Reversal of regioselectivity (straight vs. cross ring closure) in the intramolecular [2+2] photocycloaddition of phenanthrene derivatives.
Kohmoto, Shigeo; Hisamatsu, Shugo; Mitsuhashi, Hakuei; Takahashi, Masahiro; Masu, Hyuma; Azumaya, Isao; Yamaguchi, Kentaro; Kishikawa, Keiki; Organic & biomolecular chemistry 8 (2010) 2174–2179; doi:10.1039/c000179a

data_7153327
_publ_section_title
;
 Reversal of regioselectivity (straight vs. cross ring closure) in the
 intramolecular [2+2] photocycloaddition of phenanthrene derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2174
_journal_page_last               2179
_journal_paper_doi               10.1039/c000179a
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C33 H25 N O2'
_chemical_formula_weight         467.54
_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                 100.23
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.05670(10)
_cell_length_b                   9.25440(10)
_cell_length_c                   19.7847(2)
_cell_measurement_reflns_used    8803
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.44
_cell_volume                     2352.62(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26400
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                3985
_reflns_number_total             4812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000179a.txt
_cod_data_source_block           2a(a0601122mas)
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2352.65(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153327