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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/32/7123268.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_7123268
loop_
_publ_author_name
'Qiao, Yanjun'
'Lu, Yifan'
'Chen, Weinan'
'Chen, Yijing'
'Baumgarten, Martin'
'Zhou, Gang'
_publ_section_title
;
 Cyclopenta[b]thiopyran and Cyclopenta[b]selenopyran Based Heteroarenes:
 Electronic Communication Between S- and/or Se-Fused Aromatics
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01761E
_journal_year                    2019
_chemical_formula_moiety         'C38 H44 Se2'
_chemical_formula_sum            'C38 H44 Se2'
_chemical_formula_weight         658.65
_chemical_name_common            QYJ-1
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-01-13 deposited with the CCDC.    2019-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                78.341(2)
_cell_angle_beta                 88.254(2)
_cell_angle_gamma                80.527(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0411(3)
_cell_length_b                   9.2861(5)
_cell_length_c                   17.3658(10)
_cell_measurement_reflns_used    9440
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      2.60
_cell_volume                     785.30(8)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12734
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.366
_diffrn_reflns_theta_min         4.928
_exptl_absorpt_coefficient_mu    3.113
_exptl_crystal_colour            'Dark Green'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6041
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0395P)²+1.8661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2628
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc01761e2.cif
_cod_data_source_block           t_a_CCDC1
_cod_database_code               7123268
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.522
_shelx_estimated_absorpt_t_max   0.604
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Se1 Se 1.34488(9) 0.33059(5) 0.76855(3) 0.04653(17) Uani 1 1 d . .
C1 C 1.3789(9) 0.1227(5) 0.7803(3) 0.0512(10) Uani 1 1 d . .
H1 H 1.506170 0.076524 0.749406 0.061 Uiso 1 1 calc R U
C2 C 1.2356(9) 0.0365(5) 0.8293(3) 0.0503(10) Uani 1 1 d . .
H2 H 1.271238 -0.065218 0.829803 0.060 Uiso 1 1 calc R U
C3 C 1.0319(8) 0.0862(4) 0.8810(2) 0.0429(9) Uani 1 1 d . .
H3 H 0.941382 0.015473 0.911604 0.052 Uiso 1 1 calc R U
C4 C 0.9617(7) 0.2300(4) 0.8885(2) 0.0368(8) Uani 1 1 d . .
C5 C 1.0798(7) 0.3564(4) 0.8450(2) 0.0373(8) Uani 1 1 d . .
C6 C 0.9703(7) 0.4850(4) 0.8673(2) 0.0350(8) Uani 1 1 d . .
C7 C 0.7687(7) 0.4473(4) 0.9284(2) 0.0328(7) Uani 1 1 d . .
C9 C 0.5817(8) 0.2253(4) 0.9911(2) 0.0372(8) Uani 1 1 d . .
H9 H 0.579673 0.123715 0.996850 0.045 Uiso 1 1 calc R U
C8 C 0.7633(7) 0.2944(4) 0.9394(2) 0.0342(7) Uani 1 1 d . .
C10 C 0.4077(8) 0.3092(4) 1.0330(2) 0.0365(8) Uani 1 1 d . .
H10 H 0.285292 0.263323 1.066435 0.044 Uiso 1 1 calc R U
C11 C 0.4078(7) 0.4635(4) 1.02701(19) 0.0326(7) Uani 1 1 d . .
C12 C 1.0473(8) 0.6346(4) 0.8325(2) 0.0386(8) Uani 1 1 d . .
H12A H 1.218336 0.619445 0.805747 0.046 Uiso 1 1 calc R U
H12B H 1.071504 0.685482 0.874772 0.046 Uiso 1 1 calc R U
C13 C 0.8375(8) 0.7352(4) 0.7739(2) 0.0429(9) Uani 1 1 d . .
H13A H 0.668188 0.752832 0.801234 0.052 Uiso 1 1 calc R U
H13B H 0.896417 0.830708 0.756064 0.052 Uiso 1 1 calc R U
C14 C 0.7904(9) 0.6718(5) 0.7033(2) 0.0473(9) Uani 1 1 d . .
H14A H 0.736137 0.575024 0.721129 0.057 Uiso 1 1 calc R U
H14B H 0.958524 0.656774 0.675084 0.057 Uiso 1 1 calc R U
C15 C 0.5778(9) 0.7695(5) 0.6469(2) 0.0516(10) Uani 1 1 d . .
H15A H 0.412016 0.788865 0.675609 0.062 Uiso 1 1 calc R U
H15B H 0.636471 0.864370 0.626724 0.062 Uiso 1 1 calc R U
C16 C 0.5215(10) 0.7006(6) 0.5780(3) 0.0597(12) Uani 1 1 d . .
H16A H 0.689421 0.677864 0.550834 0.072 Uiso 1 1 calc R U
H16B H 0.458583 0.607047 0.598564 0.072 Uiso 1 1 calc R U
C17 C 0.3182(11) 0.7953(6) 0.5189(3) 0.0621(12) Uani 1 1 d . .
H17A H 0.148885 0.816922 0.545627 0.075 Uiso 1 1 calc R U
H17B H 0.379545 0.889364 0.498449 0.075 Uiso 1 1 calc R U
C18 C 0.2702(14) 0.7241(8) 0.4510(3) 0.0877(18) Uani 1 1 d . .
H18A H 0.206600 0.630720 0.471477 0.105 Uiso 1 1 calc R U
H18B H 0.440125 0.701163 0.424816 0.105 Uiso 1 1 calc R U
C19 C 0.0693(15) 0.8195(9) 0.3909(4) 0.109(3) Uani 1 1 d . .
H19A H 0.139491 0.907390 0.365962 0.163 Uiso 1 1 calc R U
H19B H -0.096756 0.847661 0.416672 0.163 Uiso 1 1 calc R U
H19C H 0.037819 0.763973 0.352016 0.163 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C5 Se1 C1 98.12(18) . .
C2 C1 Se1 125.2(3) . .
C2 C1 H1 117.4 . .
Se1 C1 H1 117.4 . .
C1 C2 C3 125.7(4) . .
C1 C2 H2 117.2 . .
C3 C2 H2 117.2 . .
C4 C3 C2 124.2(4) . .
C4 C3 H3 117.9 . .
C2 C3 H3 117.9 . .
C3 C4 C8 129.6(4) . .
C3 C4 C5 125.7(4) . .
C8 C4 C5 104.7(3) . .
C6 C5 C4 111.3(3) . .
C6 C5 Se1 127.6(3) . .
C4 C5 Se1 121.1(3) . .
C5 C6 C7 107.0(3) . .
C5 C6 C12 123.9(3) . .
C7 C6 C12 129.1(3) . .
C8 C7 C11 119.8(3) . 2_667
C8 C7 C6 108.1(3) . .
C11 C7 C6 132.1(3) 2_667 .
C10 C9 C8 119.2(3) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
C7 C8 C9 121.9(3) . .
C7 C8 C4 109.0(3) . .
C9 C8 C4 129.1(3) . .
C9 C10 C11 122.2(3) . .
C9 C10 H10 118.9 . .
C11 C10 H10 118.9 . .
C10 C11 C7 123.1(3) . 2_667
C10 C11 C11 119.1(4) . 2_667
C7 C11 C11 117.8(4) 2_667 2_667
C6 C12 C13 113.5(3) . .
C6 C12 H12A 108.9 . .
C13 C12 H12A 108.9 . .
C6 C12 H12B 108.9 . .
C13 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C14 C13 C12 114.2(3) . .
C14 C13 H13A 108.7 . .
C12 C13 H13A 108.7 . .
C14 C13 H13B 108.7 . .
C12 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C13 C14 C15 113.9(4) . .
C13 C14 H14A 108.8 . .
C15 C14 H14A 108.8 . .
C13 C14 H14B 108.8 . .
C15 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C16 C15 C14 113.4(4) . .
C16 C15 H15A 108.9 . .
C14 C15 H15A 108.9 . .
C16 C15 H15B 108.9 . .
C14 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C17 C16 C15 115.5(4) . .
C17 C16 H16A 108.4 . .
C15 C16 H16A 108.4 . .
C17 C16 H16B 108.4 . .
C15 C16 H16B 108.4 . .
H16A C16 H16B 107.5 . .
C18 C17 C16 114.0(5) . .
C18 C17 H17A 108.8 . .
C16 C17 H17A 108.8 . .
C18 C17 H17B 108.8 . .
C16 C17 H17B 108.8 . .
H17A C17 H17B 107.7 . .
C17 C18 C19 114.2(6) . .
C17 C18 H18A 108.7 . .
C19 C18 H18A 108.7 . .
C17 C18 H18B 108.7 . .
C19 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C5 1.876(4) .
Se1 C1 1.879(4) .
C1 C2 1.328(6) .
C1 H1 0.9300 .
C2 C3 1.425(6) .
C2 H2 0.9300 .
C3 C4 1.355(5) .
C3 H3 0.9300 .
C4 C8 1.450(5) .
C4 C5 1.465(5) .
C5 C6 1.356(5) .
C6 C7 1.478(5) .
C6 C12 1.507(5) .
C7 C8 1.399(5) .
C7 C11 1.432(5) 2_667
C9 C10 1.367(5) .
C9 C8 1.402(5) .
C9 H9 0.9300 .
C10 C11 1.416(5) .
C10 H10 0.9300 .
C11 C11 1.449(7) 2_667
C12 C13 1.544(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.504(6) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.522(6) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.520(6) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.510(6) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.508(7) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.515(9) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
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_4
C5 Se1 C1 C2 1.9(4) . .
Se1 C1 C2 C3 0.1(7) . .
C1 C2 C3 C4 -1.8(7) . .
C2 C3 C4 C8 -178.8(4) . .
C2 C3 C4 C5 0.5(6) . .
C3 C4 C5 C6 -178.5(3) . .
C8 C4 C5 C6 0.9(4) . .
C3 C4 C5 Se1 2.2(5) . .
C8 C4 C5 Se1 -178.4(2) . .
C1 Se1 C5 C6 177.9(3) . .
C1 Se1 C5 C4 -2.8(3) . .
C4 C5 C6 C7 0.0(4) . .
Se1 C5 C6 C7 179.2(2) . .
C4 C5 C6 C12 -179.2(3) . .
Se1 C5 C6 C12 0.1(5) . .
C5 C6 C7 C8 -0.9(4) . .
C12 C6 C7 C8 178.1(3) . .
C5 C6 C7 C11 180.0(4) . 2_667
C12 C6 C7 C11 -1.0(6) . 2_667
C11 C7 C8 C9 2.5(5) 2_667 .
C6 C7 C8 C9 -176.8(3) . .
C11 C7 C8 C4 -179.3(3) 2_667 .
C6 C7 C8 C4 1.5(4) . .
C10 C9 C8 C7 -1.1(5) . .
C10 C9 C8 C4 -179.0(3) . .
C3 C4 C8 C7 177.9(4) . .
C5 C4 C8 C7 -1.5(4) . .
C3 C4 C8 C9 -4.0(6) . .
C5 C4 C8 C9 176.6(3) . .
C8 C9 C10 C11 -1.2(5) . .
C9 C10 C11 C7 -178.6(3) . 2_667
C9 C10 C11 C11 2.0(6) . 2_667
C5 C6 C12 C13 103.8(4) . .
C7 C6 C12 C13 -75.1(5) . .
C6 C12 C13 C14 -61.2(5) . .
C12 C13 C14 C15 178.4(3) . .
C13 C14 C15 C16 -177.0(4) . .
C14 C15 C16 C17 -178.2(4) . .
C15 C16 C17 C18 179.3(5) . .
C16 C17 C18 C19 -179.2(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189704
