A Direct Route to Six and Seven Membered Lactones via γγ-C(sp3)-H Activation: A Simple Protocol to Build Molecular Complexity
Das, Jayabrata; Dolui, Pravas; Ali, Wajid; Biswas, Jyoti Prasad; Chandrashekar, Hediyala B.; Prakash, Gaurav; Maiti, Debabrata; Chemical Science  (2020) –; doi:10.1039/D0SC03144E

data_1558871
_publ_section_title
;
 A Direct Route to Six and Seven Membered Lactones via \g\g-C(sp3)-H
 Activation: A Simple Protocol to Build Molecular Complexity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03144E
_journal_year                    2020
_chemical_formula_moiety         'C36 H66 O12 Pd3'
_chemical_formula_sum            'C36 H66 O12 Pd3'
_chemical_formula_weight         1010.57
_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
_audit_creation_date             2020-02-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2020-02-19 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.714(3)
_cell_angle_beta                 97.035(3)
_cell_angle_gamma                107.564(4)
_cell_formula_units_Z            2
_cell_length_a                   11.4234(4)
_cell_length_b                   12.9659(5)
_cell_length_c                   15.7183(6)
_cell_measurement_reflns_used    11476
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.2680
_cell_measurement_theta_min      2.1640
_cell_volume                     2199.86(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -110.00  19.00   1.00    8.00    --  -20.00 -72.00-108.00  129
  2  \w    -87.00  19.00   1.00    8.00    --  -20.00 -72.00 108.00  106
  3  \w    -53.00  15.00   1.00    8.00    --  -20.00  72.00  36.00   68
  4  \w    -32.00 -14.00   1.00    8.00    --  -20.00   0.00  36.00   18
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0185285000
_diffrn_orient_matrix_UB_12      -0.0049523000
_diffrn_orient_matrix_UB_13      0.0441152000
_diffrn_orient_matrix_UB_21      -0.0595681000
_diffrn_orient_matrix_UB_22      -0.0362537000
_diffrn_orient_matrix_UB_23      0.0033464000
_diffrn_orient_matrix_UB_31      0.0206316000
_diffrn_orient_matrix_UB_32      -0.0443011000
_diffrn_orient_matrix_UB_33      -0.0107543000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13411
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.051
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0269P)^2^+1.4539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6699
_reflns_number_total             7723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03144e2.cif
_cod_data_source_block           dm-aj-2-22_mo
_cod_depositor_comments
;

2022-06-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C8 H14.67 O2.67 Pd0.67'
_cod_original_formula_weight         224.46
_cod_original_formula_moiety         '0.22(C36 H66 O12 Pd3)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        2199.87(15)
_cod_database_code               1558871
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.893
_reflns_odcompleteness_completeness 86.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.02
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00M(H00F,H00G), C00R(H00K,H00L), C00T(H00P,H00Q), C00X(H00Z,
 HA), C01A(H01V,H01W)
2.b Idealised Me refined as rotating group:
 C00L(H00C,H00D,H00E), C00Q(H00H,H00I,H00J), C00S(H00M,H00N,H00O), C00U(H00R,
 H00S,H00T), C00V(H00U,H00V,H00W), C00W(H00X,H00Y,H), C00Z(H00,HB,HC),
 C012(H01A,H01B,H01C), C013(H01D,H01E,H01F), C014(H01G,H01H,H01I), C015(H01J,
 H01K,H01L), C017(H01M,H01N,H01O), C018(H01P,H01Q,H01R), C019(H01S,H01T,H01U),
 C01C(H01X,H01Y,HD), C01D(H01Z,HE,HF), C01E(H01,HG,HH), C01F(H0AA,HI,HJ)
;
_shelx_res_checksum              81199
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.870