02815e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 Br N2 O2'
_chemical_formula_sum            'C21 H19 Br N2 O2'
_chemical_formula_weight         411.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-18 deposited with the CCDC.	2024-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.050(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.287(7)
_cell_length_b                   8.8974(18)
_cell_length_c                   14.848(3)
_cell_measurement_temperature    140(2)
_cell_volume                     3634.6(14)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39175
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.986
_diffrn_reflns_theta_min         2.406
_exptl_absorpt_coefficient_mu    2.280
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             1680
_refine_diff_density_max         1.588
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0967
_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^)+(0.0587P)^2^+40.8022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2100
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2580
_reflns_number_total             4360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02815e2.cif
_cod_data_source_block           f2_a
_cod_depositor_comments          'Adding full bibliography for 7133708.cif.'
_cod_original_cell_volume        3634.4(14)
_cod_database_code               7133708
_shelx_shelxl_version_number     2018/3
_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, All O(H,H) groups
2. Restrained distances
 C2-C3 \\sim C2-C3A
 with sigma of 0.02
 C3-C5 \\sim C3A-C5
 with sigma of 0.02
 O1-C5 \\sim O1-C5A
 with sigma of 0.02
 C3-C5 \\sim C3-C5A
 with sigma of 0.02
 C5-C3A \\sim C5A-C3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C5A) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C5A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(H2B)=Sof(C3A)=Sof(H3A)=1-FVAR(1)
 Sof(H2A)=Sof(C3)=Sof(H3)=FVAR(1)
 Sof(H1BB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=1-FVAR(2)
 Sof(H1AA)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C5A(H5AA,H5AB)
5.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00J(H00J),
 C00K(H00K), C00L(H00L), C2(H2A), C2(H2B), C3(H3), C3A(H3A)
5.c Tetrahedral OH refined with riding coordinates:
 O1(H1AA), O1(H1BB)
5.d Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00E)
;
_shelx_res_checksum              93199
_shelx_hkl_checksum              20953
_olex2_submission_special_instructions 'No special instructions were received'