Synthesis of 8-Aryl-Substituted Coumarins Based on Ring-Closing Metathesis and Suzuki-Miyaura Coupling: Synthesis of a Furyl Coumarin Natural Product from Galipea panamensis
Bernd Schmidt; Stefan Krehl; Alexandra Kelling; Uwe Schilde; Journal of Organic Chemistry 77 (2012) 2360–2367; doi:10.1021/jo2026564

data_4027043
_publ_contact_author_address
;
 University of Potsdam
 Institute of Chemistry
 Karl-Liebknecht-Str. 24-25
 D-14476 Potsdam
 Germany
;
_publ_contact_author_email       us@chem.uni-potsdam.de
_publ_contact_author_fax         +49-331-977-5153
_publ_contact_author_name        'Schilde, Uwe'
_publ_contact_author_phone       +49-331-977-5188
_publ_section_title
;
 Synthesis of 8-Aryl-Substituted Coumarins Based on Ring-Closing
 Metathesis and Suzuki-Miyaura Coupling: Synthesis of a Furyl Coumarin
 Natural Product from Galipea panamensis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2360
_journal_page_last               2367
_journal_paper_doi               10.1021/jo2026564
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C15 H12 O4'
_chemical_formula_sum            'C15 H21 O4'
_chemical_formula_weight         256.25
_chemical_melting_point          419(1)
_chemical_name_systematic
; 
 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 112.160(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7904(4)
_cell_length_b                   11.2095(7)
_cell_length_c                   15.2472(8)
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.44
_cell_measurement_theta_min      1.82
_cell_volume                     1233.13(12)
_computing_cell_refinement       'X-AREA (Stoe, 2004)'
_computing_data_collection       'X-AREA (Stoe, 2004)'
_computing_data_reduction        'X-RED (Stoe, 2004)'
_computing_molecular_graphics
;
  DIAMOND (Brandenburg, 2005)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 180 frames, exposure time per frame = 1 min
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       '\w scan, 1.0 \%'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7755
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.012(4)
_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   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0963P)^2^+0.3864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1799
_reflns_number_gt                1715
_reflns_number_total             2169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2026564_si_001.cif
_cod_data_source_block           krehl1
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '418-420' was changed to '419.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4027043