Copper(I)/phosphine-catalyzed tandem carboxylation/annulation of terminal alkynes with ambient pressure of CO2: one-pot access to 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
Xia, JIa-Ning; Yu, Bing; Guo, Chun-Xiang; He, Liang-Nian; Green Chem.  (2015) –; doi:10.1039/C5GC00926J

data_7220692
_publ_section_title
;
 Copper(I)/phosphine-catalyzed tandem carboxylation/annulation of terminal
 alkynes with ambient pressure of CO2: one-pot access to
 3a-hydroxyisoxazolo[3,2-a]isoindol-8(3aH)-ones
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C5GC00926J
_journal_year                    2015
_chemical_formula_sum            'C20 H17 N O6'
_chemical_formula_weight         367.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-14 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8241(16)
_cell_length_b                   24.301(5)
_cell_length_c                   9.1574(18)
_cell_measurement_reflns_used    4679
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9424
_cell_measurement_theta_min      1.6760
_cell_volume                     1737.4(6)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15793
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.035(3)
_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   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                3051
_reflns_number_total             4064
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5gc00926j2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7220692