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_1502016
_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         'C30 H26'
_chemical_formula_sum            'C30 H26'
_chemical_formula_weight         386.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_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                 97.210(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.3854(4)
_cell_length_b                   10.05033(19)
_cell_length_c                   21.6071(5)
_cell_measurement_reflns_used    6615
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.5956
_cell_measurement_theta_min      4.1212
_cell_volume                     4391.86(16)
_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
;
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
;
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
;
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      100.0
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
1 omega  -98.00  -19.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737  131.0000  148.0000 79

2 omega   31.00   62.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756 -131.0000   78.0000 31

3 omega   90.00  124.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756 -131.0000   78.0000 34

4 omega   35.00   70.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756  -28.0000   79.0000 35

5 omega   72.00  174.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756   28.0000  100.0000 102

6 omega  -40.00   22.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737   37.0000   30.0000 62

7 omega -115.00  -90.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737 -131.0000 -101.0000 25

8 omega -117.00  -45.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737  -37.0000  -90.0000 72

9 omega   36.00  133.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756  -77.0000   30.0000 97

10 omega   95.00  170.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756  125.0000   90.0000 75

11 omega   95.00  120.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756 -137.0000 -144.0000 25

12 omega   31.00   68.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756  -45.0000   60.0000 37

13 omega -119.00   -7.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737  -77.0000   30.0000 112

14 omega -117.00  -14.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-      -40.7737  -37.0000   90.0000 103

15 omega    7.00  119.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
-       40.7737   77.0000 -150.0000 112

16 omega   39.00  171.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756   15.0000  -90.0000 132

17 omega   26.00   77.00   1.0000   56.4400
omega____ theta____ kappa____ phi______ frames
-      100.5756  -45.0000 -180.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0674451
_diffrn_orient_matrix_UB_12      0.0610743
_diffrn_orient_matrix_UB_13      -0.0251727
_diffrn_orient_matrix_UB_21      0.0297826
_diffrn_orient_matrix_UB_22      0.1405108
_diffrn_orient_matrix_UB_23      0.0094343
_diffrn_orient_matrix_UB_31      0.0192696
_diffrn_orient_matrix_UB_32      -0.0034243
_diffrn_orient_matrix_UB_33      -0.0666499
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14666
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.73
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.78711
_exptl_absorpt_correction_type   multi-scan
_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)
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    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0684P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                3177
_reflns_number_total             4130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200069c_si_006.cif
_cod_data_source_block           RAJ19L
_cod_original_cell_volume        4391.87(17)
_cod_database_code               1502016