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_7057159
_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         'C17 H13 N Se2'
_chemical_formula_sum            'C17 H13 N Se2'
_chemical_formula_weight         389.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0396(3)
_cell_length_b                   18.3594(5)
_cell_length_c                   5.76067(13)
_cell_measurement_reflns_used    11262
_cell_measurement_temperature    119.98(11)
_cell_measurement_theta_max      74.1330
_cell_measurement_theta_min      4.8090
_cell_volume                     1484.86(6)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1806
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega -100.00  -31.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  120.0000 69

  2 omega  -48.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -90.0000 68

  3 omega   55.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277 -125.0000  120.0000 36

  4 omega   33.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -77.0000 -120.0000 44

  5 omega   32.00   73.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000   30.0000 41

  6 omega   39.00   68.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000  150.0000 29

  7 omega  113.00  138.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -77.0000 -120.0000 25

  8 omega   27.00  132.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -15.0000 -150.0000 105

  9 omega  -50.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   60.0000 84

 10 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000  -90.0000 97

 11 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000   30.0000 97

 12 omega   82.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000   30.0000 96

 13 omega   35.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322 -125.0000   90.0000 86

 14 omega   79.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000  -60.0000 97

 15 omega    1.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000  -30.0000 82

 16 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000  120.0000 97

 17 omega    1.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000  120.0000 82

 18 omega   25.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  150.0000 84

 19 omega   75.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   77.0000   90.0000 103

 20 omega   82.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000 -150.0000 96

 21 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000   90.0000 105

 22 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000 -180.0000 105

 23 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000  -60.0000 105

 24 omega   79.00  153.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000   60.0000 74

 25 omega   79.00  170.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000  150.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0255997000
_diffrn_orient_matrix_UB_12      0.0117098000
_diffrn_orient_matrix_UB_13      0.2574113000
_diffrn_orient_matrix_UB_21      -0.0933004000
_diffrn_orient_matrix_UB_22      0.0427560000
_diffrn_orient_matrix_UB_23      0.0354073000
_diffrn_orient_matrix_UB_31      -0.0517565000
_diffrn_orient_matrix_UB_32      -0.0712194000
_diffrn_orient_matrix_UB_33      0.0636366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17449
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.379
_diffrn_reflns_theta_min         4.817
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80525
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Rint for refined data:    0.04677 with corrections    0.02901
Rint for all data:        0.05109 with corrections    0.03403
1 observations identified as outliers and rejected
Final wR=   0.03849
Final frame scales: Min=  0.9693 Max=  1.0708
Final absorption correction factors: Amin=  0.8777 Amax=  1.0899
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_description       column
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1066
_exptl_crystal_size_mid          0.0455
_exptl_crystal_size_min          0.0264
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.009(19)
_refine_ls_extinction_coef       0.00047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0147
_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^)+(0.0230P)^2^+0.3214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0379
_refine_ls_wR_factor_ref         0.0381
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2895
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj00495a2.cif
_cod_data_source_block           vlajbm
_cod_depositor_comments
'Adding full bibliography for 7057153--7057162.cif.'
_cod_original_cell_volume        1484.86(7)
_cod_database_code               7057159
_chemical_oxdiff_formula         C17H13N1Se2
_chemical_oxdiff_usercomment     'VLAJB #15206 for VL/AJB, SN-752'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.009(19) -0.009(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'