Intra- versus intermolecular electron transfer in radical nucleophilic aromatic substitution of dihalo(hetero)arenes – a tool for estimating π-conjugation in aromatic systems
Janhsen, B.; Daniliuc, C. G.; Studer, A.; Chem. Sci. 8 (2017) 3547–; doi:10.1039/C7SC00100B

data_1545516
_publ_section_title
;
 Intra- versus intermolecular electron transfer in radical nucleophilic
 aromatic substitution of dihalo(hetero)arenes -- a tool for estimating
 \p-conjugation in aromatic systems
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3547
_journal_paper_doi               10.1039/C7SC00100B
_journal_volume                  8
_journal_year                    2017
_chemical_formula_sum            'C16 H14 I2'
_chemical_formula_weight         460.07
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-01-09 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4988(3)
_cell_length_b                   15.9491(3)
_cell_length_c                   8.2449(2)
_cell_measurement_reflns_used    3511
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      4.08
_cell_volume                     1497.71(6)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11238
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         4.15
_exptl_absorpt_coefficient_mu    4.180
_exptl_absorpt_correction_T_max  0.8848
_exptl_absorpt_correction_T_min  0.4095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0323P)^2^+5.3086P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0932
_reflns_number_gt                3202
_reflns_number_total             3703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc00100b2.cif
_cod_data_source_block           stu8104
_cod_depositor_comments
'Adding full bibliography for 1545515--1545516.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1545516