Triggering apoptosis in cancer cells with an analogue of cribrostatin 6 that elevates intracellular ROS.
Asby, D. J.; Radigois, M. G.; Wilson, D. C.; Cuda, F.; Chai, C. L. L.; Chen, A.; Bienemann, A. S.; Light, M. E.; Harrowven, D. C.; Tavassoli, A.; Organic & biomolecular chemistry 14 (2016) 9322–9330; doi:10.1039/c6ob01591c

data_7155281
_publ_section_title
;
 Triggering apoptosis in cancer cells with an analogue of cribrostatin 6
 that elevates intracellular ROS.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9322
_journal_page_last               9330
_journal_paper_doi               10.1039/c6ob01591c
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H16 N2 O3'
_chemical_formula_sum            'C20 H16 N2 O3'
_chemical_formula_weight         332.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-20 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.4411(5)
_cell_length_b                   16.0503(12)
_cell_length_c                   30.612(3)
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3390
_cell_measurement_theta_min      2.5320
_cell_volume                     3164.7(5)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -83.00   53.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   18.0000  120.0000 136

  2 omega  -84.00    4.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000  -30.0000 88

  3 omega  -95.00   36.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -18.0000  -30.0000 131

  4 omega  -54.00   25.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  120.0000 79

  5 omega -112.00  -59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -54.0000   90.0000 53
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0179192000
_diffrn_orient_matrix_UB_12      -0.0061400000
_diffrn_orient_matrix_UB_13      0.0226338000
_diffrn_orient_matrix_UB_21      0.0367560000
_diffrn_orient_matrix_UB_22      -0.0408263000
_diffrn_orient_matrix_UB_23      -0.0043075000
_diffrn_orient_matrix_UB_31      0.1022970000
_diffrn_orient_matrix_UB_32      0.0157314000
_diffrn_orient_matrix_UB_33      -0.0024219000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_av_unetI/netI     0.0777
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         3.230
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       lath
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0810
_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^)+(0.0577P)^2^+2.6528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1639
_reflns_number_total             2789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01591c2.cif
_cod_data_source_block           2015sot0019
_cod_depositor_comments
;Adding full bibliography for 7155281.cif.

 Adding full bibliography for 7155281.cif.
;
_cod_original_cell_volume        3164.7(4)
_cod_database_code               7155281
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 95.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.03
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              18459
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2015-03-19
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id FCR/7506/17
_olex2_submission_special_instructions 'No special instructions were received'