Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of Alkynes to 1,3- and 1,4-Dicarbonyl Systems.
Kier, Matthew J.; Leon, Robert M.; O'Rourke, Natasha F; Rheingold, Arnold L.; Micalizio, Glenn C.; Journal of the American Chemical Society 139 (2017) 12374–12377; doi:10.1021/jacs.7b06286

data_4131520
_publ_section_title
;
 Synthesis of Highly Oxygenated Carbocycles by Stereoselective Coupling of
 Alkynes to 1,3- and 1,4-Dicarbonyl Systems.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12374
_journal_page_last               12377
_journal_paper_doi               10.1021/jacs.7b06286
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C13 H22 O3'
_chemical_formula_sum            'C13 H22 O3'
_chemical_formula_weight         226.30
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                104.764(3)
_cell_angle_beta                 105.210(2)
_cell_angle_gamma                107.082(2)
_cell_formula_units_Z            4
_cell_length_a                   8.5418(3)
_cell_length_b                   11.8408(5)
_cell_length_c                   14.1682(6)
_cell_measurement_reflns_used    8324
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.255
_cell_measurement_theta_min      3.462
_cell_volume                     1233.26(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      100.15
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15547
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.380
_diffrn_reflns_theta_min         3.465
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0745 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.7063. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0685P)^2^+0.2841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3768
_reflns_number_total             4428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06286_si_002.cif
_cod_data_source_block           black62_0m_a
_cod_database_code               4131520
_shelx_shelxl_version_number     2016/6
_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:
 C2'(H2'), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11'(H11A,H11B), C9'(H9'A,H9'B), C10'(H10A,H10B), C12(H12C,H12D),
  C10(H10C,H10D), C11(H11C,H11D), C13(H13C,H13D), C12'(H12A,H12B), C13'(H13A,
 H13B)
2.c Idealised Me refined as rotating group:
 C6'(H6'A,H6'B,H6'C), C6(H6A,H6B,H6C), C3'(H3'A,H3'B,H3'C), C1(H1A,H1B,H1C),
 C1'(H1'A,H1'B,H1'C), C3(H3A,H3B,H3C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1'(H1'), O3'(H3'), O1(H1), O3(H3)
;
_shelx_res_checksum              31735
_shelx_hkl_checksum              69028
_olex2_submission_special_instructions 'No special instructions were received'