The cubane paradigm in bioactive molecule discovery: further scope, limitations and the cyclooctatetraene complement.
Houston, Sevan D.; Fahrenhorst-Jones, Tyler; Xing, Hui; Chalmers, Benjamin A.; Sykes, Melissa L.; Stok, Jeanette E.; Farfan Soto, Clementina; Burns, Jed M.; Bernhardt, Paul V.; De Voss, James J.; Boyle, Glen M.; Smith, Maree T.; Tsanaktsidis, John; Savage, G. Paul; Avery, Vicky M.; Williams, Craig M.; Organic & biomolecular chemistry 17 (2019) 6790–6798; doi:10.1039/c9ob01238a

data_7156942
_publ_section_title
;
 The cubane paradigm in bioactive molecule discovery: further scope,
 limitations and the cyclooctatetraene complement.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6790
_journal_page_last               6798
_journal_paper_doi               10.1039/c9ob01238a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C14 H14 N4 O3'
_chemical_formula_weight         286.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2019-03-28T17:10:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-03-28 deposited with the CCDC.    2019-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.900(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3369(14)
_cell_length_b                   9.5786(8)
_cell_length_c                   16.6878(13)
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      3.66
_cell_measurement_wavelength     0.71073
_cell_volume                     2579.9(4)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.011642
_diffrn_orient_matrix_UB_12      0.070749
_diffrn_orient_matrix_UB_13      -0.007324
_diffrn_orient_matrix_UB_21      0.000784
_diffrn_orient_matrix_UB_22      0.010454
_diffrn_orient_matrix_UB_23      0.04218
_diffrn_orient_matrix_UB_31      0.042393
_diffrn_orient_matrix_UB_32      0.019151
_diffrn_orient_matrix_UB_33      0.004125
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0
_reflns_number_gt                3020
_reflns_number_total             4541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01238a2.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7156939--7156942.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7156942
_shelx_shelxl_version_number     2018/1