Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and Highly Substituted Nanographenes from Simple Aromatics.
Zhang, Qiang; Peng, Hanqing; Zhang, Guishan; Lu, Qiongqiong; Chang, Jian; Dong, Yeye; Shi, Xianying; Wei, Junfa; Journal of the American Chemical Society 136 (2014) 5057–5064; doi:10.1021/ja413018f

data_4121611
_publ_section_title
;
 Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and
 Highly Substituted Nanographenes from Simple Aromatics.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5057
_journal_page_last               5064
_journal_paper_doi               10.1021/ja413018f
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C66 H66 O6 S3'
_chemical_formula_sum            'C66 H66 O6 S3'
_chemical_formula_weight         1051.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-26
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                98.703(11)
_cell_angle_beta                 95.789(10)
_cell_angle_gamma                108.038(15)
_cell_formula_units_Z            2
_cell_length_a                   12.1545(19)
_cell_length_b                   13.507(2)
_cell_length_c                   19.3873(17)
_cell_measurement_reflns_used    5652
_cell_measurement_temperature    105(7)
_cell_measurement_theta_max      27.3940
_cell_measurement_theta_min      3.2270
_cell_volume                     2954.4(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      105(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9902
_diffrn_measured_fraction_theta_max 0.8747
_diffrn_measurement_details
;
  1 omega  -80.00  -27.20   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  126.0000  -29.0000 44

  2 omega -102.00  -55.20   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  178.0000  150.0000 39

  3 omega  -66.00  -38.40   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -77.0000  -60.0000 23

  4 omega  -40.00   20.00   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -38.0000  -60.0000 50

  5 omega   46.00   72.40   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000  -30.0000 22

  6 omega   -1.00   56.60   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000 -150.0000 48

  7 omega   80.00  105.20   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000  -30.0000 21

  8 omega  -54.00   78.00   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -19.0000    0.0000 110

  9 omega   38.00   66.80   1.2000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000   30.0000 24
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0413011000
_diffrn_orient_matrix_UB_12      -0.0511593000
_diffrn_orient_matrix_UB_13      -0.0137677000
_diffrn_orient_matrix_UB_21      -0.0022974000
_diffrn_orient_matrix_UB_22      -0.0101414000
_diffrn_orient_matrix_UB_23      0.0348257000
_diffrn_orient_matrix_UB_31      -0.0465254000
_diffrn_orient_matrix_UB_32      0.0211058000
_diffrn_orient_matrix_UB_33      0.0026428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21794
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
;
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         11472
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1132P)^2^+3.9724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2162
_reflns_number_gt                7925
_reflns_number_total             11472
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja413018f_si_005.cif
_cod_data_source_block           shanshda0529_1
_cod_database_code               4121611
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Shared sites
{C1B, S1A}
{S1B, C1A}
{S2A, C3B}
{C3A, S2B}
{C2B, S3A}
{S3B, C2A}
2. Others
 Fixed Sof: S1A(0.6) S1B(0.4) S2A(0.6) S2B(0.4) S3A(0.6) S3B(0.4) C1A(0.6)
 H1A(0.6) C1B(0.4) H1B(0.4) C2A(0.6) H2A(0.6) C2B(0.4) H2B(0.4) C3A(0.6)
 H3A(0.6) C3B(0.4) H3B(0.4) H59A(0.7) H59B(0.7) H59C(0.3) H59D(0.3) C60A(0.7)
 H60A(0.7) H60B(0.7) C60B(0.3) H60C(0.3) H60D(0.3) C61A(0.7) H61A(0.7)
 H61B(0.7) H61C(0.7) C61B(0.3) H61D(0.3) H61E(0.3) H61F(0.3) C62A(0.6)
 H62A(0.6) C62B(0.4) H62B(0.4) C63A(0.6) H63A(0.6) C63B(0.4) H63B(0.4)
 C64A(0.6) H64A(0.6) C64B(0.4) H64B(0.4)
 Fixed Uiso: H1A(0.031) H1B(0.039) H2A(0.038) H2B(0.038) H3A(0.036) H3B(0.039)
 H6(0.029) H9(0.028) H17(0.025) H20(0.03) H34(0.025) H37(0.026) H38A(0.035)
 H38B(0.035) H48A(0.035) H48B(0.035) H40A(0.035) H40B(0.035) H39A(0.034)
 H39B(0.034) H41A(0.06) H41B(0.06) H41C(0.06) H42A(0.041) H42B(0.041)
 H43A(0.054) H43B(0.054) H44A(0.078) H44B(0.078) H45A(0.15) H45B(0.15)
 H45C(0.15) H46A(0.036) H46B(0.036) H47A(0.038) H47B(0.038) H49A(0.063)
 H49B(0.063) H49C(0.063) H50A(0.03) H50B(0.03) H51A(0.029) H51B(0.029)
 H52A(0.033) H52B(0.033) H53A(0.049) H53B(0.049) H53C(0.049) H54A(0.037)
 H54B(0.037) H55A(0.048) H55B(0.048) H56A(0.073) H56B(0.073) H57A(0.144)
 H57B(0.144) H57C(0.144) H58A(0.071) H58B(0.071) H59A(0.109) H59B(0.109)
 H59C(0.109) H59D(0.109) H60A(0.073) H60B(0.073) H60C(0.097) H60D(0.097)
 H61A(0.134) H61B(0.134) H61C(0.134) H61D(0.128) H61E(0.128) H61F(0.128)
 H62A(0.035) H62B(0.029) H63A(0.034) H63B(0.03) H64A(0.04) H64B(0.035)
 Fixed X: H1A(0.7841) H1B(0.9296) H2A(0.3966) H2B(0.4693) H3A(0.8107)
 H3B(0.5798) H6(0.6016) H9(0.3987) H17(0.8341) H20(0.7617) H34(0.3365)
 H37(0.4128) H38A(1.0013) H38B(0.8849) H39A(0.9756) H39B(1.0263) H41A(1.216)
 H41B(1.1629) H41C(1.2824) H42A(0.5381) H42B(0.6393) H43A(0.5889) H43B(0.4622)
 H44A(0.5371) H44B(0.6649) H45A(0.6064) H45B(0.4881) H45C(0.6065) H46A(0.378)
 H46B(0.2615) H47A(0.2144) H47B(0.1962) H49A(0.3185) H49B(0.2294) H49C(0.2069)
 H50A(0.1917) H50B(0.3087) H51A(0.0934) H51B(0.2095) H52A(0.0733) H52B(0.1906)
 H53A(0.0338) H53B(0.102) H53C(-0.0157) H54A(0.3771) H54B(0.2638) H55A(0.2452)
 H55B(0.2653) H56A(0.0693) H56B(0.0891) H57A(-0.041) H57B(0.075) H57C(0.049)
 H58A(1.0283) H58B(0.9948) H59A(1.1132) H59B(1.0054) H59C(1.0666) H59D(0.9603)
 H60A(1.0012) H60B(0.908) H60C(1.0625) H60D(1.1687) H61A(1.0381) H61B(1.1341)
 H61C(1.0219) H61D(1.2229) H61E(1.0966) H61F(1.1415) H62A(0.9399) H62B(0.9647)
 H63A(0.4506) H63B(0.4259) H64A(0.7674) H64B(0.7296)
 Fixed Y: H1A(-0.1022) H1B(-0.1237) H2A(0.4377) H2B(0.2313) H3A(0.2162)
 H3B(0.4047) H6(-0.1553) H9(0.0736) H17(-0.1391) H20(0.0709) H34(0.3909)
 H37(0.3167) H38A(-0.1767) H38B(-0.2741) H39A(-0.33) H39B(-0.3451) H41A(-
 0.3445) H41B(-0.3326) H41C(-0.25) H42A(-0.3099) H42B(-0.2219) H43A(-0.3884)
 H43B(-0.3844) H44A(-0.2356) H44B(-0.2369) H45A(-0.3192) H45B(-0.3932) H45C(-
 0.4095) H46A(0.0693) H46B(0.0101) H47A(0.014) H47B(-0.104) H49A(-0.0863) H49B(-
 0.0293) H49C(-0.1476) H50A(0.4618) H50B(0.5571) H51A(0.5637) H51B(0.6606)
 H52A(0.5595) H52B(0.6549) H53A(0.7179) H53B(0.7654) H53C(0.6699) H54A(0.4354)
 H54B(0.3343) H55A(0.4531) H55B(0.5423) H56A(0.3571) H56B(0.4481) H57A(0.4681)
 H57B(0.565) H57C(0.4709) H58A(-0.0318) H58B(-0.0398) H59A(0.135) H59B(0.1403)
 H59C(0.1391) H59D(0.135) H60A(0.1233) H60B(0.1483) H60C(0.1351) H60D(0.136)
 H61A(0.3124) H61B(0.2873) H61C(0.2975) H61D(0.287) H61E(0.2896) H61F(0.2954)
 H62A(-0.1411) H62B(-0.1246) H63A(0.4301) H63B(0.3911) H64A(0.3719) H64B(0.3913)
 Fixed Z: H1A(0.261) H1B(0.4759) H2A(0.379) H2B(0.201) H3A(0.775) H3B(0.7352)
 H6(0.2434) H9(0.2012) H17(0.5479) H20(0.7362) H34(0.4544) H37(0.6759)
 H38A(0.5887) H38B(0.5778) H39A(0.6757) H39B(0.6052) H41A(0.673) H41B(0.743)
 H41C(0.7359) H42A(0.159) H42B(0.1364) H43A(0.057) H43B(0.0379) H44A(-0.0137)
 H44B(0.0068) H45A(-0.1097) H45B(-0.0936) H45C(-0.0675) H46A(0.0793)
 H46B(0.1057) H47A(-0.0114) H47B(-0.0051) H49A(-0.1635) H49B(-0.1416) H49C(-
 0.134) H50A(0.4452) H50B(0.4742) H51A(0.5145) H51B(0.5261) H52A(0.3923)
 H52B(0.4031) H53A(0.3885) H53B(0.4655) H53C(0.4522) H54A(0.7586) H54B(0.7397)
 H55A(0.8357) H55B(0.7906) H56A(0.7611) H56B(0.7174) H57A(0.7948) H57B(0.8185)
 H57C(0.8596) H58A(0.7762) H58B(0.8516) H59A(0.8396) H59B(0.7911) H59C(0.7932)
 H59D(0.8327) H60A(0.93) H60B(0.8803) H60C(0.9299) H60D(0.8909) H61A(0.8814)
 H61B(0.9293) H61C(0.9589) H61D(0.9332) H61E(0.9407) H61F(0.8679) H62A(0.3284)
 H62B(0.3574) H63A(0.2618) H63B(0.2361) H64A(0.8206) H64B(0.8156)
;