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_1576859
_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         'C68 H48 O4, C1 H2 Cl2'
_chemical_formula_sum            'C69 H50 Cl2 O4'
_chemical_formula_weight         1013.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_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
;
2025-01-04 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.225(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   33.5055(11)
_cell_length_b                   10.0230(3)
_cell_length_c                   14.7840(4)
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3670
_cell_measurement_theta_min      3.7894
_cell_volume                     4935.6(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     32.00  73.00   0.50    0.48    --  104.75 -61.00 -90.00   82
  2  \w     36.00  67.00   0.50    0.48    --  104.75 -61.00 -60.00   62
  3  \w     32.00  71.00   0.50    0.48    --  104.75 -61.00 -30.00   78
  4  \w     42.00  67.00   0.50    0.48    --  104.75 -61.00   0.00   50
  5  \w    -21.00   4.00   0.50    0.12    --   46.93 -27.00-108.00   50
  6  \w    -17.00  22.00   0.50    0.12    --   46.93 -19.00  90.00   78
  7  \w     53.00  79.00   0.50    0.48    --  104.75 -94.00 150.00   52
  8  \w     41.00  77.00   0.50    0.48    --  104.75-125.00 120.00   72
  9  \w     83.00 116.00   0.50    0.48    --  104.75-125.00 120.00   66
 10  \w     92.00 171.00   0.50    0.48    --  104.75  27.00  54.00  158
 11  \w     93.00 170.00   0.50    0.48    --  104.75  45.00 150.00  154
 12  \w     69.00  95.00   0.50    0.12    --   46.93  27.00  54.00   52
 13  \w    -22.00  29.00   0.50    0.12    --  -46.93  19.00-180.00  102
 14  \w    -69.00 -31.00   0.50    0.48    -- -102.00  61.00-150.00   76
 15  \w    -67.00 -29.00   0.50    0.48    -- -102.00  61.00-120.00   76
 16  \w    -69.00 -29.00   0.50    0.48    -- -102.00  61.00 -60.00   80
 17  \w    -69.00 -33.00   0.50    0.48    -- -102.00  61.00 -30.00   72
 18  \w    -69.00 -44.00   0.50    0.48    -- -102.00  61.00  30.00   50
 19  \w    -63.00 -29.00   0.50    0.48    -- -102.00  61.00 120.00   68
 20  \w    -69.00 -37.00   0.50    0.48    -- -102.00  61.00 150.00   64
 21  \w    -82.00 -30.00   0.50    0.48    -- -102.00  77.00 150.00  104
 22  \w    -31.00  27.00   0.50    0.12    --  -46.93  27.00  54.00  116
 23  \w   -112.00 -59.00   0.50    0.12    --  -46.93 -27.00-108.00  106
 24  \w   -123.00 -89.00   0.50    0.48    -- -102.00 -27.00-108.00   68
 25  \w   -116.00 -78.00   0.50    0.12    --  -46.93-125.00 -30.00   76
;
_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      0.0369088000
_diffrn_orient_matrix_UB_12      0.0478691000
_diffrn_orient_matrix_UB_13      -0.0447760000
_diffrn_orient_matrix_UB_21      0.0268049000
_diffrn_orient_matrix_UB_22      -0.0248999000
_diffrn_orient_matrix_UB_23      0.0897772000
_diffrn_orient_matrix_UB_31      0.0076157000
_diffrn_orient_matrix_UB_32      -0.1439238000
_diffrn_orient_matrix_UB_33      -0.0303940000
_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  0.0612
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15406
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.774
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.607
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57301
_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    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.41(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     708
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0639
_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^)+(0.1086P)^2^+2.8746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1721
_reflns_Friedel_coverage         0.563
_reflns_Friedel_fraction_full    0.558
_reflns_Friedel_fraction_max     0.558
_reflns_number_gt                6121
_reflns_number_total             6803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc06584d2.cif
_cod_data_source_block           exp_22595_auto
_cod_database_code               1576859
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C1H1O1
_shelx_estimated_absorpt_t_max   0.643
_shelx_estimated_absorpt_t_min   0.602
_reflns_odcompleteness_completeness 99.04
_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
 Cl4-C2 = Cl3-C2
 1.75 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C2 \\sim Cl3 \\sim Cl4 \\sim C1 \\sim Cl1 \\sim Cl2: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(Cl3)=Sof(Cl4)=Sof(C2)=Sof(H2A)=Sof(H2B)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(C1)=Sof(H1A)=Sof(H1B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C46(H46), C47(H47), C14(H14), C5(H5), C45(H45), C17(H17),
 C29(H29), C51(H51), C22(H22), C26(H26), C34(H34), C59(H59), C30(H30), C33(H33),
  C10(H10), C9(H9), C69(H69), C58(H58), C74(H74), C68(H68), C50(H50), C25(H25),
 C44(H44), C75(H75), C37(H37), C41(H41), C48(H48), C70(H70), C38(H38), C71(H71),
  C42(H42), C49(H49), C72(H72), C73(H73)
5.c Idealised Me refined as rotating group:
 C61(H61A,H61B,H61C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C), C67(H67A,H67B,
 H67C)
;
_shelx_res_checksum              91201
_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 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.308