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_7155209
_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_formula_moiety         'C7 H3 Br F N O3'
_chemical_formula_sum            'C7 H3 Br F N O3'
_chemical_formula_weight         248.01
_chemical_name_systematic        4-bromo-2-fluoro-5-nitrobenzaldehyde
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2016-06-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-13 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.086(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6934(4)
_cell_length_b                   9.7396(3)
_cell_length_c                   7.4999(2)
_cell_measurement_reflns_used    548
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     776.71(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10688
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.836
_exptl_absorpt_coefficient_mu    5.281
_exptl_absorpt_correction_T_max  0.3874
_exptl_absorpt_correction_T_min  0.3254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_description       block
_exptl_crystal_F_000             480
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_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0298
_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^)+(0.0480P)^2^+0.1979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1765
_reflns_number_total             1777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01394e3.cif
_cod_data_source_block           import
_cod_depositor_comments
'Adding full bibliography for 7155208--7155210.cif.'
_cod_database_code               7155209
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
;
_shelx_res_checksum              73274
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'