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_4132238
_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_formula_moiety         'C32 H30 O14, 0.05(O)'
_chemical_formula_sum            'C32 H30 O14.05'
_chemical_formula_weight         639.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-20 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 101.097(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8266(6)
_cell_length_b                   13.9034(7)
_cell_length_c                   16.8142(8)
_cell_measurement_reflns_used    9649
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.663
_cell_measurement_theta_min      4.158
_cell_volume                     2942.5(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      99.89
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0577
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            74710
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.658
_diffrn_reflns_theta_max         66.658
_diffrn_reflns_theta_min         3.511
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.974
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       prism
_exptl_crystal_F_000             1338
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0500P)^2^+1.6810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4977
_reflns_number_total             5183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02535_si_003.cif
_cod_data_source_block           wu3a_0m
_cod_database_code               4132238
_publcif_datablock.id            {d2d82d57-1ba0-42e5-917a-7dad1f4daf4f}
_shelx_shelxl_version_number     2014/7
_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:
 C4(H4), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C8(H8A,H8B), C25(H25A,H25B), C30(H30A,H30B),
 C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              6383
_shelx_hkl_checksum              43223
_olex2_submission_original_sample_id wxw-gonytolide-Cs
_olex2_submission_special_instructions 'No special instructions were received'