Regioselective Substitution at the 1,3- and 6,8-Positions of Pyrene for the Construction of Small Dipolar Molecules.
Feng, Xing; Tomiyasu, Hirotsugu; Hu, Jian-Yong; Wei, Xianfu; Redshaw, Carl; Elsegood, Mark R. J.; Horsburgh, Lynne; Teat, Simon J.; Yamato, Takehiko; The Journal of organic chemistry 80 (2015) 10973–10978; doi:10.1021/acs.joc.5b02128

data_4036473
_publ_section_title
;
 Regioselective Substitution at the 1,3- and 6,8-Positions of Pyrene for
 the Construction of Small Dipolar Molecules.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10973
_journal_page_last               10978
_journal_paper_doi               10.1021/acs.joc.5b02128
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C40 H26'
_chemical_formula_sum            'C40 H26'
_chemical_formula_weight         506.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3528(6)
_cell_length_b                   12.4313(7)
_cell_length_c                   19.1537(10)
_cell_measurement_reflns_used    8904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.43
_cell_volume                     2703.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6601
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         1.953
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS v2012/1, Sheldrick, G.M., (2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.850
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 2102 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         6601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.2407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                5531
_reflns_number_total             6601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02128_si_004.cif
_cod_data_source_block           6
_cod_database_code               4036473
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
_shelx_res_checksum              79073
_shelx_hkl_checksum              10533