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_1558870
_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         'C9 H14 O4'
_chemical_formula_sum            'C9 H14 O4'
_chemical_formula_weight         186.20
_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
_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
_cell_angle_beta                 107.359(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3771(10)
_cell_length_b                   8.7126(6)
_cell_length_c                   10.1258(8)
_cell_measurement_reflns_used    2621
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.9700
_cell_measurement_theta_min      3.1360
_cell_volume                     958.00(14)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  70.00   1.00    8.00    --  -20.00   0.00 108.00  180
  2  \w    -39.00   2.00   1.00    8.00    --  -20.00  72.00  36.00   41
  3  \w   -110.00  53.00   1.00    8.00    --  -20.00   0.00-108.00  163
  4  \w    -64.00 -34.00   1.00    8.00    --  -20.00 -72.00  36.00   30
;
_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      0.0023907000
_diffrn_orient_matrix_UB_12      -0.0436562000
_diffrn_orient_matrix_UB_13      -0.0582314000
_diffrn_orient_matrix_UB_21      0.0650502000
_diffrn_orient_matrix_UB_22      -0.0044077000
_diffrn_orient_matrix_UB_23      0.0272285000
_diffrn_orient_matrix_UB_31      -0.0056252000
_diffrn_orient_matrix_UB_32      -0.0685640000
_diffrn_orient_matrix_UB_33      0.0354111000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7206
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.998
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77601
_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            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.0102
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0557
_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^)+(0.0523P)^2^+0.4173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1204
_reflns_number_total             1681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03144e2.cif
_cod_data_source_block           dm-pd-acid_mo
_cod_database_code               1558870
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 91.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.08
_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) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C008(H00C,H00D), C00B(H00E,H00F)
2.c Idealised Me refined as rotating group:
 C00C(H00G,H00H,H00I), C00D(H00J,H00K,H00L)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              75600
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.819