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_7234733
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 I N2 O5'
_chemical_formula_sum            'C14 H13 I N2 O5'
_chemical_formula_weight         416.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                90.00
_cell_angle_beta                 106.961(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.0873(10)
_cell_length_b                   9.6374(3)
_cell_length_c                   7.2450(3)
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4440
_cell_measurement_theta_min      1.8760
_cell_volume                     1541.91(11)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -16.00  10.00   1.00    7.00    --  -15.60 -99.00 -30.00   26
  2  \w    -11.00  89.00   1.00    7.00    --   17.79  19.00  30.00  100
  3  \w     -3.00  77.00   1.00    7.00    --   17.79  19.00 120.00   80
  4  \w    -88.00 -43.00   1.00    7.00    --  -15.44 178.00  60.00   45
  5  \w     56.00  88.00   1.00    7.00    --   17.79 178.00 150.00   32
  6  \w    -13.00  55.00   1.00    7.00    --   17.79 -99.00 -30.00   68
  7  \w    -59.00 -33.00   1.00    7.00    --  -15.44 178.00-120.00   26
  8  \w     -4.00  23.00   1.00    7.00    --  -15.44 -99.00   0.00   27
  9  \w     16.00  57.00   1.00    7.00    --   17.79 -99.00-150.00   41
 10  \w     42.00  74.00   1.00    7.00    --   17.79  57.00 -90.00   32
 11  \w     30.00  57.00   1.00    7.00    --   17.79 -99.00  90.00   27
 12  \w    -25.00  14.00   1.00    7.00    --   17.79 -99.00  90.00   39
 13  \w      2.00  87.00   1.00    7.00    --   17.79  38.00-180.00   85
 14  \w     -9.00  84.00   1.00    7.00    --   17.79  77.00-150.00   93
;
_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      0.0481634000
_diffrn_orient_matrix_UB_12      0.0162035000
_diffrn_orient_matrix_UB_13      -0.0267021000
_diffrn_orient_matrix_UB_21      -0.0785325000
_diffrn_orient_matrix_UB_22      -0.0193055000
_diffrn_orient_matrix_UB_23      -0.0178175000
_diffrn_orient_matrix_UB_31      -0.0331794000
_diffrn_orient_matrix_UB_32      0.0691378000
_diffrn_orient_matrix_UB_33      0.0012816000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10152
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.84
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73007
_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    1.793
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.033(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0186P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0452
_refine_ls_wR_factor_ref         0.0460
_reflns_number_gt                2623
_reflns_number_total             2731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ce01263j2.cif
_cod_data_source_block           shi_3475_fldu
_cod_original_cell_volume        1541.91(10)
_cod_database_code               7234733
_chemical_oxdiff_formula         'C20 H20 N2 O4 I1'
_chemical_oxdiff_usercomment     RT_78
_reflns_odcompleteness_completeness 100.00
_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), C3(H3), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.838