Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes and evidence for an allene intermediate in the novel base-catalyzed cyclization of 2-alkynylbiphenyls.
Wang, Yi; Burton, Donald J.; Organic letters 8 (2006) 5295–5298; doi:10.1021/ol0620850

data_1506253
_publ_section_title
;
 Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and
 9-alkylphenanthrenes and evidence for an allene intermediate in the novel
 base-catalyzed cyclization of 2-alkynylbiphenyls.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5295
_journal_page_last               5298
_journal_paper_doi               10.1021/ol0620850
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C25 H22 O2'
_chemical_formula_sum            'C25 H22 O2'
_chemical_formula_weight         354.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.591(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0057(6)
_cell_length_b                   12.2328(12)
_cell_length_c                   25.351(3)
_cell_measurement_reflns_used    6650
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1862.4(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor,1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor,1997)'
_computing_molecular_graphics    'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL v5.1 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL v5.1 (Sheldrick, 1997)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19582
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.9
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor,1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.3824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                3038
_reflns_number_total             4207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0620850si20060823_025419.cif
_cod_data_source_block           bur32
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'P 2(1)/n '
_cod_database_code               1506253