The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π–π stacking interactions and I···N halogen bonds
Mahesha, Ninganayaka; Yathirajan, Hemmige S.; Furuya, Tetsundo; Akitsu, Takashiro; Glidewell, Christopher; Acta Crystallographica Section E 75 (2019) 129–133; doi:10.1107/S205698901801811X

data_2242817
_publ_section_title
;
 The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine:
 a three-dimensional hydrogen-bonded framework, augmented by \p--\p
 stacking interactions and I&#x00B7;&#x00B7;&#x00B7;N halogen bonds
;
_journal_coeditor_code           WM5479
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              129
_journal_page_last               133
_journal_paper_doi               10.1107/S205698901801811X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H15 I N4 O'
_chemical_formula_moiety         'C15 H15 I N4 O'
_chemical_formula_sum            'C15 H15 I N4 O'
_chemical_formula_weight         394.21
_chemical_name_systematic
;
1-(2-Iodobenzoyl)-4-(pyrimidin-2-yl)piperazine
;
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.155(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   13.604(2)
_cell_length_c                   12.174(2)
_cell_measurement_reflns_used    3152
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.591
_cell_measurement_theta_min      2.290
_cell_volume                     1541.3(4)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
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SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009)
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_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_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  0.0669
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8152
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_min         2.290
_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    2.082
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Bruker, 2015)
;
_exptl_crystal_colour            colour
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_exptl_crystal_description       plate
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_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.742
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0235P)^2^+0.7279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                3188
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_database_fobs_code          2242817
_shelx_estimated_absorpt_t_min   0.336
_shelx_estimated_absorpt_t_max   0.732
_shelx_hkl_checksum              2696
_shelx_res_checksum              1018
_shelxl_version_number           2.014