Fused imidazoles as potential chemical scaffolds for inhibition of heat shock protein 70 and induction of apoptosis. Synthesis and biological evaluation of phenanthro[9,10-d]imidazoles and imidazo[4,5-f][1,10]phenanthrolines.
Patel, Alpa; Sharp, Swee Y.; Hall, Katelan; Lewis, William; Stevens, Malcolm F. G.; Workman, Paul; Moody, Christopher J.; Organic & biomolecular chemistry 14 (2016) 3889–3905; doi:10.1039/c6ob00471g

data_7155057
_publ_section_title
;
 Fused imidazoles as potential chemical scaffolds for inhibition of heat
 shock protein 70 and induction of apoptosis. Synthesis and biological
 evaluation of phenanthro[9,10-d]imidazoles and
 imidazo[4,5-f][1,10]phenanthrolines.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3889
_journal_page_last               3905
_journal_paper_doi               10.1039/c6ob00471g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-02-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-01 deposited with the CCDC.
2016-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3173(2)
_cell_length_b                   15.5645(4)
_cell_length_c                   13.0802(3)
_cell_measurement_reflns_used    10907
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.62
_cell_volume                     1489.71(7)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      90(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15358
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.389
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/2 (Bruker,2007) was used for absorption correction.
wR2(int) was 0.0760 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.9267.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_coef       0.0092(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0522P)^2^+0.2317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0795
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3111
_reflns_number_total             3166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00471g2.cif
_cod_data_source_block           apcjmj
_cod_depositor_comments
'Adding full bibliography for 7155056--7155058.cif.'
_cod_database_code               7155057
_nottingham_internal_coll_name   APCJMJ
_nottingham_internal_coll_number 11350
_nottingham_internal_coll_client AP/CJM
_nottingham_internal_coll_type   hemi
_nottingham_internal_coll_frame_method '\f and \w scans'
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 29/2/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 3/5/2013
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              39317
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'