A domino palladium-catalyzed C-C and C-O bonds formation via dual O-H bond activation: synthesis of 6,6-dialkyl-6H-benzo[c]chromenes.
Mahendar, Lodi; Krishna, Jonnada; Reddy, Alavala Gopi Krishna; Ramulu, Bokka Venkat; Satyanarayana, Gedu; Organic letters 14 (2012) 628–631; doi:10.1021/ol2032625

data_1503587
_publ_section_title
;
 A domino palladium-catalyzed C-C and C-O bonds formation via dual O-H
 bond activation: synthesis of 6,6-dialkyl-6H-benzo[c]chromenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              628
_journal_page_last               631
_journal_paper_doi               10.1021/ol2032625
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety
;
;
_chemical_formula_sum            'C19 H22 O3'
_chemical_formula_weight         298.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-23
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0822(7)
_cell_length_b                   12.7318(10)
_cell_length_c                   17.5760(14)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.3204
_cell_measurement_theta_min      4.2818
_cell_volume                     1584.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 8.0646
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
  1 omega  -43.00   21.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000   30.0000 32

  2 omega   44.00   76.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 16

  3 omega   55.00   83.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 14

  4 omega   84.00  118.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 17

  5 omega  -10.00   32.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 21

  6 omega   51.00   93.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 21

  7 omega   43.00  115.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 36

  8 omega   36.00   94.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 29

  9 omega   39.00  111.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 36

 10 omega   38.00   88.00   2.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0177890000
_diffrn_orient_matrix_UB_12      -0.1179330000
_diffrn_orient_matrix_UB_13      0.0185680000
_diffrn_orient_matrix_UB_21      -0.1784905000
_diffrn_orient_matrix_UB_22      0.0225675000
_diffrn_orient_matrix_UB_23      0.0473903000
_diffrn_orient_matrix_UB_31      -0.1228452000
_diffrn_orient_matrix_UB_32      -0.0156950000
_diffrn_orient_matrix_UB_33      -0.0714221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3557
_diffrn_reflns_theta_full        70.55
_diffrn_reflns_theta_max         70.55
_diffrn_reflns_theta_min         4.29
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.264
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.264
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0928
_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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3066
_refine_ls_wR_factor_ref         0.3088
_reflns_number_gt                2342
_reflns_number_total             2523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2032625_si_003.cif
_cod_data_source_block           exp_19
_cod_database_code               1503587
_chemical_oxdiff_formula         'C19 H22 O3'
_reflns_odcompleteness_completeness 96.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97