Discovery and Mechanistic Study of a Totally Organic C<sub>(aryl)</sub>-C<sub>(alkyl)</sub>Oxygen Insertion Reaction.
Kazim, Muhammad; Foy, Hayden; Siegler, Maxime A.; Dudding, Travis; Lectka, Thomas; The Journal of organic chemistry 84 (2019) 14349–14353; doi:10.1021/acs.joc.9b02238

data_4034514
_publ_section_title
;
 Discovery and Mechanistic Study of a Totally Organic
 C<sub>(aryl)</sub>-C<sub>(alkyl)</sub>Oxygen Insertion Reaction.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14349
_journal_page_last               14353
_journal_paper_doi               10.1021/acs.joc.9b02238
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C29 H20 O5'
_chemical_formula_sum            'C29 H20 O5'
_chemical_formula_weight         448.45
_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.324(5)
_cell_angle_beta                 103.153(6)
_cell_angle_gamma                102.371(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0663(5)
_cell_length_b                   12.7882(6)
_cell_length_c                   13.3392(11)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      67.29
_cell_measurement_theta_min      3.46
_cell_volume                     1258.07(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
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_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.250
_diffrn_reflns_theta_max         67.250
_diffrn_reflns_theta_min         3.540
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       'small plate'
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0816P)^2^+1.0935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3584
_reflns_number_total             4504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02238_si_003.cif
_cod_data_source_block           xs1924a
_cod_database_code               4034514
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.767
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              95855
_shelx_hkl_checksum              81534
_shelx_fab_checksum              66624