Solvent-Controlled Switchable C-H Alkenylation of 4-Aryl-1H-pyrrole-3-carboxylates: Application to the Total Synthesis of (±)-Rhazinilam.
Su, Youla; Zhou, Haipin; Chen, Jiaxuan; Xu, Jinyi; Wu, Xiaoming; Lin, Aijun; Yao, Hequan; Organic letters 16 (2014) 4884–4887; doi:10.1021/ol5023933

data_1517607
_publ_section_title
;
 Solvent-Controlled Switchable C-H Alkenylation of
 4-Aryl-1H-pyrrole-3-carboxylates: Application to the Total Synthesis of
 (+-)-Rhazinilam.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4884
_journal_page_last               4887
_journal_paper_doi               10.1021/ol5023933
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C25 H30 N2 O6'
_chemical_formula_weight         454.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.88(3)
_cell_angle_beta                 91.47(3)
_cell_angle_gamma                101.15(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7470(17)
_cell_length_b                   11.114(2)
_cell_length_c                   13.238(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1210.2(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4345
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0671
_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^)+(0.1000P)^2^+0.1600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                2679
_reflns_number_total             4078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5023933_si_003.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517607--1517608.cif.
;
_cod_original_cell_volume        1210.2(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1517607