Through-Space Activation Can Override Substituent Effects in Electrophilic Aromatic Substitution.
Guan, Liangyu; Holl, Maxwell Gargiulo; Pitts, Cody Ross; Struble, Mark D.; Siegler, Maxime A.; Lectka, Thomas; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b09792

data_4126601
_publ_section_title
;
 Through-Space Activation Can Override Substituent Effects in
 Electrophilic Aromatic Substitution.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b09792
_journal_year                    2017
_chemical_formula_moiety         'C23 H15 Br N2 O8'
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_symmetry_space_group_name_H-M   'P 1 n 1'
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_cell_measurement_reflns_used    15032
_cell_measurement_temperature    110(2)
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_cell_volume                     1950.93(5)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_number            22369
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.891
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_exptl_absorpt_coefficient_mu    3.415
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.617
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.22(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         6422
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.9959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6199
_reflns_number_total             6422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09792_si_003.cif
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_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              80362
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