Functionalized chromans and isochromans via a diastereoselective Pd(0)-catalyzed carboiodination.
Petrone, David A.; Malik, Hasnain A.; Clemenceau, Antonin; Lautens, Mark; Organic letters 14 (2012) 4806–4809; doi:10.1021/ol302111y

data_1508636
_publ_section_title
;
 Functionalized chromans and isochromans via a diastereoselective
 Pd(0)-catalyzed carboiodination.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4806
_journal_page_last               4809
_journal_paper_doi               10.1021/ol302111y
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H17 Cl I N O'
_chemical_formula_sum            'C20 H17 Cl I N O'
_chemical_formula_weight         449.70
_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                91.746(3)
_cell_angle_beta                 99.673(4)
_cell_angle_gamma                90.051(4)
_cell_formula_units_Z            4
_cell_length_a                   9.3159(14)
_cell_length_b                   11.7847(18)
_cell_length_c                   15.718(2)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.76
_cell_volume                     1700.2(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Bruker Triumph'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24722
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    2.047
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.791
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+5.4015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                6178
_reflns_number_total             7601
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol302111y_si_003.cif
_cod_data_source_block           d12196
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
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_cod_database_code               1508636