#------------------------------------------------------------------------------
#$Date: 2025-11-29 18:56:37 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303580 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/51/7135115.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_7135115
loop_
_publ_author_name
'Schmiedtchen, Marco'
'Thulaseedharan Nair Sailaja, Sidharth'
'Lorberg, Rick Y.'
'Wölper, Christoph'
'Galstyan, Anzhela'
'Voskuhl, Jens'
_publ_section_title
;
 Tuneable phosphorescence and singlet oxygen production of bridged ethers
 via chalcogen variation and photocyclisation.
;
_journal_issue                   95
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              18810
_journal_page_last               18813
_journal_paper_doi               10.1039/d5cc05206h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C31.5 H26 N2 O2 S2 Se2'
_chemical_formula_weight         686.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2025-07-29 deposited with the CCDC.	2025-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                104.048(3)
_cell_angle_beta                 91.718(3)
_cell_angle_gamma                99.820(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2952(3)
_cell_length_b                   11.3991(6)
_cell_length_c                   20.6848(11)
_cell_measurement_reflns_used    9278
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.84
_cell_measurement_theta_min      2.35
_cell_volume                     1414.88(13)
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_collection       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/Queen'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            102276
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.295
_diffrn_reflns_theta_min         1.873
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.794
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Blessing, Acta Cryst 1995 A51 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       tablet
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.725
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         10886
_refine_ls_number_restraints     378
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+1.0204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8624
_reflns_number_total             10886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc05206h2.cif
_cod_data_source_block           ms_sp02m_sq
_cod_depositor_comments
'Adding full bibliography for 7135109--7135115.cif.'
_cod_original_formula_sum        'C31.50 H26 N2 O2 S2 Se2'
_cod_database_code               7135115
_shelx_shelxl_version_number     2017/1
_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   0.429
_shelx_estimated_absorpt_t_max   0.841
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.71669(3) 0.39169(2) 0.50162(2) 0.01422(4) Uani 1 1 d . . . . .
Se2 Se 0.22305(3) 0.24063(2) 0.52152(2) 0.01763(5) Uani 1 1 d . . . . .
S1 S 0.84632(8) 0.57032(4) 0.77918(2) 0.02233(9) Uani 1 1 d . . . . .
S2 S 0.37450(9) 0.41190(5) 0.79661(2) 0.02420(10) Uani 1 1 d . . . . .
N1 N -0.0294(3) 0.21704(16) 0.67241(10) 0.0277(4) Uani 1 1 d . . . . .
N2 N 1.1420(3) 0.56657(16) 0.63374(9) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.6226(3) 0.38940(14) 0.58819(8) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.4184(3) 0.32714(14) 0.59628(8) 0.0143(3) Uani 1 1 d . . . . .
C3 C 0.3527(3) 0.33160(15) 0.66113(9) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.4825(3) 0.40317(15) 0.71808(9) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.6835(3) 0.46988(15) 0.71002(8) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.7548(3) 0.45752(14) 0.64517(9) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.6242(3) 0.22056(15) 0.45940(8) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.4218(3) 0.15806(15) 0.46854(8) 0.0152(3) Uani 1 1 d . . . . .
C9 C 0.3563(3) 0.03334(16) 0.43654(9) 0.0192(3) Uani 1 1 d . . . . .
H9 H 0.219991 -0.009932 0.443881 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4921(3) -0.02665(16) 0.39399(10) 0.0228(4) Uani 1 1 d . . . . .
H10 H 0.446889 -0.110828 0.371262 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6932(3) 0.03537(17) 0.38442(10) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.785140 -0.006546 0.355248 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7615(3) 0.15904(16) 0.41738(9) 0.0186(3) Uani 1 1 d . . . . .
H12 H 0.900330 0.201091 0.411297 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1408(3) 0.26669(16) 0.66862(9) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.9699(3) 0.51919(16) 0.63806(9) 0.0175(3) Uani 1 1 d . . . . .
O1 O 1.1716(13) 1.0204(6) 0.7843(5) 0.0399(15) Uani 0.65(3) 1 d . . P A 3
C15 C 0.8327(16) 0.7133(9) 0.7575(6) 0.0175(13) Uani 0.65(3) 1 d . . P A 3
C16 C 1.0124(15) 0.8064(8) 0.7791(5) 0.0204(12) Uani 0.65(3) 1 d . . P A 3
H16 H 1.134768 0.792676 0.802250 0.024 Uiso 0.65(3) 1 calc R U P A 3
C17 C 1.0082(14) 0.9213(7) 0.7659(5) 0.0266(12) Uani 0.65(3) 1 d . . P A 3
C18 C 0.8373(15) 0.9376(7) 0.7286(4) 0.0303(13) Uani 0.65(3) 1 d . . P A 3
H18 H 0.840815 1.013461 0.716904 0.036 Uiso 0.65(3) 1 calc R U P A 3
C19 C 0.6606(19) 0.8446(7) 0.7080(5) 0.0349(17) Uani 0.65(3) 1 d . . P A 3
H19 H 0.540363 0.858171 0.683735 0.042 Uiso 0.65(3) 1 calc R U P A 3
C20 C 0.6557(17) 0.7304(8) 0.7222(5) 0.0259(14) Uani 0.65(3) 1 d . . P A 3
H20 H 0.533703 0.666229 0.707984 0.031 Uiso 0.65(3) 1 calc R U P A 3
C21 C 1.3475(11) 1.0088(7) 0.8247(8) 0.049(2) Uani 0.65(3) 1 d . . P A 3
H21A H 1.294921 0.988139 0.865402 0.059 Uiso 0.65(3) 1 calc R U P A 3
H21B H 1.450975 1.086655 0.836697 0.059 Uiso 0.65(3) 1 calc R U P A 3
H21C H 1.418770 0.943356 0.800024 0.059 Uiso 0.65(3) 1 calc R U P A 3
C15' C 0.882(3) 0.713(2) 0.7593(12) 0.021(2) Uani 0.35(3) 1 d . . P A 4
O1' O 1.224(3) 1.0171(12) 0.8031(9) 0.050(3) Uani 0.35(3) 1 d . . P A 4
C16' C 1.059(3) 0.8013(19) 0.7874(11) 0.031(3) Uani 0.35(3) 1 d . . P A 4
H16' H 1.170849 0.783827 0.813420 0.037 Uiso 0.35(3) 1 calc R U P A 4
C17' C 1.068(4) 0.9191(17) 0.7760(10) 0.039(3) Uani 0.35(3) 1 d . . P A 4
C18' C 0.907(4) 0.9475(12) 0.7417(9) 0.041(3) Uani 0.35(3) 1 d . . P A 4
H18' H 0.912976 1.029247 0.737714 0.050 Uiso 0.35(3) 1 calc R U P A 4
C19' C 0.735(4) 0.8562(15) 0.7123(9) 0.034(3) Uani 0.35(3) 1 d . . P A 4
H19' H 0.626754 0.873013 0.684588 0.040 Uiso 0.35(3) 1 calc R U P A 4
C20' C 0.718(3) 0.7398(16) 0.7233(10) 0.026(2) Uani 0.35(3) 1 d . . P A 4
H20' H 0.593938 0.678710 0.706006 0.031 Uiso 0.35(3) 1 calc R U P A 4
C21' C 1.373(3) 1.0003(17) 0.8492(9) 0.058(4) Uani 0.35(3) 1 d . . P A 4
H21D H 1.453116 0.937130 0.827240 0.070 Uiso 0.35(3) 1 calc R U P A 4
H21E H 1.296722 0.973978 0.885428 0.070 Uiso 0.35(3) 1 calc R U P A 4
H21F H 1.473531 1.077841 0.867690 0.070 Uiso 0.35(3) 1 calc R U P A 4
C27 C 0.7160(3) 0.2917(2) 0.81390(11) 0.0267(4) Uani 1 1 d . U . . .
H27 H 0.722345 0.272772 0.766753 0.032 Uiso 0.5 1 calc R U P B 1
H27' H 0.715690 0.261540 0.766854 0.032 Uiso 0.5 1 calc R U P C 2
O2 O 0.7843(6) 0.4391(4) 1.01639(15) 0.0404(9) Uani 0.5 1 d . U P D 1
C22 C 0.5435(12) 0.3559(10) 0.8413(6) 0.0167(13) Uani 0.5 1 d . U P D 1
C23 C 0.6175(7) 0.4179(4) 0.91148(19) 0.0236(7) Uani 0.5 1 d . U P D 1
H23 H 0.554250 0.486032 0.932463 0.028 Uiso 0.5 1 calc R U P D 1
C24 C 0.7734(7) 0.3846(4) 0.94970(19) 0.0260(8) Uani 0.5 1 d . U P D 1
C25 C 0.9041(8) 0.3043(5) 0.9190(3) 0.0263(9) Uani 0.5 1 d . U P D 1
H25 H 1.012517 0.284135 0.945169 0.032 Uiso 0.5 1 calc R U P D 1
C26 C 0.879(2) 0.2540(14) 0.8519(6) 0.0236(15) Uani 0.5 1 d . U P D 1
H26 H 0.963589 0.196541 0.830707 0.028 Uiso 0.5 1 calc R U P D 1
C28 C 0.9438(10) 0.4114(6) 1.0583(2) 0.0419(12) Uani 0.5 1 d . U P D 1
H28A H 0.906974 0.324735 1.059215 0.063 Uiso 0.5 1 calc R U P D 1
H28B H 0.947668 0.463672 1.103721 0.063 Uiso 0.5 1 calc R U P D 1
H28C H 1.085820 0.426679 1.040673 0.063 Uiso 0.5 1 calc R U P D 1
O2' O 0.5670(13) 0.3467(5) 1.0152(2) 0.0829(19) Uani 0.5 1 d . U P D 2
C22' C 0.5982(12) 0.3692(11) 0.8434(7) 0.0198(15) Uani 0.5 1 d . U P D 2
C23' C 0.5019(11) 0.3722(4) 0.9088(2) 0.0346(10) Uani 0.5 1 d . U P D 2
H23' H 0.370730 0.399811 0.920349 0.042 Uiso 0.5 1 calc R U P D 2
C24' C 0.6296(13) 0.3292(5) 0.9504(2) 0.0492(14) Uani 0.5 1 d . U P D 2
C25' C 0.8011(13) 0.2740(5) 0.9267(3) 0.0474(14) Uani 0.5 1 d . U P D 2
H25' H 0.891593 0.246411 0.955248 0.057 Uiso 0.5 1 calc R U P D 2
C26' C 0.836(2) 0.2605(15) 0.8582(7) 0.035(2) Uani 0.5 1 d . U P D 2
H26' H 0.957393 0.225606 0.842565 0.043 Uiso 0.5 1 calc R U P D 2
C28' C 0.704(2) 0.3165(9) 1.0625(3) 0.130(5) Uani 0.5 1 d . U P D 2
H28D H 0.656007 0.343698 1.107462 0.195 Uiso 0.5 1 calc R U P D 2
H28E H 0.853313 0.357786 1.061224 0.195 Uiso 0.5 1 calc R U P D 2
H28F H 0.697462 0.227274 1.051463 0.195 Uiso 0.5 1 calc R U P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
_geom_angle_publ_flag
C1 Se1 C7 98.03(7) . . ?
C2 Se2 C8 97.93(7) . . ?
C15' S1 C5 103.6(8) . . ?
C5 S1 C15 98.0(3) . . ?
C22 S2 C4 105.9(4) . . ?
C4 S2 C22' 100.5(4) . . ?
C2 C1 C6 118.79(15) . . ?
C2 C1 Se1 121.35(12) . . ?
C6 C1 Se1 119.74(12) . . ?
C1 C2 C3 119.42(15) . . ?
C1 C2 Se2 121.33(13) . . ?
C3 C2 Se2 119.22(12) . . ?
C4 C3 C2 121.63(15) . . ?
C4 C3 C13 119.53(16) . . ?
C2 C3 C13 118.72(15) . . ?
C5 C4 C3 119.00(15) . . ?
C5 C4 S2 123.14(13) . . ?
C3 C4 S2 117.73(13) . . ?
C4 C5 C6 118.90(15) . . ?
C4 C5 S1 121.26(13) . . ?
C6 C5 S1 119.83(13) . . ?
C1 C6 C5 121.97(16) . . ?
C1 C6 C14 119.72(15) . . ?
C5 C6 C14 118.30(15) . . ?
C8 C7 C12 119.92(15) . . ?
C8 C7 Se1 121.22(12) . . ?
C12 C7 Se1 118.84(13) . . ?
C7 C8 C9 120.30(16) . . ?
C7 C8 Se2 121.30(12) . . ?
C9 C8 Se2 118.35(13) . . ?
C10 C9 C8 119.44(17) . . ?
C11 C10 C9 120.45(17) . . ?
C10 C11 C12 120.36(17) . . ?
C11 C12 C7 119.50(17) . . ?
N1 C13 C3 177.2(2) . . ?
N2 C14 C6 178.1(2) . . ?
C17 O1 C21 116.7(6) . . ?
C20 C15 C16 121.7(8) . . ?
C20 C15 S1 122.7(6) . . ?
C16 C15 S1 115.6(6) . . ?
C15 C16 C17 118.3(6) . . ?
O1 C17 C18 115.0(6) . . ?
O1 C17 C16 124.6(6) . . ?
C18 C17 C16 120.3(6) . . ?
C17 C18 C19 120.4(5) . . ?
C18 C19 C20 120.8(5) . . ?
C15 C20 C19 118.3(6) . . ?
C16' C15' C20' 121.1(17) . . ?
C16' C15' S1 119.5(13) . . ?
C20' C15' S1 118.8(13) . . ?
C17' O1' C21' 116.0(13) . . ?
C15' C16' C17' 117.3(13) . . ?
C18' C17' O1' 112.9(14) . . ?
C18' C17' C16' 122.5(13) . . ?
O1' C17' C16' 124.3(13) . . ?
C17' C18' C19' 119.0(12) . . ?
C18' C19' C20' 120.1(11) . . ?
C15' C20' C19' 119.9(13) . . ?
C22' C27 C26' 110.8(8) . . ?
C26 C27 C22 126.3(7) . . ?
C24 O2 C28 117.4(4) . . ?
C27 C22 C23 105.9(6) . . ?
C27 C22 S2 124.9(8) . . ?
C23 C22 S2 121.9(7) . . ?
C24 C23 C22 125.3(6) . . ?
O2 C24 C25 125.4(4) . . ?
O2 C24 C23 114.4(4) . . ?
C25 C24 C23 120.2(4) . . ?
C26 C25 C24 120.7(6) . . ?
C25 C26 C27 117.4(7) . . ?
C24' O2' C28' 116.8(7) . . ?
C27 C22' C23' 126.1(10) . . ?
C27 C22' S2 122.0(8) . . ?
C23' C22' S2 100.1(6) . . ?
C24' C23' C22' 110.9(7) . . ?
C25' C24' O2' 125.2(5) . . ?
C25' C24' C23' 121.0(5) . . ?
O2' C24' C23' 113.7(6) . . ?
C24' C25' C26' 117.1(6) . . ?
C27 C26' C25' 126.3(8) . . ?
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
Se1 C1 1.9077(17) . ?
Se1 C7 1.9136(16) . ?
Se2 C2 1.8993(16) . ?
Se2 C8 1.9067(17) . ?
S1 C15' 1.75(2) . ?
S1 C5 1.7677(17) . ?
S1 C15 1.808(10) . ?
S2 C22 1.689(12) . ?
S2 C4 1.7668(18) . ?
S2 C22' 1.881(11) . ?
N1 C13 1.137(3) . ?
N2 C14 1.141(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.407(2) . ?
C3 C4 1.404(2) . ?
C3 C13 1.443(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.409(2) . ?
C6 C14 1.445(2) . ?
C7 C8 1.392(2) . ?
C7 C12 1.396(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.388(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.395(3) . ?
O1 C17 1.360(10) . ?
O1 C21 1.412(8) . ?
C15 C20 1.380(8) . ?
C15 C16 1.391(9) . ?
C16 C17 1.407(8) . ?
C17 C18 1.368(7) . ?
C18 C19 1.376(7) . ?
C19 C20 1.398(10) . ?
C15' C16' 1.37(2) . ?
C15' C20' 1.373(17) . ?
O1' C17' 1.348(19) . ?
O1' C21' 1.385(16) . ?
C16' C17' 1.41(2) . ?
C17' C18' 1.345(16) . ?
C18' C19' 1.379(15) . ?
C19' C20' 1.39(2) . ?
C27 C22' 1.301(13) . ?
C27 C26' 1.321(14) . ?
C27 C26 1.454(11) . ?
C27 C22 1.464(11) . ?
O2 C24 1.363(5) . ?
O2 C28 1.431(5) . ?
C22 C23 1.474(12) . ?
C23 C24 1.399(6) . ?
C24 C25 1.387(6) . ?
C25 C26 1.360(13) . ?
O2' C24' 1.386(7) . ?
O2' C28' 1.428(10) . ?
C22' C23' 1.494(14) . ?
C23' C24' 1.387(8) . ?
C24' C25' 1.383(10) . ?
C25' C26' 1.416(14) . ?
