Pyrene-embedded nanohoops: synthesis and dopant engineering for organic solar cells with an enhanced efficiency of 19.96.
He, Jing; Liu, Wenlong; Wu, Siwei; Xie, Qi; Lian, Zhe; Li, Xiaonan; Guo, Shengzhu; Wang, Ying; Xu, Xinjun; Jiang, Hua; Chemical science 17 (2026) 5192–5200; doi:10.1039/d5sc06584d

data_1576858
_publ_section_title
;
 Pyrene-embedded nanohoops: synthesis and dopant engineering for organic
 solar cells with an enhanced efficiency of 19.96.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              5192
_journal_page_last               5200
_journal_paper_doi               10.1039/d5sc06584d
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C66 H44 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C68 H48 Cl4 O2'
_chemical_formula_weight         1038.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-10-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-01-02 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.052(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.3171(4)
_cell_length_b                   9.62150(15)
_cell_length_c                   16.4770(4)
_cell_measurement_reflns_used    10037
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4330
_cell_measurement_theta_min      4.5950
_cell_volume                     2594.96(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_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     38.00  65.00   0.50    1.02    --  104.75 -61.00 -60.00   54
  2  \w     32.00  73.00   0.50    1.02    --  104.75 -61.00 -30.00   82
  3  \w     38.00  71.00   0.50    1.02    --  104.75 -61.00   0.00   66
  4  \w     35.00  64.00   0.50    1.02    --  104.75 -61.00  30.00   58
  5  \w     41.00  66.00   0.50    1.02    --  104.75 -61.00 150.00   50
  6  \w     41.00 100.00   0.50    0.26    --   46.80  33.00 105.00  118
  7  \w     91.00 178.00   0.50    1.02    --  104.75  33.00 105.00  174
  8  \w     81.00 110.00   0.50    1.02    --  104.75-125.00-180.00   58
  9  \w    -20.00  24.00   0.50    0.26    --  -46.80  19.00-120.00   88
 10  \w    -35.00  18.00   0.50    0.26    --  -46.80  37.00 -90.00  106
 11  \w    -18.00   7.00   0.50    0.26    --   46.80 -33.00 -52.00   50
 12  \w     36.00  77.00   0.50    1.02    --  104.75-125.00-180.00   82
 13  \w    -27.00  18.00   0.50    0.26    --  -46.80  33.00 105.00   90
 14  \w    -66.00 -33.00   0.50    1.02    -- -102.00  77.00  90.00   66
 15  \w    -61.00 -33.00   0.50    1.02    -- -102.00  61.00 -60.00   56
 16  \w    -67.00 -33.00   0.50    1.02    -- -102.00  61.00 -90.00   68
 17  \w    -66.00 -32.00   0.50    1.02    -- -102.00  61.00 120.00   68
 18  \w    -65.00 -40.00   0.50    1.02    -- -102.00  61.00-120.00   50
 19  \w    -68.00 -41.00   0.50    1.02    -- -102.00  61.00-150.00   54
 20  \w    -63.00 -33.00   0.50    1.02    -- -102.00  61.00-180.00   60
 21  \w    -75.00 -45.00   0.50    1.02    -- -102.00  77.00-150.00   60
 22  \w   -115.00 -32.00   0.50    1.02    -- -102.00 125.00-150.00  166
 23  \w   -171.00 -88.00   0.50    1.02    -- -102.00 -15.00-180.00  166
 24  \w   -119.00 -45.00   0.50    0.26    --  -46.80 -33.00 -52.00  148
 25  \w   -120.00 -94.00   0.50    1.02    -- -102.00 -33.00 -52.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0452261000
_diffrn_orient_matrix_UB_12      0.0603706000
_diffrn_orient_matrix_UB_13      -0.0895037000
_diffrn_orient_matrix_UB_21      0.0824743000
_diffrn_orient_matrix_UB_22      0.0304912000
_diffrn_orient_matrix_UB_23      -0.0130434000
_diffrn_orient_matrix_UB_31      -0.0015084000
_diffrn_orient_matrix_UB_32      -0.1451459000
_diffrn_orient_matrix_UB_33      -0.0400860000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16635
_diffrn_reflns_point_group_measured_fraction_full 0.794
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.099
_diffrn_reflns_theta_min         4.596
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 2387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.152(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     764
_refine_ls_number_reflns         8049
_refine_ls_number_restraints     297
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0786
_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/[\s^2^(Fo^2^)+(0.1560P)^2^+1.5228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2152
_refine_ls_wR_factor_ref         0.2220
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_full    0.593
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                7390
_reflns_number_total             8049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06584d2.cif
_cod_data_source_block           exp_22592_auto
_cod_original_cell_volume        2594.97(10)
_cod_database_code               1576858
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1O1
_shelx_estimated_absorpt_t_max   0.528
_shelx_estimated_absorpt_t_min   0.482
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl3-C3 = Cl2-C3
 1.75 with sigma of 0.001
 O2-C5 = O3-C4
 1.55 with sigma of 0.001
 C67-C5
 2.5 with sigma of 0.001
 O76-C77 = O1-C8
 1.55 with sigma of 0.001
 Cl4-C6 = Cl1-C6
 1.75 with sigma of 0.001
 Cl5-C1 = Cl6-C1
 1.75 with sigma of 0.001
 Cl8-C2 = Cl7-C2
 1.75 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C8 \\sim O1 \\sim O76 \\sim C77 \\sim C11 \\sim C10 \\sim C54 \\sim C50 \\sim
C51 \\sim C52 \\sim C53 \\sim C14 \\sim C13 \\sim C12 \\sim O3 \\sim O2 \\sim
C5 \\sim C4: within 2A with sigma of 0.004 and sigma for terminal atoms of 0.01
within 2A
C2 \\sim Cl7 \\sim Cl8 \\sim C3 \\sim Cl2 \\sim Cl3: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.01 within 2A
C1 \\sim Cl6 \\sim Cl5 \\sim C6 \\sim Cl1 \\sim Cl4: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(O1)=1-FVAR(1)
 Sof(O76)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=FVAR(1)
 Sof(O2)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=1-FVAR(2)
 Sof(O3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(2)
 Sof(Cl6)=Sof(Cl5)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(3)
 Sof(Cl1)=Sof(Cl4)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(3)
 Sof(Cl7)=Sof(Cl8)=Sof(C2)=Sof(H2A)=Sof(H2B)=1-FVAR(4)
 Sof(Cl2)=Sof(Cl3)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(4)
5.a Riding coordinates:
 C5(H5A,H5B,H5C)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C1(H1A,H1B), C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C69(H69), C16(H16), C60(H60), C20(H20), C68(H68), C67(H67), C19(H19),
 C39(H39), C56(H56), C40(H40), C72(H72), C63(H63), C47(H47), C59(H59), C31(H31),
  C73(H73), C64(H64), C51(H51), C55(H55), C23(H23), C58(H58), C32(H32),
 C43(H43), C57(H57), C54(H54), C28(H28), C70(H70), C44(H44), C62(H62), C27(H27),
  C35(H35), C66(H66), C24(H24), C36(H36), C71(H71), C61(H61), C48(H48), C65(H65)
5.d Idealised Me refined as rotating group:
 C77(H77A,H77B,H77C), C8(H8A,H8B,H8C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              59320
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.782