Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state and predicted by solution 13C-NMR spectroscopy
Popa, Marcel Mirel; Man, Isabela; Draghici, Constantin; Sova, Sergiu; Caira, M. R.; Dumitrascu, Florea; Dumitrescu, Denisa; CrystEngComm  (2019) –; doi:10.1039/C9CE01263J

data_7234732
_publ_section_title
;
 Halogen bonding in 5-iodo-1-arylpyrazoles investigated in the solid state
 and predicted by solution 13C-NMR spectroscopy
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01263J
_journal_year                    2019
_chemical_formula_moiety         'C14 H12 Cl I N2 O4'
_chemical_formula_sum            'C14 H12 Cl I N2 O4'
_chemical_formula_weight         434.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-09 deposited with the CCDC.    2019-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                111.275(8)
_cell_angle_beta                 96.662(7)
_cell_angle_gamma                95.904(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3915(7)
_cell_length_b                   10.0389(8)
_cell_length_c                   10.2106(9)
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      25.4880
_cell_measurement_theta_min      2.1640
_cell_volume                     786.30(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      3.00  83.00   1.00    7.00    --   17.87  38.00  60.00   80
  2  \w      3.00  68.00   1.00    7.00    --   17.87  57.00  90.00   65
  3  \w     -9.00  85.00   1.00    7.00    --   17.87  77.00 -90.00   94
  4  \w    -50.00  45.00   1.00    7.00    --   17.87 -77.00 150.00   95
  5  \w    -60.00 -35.00   1.00    7.00    --  -15.52-178.00 120.00   25
  6  \w    -78.00   1.00   1.00    7.00    --  -15.29 -57.00 150.00   79
  7  \w    -24.00  57.00   1.00    7.00    --   17.71 -99.00  60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0519668000
_diffrn_orient_matrix_UB_12      -0.0059154000
_diffrn_orient_matrix_UB_13      0.0483323000
_diffrn_orient_matrix_UB_21      -0.0576344000
_diffrn_orient_matrix_UB_22      0.0324072000
_diffrn_orient_matrix_UB_23      -0.0298947000
_diffrn_orient_matrix_UB_31      -0.0374418000
_diffrn_orient_matrix_UB_32      -0.0693423000
_diffrn_orient_matrix_UB_33      -0.0498397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7393
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.17
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         2.304
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+1.3028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                2427
_reflns_number_total             2768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ce01263j2.cif
_cod_data_source_block           shi_3466_fldu
_cod_original_cell_volume        786.30(11)
_cod_database_code               7234732
_chemical_oxdiff_formula         'C20 H20 N4 O2'
_chemical_oxdiff_usercomment     D_26
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.872