#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:53:58 +0300 (Wed, 05 May 2021) $
#$Revision: 264915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060492.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_7060492
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_formula_moiety         'C27 H20 Se'
_chemical_formula_sum            'C27 H20 Se'
_chemical_formula_weight         423.419
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-07
_audit_update_record
;
2020-11-06 deposited with the CCDC.	2021-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.3292(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.79929(10)
_cell_length_b                   7.77564(4)
_cell_length_c                   17.03739(11)
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      75.0
_cell_measurement_theta_min      0.9
_cell_volume                     1986.85(2)
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22517
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9988
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.37
_diffrn_reflns_theta_min         5.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_T_max  0.93601
_exptl_absorpt_correction_T_min  0.60153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.4133
_refine_diff_density_min         -0.4396
_refine_diff_density_rms         0.0556
_refine_ls_d_res_high            0.7901
_refine_ls_d_res_low             8.2896
_refine_ls_goodness_of_fit_ref   1.0370
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0370
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+1.0935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0756
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -19
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                4044
_reflns_number_total             4210
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1nj00401h2.cif
_cod_data_source_block           A753
_cod_depositor_comments
'Adding full bibliography for 7060487--7060492.cif.'
_cod_database_code               7060492
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.613
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
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
C1 C 0.13676(11) 0.5489(2) 0.74490(10) 0.0287(3) Uani 1.000000 .
H1 H 0.11089(11) 0.5683(2) 0.68854(10) 0.0344(4) Uiso 1.000000 R
C2 C 0.12510(11) 0.6690(2) 0.80030(11) 0.0332(3) Uani 1.000000 .
C3 C 0.16397(13) 0.6361(2) 0.88498(12) 0.0387(4) Uani 1.000000 .
H3 H 0.15435(13) 0.7128(2) 0.92319(12) 0.0464(5) Uiso 1.000000 R
C4 C 0.21583(12) 0.4935(3) 0.91280(11) 0.0362(4) Uani 1.000000 .
H4 H 0.2382(17) 0.472(3) 0.9711(16) 0.049(6) Uiso 1.000000 .
C4A C 0.23025(10) 0.3712(2) 0.85686(9) 0.0276(3) Uani 1.000000 .
C4B C 0.28490(10) 0.2196(2) 0.88441(9) 0.0276(3) Uani 1.000000 .
C5 C 0.33690(11) 0.1957(2) 0.96827(10) 0.0329(3) Uani 1.000000 .
H5 H 0.3379(15) 0.282(3) 1.0062(14) 0.040(6) Uiso 1.000000 .
C6 C 0.38487(12) 0.0480(2) 0.99376(11) 0.0369(4) Uani 1.000000 .
H6 H 0.41905(12) 0.0351(2) 1.04889(11) 0.0443(5) Uiso 1.000000 R
C7 C 0.38258(12) -0.0835(3) 0.93709(11) 0.0379(4) Uani 1.000000 .
H7 H 0.41342(12) -0.1854(3) 0.95497(11) 0.0454(5) Uiso 1.000000 R
C8 C 0.33486(12) -0.0622(2) 0.85512(11) 0.0334(4) Uani 1.000000 .
H8 H 0.33435(12) -0.1498(2) 0.81782(11) 0.0401(4) Uiso 1.000000 R
C8A C 0.28658(10) 0.0902(2) 0.82645(9) 0.0272(3) Uani 1.000000 .
C9 C 0.23938(10) 0.1198(2) 0.73943(9) 0.0259(3) Uani 1.000000 .
C10 C 0.19323(10) 0.2667(2) 0.71253(9) 0.0254(3) Uani 1.000000 .
C10A C 0.18699(10) 0.3972(2) 0.77153(9) 0.0258(3) Uani 1.000000 .
C11 C 0.07074(13) 0.8295(2) 0.77101(13) 0.0415(4) Uani 1.000000 .
H11a H 0.0578(9) 0.8408(12) 0.7123(2) 0.0622(6) Uiso 1.000000 GR
H11b H 0.0160(5) 0.8218(10) 0.7840(9) 0.0622(6) Uiso 1.000000 GR
H11c H 0.1039(5) 0.9280(3) 0.7981(8) 0.0622(6) Uiso 1.000000 GR
Se12 Se 0.244229(11) -0.05376(2) 0.659625(10) 0.02912(8) Uani 1.000000 .
C13 C 0.36363(11) -0.0175(2) 0.65754(9) 0.0272(3) Uani 1.000000 .
C14 C 0.41442(13) 0.1239(2) 0.69367(12) 0.0388(4) Uani 1.000000 .
H14 H 0.39123(13) 0.2065(2) 0.72070(12) 0.0466(5) Uiso 1.000000 R
C15 C 0.50020(14) 0.1412(3) 0.68916(14) 0.0492(5) Uani 1.000000 .
H15 H 0.53425(14) 0.2363(3) 0.71315(14) 0.0590(6) Uiso 1.000000 R
C16 C 0.53575(14) 0.0192(3) 0.64957(13) 0.0460(5) Uani 1.000000 .
H16 H 0.59365(14) 0.0310(3) 0.64767(13) 0.0552(5) Uiso 1.000000 R
C17 C 0.48456(13) -0.1205(3) 0.61286(12) 0.0435(4) Uani 1.000000 .
H17 H 0.50780(13) -0.2025(3) 0.58560(12) 0.0522(5) Uiso 1.000000 R
C18 C 0.39845(12) -0.1387(2) 0.61655(11) 0.0361(4) Uani 1.000000 .
H18 H 0.36404(12) -0.2326(2) 0.59143(11) 0.0433(4) Uiso 1.000000 R
C19 C 0.14706(10) 0.2977(2) 0.62236(9) 0.0277(3) Uani 1.000000 .
C20 C 0.18675(12) 0.4024(2) 0.57785(11) 0.0345(4) Uani 1.000000 .
H20 H 0.24041(12) 0.4571(2) 0.60469(11) 0.0414(4) Uiso 1.000000 R
C21 C 0.14658(14) 0.4258(3) 0.49335(11) 0.0411(4) Uani 1.000000 .
H21 H 0.17394(14) 0.4944(3) 0.46364(11) 0.0494(5) Uiso 1.000000 R
C22 C 0.06653(14) 0.3478(3) 0.45375(11) 0.0439(5) Uani 1.000000 .
H22 H 0.03982(14) 0.3638(3) 0.39725(11) 0.0527(5) Uiso 1.000000 R
C23 C 0.02543(13) 0.2455(3) 0.49738(11) 0.0431(4) Uani 1.000000 .
H23 H -0.02895(13) 0.1935(3) 0.47039(11) 0.0517(5) Uiso 1.000000 R
C24 C 0.06570(11) 0.2206(2) 0.58191(10) 0.0345(4) Uani 1.000000 .
H24 H 0.03801(11) 0.1521(2) 0.61136(10) 0.0415(4) Uiso 1.000000 R
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'
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
C2 C1 H1 119.11(10) . . ?
C10A C1 H1 119.11(9) . . ?
C10A C1 C2 121.78(16) . . ?
C3 C2 C1 118.07(16) . . ?
C11 C2 C1 121.19(16) . . ?
C11 C2 C3 120.72(16) . . ?
H3 C3 C2 119.21(10) . . ?
C4 C3 C2 121.58(16) . . ?
C4 C3 H3 119.21(10) . . ?
H4 C4 C3 119.0(15) . . ?
C4A C4 C3 121.04(16) . . ?
C4A C4 H4 119.7(15) . . ?
C4B C4A C4 122.29(15) . . ?
C10A C4A C4 117.98(15) . . ?
C10A C4A C4B 119.69(14) . . ?
C5 C4B C4A 122.00(15) . . ?
C8A C4B C4A 119.49(14) . . ?
C8A C4B C5 118.51(15) . . ?
H5 C5 C4B 118.8(14) . . ?
C6 C5 C4B 121.11(17) . . ?
C6 C5 H5 120.0(14) . . ?
H6 C6 C5 119.92(10) . . ?
C7 C6 C5 120.16(16) . . ?
C7 C6 H6 119.92(10) . . ?
H7 C7 C6 119.97(10) . . ?
C8 C7 C6 120.07(17) . . ?
C8 C7 H7 119.97(11) . . ?
H8 C8 C7 119.41(11) . . ?
C8A C8 C7 121.18(17) . . ?
C8A C8 H8 119.41(10) . . ?
C8 C8A C4B 118.83(14) . . ?
C9 C8A C4B 118.86(14) . . ?
C9 C8A C8 122.31(15) . . ?
C10 C9 C8A 121.84(14) . . ?
Se12 C9 C8A 119.05(12) . . ?
Se12 C9 C10 119.10(11) . . ?
C10A C10 C9 120.06(14) . . ?
C19 C10 C9 121.27(14) . . ?
C19 C10 C10A 118.67(14) . . ?
C4A C10A C1 119.35(14) . . ?
C10 C10A C1 120.91(14) . . ?
C10 C10A C4A 119.73(14) . . ?
H11a C11 C2 109.5 . . ?
H11b C11 C2 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C2 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C13 Se12 C9 99.62(7) . . ?
C14 C13 Se12 122.93(13) . . ?
C18 C13 Se12 117.25(13) . . ?
C18 C13 C14 119.81(16) . . ?
H14 C14 C13 120.29(10) . . ?
C15 C14 C13 119.42(17) . . ?
C15 C14 H14 120.29(11) . . ?
H15 C15 C14 119.51(11) . . ?
C16 C15 C14 120.98(18) . . ?
C16 C15 H15 119.51(12) . . ?
H16 C16 C15 120.30(12) . . ?
C17 C16 C15 119.40(18) . . ?
C17 C16 H16 120.30(11) . . ?
H17 C17 C16 119.92(11) . . ?
C18 C17 C16 120.17(17) . . ?
C18 C17 H17 119.92(11) . . ?
C17 C18 C13 120.20(17) . . ?
H18 C18 C13 119.90(10) . . ?
H18 C18 C17 119.90(11) . . ?
C20 C19 C10 119.73(15) . . ?
C24 C19 C10 121.04(15) . . ?
C24 C19 C20 119.22(15) . . ?
H20 C20 C19 119.85(10) . . ?
C21 C20 C19 120.29(18) . . ?
C21 C20 H20 119.85(12) . . ?
H21 C21 C20 119.98(12) . . ?
C22 C21 C20 120.03(18) . . ?
C22 C21 H21 119.98(11) . . ?
H22 C22 C21 119.81(11) . . ?
C23 C22 C21 120.39(16) . . ?
C23 C22 H22 119.81(11) . . ?
H23 C23 C22 120.10(11) . . ?
C24 C23 C22 119.81(18) . . ?
C24 C23 H23 120.10(12) . . ?
C23 C24 C19 120.24(17) . . ?
H24 C24 C19 119.88(10) . . ?
H24 C24 C23 119.88(12) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.380(2) . ?
C1 C10A 1.415(2) . ?
C2 C3 1.403(3) . ?
C2 C11 1.508(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(3) . ?
C4 H4 0.96(3) . ?
C4 C4A 1.414(2) . ?
C4A C4B 1.450(2) . ?
C4A C10A 1.413(2) . ?
C4B C5 1.419(2) . ?
C4B C8A 1.416(2) . ?
C5 H5 0.93(2) . ?
C5 C6 1.369(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(2) . ?
C8 H8 0.9300 . ?
C8 C8A 1.411(2) . ?
C8A C9 1.453(2) . ?
C9 C10 1.355(2) . ?
C9 Se12 1.9341(15) . ?
C10 C10A 1.453(2) . ?
C10 C19 1.498(2) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
Se12 C13 1.9187(16) . ?
C13 C14 1.386(2) . ?
C13 C18 1.386(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(2) . ?
C19 C24 1.389(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(2) . ?
C24 H24 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 3.12(19) . . . . ?
C1 C10A C4A C4 4.60(18) . . . . ?
C1 C10A C4A C4B -177.43(14) . . . . ?
C1 C10A C10 C9 -177.95(15) . . . . ?
C1 C10A C10 C19 1.42(17) . . . . ?
C2 C3 C4 C4A -1.7(2) . . . . ?
C3 C4 C4A C4B 179.83(17) . . . . ?
C3 C4 C4A C10A -2.3(2) . . . . ?
C4 C4A C4B C5 -8.60(19) . . . . ?
C4 C4A C4B C8A 171.07(16) . . . . ?
C4 C4A C10A C10 -174.24(14) . . . . ?
C4A C4B C5 C6 176.95(16) . . . . ?
C4A C4B C8A C8 -175.42(15) . . . . ?
C4A C4B C8A C9 5.28(16) . . . . ?
C4A C10A C10 C9 0.88(17) . . . . ?
C4A C10A C10 C19 -179.75(14) . . . . ?
C4B C5 C6 C7 -0.6(2) . . . . ?
C4B C8A C8 C7 -2.59(18) . . . . ?
C4B C8A C9 C10 -0.69(17) . . . . ?
C4B C8A C9 Se12 178.26(11) . . . . ?
C5 C6 C7 C8 2.4(2) . . . . ?
C6 C7 C8 C8A -0.8(2) . . . . ?
C7 C8 C8A C9 176.68(16) . . . . ?
C8 C8A C9 C10 -179.96(16) . . . . ?
C8 C8A C9 Se12 -1.01(17) . . . . ?
C8A C9 C10 C10A -2.43(18) . . . . ?
C8A C9 C10 C19 178.21(14) . . . . ?
C9 C10 C19 C20 -100.41(17) . . . . ?
C9 C10 C19 C24 78.35(17) . . . . ?
C10 C19 C20 C21 177.02(16) . . . . ?
C10 C19 C24 C23 -177.49(16) . . . . ?
Se12 C13 C14 C15 -179.73(17) . . . . ?
Se12 C13 C18 C17 -179.85(14) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C13 C18 C17 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C19 C20 C21 C22 1.2(2) . . . . ?
C19 C24 C23 C22 -0.2(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
