Toward cove-edged low band gap graphene nanoribbons.
Liu, Junzhi; Li, Bo-Wei; Tan, Yuan-Zhi; Giannakopoulos, Angelos; Sanchez-Sanchez, Carlos; Beljonne, David; Ruffieux, Pascal; Fasel, Roman; Feng, Xinliang; Müllen, Klaus; Journal of the American Chemical Society 137 (2015) 6097–6103; doi:10.1021/jacs.5b03017

data_4123602
_publ_section_title
;
 Toward cove-edged low band gap graphene nanoribbons.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6097
_journal_page_last               6103
_journal_paper_doi               10.1021/jacs.5b03017
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C88 H62'
_chemical_formula_sum            'C88 H62'
_chemical_formula_weight         1119.38
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.405(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.8791(8)
_cell_length_b                   21.8851(10)
_cell_length_c                   36.4305(15)
_cell_measurement_reflns_used    12309
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      61.5730
_cell_volume                     14804.5(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3415
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
  1 omega  -90.00  -36.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.8591 -178.0000  -90.0000 54

  2 omega  -83.00  -39.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        0.8591  178.0000 -120.0000 44

  3 omega  -88.00  -39.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        0.8591  178.0000   90.0000 49

  4 omega  -60.00  -34.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        0.8591  178.0000  120.0000 26

  5 omega  -86.00  -58.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -        0.8591  178.0000 -180.0000 28

  6 omega   17.00   85.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440  -30.0000  -60.0000 68

  7 omega   54.00  149.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440   61.0000 -120.0000 95

  8 omega   77.00  107.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440 -125.0000 -180.0000 30

  9 omega   50.00   76.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440 -125.0000  150.0000 26

 10 omega   11.00  108.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440  -61.0000   90.0000 97

 11 omega   12.00  110.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.8440  -61.0000  -90.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0386311000
_diffrn_orient_matrix_UB_12      0.0606653000
_diffrn_orient_matrix_UB_13      -0.0047731000
_diffrn_orient_matrix_UB_21      0.0279995000
_diffrn_orient_matrix_UB_22      -0.0268370000
_diffrn_orient_matrix_UB_23      -0.0337938000
_diffrn_orient_matrix_UB_31      -0.0678751000
_diffrn_orient_matrix_UB_32      0.0235522000
_diffrn_orient_matrix_UB_33      -0.0261486000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            48736
_diffrn_reflns_theta_full        62.49
_diffrn_reflns_theta_max         62.49
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.9190
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             4720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1654
_refine_ls_number_reflns         22755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2355
_reflns_number_gt                15101
_reflns_number_total             22755
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03017_si_004.cif
_cod_data_source_block           2
_cod_depositor_comments          'Adding full bibliography for 4123602.cif.'
_cod_database_code               4123602
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_olex2_refinement_description
;
1. Shared sites
{H2DC, H1YA}
{H2LB, H2IA}
2. Others
 Fixed Sof: C1E(0.85) H1EA(0.85) H1EB(0.85) H1EC(0.85) C1F(0.85) H1FA(0.85)
 H1FB(0.85) H1FC(0.85) C1Y(0.75) H1YA(0.75) H1YB(0.75) H1YC(0.75) C1Z(0.75)
 H1ZA(0.75) H1ZB(0.75) H1ZC(0.75) C2B(0.75) H2BA(0.75) H2BB(0.75) H2BC(0.75)
 C144(0.85) H14A(0.85) H14B(0.85) H14C(0.85) C1M(0.5) H1MA(0.5) H1MB(0.5)
 H1MC(0.5) C2C(0.5) H2CA(0.5) H2CB(0.5) H2CC(0.5) C2L(0.5) H2LA(0.5) H2LB(0.5)
 H2LC(0.5) C2A(0.25) H2AA(0.25) H2AB(0.25) H2AC(0.25) C2D(0.25) H2DA(0.25)
 H2DB(0.25) H2DC(0.25) C2G(0.25) H2GA(0.25) H2GB(0.25) H2GC(0.25) C2I(0.5)
 H2IA(0.5) H2IB(0.5) H2IC(0.5) C2J(0.5) H2JA(0.5) H2JB(0.5) H2JC(0.5) C2K(0.5)
 H2KA(0.5) H2KB(0.5) H2KC(0.5) C2F(0.15) H2FA(0.15) H2FB(0.15) H2FC(0.15)
 C2H(0.15) H2HA(0.15) H2HB(0.15) H2HC(0.15) C2M(0.15) H2MA(0.15) H2MB(0.15)
 H2MC(0.15)
 Fixed Uiso: H1B(0.073) H1EA(0.1) H1EB(0.1) H1EC(0.1) H1FA(0.099) H1FB(0.099)
 H1FC(0.099) H1GA(0.121) H1GB(0.121) H1GC(0.121) H1LA(0.141) H1LB(0.141)
 H1LC(0.141) H1NA(0.145) H1NB(0.145) H1NC(0.145) H1U(0.081) H1XA(0.134)
 H1XB(0.134) H1XC(0.134) H1YA(0.101) H1YB(0.101) H1YC(0.101) H1ZA(0.103)
 H1ZB(0.103) H1ZC(0.103) H2BA(0.138) H2BB(0.138) H2BC(0.138) H6(0.044)
 H11(0.044) H17(0.047) H38(0.048) H48(0.051) H50(0.048) H53(0.051) H55(0.051)
 H67(0.047) H74(0.054) H78(0.053) H80(0.055) H88(0.062) H102(0.063) H106(0.064)
 H107(0.059) H114(0.062) H11A(0.163) H11B(0.163) H11C(0.163) H126(0.071)
 H128(0.067) H129(0.071) H138(0.079) H13A(0.109) H13B(0.109) H13C(0.109)
 H141(0.07) H142(0.074) H14A(0.085) H14B(0.085) H14C(0.085) H147(0.077)
 H1C(0.094) H1D(0.085) H1I(0.097) H1JA(0.182) H1JB(0.182) H1JC(0.182)
 H1K(0.087) H1MA(0.113) H1MB(0.113) H1MC(0.113) H1OA(0.2) H1OB(0.2) H1OC(0.2)
 H1P(0.098) H1Q(0.088) H1R(0.12) H1SA(0.251) H1SB(0.251) H1SC(0.251)
 H1TA(0.146) H1TB(0.146) H1TC(0.146) H1V(0.087) H1W(0.131) H2CA(0.15)
 H2CB(0.15) H2CC(0.15) H2LA(0.094) H2LB(0.094) H2LC(0.094) H18(0.045)
 H27(0.065) H31(0.045) H49(0.058) H61(0.049) H65(0.057) H71(0.051) H75(0.049)
 H79(0.052) H81(0.055) H82(0.049) H84(0.055) H93(0.064) H96(0.057) H10A(0.135)
 H10B(0.135) H10C(0.135) H11D(0.112) H11E(0.112) H11F(0.112) H12A(0.147)
 H12B(0.147) H12C(0.147) H13D(0.104) H13E(0.104) H13F(0.104) H133(0.073)
 H13G(0.112) H13H(0.112) H13I(0.112) H137(0.066) H140(0.079) H2AA(0.101)
 H2AB(0.101) H2AC(0.101) H2DA(0.11) H2DB(0.11) H2DC(0.11) H2GA(0.1) H2GB(0.1)
 H2GC(0.1) H2IA(0.211) H2IB(0.211) H2IC(0.211) H2JA(0.203) H2JB(0.203)
 H2JC(0.203) H2KA(0.114) H2KB(0.114) H2KC(0.114) H2FA(0.121) H2FB(0.121)
 H2FC(0.121) H2HA(0.131) H2HB(0.131) H2HC(0.131) H2MA(0.173) H2MB(0.173)
 H2MC(0.173)
 Fixed X: H1B(0.704) H1EA(0.2322) H1EB(0.1985) H1EC(0.185) H1FA(0.287)
 H1FB(0.3655) H1FC(0.3304) H1GA(-0.0021) H1GB(0.0309) H1GC(-0.0223)
 H1LA(0.1824) H1LB(0.1456) H1LC(0.1204) H1NA(0.1243) H1NB(0.1544) H1NC(0.0752)
 H1U(-0.0839) H1XA(0.7146) H1XB(0.6709) H1XC(0.6351) H1YA(0.3892) H1YB(0.4102)
 H1YC(0.4493) H1ZA(0.528) H1ZB(0.549) H1ZC(0.469) H2BA(0.5364) H2BB(0.5896)
 H2BC(0.57) H6(0.3715) H11(0.2701) H17(0.3073) H38(0.5247) H48(0.4498)
 H50(0.1771) H53(0.4935) H55(0.1053) H67(0.3394) H74(0.187) H78(0.3527)
 H80(0.5512) H88(0.5637) H102(0.7114) H106(0.0863) H107(0.1349) H114(0.7099)
 H11A(0.5653) H11B(0.541) H11C(0.5316) H126(-0.0278) H128(0.6487) H129(0.7073)
 H138(-0.0159) H13A(0.7321) H13B(0.6639) H13C(0.6876) H141(-0.057) H142(-
 0.0878) H14A(0.3535) H14B(0.3868) H14C(0.3225) H147(-0.1121) H1C(0.4865) H1D(-
 0.2312) H1I(0.4436) H1JA(-0.1307) H1JB(-0.0533) H1JC(-0.098) H1K(-0.2265)
 H1MA(0.0061) H1MB(-0.0694) H1MC(-0.0556) H1OA(-0.2398) H1OB(-0.2379) H1OC(-
 0.2138) H1P(0.563) H1Q(0.5281) H1R(-0.2213) H1SA(0.3844) H1SB(0.3739)
 H1SC(0.4417) H1TA(0.2652) H1TB(0.2402) H1TC(0.2511) H1V(0.5564) H1W(-0.2189)
 H2CA(-0.1049) H2CB(-0.0948) H2CC(-0.0488) H2LA(0.0418) H2LB(0.0838)
 H2LC(0.0101) H18(0.1709) H27(-0.0519) H31(0.2025) H49(-0.0149) H61(0.1509)
 H65(0.3251) H71(0.2218) H75(0.046) H79(0.1197) H81(-0.0391) H82(0.3209)
 H84(0.3741) H93(0.4251) H96(0.3099) H10A(0.127) H10B(0.1666) H10C(0.1901)
 H11D(0.312) H11E(0.287) H11F(0.3342) H12A(0.402) H12B(0.3258) H12C(0.3292)
 H13D(0.2348) H13E(0.193) H13F(0.1538) H133(-0.1787) H13G(-0.1185) H13H(-
 0.0994) H13I(-0.0467) H137(-0.0942) H140(0.5131) H2AA(0.5872) H2AB(0.5921)
 H2AC(0.5579) H2DA(0.4658) H2DB(0.4484) H2DC(0.3966) H2GA(0.4559) H2GB(0.5253)
 H2GC(0.5331) H2IA(0.086) H2IB(0.0778) H2IC(0.0264) H2JA(-0.0521) H2JB(-0.0381)
 H2JC(0.0274) H2KA(-0.0566) H2KB(-0.1077) H2KC(-0.0842) H2FA(0.3761)
 H2FB(0.3886) H2FC(0.37) H2HA(0.2916) H2HB(0.2109) H2HC(0.2532) H2MA(0.2174)
 H2MB(0.2706) H2MC(0.2021)
 Fixed Y: H1B(0.7497) H1EA(0.3288) H1EB(0.3788) H1EC(0.3076) H1FA(0.2424)
 H1FB(0.2721) H1FC(0.2601) H1GA(0.1526) H1GB(0.0942) H1GC(0.0852) H1LA(0.1502)
 H1LB(0.1427) H1LC(0.1964) H1NA(0.0312) H1NB(0.0475) H1NC(0.0197) H1U(0.2034)
 H1XA(0.6065) H1XB(0.6042) H1XC(0.5783) H1YA(0.3659) H1YB(0.4323) H1YC(0.3729)
 H1ZA(0.3099) H1ZB(0.3318) H1ZC(0.3088) H2BA(0.4723) H2BB(0.4338) H2BC(0.4095)
 H6(0.3688) H11(0.4022) H17(0.5113) H38(0.4991) H48(0.6494) H50(0.3532)
 H53(0.587) H55(0.2825) H67(0.4223) H74(0.2913) H78(0.6018) H80(0.6194)
 H88(0.6571) H102(0.7432) H106(0.318) H107(0.1956) H114(0.7457) H11A(0.673)
 H11B(0.7173) H11C(0.6449) H126(0.0738) H128(0.7151) H129(0.7482) H138(0.2764)
 H13A(0.7185) H13B(0.7617) H13C(0.7135) H141(0.0972) H142(0.1243) H14A(0.3673)
 H14B(0.3794) H14C(0.4214) H147(0.1472) H1C(0.8354) H1D(0.2226) H1I(0.8171)
 H1JA(0.3728) H1JB(0.3982) H1JC(0.4321) H1K(0.2675) H1MA(0.3744) H1MB(0.3892)
 H1MC(0.4092) H1OA(0.4842) H1OB(0.424) H1OC(0.4884) H1P(0.871) H1Q(0.8493)
 H1R(0.3083) H1SA(0.6456) H1SB(0.6771) H1SC(0.6947) H1TA(0.6753) H1TB(0.7453)
 H1TC(0.7097) H1V(0.8505) H1W(0.3579) H2CA(0.5152) H2CB(0.5069) H2CC(0.5573)
 H2LA(0.5392) H2LB(0.4774) H2LC(0.4935) H18(0.6199) H27(0.46) H31(0.5364)
 H49(0.313) H61(0.4771) H65(0.6775) H71(0.4779) H75(0.4224) H79(0.5119)
 H81(0.4009) H82(0.7392) H84(0.5958) H93(0.7189) H96(0.5058) H10A(0.7558)
 H10B(0.8051) H10C(0.7971) H11D(0.7889) H11E(0.7823) H11F(0.7297) H12A(0.8006)
 H12B(0.7836) H12C(0.8259) H13D(0.6595) H13E(0.7184) H13F(0.6724) H133(0.2072)
 H13G(0.5364) H13H(0.5304) H13I(0.5016) H137(0.2324) H140(0.7931) H2AA(0.3538)
 H2AB(0.4106) H2AC(0.3474) H2DA(0.3357) H2DB(0.3136) H2DC(0.3617) H2GA(0.4616)
 H2GB(0.4839) H2GC(0.4328) H2IA(0.4815) H2IB(0.4105) H2IC(0.441) H2JA(0.5252)
 H2JB(0.5487) H2JC(0.5444) H2KA(0.3825) H2KB(0.4393) H2KC(0.4262) H2FA(0.2909)
 H2FB(0.3608) H2FC(0.3113) H2HA(0.4227) H2HB(0.4009) H2HC(0.3748) H2MA(0.2595)
 H2MB(0.2486) H2MC(0.2923)
 Fixed Z: H1B(0.3168) H1EA(-0.0029) H1EB(0.021) H1EC(0.0272) H1FA(0.0613)
 H1FB(0.0717) H1FC(0.029) H1GA(0.3745) H1GB(0.398) H1GC(0.3589) H1LA(0.3651)
 H1LB(0.4011) H1LC(0.3719) H1NA(0.3777) H1NB(0.3405) H1NC(0.3376) H1U(0.0661)
 H1XA(0.0914) H1XB(0.0495) H1XC(0.0829) H1YA(0.3922) H1YB(0.4093) H1YC(0.4291)
 H1ZA(0.3964) H1ZB(0.3578) H1ZC(0.3589) H2BA(0.4075) H2BB(0.3868) H2BC(0.4251)
 H6(0.3304) H11(0.3318) H17(0.1023) H38(0.3473) H48(0.1212) H50(0.3537)
 H53(0.3548) H55(0.3162) H67(0.1015) H74(0.0868) H78(0.0839) H80(0.1216)
 H88(0.3929) H102(0.1365) H106(0.0793) H107(0.3116) H114(0.1989) H11A(0.0313)
 H11B(0.0617) H11C(0.0649) H126(0.2992) H128(0.3702) H129(0.2547) H138(0.0419)
 H13A(0.0835) H13B(0.0704) H13C(0.0419) H141(0.2373) H142(0.1828) H14A(0.0153)
 H14B(0.0582) H14C(0.0373) H147(0.1206) H1C(0.4263) H1D(0.185) H1I(0.4796)
 H1JA(-0.0246) H1JB(-0.0054) H1JC(-0.0412) H1K(0.1292) H1MA(0.3891)
 H1MB(0.3628) H1MC(0.4058) H1OA(0.0059) H1OB(-0.0189) H1OC(-0.0334) H1P(0.3233)
 H1Q(0.3785) H1R(0.08) H1SA(0.5031) H1SB(0.5414) H1SC(0.5228) H1TA(0.4744)
 H1TB(0.4722) H1TC(0.5112) H1V(0.2556) H1W(0.0253) H2CA(0.3767) H2CB(0.3343)
 H2CC(0.3602) H2LA(0.3994) H2LB(0.4129) H2LC(0.4266) H18(0.1451) H27(0.0746)
 H31(0.1313) H49(0.3011) H61(0.081) H65(0.4303) H71(0.3729) H75(0.083)
 H79(0.3594) H81(0.3104) H82(0.1936) H84(0.4208) H93(0.205) H96(0.4222)
 H10A(0.1368) H10B(0.1152) H10C(0.1594) H11D(0.144) H11E(0.0998) H11F(0.123)
 H12A(0.5307) H12B(0.5414) H12C(0.5059) H13D(0.0917) H13E(0.073) H13F(0.097)
 H133(0.2519) H13G(0.03) H13H(-0.0109) H13I(0.0242) H137(0.3036) H140(0.2035)
 H2AA(0.3973) H2AB(0.3702) H2AC(0.3535) H2DA(0.4163) H2DB(0.3737) H2DC(0.3888)
 H2GA(0.4177) H2GB(0.4019) H2GC(0.4338) H2IA(0.4156) H2IB(0.405) H2IC(0.4304)
 H2JA(0.4009) H2JB(0.3612) H2JC(0.3958) H2KA(0.367) H2KB(0.3529) H2KC(0.3967)
 H2FA(0.0713) H2FB(0.0613) H2FC(0.0286) H2HA(0.0296) H2HB(0.0302) H2HC(-0.0008)
 H2MA(0.0536) H2MB(0.0246) H2MC(0.0136)
;