Unravelling Nucleophilic Aromatic Substitution Pathways with Bimetallic Nucleophiles
Garçon, Martí; Bakewell, Clare; White, Andrew J. P.; Crimmin, Mark Richard; Chemical Communications  (2019) –; doi:10.1039/C8CC09701A

data_7122832
_publ_section_title
;
 Unravelling Nucleophilic Aromatic Substitution Pathways with Bimetallic
 Nucleophiles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09701A
_journal_year                    2019
_chemical_formula_moiety         'C18 H9 F4 Fe N O2'
_chemical_formula_sum            'C18 H9 F4 Fe N O2'
_chemical_formula_weight         403.11
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-11-02 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5632(3)
_cell_length_b                   11.0014(5)
_cell_length_c                   16.3358(5)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.1740
_cell_measurement_theta_min      3.0270
_cell_volume                     1538.95(10)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0382
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3712
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.249
_diffrn_reflns_theta_min         2.686
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  0.774
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
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) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       blocks
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.032(13)
_refine_ls_extinction_coef       0.0107(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0235P)^2^+0.5151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0637
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_full    0.792
_reflns_Friedel_fraction_max     0.611
_reflns_number_gt                2595
_reflns_number_total             2786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09701a2.cif
_cod_data_source_block           3c
_cod_database_code               7122832
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              90065