#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:53:58 +0300 (Wed, 05 May 2021) $
#$Revision: 264915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060488.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7060488
loop_
_publ_author_name
'Arsenyan, Pavel'
'Petrenko, Alla'
'Belyakov, Sergey'
_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_absolute_configuration ad
_chemical_formula_moiety         'C27 H17 N Se'
_chemical_formula_sum            'C27 H17 N Se'
_chemical_formula_weight         434.40
_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_Int_Tables_number      33
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-01
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2020-06-05 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.83567(8)
_cell_length_b                   15.85744(8)
_cell_length_c                   7.87700(3)
_cell_measurement_reflns_used    18777
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      76.9820
_cell_measurement_theta_min      3.9390
_cell_volume                     1978.019(16)
_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    'ShelXS (Sheldrick, 2008)'
_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 0.98
_diffrn_measured_fraction_theta_max 0.8213
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  22.00   0.50    0.25    --  -49.35  23.00-136.00  102
  2  ω    -93.00 -67.00   0.50    0.25    --  -84.25 128.00  79.00   52
  3  ω   -141.00-116.00   0.50    0.25    --  -84.25 -23.00  58.00   50
  4  ω    144.00 170.00   0.50    0.25    --  105.75 128.00  79.00   52
  5  ω     90.00 129.00   0.50    0.25    --  105.75 128.00  79.00   78
  6  ω     69.00  95.00   0.50    0.25    --  105.75-102.00-101.00   52
  7  ω    -21.00  19.00   0.50    0.25    --  -49.35  19.00   0.00   80
  8  ω   -116.00 -88.00   0.50    0.25    --  -49.35-125.00 120.00   56
  9  ω   -117.00 -88.00   0.50    0.25    --  -49.35 -77.00 150.00   58
 10  ω   -120.00 -95.00   0.50    0.25    --  -49.35 -77.00 -60.00   50
 11  ω    -17.00  26.00   0.50    0.25    --   49.66 -19.00 -30.00   86
 12  ω    121.00 167.00   0.50    0.25    --  105.75 125.00  90.00   92
 13  ω    146.00 177.00   0.50    0.25    --  105.75 125.00 120.00   62
 14  ω     36.00  71.00   0.50    0.25    --  105.75 -61.00  60.00   70
 15  ω     92.00 119.00   0.50    0.25    --  105.75 125.00 120.00   54
 16  ω    147.00 172.00   0.50    0.25    --  105.75  15.00   0.00   50
 17  ω     88.00 147.00   0.50    0.25    --  105.75  77.00  30.00  118
 18  ω     35.00  65.00   0.50    0.25    --  105.75 -77.00  60.00   60
 19  ω     80.00 105.00   0.50    0.25    --  105.75 -77.00  60.00   50
 20  ω     78.00 104.00   0.50    0.25    --  105.75 -94.00-150.00   52
 21  ω     43.00  68.00   0.50    0.25    --  105.75 -61.00 -90.00   50
 22  ω     64.00  90.00   0.50    0.25    --  105.75-125.00  30.00   52
 23  ω    122.00 165.00   0.50    0.25    --  105.75 125.00-120.00   86
 24  ω     61.00 100.00   0.50    0.25    --  105.75 -77.00  30.00   78
 25  ω     42.00  68.00   0.50    0.25    --  105.75 -81.00-167.72   52
 26  ω    100.00 127.00   0.50    0.25    --  105.75 -81.00-167.72   54
 27  ω     40.00  65.00   0.50    0.25    --  105.75 -61.00 -60.00   50
 28  ω    123.00 161.00   0.50    0.25    --  105.75  15.00  90.00   76
 29  ω     78.00 132.00   0.50    0.25    --  105.75 148.00 153.56  108
 30  ω     40.00  65.00   0.50    0.25    --  105.75 -77.00 -90.00   50
 31  ω     75.00 101.00   0.50    0.25    --  105.75 -77.00 -90.00   52
 32  ω     38.00  63.00   0.50    0.25    --  105.75 -77.00 -30.00   50
 33  ω     34.00  82.00   0.50    0.25    --  105.75 -77.00 150.00   96
 34  ω     40.00  66.00   0.50    0.25    --  105.75 -94.00-150.00   52
 35  ω     98.00 123.00   0.50    0.25    --  105.75  77.00-180.00   50
 36  ω    100.00 178.00   0.50    0.25    --  105.75  15.00 -60.00  156
 37  ω     35.00  87.00   0.50    0.25    --  105.75 -94.00  30.00  104
 38  ω     37.00  66.00   0.50    0.25    --  105.75 -61.00 -30.00   58
 39  ω    102.00 127.00   0.50    0.25    --  105.75   0.00-180.00   50
 40  ω    124.00 153.00   0.50    0.25    --  105.75   0.00   0.00   58
 41  ω    112.00 138.00   0.50    0.25    --  105.75  23.00-136.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0725789000
_diffrn_orient_matrix_UB_12      -0.0606087000
_diffrn_orient_matrix_UB_13      0.0455934000
_diffrn_orient_matrix_UB_21      0.0645879000
_diffrn_orient_matrix_UB_22      0.0703381000
_diffrn_orient_matrix_UB_23      -0.0367214000
_diffrn_orient_matrix_UB_31      -0.0050261000
_diffrn_orient_matrix_UB_32      0.0286213000
_diffrn_orient_matrix_UB_33      0.1865870000
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            20221
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         77.24
_diffrn_reflns_theta_min         3.95
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.651
_exptl_absorpt_correction_T_max  0.96704
_exptl_absorpt_correction_T_min  0.73145
_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    1.4586
_exptl_crystal_description       Plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.2673
_refine_diff_density_min         -0.5366
_refine_diff_density_rms         0.0462
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.005(14)
_refine_ls_d_res_high            0.7904
_refine_ls_d_res_low             11.2052
_refine_ls_goodness_of_fit_ref   1.0500
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0500
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0712P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.615
_reflns_limit_h_max              20
_reflns_limit_h_min              -19
_reflns_limit_k_max              20
_reflns_limit_k_min              -19
_reflns_limit_l_max              9
_reflns_limit_l_min              -7
_reflns_number_gt                3405
_reflns_number_total             3428
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1nj00401h2.cif
_cod_data_source_block           A546new
_cod_depositor_comments
'Adding full bibliography for 7060487--7060492.cif.'
_cod_original_cell_volume        1978.020(16)
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7060488
_chemical_oxdiff_formula         'C108 H68 N4 Se4'
_chemical_oxdiff_usercomment     'from Pavel'
_diffrn_oxdiff_digest_frames
;
01845d136f852998c3f8457f4f045b4c3000072ab60
;
_diffrn_oxdiff_digest_hkl
;
01199cb2a695c653d044f5e38df3fed12fc049
;
_reflns_odcompleteness_completeness 99.26
_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:
 C4(H4), C17(H17), C25(H25), C23(H23), C1(H1), C6(H6), C15(H15), C8(H8),
 C3(H3), C19(H19), C24(H24), C7(H7), C16(H16), C21(H21), C18(H18), C22(H22),
 C5(H5)
;
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.665
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y+1/2,z+1/2
4 x+1/2,-y+1/2,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Se13 Se -0.733347(12) -0.410599(12) -0.59660(3) 0.02740(10) Uani 1.000000 .
C14 C -0.81835(11) -0.32415(11) -0.5953(3) 0.0236(4) Uani 1.000000 .
C4 C -0.87882(11) -0.67205(12) -0.0951(4) 0.0288(4) Uani 1.000000 .
H4 H -0.92499(11) -0.70522(12) -0.1245(4) 0.0346(5) Uiso 1.000000 R
N12 N -0.69227(14) -0.66458(15) 0.3841(3) 0.0425(5) Uani 1.000000 .
C17 C -0.93393(12) -0.19233(12) -0.5940(4) 0.0307(4) Uani 1.000000 .
H17 H -0.97264(12) -0.14822(12) -0.5934(4) 0.0369(5) Uiso 1.000000 R
C25 C -0.68567(15) -0.37894(15) -0.1149(4) 0.0368(5) Uani 1.000000 .
H25 H -0.74025(15) -0.36403(15) -0.0833(4) 0.0441(6) Uiso 1.000000 R
C10a C -0.78034(13) -0.55932(13) -0.1632(3) 0.0217(4) Uani 1.000000 .
C23 C -0.53579(16) -0.35614(17) -0.0977(4) 0.0448(6) Uani 1.000000 .
H23 H -0.48996(16) -0.32625(17) -0.0549(4) 0.0538(7) Uiso 1.000000 R
C1 C -0.74069(15) -0.57419(16) -0.0061(4) 0.0245(5) Uani 1.000000 .
H1 H -0.69458(15) -0.54145(16) 0.0256(4) 0.0294(6) Uiso 1.000000 R
C6 C -1.01104(14) -0.61755(14) -0.5612(4) 0.0351(6) Uani 1.000000 .
H6 H -1.06171(14) -0.64449(14) -0.5861(4) 0.0422(7) Uiso 1.000000 R
C2 C -0.76923(11) -0.63669(15) 0.1018(3) 0.0261(5) Uani 1.000000 .
C10 C -0.74733(14) -0.49745(13) -0.2815(3) 0.0234(4) Uani 1.000000 .
C15 C -0.82212(14) -0.26920(13) -0.7328(3) 0.0268(4) Uani 1.000000 .
H15 H -0.78651(14) -0.27677(13) -0.8254(3) 0.0322(5) Uiso 1.000000 R
C8 C -0.90070(14) -0.52014(13) -0.6403(3) 0.0295(5) Uani 1.000000 .
H8 H -0.87736(14) -0.48294(13) -0.7186(3) 0.0354(5) Uiso 1.000000 R
C3 C -0.83925(13) -0.68673(14) 0.0553(3) 0.0301(5) Uani 1.000000 .
H3 H -0.85816(13) -0.72938(14) 0.1269(3) 0.0362(6) Uiso 1.000000 R
C11 C -0.72634(13) -0.65182(16) 0.2600(4) 0.0305(5) Uani 1.000000 .
C19 C -0.87251(13) -0.31400(13) -0.4578(3) 0.0268(4) Uani 1.000000 .
H19 H -0.87016(13) -0.35103(13) -0.3663(3) 0.0322(5) Uiso 1.000000 R
C24 C -0.6172(2) -0.33324(18) -0.0530(4) 0.0461(7) Uani 1.000000 .
H24 H -0.6261(2) -0.28737(18) 0.0184(4) 0.0553(8) Uiso 1.000000 R
C7 C -0.97532(16) -0.56194(15) -0.6792(3) 0.0339(5) Uani 1.000000 .
H7 H -1.00150(16) -0.55302(15) -0.7833(3) 0.0407(6) Uiso 1.000000 R
C9 C -0.78432(13) -0.48732(13) -0.4366(3) 0.0229(4) Uani 1.000000 .
C4a C -0.85222(12) -0.60806(12) -0.2084(3) 0.0224(4) Uani 1.000000 .
C16 C -0.87974(14) -0.20263(13) -0.7306(3) 0.0296(5) Uani 1.000000 .
H16 H -0.88179(14) -0.16505(13) -0.8211(3) 0.0355(5) Uiso 1.000000 R
C21 C -0.59068(14) -0.46871(15) -0.2703(4) 0.0352(5) Uani 1.000000 .
H21 H -0.58122(14) -0.51349(15) -0.3441(4) 0.0423(6) Uiso 1.000000 R
C18 C -0.93037(13) -0.24774(13) -0.4585(3) 0.0293(4) Uani 1.000000 .
H18 H -0.96688(13) -0.24071(13) -0.3671(3) 0.0352(5) Uiso 1.000000 R
C22 C -0.52280(18) -0.42321(19) -0.2055(5) 0.0461(8) Uani 1.000000 .
H22 H -0.46803(18) -0.43827(19) -0.2354(5) 0.0553(9) Uiso 1.000000 R
C20 C -0.67275(13) -0.44713(12) -0.2244(3) 0.0255(4) Uani 1.000000 .
C8a C -0.86002(13) -0.53348(12) -0.4837(3) 0.0234(4) Uani 1.000000 .
C5 C -0.97164(12) -0.63244(13) -0.4092(3) 0.0293(5) Uani 1.000000 .
H5 H -0.99583(12) -0.66966(13) -0.3320(3) 0.0352(6) Uiso 1.000000 R
C4b C -0.89436(14) -0.59182(11) -0.3680(3) 0.0238(5) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 Se13 C14 98.82(9) . . ?
C15 C14 Se13 118.22(17) . . ?
C19 C14 Se13 121.24(17) . . ?
C19 C14 C15 120.48(18) . . ?
C4a C4 C3 122.33(19) . . ?
C18 C17 C16 119.93(19) . . ?
C20 C25 C24 120.3(2) . . ?
C10 C10a C1 121.2(2) . . ?
C4a C10a C1 119.1(2) . . ?
C4a C10a C10 119.7(2) . . ?
C22 C23 C24 119.9(2) . . ?
C2 C1 C10a 121.0(2) . . ?
C5 C6 C7 120.3(2) . . ?
C3 C2 C1 120.0(2) . . ?
C11 C2 C1 119.9(2) . . ?
C11 C2 C3 120.1(2) . . ?
C9 C10 C10a 120.0(2) . . ?
C20 C10 C10a 116.9(2) . . ?
C20 C10 C9 123.1(2) . . ?
C16 C15 C14 119.5(2) . . ?
C8a C8 C7 120.7(2) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C11 N12 179.3(3) . . ?
C18 C19 C14 119.3(2) . . ?
C23 C24 C25 120.0(3) . . ?
C8 C7 C6 119.9(2) . . ?
C10 C9 Se13 118.67(16) . . ?
C8a C9 Se13 119.74(17) . . ?
C8a C9 C10 121.6(2) . . ?
C10a C4a C4 118.0(2) . . ?
C4b C4a C4 122.58(19) . . ?
C4b C4a C10a 119.37(19) . . ?
C15 C16 C17 120.2(2) . . ?
C20 C21 C22 119.9(3) . . ?
C19 C18 C17 120.6(2) . . ?
C21 C22 C23 120.8(3) . . ?
C10 C20 C25 118.89(19) . . ?
C21 C20 C25 119.1(2) . . ?
C21 C20 C10 121.9(2) . . ?
C9 C8a C8 121.7(2) . . ?
C4b C8a C8 119.29(19) . . ?
C4b C8a C9 119.0(2) . . ?
C4b C5 C6 120.9(2) . . ?
C8a C4b C4a 120.09(19) . . ?
C5 C4b C4a 121.0(2) . . ?
C5 C4b C8a 118.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se13 C14 1.9212(18) . ?
Se13 C9 1.929(2) . ?
C14 C15 1.391(3) . ?
C14 C19 1.391(3) . ?
C4 C3 1.360(4) . ?
C4 C4a 1.415(3) . ?
N12 C11 1.135(4) . ?
C17 C16 1.386(4) . ?
C17 C18 1.384(4) . ?
C25 C24 1.393(3) . ?
C25 C20 1.398(3) . ?
C10a C1 1.408(4) . ?
C10a C10 1.451(3) . ?
C10a C4a 1.421(3) . ?
C23 C24 1.384(4) . ?
C23 C22 1.377(5) . ?
C1 C2 1.382(4) . ?
C6 C7 1.400(4) . ?
C6 C5 1.370(3) . ?
C2 C3 1.412(3) . ?
C2 C11 1.439(4) . ?
C10 C9 1.364(3) . ?
C10 C20 1.495(3) . ?
C15 C16 1.395(3) . ?
C8 C7 1.389(3) . ?
C8 C8a 1.408(3) . ?
C19 C18 1.394(3) . ?
C9 C8a 1.453(3) . ?
C4a C4b 1.446(3) . ?
C21 C22 1.392(4) . ?
C21 C20 1.392(3) . ?
C8a C4b 1.408(3) . ?
C5 C4b 1.421(3) . ?
