Elaboration of tetra-orthogonally-substituted aromatic scaffolds towards novel EGFR-kinase inhibitors.
Close, Adam J.; Jones, Rhiannon N.; Ocasio, Cory A.; Kemmitt, Paul; Roe, S. Mark; Spencer, John; Organic & biomolecular chemistry 14 (2016) 8246–8252; doi:10.1039/c6ob01394e

data_7155208
_publ_section_title
;
 Elaboration of tetra-orthogonally-substituted aromatic scaffolds towards
 novel EGFR-kinase inhibitors.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8246
_journal_page_last               8252
_journal_paper_doi               10.1039/c6ob01394e
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C7 H3 Br1 F1 N1 O3'
_chemical_formula_sum            'C7 H3 Br F N O3'
_chemical_formula_weight         248.01
_chemical_name_systematic        5-bromo-4-fluoro-2-nitrobenzaldehyde
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-06-25T17:12:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-06-13 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.211(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9191(2)
_cell_length_b                   6.2146(2)
_cell_length_c                   13.1151(6)
_cell_measurement_reflns_used    525
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_measurement_wavelength     0.71073
_cell_volume                     399.27(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.9901
_diffrn_measured_fraction_theta_max 0.6144
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.2987E-3
_diffrn_orient_matrix_UB_12      0.104744
_diffrn_orient_matrix_UB_13      0.578922E-1
_diffrn_orient_matrix_UB_21      0.204132
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      0.68065E-2
_diffrn_orient_matrix_UB_31      -0.2561E-3
_diffrn_orient_matrix_UB_32      0.122153
_diffrn_orient_matrix_UB_33      -0.496415E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5492
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         3.63
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    5.135
_exptl_absorpt_correction_T_max  0.3427
_exptl_absorpt_correction_T_min  0.2795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.063
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.042
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.264
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1205P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                1587
_reflns_number_total             1734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01394e3.cif
_cod_data_source_block           import
_cod_depositor_comments
'Adding full bibliography for 7155208--7155210.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7155208