Indolo[2,3-e]benzazocines and indolo[2,3-f]benzazonines and their copper(II) complexes as microtubule destabilizing agents
Arion, Vladimir; Wittmann, Christopher; Dömötör, Orsolya; Kuznetcova, Irina; Spengler, Gabriella; Reynisson, Johannes; Holder, Lauren; Miller, Gavin John; Enyedy, Eva A.; Bai, Ruoli; Hamel, Ernest; Dalton Transactions  (2023) –; doi:10.1039/D3DT01632C

data_7713373
_publ_section_title
;
 Indolo[2,3-e]benzazocines and indolo[2,3-f]benzazonines and their
 copper(II) complexes as microtubule destabilizing agents
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01632C
_journal_year                    2023
_chemical_formula_moiety         'C24 H20 Br N5'
_chemical_formula_sum            'C24 H20 Br N5'
_chemical_formula_weight         458.36
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0799(3)
_cell_length_b                   15.5637(5)
_cell_length_c                   15.6684(6)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.927
_cell_measurement_theta_min      2.841
_cell_volume                     1970.35(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11561
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.049
_diffrn_reflns_theta_min         2.600
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_T_max  0.6042
_exptl_absorpt_correction_T_min  0.4749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.016(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0708P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.539
_reflns_Friedel_fraction_full    0.804
_reflns_Friedel_fraction_max     0.567
_reflns_number_gt                3478
_reflns_number_total             4521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt01632c2.cif
_cod_data_source_block           chwi685
_cod_database_code               7713373
_shelx_estimated_absorpt_t_min   0.509
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           2014-3
_shelx_res_checksum              92556