Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.
Wu, Xiaowei; Iwata, Takayuki; Scharf, Adam; Qin, Tian; Reichl, Kyle D.; Porco, Jr, John A; Journal of the American Chemical Society 140 (2018) 5969–5975; doi:10.1021/jacs.8b02535

data_4132237
_publ_section_title
;
 Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide
 Blocking Group for Oxidative Coupling.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5969
_journal_page_last               5975
_journal_paper_doi               10.1021/jacs.8b02535
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H15 Br O7'
_chemical_formula_sum            'C16 H15 Br O7'
_chemical_formula_weight         399.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-22 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6776(2)
_cell_length_b                   14.2324(5)
_cell_length_c                   19.4060(7)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.684
_cell_measurement_theta_min      3.850
_cell_volume                     1568.12(10)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_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      100.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 Proteum-R'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31910
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.741
_diffrn_reflns_theta_min         3.851
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    3.922
_exptl_absorpt_correction_T_max  0.7043
_exptl_absorpt_correction_T_min  0.5954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2016)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_description       bar
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0220P)^2^+1.1480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0553
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2642
_reflns_number_total             2765
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {9d769a91-9857-4c55-a124-8df6e4f568c4}
_cod_data_source_file            ja8b02535_si_002.cif
_cod_data_source_block           wu4a_0m
_cod_database_code               4132237
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.94(2)
 0.06(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              87114
_shelx_hkl_checksum              9933
_olex2_submission_special_instructions 'No special instructions were received'