On the importance of antiparallel π–π interactions in the solid state of isatin-based hydrazides
Ahmed, Muhammad Naeem; Arif, Maryam; Jabeen, Farah; Khan, Haroon Ahmed; Yasin, Khawaja Ansar; Tahir, Muhammad Nawaz; Franconetti, Antonio; Frontera, Antonio; New Journal of Chemistry 43 (2019) 8122–; doi:10.1039/C9NJ00405J

data_7058389
_publ_section_title
;
 On the importance of antiparallel \p--\p interactions in the solid state
 of isatin-based hydrazides
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8122
_journal_paper_doi               10.1039/C9NJ00405J
_journal_volume                  43
_journal_year                    2019
_chemical_formula_iupac          'C18 H16 Br N3 O2'
_chemical_formula_moiety         'C18 H16 Br N3 O2'
_chemical_formula_sum            'C18 H16 Br N3 O2'
_chemical_formula_weight         386.25
_chemical_name_systematic
;
2-Bromo-N'-[(3Z)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-29 deposited with the CCDC.    2019-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.512(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9365(8)
_cell_length_b                   19.667(2)
_cell_length_c                   10.9290(12)
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.138
_cell_measurement_theta_min      2.135
_cell_volume                     1702.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.76
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13928
_diffrn_reflns_theta_full        27.138
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_min         2.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.064
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0612P)^2^+0.2153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                2070
_reflns_number_total             3754
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c9nj00405j2.cif
_cod_data_source_block           P5
_cod_depositor_comments
'Adding full bibliography for 7058386--7058390.cif.'
_cod_database_code               7058389
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              6181