Thiophene-backbone arcuate graphene nanoribbons: shotgun synthesis and length dependent properties
Zhang, Ruiying; Chen, Xinyu; Zhu, Lingyun; Huang, Yanxia; Zhai, Zi'ang; Wang, Qiang; Wang, Lingding; Wang, Taosong; Wang, Wei-Zhen; Ye, Ke-Yin; Li, Yuanming; Chemical Science 16 (2025) 7366–7373; doi:10.1039/D4SC08353A

data_1574192
_publ_section_title
;
 Thiophene-backbone arcuate graphene nanoribbons: shotgun synthesis and
 length dependent properties
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7366
_journal_page_last               7373
_journal_paper_doi               10.1039/D4SC08353A
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C82 H78 O4 S2, 2(C H Cl3)'
_chemical_formula_sum            'C84 H80 Cl6 O4 S2'
_chemical_formula_weight         1430.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-26 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.188(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.5478(5)
_cell_length_b                   20.7666(2)
_cell_length_c                   31.3909(5)
_cell_measurement_reflns_used    34641
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      55.9220
_cell_measurement_theta_min      2.2670
_cell_volume                     15631.0(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -73.00  15.00   0.50    0.64    --   -1.41 -53.00 123.00  176
  2  \w      5.00  67.00   0.50    0.64    --   -1.41  53.00 -91.00  124
  3  \w     47.00 137.00   0.50    2.54    --   67.13  53.00 -91.00  180
  4  \w      7.00  74.00   0.50    2.54    --   67.13 -53.00 123.00  134
  5  \w    -60.00   3.00   0.50    2.54    --  -69.95  53.00 -91.00  126
  6  \w   -142.00 -56.00   0.50    2.54    --  -69.95 -53.00 123.00  172
  7  \w     -4.00  29.00   0.50    0.64    --   -1.41 -99.00-180.00   66
  8  \w      6.00  31.00   0.50    0.64    --   -1.41 -99.00   0.00   50
  9  \w     11.00  95.00   0.50    2.54    --   67.13 -77.00 120.00  168
 10  \w     63.00  89.00   0.50    2.54    --   67.13  77.00 -60.00   52
 11  \w     22.00  92.00   0.50    2.54    --   67.13-125.00 120.00  140
 12  \w    113.00 138.00   0.50    2.54    --   67.13  77.00 -60.00   50
 13  \w     69.00  95.00   0.50    2.54    --   67.13 -99.00-150.00   52
 14  \w     -4.00  64.00   0.50    2.54    --   67.13 -99.00-150.00  136
 15  \w    -22.00   4.00   0.50    2.54    --  -69.95  57.00  60.00   52
 16  \w    -93.00 -47.00   0.50    2.54    --  -69.95  57.00  60.00   92
 17  \w   -109.00 -20.00   0.50    2.54    --  -69.95 125.00 -90.00  178
 18  \w    -73.00 -48.00   0.50    2.54    --  -69.95 -57.00-120.00   50
 19  \w   -134.00-102.00   0.50    2.54    --  -69.95 -57.00-120.00   64
 20  \w   -132.00 -92.00   0.50    2.54    --  -69.95 -99.00-120.00   80
 21  \w   -119.00 -83.00   0.50    2.54    --  -69.95-125.00-150.00   72
 22  \w   -110.00 -22.00   0.50    2.54    --  -69.95 125.00   0.00  176
 23  \w   -140.00 -81.00   0.50    2.54    --  -69.95-125.00-120.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0437449000
_diffrn_orient_matrix_UB_12      0.0321592000
_diffrn_orient_matrix_UB_13      -0.0281568000
_diffrn_orient_matrix_UB_21      0.0346854000
_diffrn_orient_matrix_UB_22      0.0426333000
_diffrn_orient_matrix_UB_23      -0.0082310000
_diffrn_orient_matrix_UB_31      0.0020402000
_diffrn_orient_matrix_UB_32      -0.0361457000
_diffrn_orient_matrix_UB_33      -0.0347038000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            79840
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        52.932
_diffrn_reflns_theta_max         52.932
_diffrn_reflns_theta_min         2.263
_diffrn_source                   'Ga K\a'
_exptl_absorpt_coefficient_mu    1.903
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             6000
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.991
_refine_diff_density_min         -1.194
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         13676
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0842
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1610P)^2^+58.5928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2435
_refine_ls_wR_factor_ref         0.2535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11243
_reflns_number_total             13676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08353a2.cif
_cod_data_source_block           ARO-11
_cod_depositor_comments
'Adding full bibliography for 1574192--1574193.cif.'
_cod_database_code               1574192
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHOSCl
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     53.78
_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. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C84) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(Cl1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C83(H83), C84(H84)
3.b Aromatic/amide H refined with riding coordinates:
 C53(H53), C48(H48), C47(H47), C56(H56), C39(H39), C67(H67), C54(H54),
 C75(H75), C86(H86), C40(H40), C11(H11), C76(H76), C70(H70), C2(H2), C9(H9),
 C29(H29), C8(H8), C78(H78), C44(H44), C43(H43), C32(H32), C1(H1), C31(H31),
 C69(H69)
3.c Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C58(H58A,H58B,
 H58C), C22(H22A,H22B,H22C), C16(H16A,H16B,H16C), C59(H59A,H59B,H59C), C73(H73A,
 H73B,H73C), C74(H74A,H74B,H74C), C80(H80A,H80B,H80C), C82(H82A,H82B,H82C),
 C34(H34A,H34B,H34C), C81(H81A,H81B,H81C), C36(H36A,H36B,H36C), C72(H72A,H72B,
 H72C), C17(H17A,H17B,H17C), C35(H35A,H35B,H35C), C18(H18A,H18B,H18C)
;
_smtbx_masks_void_probe_radius   1.0
_smtbx_masks_void_truncation_radius 1.0
_shelx_res_checksum              75477
_shelx_fab_checksum              26318
_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 2.008
_oxdiff_exptl_absorpt_empirical_full_min 0.572