Curved graphene nanoribbons derived from tetrahydropyrene-based polyphenylenes <i>via</i> one-pot K-region oxidation and Scholl cyclization.
Obermann, Sebastian; Zheng, Wenhao; Melidonie, Jason; Böckmann, Steffen; Osella, Silvio; Arisnabarreta, Nicolás; Guerrero-León, L Andrés; Hennersdorf, Felix; Beljonne, David; Weigand, Jan J.; Bonn, Mischa; De Feyter, Steven; Hansen, Michael Ryan; Wang, Hai I.; Ma, Ji; Feng, Xinliang; Chemical science 14 (2023) 8607–8614; doi:10.1039/d3sc02824k

data_1569586
_publ_section_title
;
 Curved graphene nanoribbons derived from tetrahydropyrene-based
 polyphenylenes <i>via</i> one-pot K-region oxidation and Scholl
 cyclization.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              8607
_journal_page_last               8614
_journal_paper_doi               10.1039/d3sc02824k
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '1.301(C S2), C178 H134'
_chemical_formula_sum            'C183 H134 S10'
_chemical_formula_weight         2653.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.217(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.6811(6)
_cell_length_b                   28.4303(9)
_cell_length_c                   21.9446(4)
_cell_measurement_reflns_used    9313
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3320
_cell_measurement_theta_min      2.5560
_cell_volume                     14492.2(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     90.00 115.00   0.50   15.00    --   42.50  37.00 108.00   50
  2  \w     51.00  79.00   0.50   15.00    --   42.50  37.00 108.00   56
  3  \w     -7.00  18.00   0.50   15.00    --   42.50 -37.00 -47.00   50
  4  \w     96.00 128.00   0.50   60.00    --  111.00 -37.00 -47.00   64
  5  \w     38.00  88.00   0.50   60.00    --  111.00 -37.00 -47.00  100
  6  \w    115.00 169.00   0.50   60.00    --  111.00  37.00 108.00  108
  7  \w   -111.00 -16.00   0.50   15.00    --  -38.50 -37.00 -47.00  190
  8  \w    -26.00  29.00   0.50   15.00    --  -38.50  38.00 -60.00  110
  9  \w    -43.00  -5.00   0.50   15.00    --  -38.50  37.00 108.00   76
 10  \w     47.00 114.00   0.50   15.00    --   42.50  38.00-180.00  134
 11  \w     17.00 112.00   0.50   15.00    --   42.50  57.00 -90.00  190
 12  \w     22.00  89.00   0.50   15.00    --   42.50  38.00 -90.00  134
 13  \w     33.00  95.00   0.50   15.00    --   42.50-125.00 150.00  124
 14  \w     17.00  58.00   0.50   15.00    --   42.50  57.00-120.00   82
 15  \w     54.00  97.00   0.50   15.00    --   42.50-125.00 -60.00   86
 16  \w     83.00 111.00   0.50   60.00    --  111.00  62.00-129.34   56
 17  \w    138.00 166.00   0.50   60.00    --  111.00  61.00-180.00   56
 18  \w     83.00 110.00   0.50   60.00    --  111.00  61.00-180.00   54
 19  \w     85.00 168.00   0.50   60.00    --  111.00  56.00-151.02  166
 20  \w     42.00  90.00   0.50   60.00    --  111.00-125.00-120.00   96
 21  \w     91.00 119.00   0.50   60.00    --  111.00 -45.00-120.00   56
 22  \w     32.00  71.00   0.50   60.00    --  111.00 -94.00 -90.00   78
 23  \w    135.00 169.00   0.50   60.00    --  111.00  61.00 -90.00   68
 24  \w     83.00 110.00   0.50   60.00    --  111.00  65.00-171.47   54
 25  \w    103.00 131.00   0.50   60.00    --  111.00 125.00  90.00   56
 26  \w     87.00 116.00   0.50   60.00    --  111.00  61.00 -90.00   58
 27  \w     43.00 136.00   0.50   60.00    --  111.00 -61.00  60.00  186
 28  \w     87.00 113.00   0.50   60.00    --  111.00  45.00-180.00   52
 29  \w     83.00 111.00   0.50   60.00    --  111.00  61.00-120.00   56
 30  \w     87.00 155.00   0.50   60.00    --  111.00  45.00-120.00  136
 31  \w     83.00 111.00   0.50   60.00    --  111.00  62.00 -96.65   56
 32  \w     43.00  68.00   0.50   60.00    --  111.00 -61.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0583850000
_diffrn_orient_matrix_UB_12      0.0219379000
_diffrn_orient_matrix_UB_13      -0.0295714000
_diffrn_orient_matrix_UB_21      0.0238502000
_diffrn_orient_matrix_UB_22      0.0125699000
_diffrn_orient_matrix_UB_23      -0.0584026000
_diffrn_orient_matrix_UB_31      -0.0204774000
_diffrn_orient_matrix_UB_32      -0.0478911000
_diffrn_orient_matrix_UB_33      -0.0288652000
_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  0.0908
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            112827
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       block
_exptl_crystal_F_000             5568
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1689
_refine_ls_number_reflns         25693
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1636
_refine_ls_R_factor_gt           0.0902
_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^)+(0.1181P)^2^+19.5903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2928
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13105
_reflns_number_total             25693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02824k2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1569585--1569586.cif.'
_cod_database_code               1569586
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C183H134S10
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.743
_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. Restrained distances
 H12G-H15H_$1
 -2.1 with sigma of 0.02
3. Same fragment restrains
{S2, S1, C179} sigma for 1-2: 0.02, 1-3: 0.02
as in
{S3, S4, C180}
4. Others
 Sof(S2)=Sof(S1)=Sof(C179)=FVAR(1)
 Sof(S3)=Sof(S4)=Sof(C180)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C20(H20), C22(H22), C25(H25), C27(H27),
 C31(H31), C33(H33), C42(H42), C44(H44), C47(H47), C49(H49), C56(H56), C58(H58),
  C65(H65), C67(H67), C75(H75), C77(H77), C82(H82), C84(H84), C88(H88),
 C90(H90), C97(H97), C99(H99), C112(H112), C116(H116), C118(H118), C123(H123),
 C132(H132), C136(H136), C138(H138), C143(H143), C146(H146), C148(H148),
 C151(H151), C153(H153), C158(H158), C160(H160), C163(H163), C165(H165),
 C172(H172), C174(H174)
5.b Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C60(H60A,H60B,
 H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C69(H69A,H69B,H69C), C70(H70A,
 H70B,H70C), C71(H71A,H71B,H71C), C79(H79A,H79B,H79C), C80(H80A,H80B,H80C),
 C81(H81A,H81B,H81C), C92(H92A,H92B,H92C), C93(H93A,H93B,H93C), C94(H94A,H94B,
 H94C), C120(H12A,H12B,H12C), C121(H12D,H12E,H12F), C122(H12G,H12H,H12I),
 C140(H14A,H14B,H14C), C141(H14D,H14E,H14F), C142(H14G,H14H,H14I), C155(H15A,
 H15B,H15C), C156(H15D,H15E,H15F), C157(H15G,H15H,H15I), C167(H16A,H16B,H16C),
 C168(H16D,H16E,H16F), C169(H16G,H16H,H16I), C176(H17A,H17B,H17C), C177(H17D,
 H17E,H17F), C178(H17G,H17H,H17I)
;
_shelx_res_checksum              12
_shelx_hkl_checksum              99985
_shelx_fab_checksum              96781
_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 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.755