Oxidative Arylation of Isochroman
Soo J. Park; Jason R. Price; Matthew H. Todd; Journal of Organic Chemistry 77 (2012) 949–955; doi:10.1021/jo2021373

data_4026892
_publ_contact_author_address
;
School of Chemistry
The University of Sydney
NSW 2006 (Australia)
;
_publ_contact_author_email
;
matthew.todd@sydney.edu.au
;
_publ_contact_author_fax         '(+61) 2-9351-3329'
_publ_contact_author_name
;
Matthew H. Todd
;
_publ_section_title
;
 Oxidative Arylation of Isochroman
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              949
_journal_page_last               955
_journal_paper_doi               10.1021/jo2021373
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_chemical_name_systematic
; 
1-(6-bromo-2-methoxynaphthalen-1-yl)isochroman 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 103.762(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6060(2)
_cell_length_b                   18.2870(2)
_cell_length_c                   7.13960(10)
_cell_measurement_reflns_used    15494
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.8
_cell_measurement_theta_min      2.93
_cell_volume                     1471.80(4)
_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
 WinGX (Farrugia, 1999)
 SHELXTL (Bruker, 2003)
 ORTEP-3 (Farrugia, 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_crystal_treatment
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream.
;
_diffrn_detector_area_resol_mean 10.5861
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26003
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       chunk
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0400P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2609
_reflns_number_total             2877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2021373_si_002.cif
_cod_data_source_block           mht11jp02_p21onc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026892