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_7057161
_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 Cl N Se, C11 H9 Cl N Se, I3'
_chemical_formula_sum            'C22 H17 Cl2 I3 N2 Se2'
_chemical_formula_weight         918.90
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2291(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7709(3)
_cell_length_b                   12.4525(3)
_cell_length_c                   18.3447(4)
_cell_measurement_reflns_used    11167
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.38
_cell_measurement_theta_min      4.25
_cell_volume                     2673.04(11)
_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-2014 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1806
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega -109.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  -30.0000 97

  2 omega -111.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000 -120.0000 95

  3 omega   25.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000    0.0000 84

  4 omega   25.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  -90.0000 84

  5 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  -30.0000 60

  6 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000    0.0000 60

  7 omega   82.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  120.0000 95

  8 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  120.0000 60

  9 omega   94.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  125.0000   60.0000 84

 10 omega  -50.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   60.0000 84

 11 omega -112.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000  120.0000 105

 12 omega    1.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000 -180.0000 82

 13 omega   82.00  143.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000 -150.0000 61

 14 omega   82.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000   30.0000 96

 15 omega   82.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000  -60.0000 96
;
_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      0.1267093000
_diffrn_orient_matrix_UB_12      -0.0064346000
_diffrn_orient_matrix_UB_13      0.0311879000
_diffrn_orient_matrix_UB_21      -0.0336940000
_diffrn_orient_matrix_UB_22      0.0182661000
_diffrn_orient_matrix_UB_23      0.0779493000
_diffrn_orient_matrix_UB_31      -0.0118363000
_diffrn_orient_matrix_UB_32      -0.1221112000
_diffrn_orient_matrix_UB_33      0.0098919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20473
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         4.706
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    32.609
_exptl_absorpt_correction_T_max  0.318
_exptl_absorpt_correction_T_min  0.073
_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.
Refinement stage 1: ABSORPTION CORRECTION
Frame scaling turned off
Absorption correction model - max even order: 8, max odd order: 7 (80 parameters)
Refinement control: 80 pars with 3240 matrix size
Enough LS memory for 2 threads!
Cycle 1
wR=   0.07912
Using Levenberg-Marquardt:    0.00010
New wR=   0.05221
Rint for refined data:    0.07142 with corrections    0.04128
Rint for all data:        0.07306 with corrections    0.04320
15 observations identified as outliers and rejected
Cycle 2
wR=   0.04512
Using Levenberg-Marquardt:    0.00001
New wR=   0.04461
Rint for refined data:    0.07009 with corrections    0.03938
Rint for all data:        0.07306 with corrections    0.04283
3 observations identified as outliers and rejected
Cycle 3
wR=   0.04447
Using Levenberg-Marquardt:    0.00000
New wR=   0.04451
Rint for refined data:    0.06977 with corrections    0.03933
Rint for all data:        0.07306 with corrections    0.04295
Final wR=   0.04451
Final absorption correction factors: Amin=  0.7491 Amax=  1.2109
;
_exptl_crystal_colour            'translucent dark orange'
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.98
_refine_diff_density_min         -1.83
_refine_diff_density_rms         0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                5140
_reflns_number_total             5329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj00495a2.cif
_cod_data_source_block           vlajbk
_cod_depositor_comments
'Adding full bibliography for 7057153--7057162.cif.'
_cod_database_code               7057161
_chemical_oxdiff_usercomment
'VLAJBK #15204 for VL/AJB, 120 K in Fomblin film'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1'(H1'A), C2'(H2'), C3'(H3'), C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'),
 C11'(H11'), C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-08
_olex2_date_sample_submission    2015-10-02
_olex2_exptl_crystal_mounting_method 'In Fomblin on MicroMount'
_olex2_submission_original_sample_id VLAJBK
_olex2_submission_special_instructions 'No special instructions were received'