Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant.
Navale, Tushar S.; Thakur, Khushabu; Rathore, Rajendra; Organic letters 13 (2011) 1634–1637; doi:10.1021/ol200069c

data_1502015
_publ_section_title
;
 Sequential oxidative transformation of tetraarylethylenes to
 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an
 oxidant.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1634
_journal_page_last               1637
_journal_paper_doi               10.1021/ol200069c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C26 H14 Br4'
_chemical_formula_sum            'C26 H14 Br4'
_chemical_formula_weight         646.01
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.5244(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.7871(3)
_cell_length_b                   9.92103(17)
_cell_length_c                   22.1583(3)
_cell_measurement_reflns_used    17578
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.7677
_cell_measurement_theta_min      3.488
_cell_volume                     4530.35(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics
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OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
1 omega  -59.00   54.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-       19.9198  -77.0000  -90.0000 113

2 omega   -7.00   49.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-       19.9198  -77.0000   90.0000 56

3 omega   15.00   54.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-      -20.0760   37.0000  150.0000 39

4 omega  -54.00  -26.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-      -20.0760  102.0000   -3.0000 28

5 omega   -6.00   96.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-       19.9198   37.0000  -90.0000 102

6 omega   -6.00   96.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-       19.9198   37.0000 -180.0000 102

7 omega  -14.00   99.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-       19.9198   77.0000    0.0000 113

8 omega  -64.00  -12.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-      -20.0760  102.0000   -3.0000 52

9 omega  -64.00   -4.00   1.0000   54.6900
omega____ theta____ kappa____ phi______ frames
-      -20.0760  102.0000  176.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0286044
_diffrn_orient_matrix_UB_12      -0.0395887
_diffrn_orient_matrix_UB_13      0.0052826
_diffrn_orient_matrix_UB_21      -0.0170877
_diffrn_orient_matrix_UB_22      -0.0560324
_diffrn_orient_matrix_UB_23      -0.0140679
_diffrn_orient_matrix_UB_31      0.0085997
_diffrn_orient_matrix_UB_32      0.0202399
_diffrn_orient_matrix_UB_33      -0.0285693
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42334
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.84
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    7.118
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.3544
_exptl_crystal_size_mid          0.1255
_exptl_crystal_size_min          0.0254
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0271P)^2^+33.3882P] where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                5180
_reflns_number_total             7976
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200069c_si_005.cif
_cod_data_source_block           RAJ19E
_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 
;
_cod_original_cell_volume        4530.34(12)
_cod_database_code               1502015