Synthesis and biological evaluation of benzocyclooctene-based and indene-based anticancer agents that function as inhibitors of tubulin polymerization
Herdman, Christine A.; Strecker, Tracy E.; Tanpure, Rajendra P.; Chen, Zhi; Winters, Alex; Gerberich, Jeni; Liu, Li; Hamel, Ernest; Mason, Ralph P.; Chaplin, David J.; Trawick, Mary Lynn; Pinney, Kevin G.; Med. Chem. Commun. 7 (2016) 2418–; doi:10.1039/C6MD00459H

data_7119185
_publ_section_title
;
 Synthesis and biological evaluation of benzocyclooctene-based and
 indene-based anticancer agents that function as inhibitors of tubulin
 polymerization
;
_journal_issue                   12
_journal_name_full               'Med. Chem. Commun.'
_journal_page_first              2418
_journal_paper_doi               10.1039/C6MD00459H
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C22 H26 O5'
_chemical_formula_weight         370.43
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-29 deposited with the CCDC.
2016-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   11.1239(8)
_cell_length_c                   20.5570(13)
_cell_measurement_reflns_used    9721
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.41
_cell_volume                     3805.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
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_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.242
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_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
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_exptl_crystal_description       Block
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_exptl_crystal_size_mid          0.130
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0418P)^2^+1.6747P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3206
_reflns_number_total             3865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6md00459h2.cif
_cod_data_source_block           KP76
_cod_depositor_comments
'Adding full bibliography for 7119184--7119185.cif.'
_cod_database_code               7119185
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
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