Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions
Mahesha, Ninganayaka; Sagar, Belakavadi K.; Yathirajan, Hemmige S.; Furuya, Tetsundo; Haraguchi, Tomoyuki; Akitsu, Takashiro; Glidewell, Christopher; Acta Crystallographica Section E 75 (2019) 202–207; doi:10.1107/S2056989019000458

data_2242804
_publ_section_title
;
 Three closely related
 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar
 molecular structures but different intermolecular interactions
;
_journal_coeditor_code           ZL2747
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              202
_journal_page_last               207
_journal_paper_doi               10.1107/S2056989019000458
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C19 H18 F2 N2 O3'
_chemical_formula_moiety         'C19 H18 F2 N2 O3'
_chemical_formula_sum            'C19 H18 F2 N2 O3'
_chemical_formula_weight         360.35
_chemical_name_systematic
;
1-[(1,3-Benzodioxol-5-yl)methyl]-4-(2,6-difluorobenzoyl)piperazine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2762(9)
_cell_length_b                   15.9821(10)
_cell_length_c                   7.3753(5)
_cell_measurement_reflns_used    3743
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.503
_cell_measurement_theta_min      1.913
_cell_volume                     1682.78(19)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9016
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         1.913
_diffrn_source                   'fine focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1369 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0960P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                3449
_reflns_number_total             3743
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2747sup1.cif
_cod_data_source_block           II
_cod_database_code               2242804
_cod_database_fobs_code          2242804
_shelx_estimated_absorpt_t_min   0.905
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              9447
_shelx_res_checksum              16120
_shelxl_version_number           2.014