Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives.
Karad, Somnath Narayan; Chung, Wei-Kang; Liu, Rai-Shung; Chemical communications (Cambridge, England) 51 (2015) 13004–13007; doi:10.1039/c5cc04538j

data_7117597
_publ_section_title
;
 Gold-catalyzed formal [4\p+2\p]-cycloadditions of tert-butyl propiolates
 with aldehydes and ketones to form 4H-1,3-dioxine derivatives.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13004
_journal_page_last               13007
_journal_paper_doi               10.1039/c5cc04538j
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-04-29 deposited with the CCDC.
2015-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.598(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0914(7)
_cell_length_b                   8.5177(11)
_cell_length_c                   23.947(3)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.1969
_cell_measurement_theta_min      2.9349
_cell_volume                     1242.4(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8860
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_min         0.850
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.866
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.300
_refine_ls_extinction_coef       0.27(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.388
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.1269
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3426
_refine_ls_wR_factor_ref         0.3920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1579
_reflns_number_total             2531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04538j2.cif
_cod_data_source_block           141246_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_database_code               7117597
_shelxl_version_number           2014/6
_shelx_res_checksum              56587