Synergistic Effects of Halogen Bond and π-π Interactions in Thiophene-based Building Blocks
Wilson, Jamey; Williams, Jon; Petkovsek, Chesney; Reves, Peyton; Jurss, Jonah W.; Hammer, Nathan I.; Tschumper, Gregory S.; Watkins, Davita; RSC Adv.  (2015) –; doi:10.1039/C5RA16680B

data_7222272
_publ_section_title
;
 Synergistic Effects of Halogen Bond and \p-\p Interactions in
 Thiophene-based Building Blocks
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA16680B
_journal_year                    2015
_chemical_formula_moiety         'C9 H7 N S, C6 F5 I'
_chemical_formula_sum            'C15 H7 F5 I N S'
_chemical_formula_weight         455.18
_chemical_name_common            Pyr-T_IPFB
_chemical_name_systematic
;
 ?
;
_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_date             2015-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-07-07 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.757(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7694(5)
_cell_length_b                   7.5097(4)
_cell_length_c                   22.9574(13)
_cell_measurement_reflns_used    9784
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.46
_cell_volume                     1511.16(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26339
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         1.77
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_T_max  0.7693
_exptl_absorpt_correction_T_min  0.5256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0158
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0084P)^2^+1.7652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0377
_reflns_number_gt                2977
_reflns_number_total             3130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra16680b2.cif
_cod_data_source_block           shelxl
_cod_database_code               7222272
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C9, S1A}
{C9A, S1}
3. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(S1A)
Uanis(C9A) = Uanis(S1)
4. Others
 Sof(C9A)=Sof(H9A)=Sof(S1A)=1-FVAR(1)
 Sof(C9)=Sof(H9)=Sof(S1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C9A(H9A), C12(H12), C13(H13), C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'