Highly regiospecific synthetic approach to monobay-functionalized perylene bisimide and di(perylene bisimide).
Zhen, Yonggang; Qian, Hualei; Xiang, Junfeng; Qu, Jianqiang; Wang, Zhaohui; Organic letters 11 (2009) 3084–3087; doi:10.1021/ol901168k

data_1504019
_publ_section_title
;
 Highly regiospecific synthetic approach to monobay-functionalized
 perylene bisimide and di(perylene bisimide).
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3084
_journal_page_last               3087
_journal_paper_doi               10.1021/ol901168k
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C49 H44 Cl2 N2 O5'
_chemical_formula_weight         811.76
_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                 103.60(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5797(17)
_cell_length_b                   33.294(7)
_cell_length_c                   15.726(3)
_cell_measurement_reflns_used    10896
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      1.22
_cell_volume                     4366.2(16)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41787
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.22
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_platon_squeeze_details
;
;
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         8581
_refine_ls_number_restraints     428
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0794
_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^)+(0.0465P)^2^+3.7726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1661
_reflns_number_gt                7560
_reflns_number_total             8581
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901168k_si_001.cif
_cod_data_source_block           mx120
_cod_original_cell_volume        4366.2(15)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1504019