Selanyl and tellanyl electrophiles as a driving force in the construction of sophisticated polyaromatic hydrocarbons
Arsenyan, Pavel; Petrenko, Alla; Belyakov, Sergey; New Journal of Chemistry 45 (2021) 7247–7255; doi:10.1039/D1NJ00401H

data_7060491
_publ_section_title
;
 Selanyl and tellanyl electrophiles as a driving force in the construction
 of sophisticated polyaromatic hydrocarbons
;
_journal_issue                   16
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7247
_journal_page_last               7255
_journal_paper_doi               10.1039/D1NJ00401H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C36 H22 Se'
_chemical_formula_sum            'C36 H22 Se'
_chemical_formula_weight         533.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-14
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2020-06-07 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                73.366(1)
_cell_angle_beta                 82.145(1)
_cell_angle_gamma                80.121(1)
_cell_formula_units_Z            2
_cell_length_a                   9.3198(1)
_cell_length_b                   11.5015(2)
_cell_length_c                   11.9566(2)
_cell_measurement_reflns_used    41769
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      76.9160
_cell_measurement_theta_min      3.8850
_cell_volume                     1204.59(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9930
_diffrn_measured_fraction_theta_max 0.9930
_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   -119.00 -79.00   0.50    0.07    --  -49.35 -47.00  43.00   80
  2  \w    -49.00  22.00   0.50    0.07    --  -49.35  47.00-167.00  142
  3  \w    -21.00  48.00   0.50    0.07    --   49.66 -47.00  43.00  138
  4  \w     81.00 121.00   0.50    0.07    --   49.66  47.00-167.00   80
  5  \w    -53.00 -28.00   0.50    0.26    --  -84.25  47.00-167.00   50
  6  \w   -124.00 -99.00   0.50    0.26    --  -84.25 -47.00  43.00   50
  7  \w    131.00 157.00   0.50    0.26    --  105.75  47.00-167.00   52
  8  \w    -36.00 -10.00   0.50    0.07    --    4.00 120.00  88.70   52
  9  \w    -25.00   0.00   0.50    0.07    --   12.00 109.00-120.06   50
 10  \w    -12.00  13.00   0.50    0.07    --   20.00 101.00  22.53   50
 11  \w      6.00  31.00   0.50    0.07    --   28.00  80.00-145.93   50
 12  \w     11.00  37.00   0.50    0.07    --   32.00  77.00-164.37   52
 13  \w     13.00  38.00   0.50    0.07    --   32.00  74.00 -57.63   50
 14  \w    -48.00 -19.00   0.50    0.07    --  -36.00 -71.00  54.41   58
 15  \w     18.00  43.00   0.50    0.07    --   36.00  72.00  18.06   50
 16  \w    -53.00 -26.00   0.50    0.07    --  -36.00 -69.00  33.27   54
 17  \w     18.00  43.00   0.50    0.07    --   36.00  73.00  65.79   50
 18  \w    -43.00 -18.00   0.50    0.07    --  -36.00 -73.00-135.96   50
 19  \w     34.00  61.00   0.50    0.07    --   48.00  66.00 -40.46   54
 20  \w     85.00 111.00   0.50    0.07    --   48.00  66.00 -40.46   52
 21  \w     33.00  60.00   0.50    0.07    --   48.00  66.00  84.50   54
 22  \w    -69.00 -42.00   0.50    0.07    --  -49.35 -57.00 150.00   54
 23  \w    -87.00 -41.00   0.50    0.07    --  -49.35 -16.00  45.66   92
 24  \w     33.00  95.00   0.50    0.07    --   49.66-125.00 -90.00  124
 25  \w     36.00  63.00   0.50    0.07    --   52.00  65.00 113.38   54
 26  \w   -126.00 -93.00   0.50    0.07    --  -56.00 -64.00-125.12   66
 27  \w    -67.00 -40.00   0.50    0.07    --  -56.00 -64.00-125.12   54
 28  \w     41.00  66.00   0.50    0.07    --   56.00  67.00 122.93   50
 29  \w   -122.00 -87.00   0.50    0.07    --  -56.00 -66.00-162.50   70
 30  \w     42.00  69.00   0.50    0.07    --   56.00  65.00-133.47   54
 31  \w     41.00  66.00   0.50    0.07    --   56.00  66.00 170.16   50
 32  \w    -72.00 -40.00   0.50    0.07    --  -56.00 -66.00-162.50   64
 33  \w     41.00  68.00   0.50    0.07    --   56.00  66.00   0.72   54
 34  \w     40.00  95.00   0.50    0.07    --   56.00  67.00  29.34  110
 35  \w    -69.00 -40.00   0.50    0.07    --  -56.00 -66.00 146.65   58
 36  \w     45.00  71.00   0.50    0.07    --   60.00  66.00 -23.91   52
 37  \w    -72.00 -43.00   0.50    0.07    --  -60.00 -67.00  81.47   58
 38  \w    -78.00 -52.00   0.50    0.26    --  -68.00 -66.00-127.25   52
 39  \w    -78.00 -52.00   0.50    0.26    --  -68.00 -64.00 -92.91   52
 40  \w    -81.00 -54.00   0.50    0.26    --  -68.00 -60.00 126.75   54
 41  \w   -137.00-109.00   0.50    0.26    --  -68.00 -65.00  19.58   56
 42  \w    -77.00 -52.00   0.50    0.26    --  -68.00 -65.00  19.58   50
 43  \w    -84.00 -59.00   0.50    0.26    --  -72.00 -58.00  51.24   50
 44  \w    -81.00 -56.00   0.50    0.26    --  -72.00 -64.00  12.15   50
 45  \w    -82.00 -56.00   0.50    0.26    --  -72.00 -66.00-138.01   52
 46  \w    -84.00 -57.00   0.50    0.26    --  -72.00 -65.00  46.98   54
 47  \w    -87.00 -61.00   0.50    0.26    --  -76.00 -63.00 -27.17   52
 48  \w    -88.00 -61.00   0.50    0.26    --  -76.00 -63.00  38.69   54
 49  \w    -89.00 -62.00   0.50    0.26    --  -76.00 -60.00 150.44   54
 50  \w    -88.00 -61.00   0.50    0.26    --  -76.00 -65.00 -50.67   54
 51  \w    -90.00 -65.00   0.50    0.26    --  -80.00 -63.00 -35.51   50
 52  \w    -93.00 -67.00   0.50    0.26    --  -80.00 -59.00  71.03   52
 53  \w    -97.00 -68.00   0.50    0.26    --  -84.25 -66.00   4.84   58
 54  \w    -95.00 -69.00   0.50    0.26    --  -84.25 -65.00  66.04   52
 55  \w   -149.00 -68.00   0.50    0.26    --  -84.25 -66.00 175.36  162
 56  \w    -96.00 -70.00   0.50    0.26    --  -84.25 -65.00 -53.88   52
 57  \w    -95.00 -68.00   0.50    0.26    --  -84.25 -65.00 127.85   54
 58  \w    -96.00 -70.00   0.50    0.26    --  -84.25 -61.00  20.16   52
 59  \w    -94.00 -68.00   0.50    0.26    --  -84.25 -65.00 -71.08   52
 60  \w    -96.00 -69.00   0.50    0.26    --  -84.25 -66.00-172.98   54
 61  \w    -97.00 -70.00   0.50    0.26    --  -84.25 -65.00 116.05   54
 62  \w   -114.00 -68.00   0.50    0.26    --  -84.25 -65.00-121.13   92
 63  \w    -66.00 -30.00   0.50    0.26    --  -84.25  61.00-180.00   72
 64  \w    -95.00 -70.00   0.50    0.26    --  -84.25 -61.00  90.00   50
 65  \w    -96.00 -69.00   0.50    0.26    --  -84.25 -63.00-169.64   54
 66  \w   -113.00 -73.00   0.50    0.26    --  -84.25 -54.00 127.31   80
 67  \w   -135.00 -72.00   0.50    0.26    --  -84.25 -58.00-166.39  126
 68  \w    -95.00 -69.00   0.50    0.26    --  -84.25 -64.00 -95.38   52
 69  \w    -98.00 -71.00   0.50    0.26    --  -84.25 -61.00 -23.58   54
 70  \w    -96.00 -70.00   0.50    0.26    --  -84.25 -66.00-104.83   52
 71  \w    -97.00 -70.00   0.50    0.26    --  -84.25 -61.00-150.00   54
 72  \w     35.00 116.00   0.50    0.26    --  105.75-125.00-180.00  162
 73  \w     91.00 118.00   0.50    0.26    --  105.75   0.00  90.00   54
 74  \w     88.00 141.00   0.50    0.26    --  105.75  77.00-150.00  106
 75  \w     36.00  89.00   0.50    0.26    --  105.75 -94.00  90.00  106
 76  \w     39.00  64.00   0.50    0.26    --  105.75 -61.00 120.00   50
 77  \w     45.00  70.00   0.50    0.26    --  105.75 -61.00  60.00   50
 78  \w     72.00 109.00   0.50    0.26    --  105.75 -94.00  60.00   74
 79  \w     92.00 155.00   0.50    0.26    --  105.75  61.00 120.00  126
 80  \w    139.00 165.00   0.50    0.26    --  105.75  61.00 -30.00   52
 81  \w     39.00  65.00   0.50    0.26    --  105.75 -94.00  60.00   52
 82  \w     65.00 102.00   0.50    0.26    --  105.75 -77.00-150.00   74
 83  \w     94.00 124.00   0.50    0.26    --  105.75  61.00 -30.00   60
 84  \w     92.00 160.00   0.50    0.26    --  105.75  61.00  90.00  136
 85  \w    143.00 178.00   0.50    0.26    --  105.75  30.00-120.00   70
 86  \w    146.00 171.00   0.50    0.26    --  105.75  61.00 150.00   50
 87  \w     92.00 138.00   0.50    0.26    --  105.75  61.00 150.00   92
 88  \w     90.00 153.00   0.50    0.26    --  105.75  77.00-180.00  126
 89  \w     72.00 116.00   0.50    0.26    --  105.75-125.00 -30.00   88
 90  \w    140.00 167.00   0.50    0.26    --  105.75  77.00-120.00   54
 91  \w     80.00 109.00   0.50    0.26    --  105.75 -94.00  30.00   58
 92  \w     38.00  65.00   0.50    0.26    --  105.75-125.00 -30.00   54
 93  \w     95.00 128.00   0.50    0.26    --  105.75 -82.00 -85.68   66
 94  \w     88.00 117.00   0.50    0.26    --  105.75  77.00-120.00   58
 95  \w     59.00  84.00   0.50    0.26    --  105.75 -82.00 -85.68   50
 96  \w    145.00 173.00   0.50    0.26    --  105.75  77.00   0.00   56
 97  \w     36.00  74.00   0.50    0.26    --  105.75 -94.00  30.00   76
 98  \w    108.00 135.00   0.50    0.26    --  105.75  30.00-120.00   54
 99  \w     36.00  69.00   0.50    0.26    --  105.75 -61.00-180.00   66
100  \w     92.00 119.00   0.50    0.26    --  105.75  61.00-180.00   54
101  \w     90.00 115.00   0.50    0.26    --  105.75  77.00   0.00   50
102  \w     78.00 116.00   0.50    0.26    --  105.75-125.00  30.00   76
103  \w     35.00  67.00   0.50    0.26    --  105.75-125.00  30.00   64
104  \w     49.00  75.00   0.50    0.26    --  105.75 -77.00 150.00   52
105  \w     84.00 116.00   0.50    0.26    --  105.75-125.00-120.00   64
106  \w     41.00  66.00   0.50    0.26    --  105.75-125.00-120.00   50
107  \w     41.00  70.00   0.50    0.26    --  105.75-125.00 150.00   58
108  \w     77.00 106.00   0.50    0.26    --  105.75-125.00 150.00   58
109  \w     93.00 156.00   0.50    0.26    --  105.75  61.00  60.00  126
110  \w     98.00 144.00   0.50    0.26    --  105.75  61.00-150.00   92
111  \w     92.00 141.00   0.50    0.26    --  105.75  61.00 -60.00   98
112  \w     88.00 157.00   0.50    0.26    --  105.75  77.00 -30.00  138
113  \w    128.00 163.00   0.50    0.26    --  105.75  61.00   0.00   70
114  \w    127.00 163.00   0.50    0.26    --  105.75  77.00  30.00   72
115  \w     87.00 115.00   0.50    0.26    --  105.75-125.00   0.00   56
116  \w     89.00 119.00   0.50    0.26    --  105.75  77.00  30.00   60
117  \w     96.00 122.00   0.50    0.26    --  105.75  61.00   0.00   52
118  \w     34.00  65.00   0.50    0.26    --  105.75 -61.00-150.00   62
119  \w     36.00  78.00   0.50    0.26    --  105.75-125.00   0.00   84
120  \w    149.00 176.00   0.50    0.26    --  105.75  30.00  90.00   54
121  \w    104.00 140.00   0.50    0.26    --  105.75  30.00  90.00   72
122  \w     35.00  60.00   0.50    0.26    --  105.75 -77.00   0.00   50
123  \w     58.00  84.00   0.50    0.26    --  105.75 -77.00  30.00   52
124  \w     42.00  69.00   0.50    0.26    --  105.75 -77.00 120.00   54
125  \w     78.00 103.00   0.50    0.26    --  105.75 -77.00 120.00   50
126  \w     82.00 107.00   0.50    0.26    --  105.75 -94.00-120.00   50
127  \w     91.00 154.00   0.50    0.26    --  105.75  77.00 -60.00  126
128  \w     88.00 116.00   0.50    0.26    --  105.75-125.00  90.00   56
129  \w     38.00  79.00   0.50    0.26    --  105.75   0.00  90.00   82
130  \w     35.00  60.00   0.50    0.26    --  105.75-125.00  90.00   50
131  \w    129.00 154.00   0.50    0.26    --  105.75  61.00 -90.00   50
132  \w     48.00  75.00   0.50    0.26    --  105.75-125.00  60.00   54
133  \w     88.00 115.00   0.50    0.26    --  105.75  77.00 150.00   54
134  \w     95.00 121.00   0.50    0.26    --  105.75  61.00 -90.00   52
135  \w     34.00  83.00   0.50    0.26    --  105.75 -77.00-180.00   98
136  \w    142.00 178.00   0.50    0.26    --  105.75  77.00  60.00   72
137  \w    111.00 136.00   0.50    0.26    --  105.75 125.00   0.00   50
138  \w     89.00 126.00   0.50    0.26    --  105.75  77.00  60.00   74
139  \w     98.00 130.00   0.50    0.26    --  105.75  45.00-180.00   64
140  \w    141.00 178.00   0.50    0.26    --  105.75  45.00 120.00   74
141  \w    147.00 175.00   0.50    0.26    --  105.75  30.00 150.00   56
142  \w    114.00 147.00   0.50    0.26    --  105.75  30.00-180.00   66
143  \w     94.00 134.00   0.50    0.26    --  105.75  61.00  30.00   80
144  \w     73.00 108.00   0.50    0.26    --  105.75 -94.00-180.00   70
145  \w     35.00  61.00   0.50    0.26    --  105.75 -94.00-180.00   52
146  \w     99.00 126.00   0.50    0.26    --  105.75  61.00-120.00   54
147  \w    139.00 168.00   0.50    0.26    --  105.75 125.00   0.00   58
148  \w    117.00 145.00   0.50    0.26    --  105.75 125.00  90.00   56
149  \w     91.00 138.00   0.50    0.26    --  105.75  77.00 120.00   94
150  \w     35.00  63.00   0.50    0.26    --  105.75 -61.00-120.00   56
151  \w    153.00 178.00   0.50    0.26    --  105.75  77.00-150.00   50
152  \w    100.00 125.00   0.50    0.26    --  105.75  45.00 120.00   50
153  \w     35.00  60.00   0.50    0.26    --  105.75 -77.00  60.00   50
154  \w     35.00  75.00   0.50    0.26    --  105.75 -80.00 -40.72   80
155  \w     96.00 122.00   0.50    0.26    --  105.75 -80.00 -40.72   52
156  \w     99.00 176.00   0.50    0.26    --  105.75  15.00 -60.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1653300000
_diffrn_orient_matrix_UB_12      0.0191351000
_diffrn_orient_matrix_UB_13      0.0372734000
_diffrn_orient_matrix_UB_21      -0.0246060000
_diffrn_orient_matrix_UB_22      -0.0881174000
_diffrn_orient_matrix_UB_23      -0.0691024000
_diffrn_orient_matrix_UB_31      0.0213958000
_diffrn_orient_matrix_UB_32      -0.1086267000
_diffrn_orient_matrix_UB_33      0.1098882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47319
_diffrn_reflns_theta_full        77.3575
_diffrn_reflns_theta_max         77.36
_diffrn_reflns_theta_min         3.88
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  0.72469
_exptl_absorpt_correction_T_min  0.63050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.4709
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.0814
_refine_diff_density_min         -0.7651
_refine_diff_density_rms         0.0764
_refine_ls_d_res_high            0.7901
_refine_ls_d_res_low             11.4069
_refine_ls_goodness_of_fit_ref   1.0395
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0395
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.6980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                5005
_reflns_number_total             5082
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1nj00401h2.cif
_cod_data_source_block           A574
_cod_depositor_comments
'Adding full bibliography for 7060487--7060492.cif.'
_cod_database_code               7060491
_chemical_oxdiff_formula         'C72 H44 Se2 '
_chemical_oxdiff_usercomment     'from Pavel'
_diffrn_oxdiff_digest_frames
;
010bad3eae4b50f8a41c425ff493419dfc0008053c7
;
_diffrn_oxdiff_digest_hkl
;
01b5686acb733594bc4cf5e02874485a4519bb
;
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C33(H33), C35(H35), C36(H36), C37(H37)
;
_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.812