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_7155058
_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         'C23 H20 N2 O2'
_chemical_formula_sum            'C23 H20 N2 O2'
_chemical_formula_weight         356.41
_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     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                 93.765(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5059(10)
_cell_length_b                   32.640(2)
_cell_length_c                   9.2776(6)
_cell_measurement_reflns_used    3368
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.30
_cell_measurement_theta_min      3.54
_cell_volume                     3778.9(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -65.00   26.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  150.0000 91

  2 omega    1.00   27.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  -90.0000 26

  3 omega  -69.00   24.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   57.0000    0.0000 93

  4 omega   43.00   75.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000 -180.0000 32

  5 omega   42.00   71.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -60.0000 29

  6 omega   80.00  147.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   77.0000   30.0000 67

  7 omega   36.00   71.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -90.0000 35

  8 omega   36.00   68.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  120.0000 32

  9 omega   33.00   67.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 34

 10 omega   68.00  133.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  -90.0000 65

 11 omega  103.00  151.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000   30.0000 48

 12 omega   34.00   61.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   60.0000 27

 13 omega   35.00   64.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -77.0000  -90.0000 29

 14 omega   35.00   68.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 33

 15 omega   28.00  135.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -15.0000 -150.0000 107
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0365261000
_diffrn_orient_matrix_UB_12      -0.0395033000
_diffrn_orient_matrix_UB_13      -0.0795372000
_diffrn_orient_matrix_UB_21      -0.1173986000
_diffrn_orient_matrix_UB_22      0.0099017000
_diffrn_orient_matrix_UB_23      0.0279277000
_diffrn_orient_matrix_UB_31      -0.0120656000
_diffrn_orient_matrix_UB_32      0.0238593000
_diffrn_orient_matrix_UB_33      -0.1433602000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_unetI/netI     0.1119
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6629
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.113
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.2866
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         6629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0919
_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^)+8.4171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1916
_refine_ls_wR_factor_ref         0.2091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4342
_reflns_number_total             6629
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00471g2.cif
_cod_data_source_block           apcjmk
_cod_depositor_comments
'Adding full bibliography for 7155056--7155058.cif.'
_cod_original_cell_volume        3778.8(5)
_cod_database_code               7155058
_nottingham_internal_coll_name   APCJMK
_nottingham_internal_coll_number 11427
_nottingham_internal_coll_client AP/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '100.0000 and 400.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   25/5/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 30/05/2012
_nottingham_internal_process_user WL
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_user WL
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 H20 N2 O2'
_chemical_oxdiff_usercomment
'APCJMK #11427 IN FOMBLIN FIML ON MICROMOUNT FOR AP/CJM'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.503(3) 0.497(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C25(H25), N30(H30), C34(H34),
  C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43),
 C44(H44), C48(H48), C49(H49), C51(H51), C52(H52)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C46(H46A,H46B,H46C), C54(H54A,H54B,
 H54C)
;
_shelx_res_checksum              86096
_olex2_submission_special_instructions 'No special instructions were received'