Structural diversity in the products formed by the reactions of 2-arylselanyl pyridine derivatives and dihalogens
Montis, Riccardo; Arca, Massimiliano; Aragoni, M. Carla; Blake, Alexander J.; Castellano, Carlo; Demartin, Francesco; Isaia, Francesco; Lippolis, Vito; Pintus, Anna; Lenardão, Eder J.; Perin, Gelson; O'Connor, Alice E.; Thurow, Samuel; New Journal of Chemistry 42 (2018) 10592–; doi:10.1039/C8NJ00495A

data_7057160
_publ_section_title
;
 Structural diversity in the products formed by the reactions of
 2-arylselanyl pyridine derivatives and dihalogens
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10592
_journal_paper_doi               10.1039/C8NJ00495A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C11 H8 Cl1.27 F0.32 I1.41 N Se'
_chemical_formula_sum            'C11 H8 Cl1.27 F0.32 I1.41 N Se'
_chemical_formula_weight         463.17
_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_date             2018-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.19(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.260(2)
_cell_length_b                   13.1618(4)
_cell_length_c                   10.964(9)
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.0380
_cell_measurement_theta_min      3.3380
_cell_volume                     1339.8(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -64.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 52

  2 omega  -44.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   30.0000 64

  3 omega -106.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 27

  4 omega  -78.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  150.0000 76

  5 omega   57.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000    0.0000 78

  6 omega   73.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  150.0000 81

  7 omega   34.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 64

  8 omega   30.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   60.0000 30

  9 omega   82.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  125.0000   90.0000 94

 10 omega   35.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  -30.0000 29

 11 omega   31.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000    0.0000 56

 12 omega   16.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000  -90.0000 97

 13 omega   20.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000 -180.0000 95

 14 omega   20.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000   30.0000 95

 15 omega   80.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   60.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1797209000
_diffrn_orient_matrix_UB_12      0.0813391000
_diffrn_orient_matrix_UB_13      -0.1096477000
_diffrn_orient_matrix_UB_21      0.2023443000
_diffrn_orient_matrix_UB_22      0.0680370000
_diffrn_orient_matrix_UB_23      0.0684280000
_diffrn_orient_matrix_UB_31      -0.0176918000
_diffrn_orient_matrix_UB_32      -0.0495241000
_diffrn_orient_matrix_UB_33      -0.0860931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6664
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        65.072
_diffrn_reflns_theta_max         65.072
_diffrn_reflns_theta_min         4.948
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              '(Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    31.449
_exptl_absorpt_correction_T_max  0.082
_exptl_absorpt_correction_T_min  0.005
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Rint for refined data:    0.20163 with corrections    0.10354
Rint for all data:        0.20257 with corrections    0.10505
Final wR=   0.11407
Final frame scales: Min=  0.6961 Max=  1.7957
Final absorption correction factors: Amin=  0.3526 Amax=  1.8847
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_F_000             856.8
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.172
_refine_diff_density_max         2.830
_refine_diff_density_min         -1.800
_refine_diff_density_rms         0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0601
_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^)+(0.1101P)^2^+1.5760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2191
_reflns_number_total             2259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj00495a2.cif
_cod_data_source_block           vlajbo
_cod_depositor_comments
'Adding full bibliography for 7057153--7057162.cif.'
_cod_original_cell_volume        1339.8(13)
_cod_database_code               7057160
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{I2', Cl2}
3. Restrained distances
 C10-F1
 1.34 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(I2') = Uanis(Cl2)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(I2')=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Sof(F1)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'