Radical directed regioselective functionalization of diverse alkene derivatives
Suresh, Pavithira; Prasanna Kumari, Subramaniyan; Krishna Reddy, Singarajanahalli Mundarinti; Anthony, Savarimuthu Philip; Thamotharan, Subbiah; Selva Ganesan, Subramaniapillai; New Journal of Chemistry 46 (2022) 20951–20956; doi:10.1039/D2NJ02824G

data_7061983
_publ_section_title
;
 Radical directed regioselective functionalization of diverse alkene
 derivatives
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20951
_journal_page_last               20956
_journal_paper_doi               10.1039/D2NJ02824G
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C24 H28 O4'
_chemical_formula_sum            'C24 H28 O4'
_chemical_formula_weight         380.487
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_audit_creation_date             2022-10-04
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2022.09.28 svn.r5c12d49f for OlexSys, GUI svn.r6444)
;
_audit_update_record
;
2022-10-05 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.8790(18)
_cell_length_b                   17.290(4)
_cell_length_c                   28.075(6)
_cell_measurement_reflns_used    104546
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.548
_cell_measurement_theta_min      0.361
_cell_volume                     4310.0(16)
_computing_cell_refinement       '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_data_collection
'<i>PAL BL2D-SMDC Program</i>(Shin et.al, 2016)'
_computing_data_reduction        '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    '<i>SHELXT-2018</i>(Sheldrick, 2018)'
_diffrn_ambient_temperature      220.00
_diffrn_measured_fraction_theta_full 0.9942
_diffrn_measured_fraction_theta_max 0.9942
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.63000
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.9942
_diffrn_reflns_Laue_measured_fraction_max 0.9942
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            54242
_diffrn_reflns_point_group_measured_fraction_full 0.9942
_diffrn_reflns_point_group_measured_fraction_max 0.9942
_diffrn_reflns_theta_full        21.9998
_diffrn_reflns_theta_max         22.00
_diffrn_reflns_theta_min         1.29
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'<i>HKL3000sm Scalepack</i>(Otwinowski et.al,2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       block
_exptl_crystal_F_000             1632.659
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.4249
_refine_diff_density_min         -0.3052
_refine_diff_density_rms         0.0448
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             14.0375
_refine_ls_extinction_coef       0.0012
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0419
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     364
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.0015
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1316P)^2^+1.3992P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2153
_refine_ls_wR_factor_ref         0.2302
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                2753
_reflns_number_total             3784
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj02824g2.cif
_cod_data_source_block           SPA694
_cod_original_cell_volume        4310.0(15)
_cod_database_code               7061983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11B-C12B \\sim C11B-C13B \\sim C11B-C14B
 with sigma of 0.02
 C12B-C13B \\sim C13B-C14B \\sim C14B-C12B
 with sigma of 0.04
 C19A-C20A \\sim C20A-C21A \\sim C21A-C22A \\sim C22A-C23A \\sim C23A-C24A
\\sim C24A-C19A
 with sigma of 0.02
 C19A-C21A \\sim C19A-C23A \\sim C20A-C22A \\sim C20A-C24A \\sim C21A-C23A
\\sim C22A-C24A
 with sigma of 0.04
 C19B-C20B \\sim C20B-C21B \\sim C21B-C22B \\sim C22B-C23B \\sim C23B-C24B
\\sim C24B-C19B
 with sigma of 0.02
 C19B-C21B \\sim C19B-C23B \\sim C20B-C22B \\sim C20B-C24B \\sim C21B-C23B
\\sim C22B-C24B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C3, C4, C5, C6, C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10A, C11A, C12A, C13A, C14A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10B, C11B, C12B, C13B, C14B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10A, C11A, C12A, C13A, C14A, C19A, C20A, C21A, C22A, C23A, C24A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10B, C11B, C12B, C13B, C14B, C19B, C20B, C21B, C22B, C23B, C24B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(C12B)=Sof(H12d)=Sof(H12e)=Sof(H12f)=
 Sof(C13B)=Sof(H13d)=Sof(H13e)=Sof(H13f)=Sof(C14B)=Sof(H14d)=Sof(H14e)=
 Sof(H14f)=1-FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12a)=Sof(H12b)=Sof(H12c)=
 Sof(C13A)=Sof(H13a)=Sof(H13b)=Sof(H13c)=Sof(C14A)=Sof(H14a)=Sof(H14b)=
 Sof(H14c)=FVAR(1)
 Sof(C19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=
 Sof(C23B)=Sof(H23B)=Sof(C24B)=Sof(H24B)=1-FVAR(2)
 Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C10A(H10A), C10B(H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C20A(H20A), C21A(H21A), C22A(H22A),
 C23A(H23A), C24A(H24A), C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B),
 C24B(H24B)
5.c Idealised Me refined as rotating group:
 C12A(H12a,H12b,H12c), C13A(H13a,H13b,H13c), C14A(H14a,H14b,H14c), C12B(H12d,
 H12e,H12f), C13B(H13d,H13e,H13f), C14B(H14d,H14e,H14f), C16(H16a,H16b,H16c),
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_olex2_submission_special_instructions 'No special instructions were received'