Concise synthesis of halogenated chrysenes ([4]phenacenes) that favor pi-stack packing in single crystals.
Isobe, Hiroyuki; Hitosugi, Shunpei; Matsuno, Taisuke; Iwamoto, Takeaki; Ichikawa, Junji; Organic letters 11 (2009) 4026–4028; doi:10.1021/ol901693y

data_1504146
_publ_section_title
;
 Concise synthesis of halogenated chrysenes ([4]phenacenes) that favor
 pi-stack packing in single crystals.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4026
_journal_page_last               4028
_journal_paper_doi               10.1021/ol901693y
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C20 H14 Br2'
_chemical_formula_weight         414.13
_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                 110.436(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.496(5)
_cell_length_b                   4.0216(7)
_cell_length_c                   29.455(5)
_cell_measurement_reflns_used    3862
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.58
_cell_volume                     3163.1(9)
_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      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  '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  0.0729
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32065
_diffrn_reflns_theta_full        26.83
_diffrn_reflns_theta_max         26.83
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    5.119
_exptl_absorpt_correction_T_max  0.9045
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    empirical
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0497
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                4737
_reflns_number_total             6735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901693y_si_009.cif
_cod_data_source_block           sh10-2
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3163.0(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504146