Toward Full Zigzag-Edged Nanographenes: peri-Tetracene and Its Corresponding Circumanthracene.
Ajayakumar, M. R.; Fu, Yubin; Ma, Ji; Hennersdorf, Felix; Komber, Hartmut; Weigand, Jan J.; Alfonsov, Alexey; Popov, Alexey A.; Berger, Reinhard; Liu, Junzhi; Müllen, Klaus; Feng, Xinliang; Journal of the American Chemical Society 140 (2018) 6240–6244; doi:10.1021/jacs.8b03711

data_4132405
_publ_section_title
;
 Toward Full Zigzag-Edged Nanographenes: peri-Tetracene and Its
 Corresponding Circumanthracene.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6240
_journal_page_last               6244
_journal_paper_doi               10.1021/jacs.8b03711
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         '1.5(C2 H2 Cl4), C74 H62'
_chemical_formula_sum            'C77 H65 Cl6'
_chemical_formula_weight         1202.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                108.7010(10)
_cell_angle_beta                 107.2900(10)
_cell_angle_gamma                101.4190(10)
_cell_formula_units_Z            2
_cell_length_a                   13.7112(2)
_cell_length_b                   15.3522(2)
_cell_length_c                   16.2553(2)
_cell_measurement_reflns_used    20304
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      76.4900
_cell_measurement_theta_min      3.2010
_cell_volume                     2927.37(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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     17.00 105.00   0.50    3.50    --   42.87  57.00 -90.00  176
  2  \w    127.00 153.00   0.50   14.00    --  111.00  15.00 -30.00   52
  3  \w     98.00 177.00   0.50   14.00    --  111.00  61.00-150.00  158
  4  \w     96.00 123.00   0.50   14.00    --  111.00 125.00 -90.00   54
  5  \w     88.00 141.00   0.50   14.00    --  111.00  45.00   0.00  106
  6  \w    125.00 158.00   0.50   14.00    --  111.00  30.00  90.00   66
  7  \w     99.00 138.00   0.50   14.00    --  111.00 -61.00 120.00   78
  8  \w     92.00 121.00   0.50   14.00    --  111.00-125.00   0.00   58
  9  \w     71.00  98.00   0.50   14.00    --  111.00 -94.00   0.00   54
 10  \w     72.00 134.00   0.50   14.00    --  111.00 -45.00   0.00  124
 11  \w     67.00 105.00   0.50   14.00    --  111.00  15.00 -30.00   76
 12  \w     92.00 178.00   0.50   14.00    --  111.00  45.00 -30.00  172
 13  \w     94.00 174.00   0.50   14.00    --  111.00 125.00  60.00  160
 14  \w    100.00 148.00   0.50   14.00    --  111.00 125.00 150.00   96
 15  \w     57.00 135.00   0.50   14.00    --  111.00 -61.00-120.00  156
 16  \w     91.00 121.00   0.50   14.00    --  111.00-125.00-150.00   60
 17  \w     57.00 116.00   0.50   14.00    --  111.00-125.00 -60.00  118
 18  \w     56.00  83.00   0.50    3.50    --   42.87-125.00 -60.00   54
 19  \w     31.00  87.00   0.50   14.00    --  111.00 -94.00-150.00  112
 20  \w     54.00 100.00   0.50   14.00    --  111.00 -30.00-180.00   92
 21  \w     30.00 106.00   0.50   14.00    --  111.00 -94.00-180.00  152
 22  \w     40.00  97.00   0.50   14.00    --  111.00-125.00-180.00  114
 23  \w     45.00  70.00   0.50   14.00    --  111.00-125.00   0.00   50
 24  \w     38.00  70.00   0.50   14.00    --  111.00 -94.00  30.00   64
 25  \w     39.00 121.00   0.50   14.00    --  111.00-125.00  90.00  164
 26  \w     55.00  98.00   0.50   14.00    --  111.00-125.00 120.00   86
 27  \w     49.00 107.00   0.50   14.00    --  111.00-125.00 150.00  116
 28  \w     20.00  61.00   0.50    3.50    --   42.87 -77.00 150.00   82
 29  \w    -61.00  33.00   0.50    3.50    --  -38.50  38.00 150.00  188
 30  \w    -39.00  -7.00   0.50    3.50    --  -38.50 125.00 -30.00   64
 31  \w    -94.00 -57.00   0.50    3.50    --  -38.50 125.00 -30.00   74
 32  \w   -110.00 -16.00   0.50    3.50    --  -38.50 -38.00 -30.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288133000
_diffrn_orient_matrix_UB_12      0.0703781000
_diffrn_orient_matrix_UB_13      -0.0451343000
_diffrn_orient_matrix_UB_21      0.1179296000
_diffrn_orient_matrix_UB_22      0.0010584000
_diffrn_orient_matrix_UB_23      0.0341934000
_diffrn_orient_matrix_UB_31      -0.0271513000
_diffrn_orient_matrix_UB_32      -0.0871106000
_diffrn_orient_matrix_UB_33      -0.0926506000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31486
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.730
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_T_max  0.797
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.365
_exptl_crystal_description       plate
_exptl_crystal_F_000             1258
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.126
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         12207
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0762P)^2^+2.5596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11820
_reflns_number_total             12207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03711_si_003.cif
_cod_data_source_block           feng069
_cod_original_cell_volume        2927.36(7)
_cod_database_code               4132405
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C153 H128 Cl12 '
_chemical_oxdiff_usercomment     'NMR Nr 4, terachlorothan'
_shelx_estimated_absorpt_t_max   0.793
_shelx_estimated_absorpt_t_min   0.442
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
 Cl6-C77 \\sim Cl5-C77 \\sim Cl9-C79 \\sim Cl10-C79 \\sim Cl8-C78 \\sim Cl7-C78
\\sim Cl11-C80 \\sim Cl12-
 C80
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl5 \\sim Cl6 \\sim C77 \\sim C78 \\sim Cl7 \\sim Cl8 \\sim Cl9 \\sim Cl10
\\sim C79 \\sim C80 \\sim Cl11 \\sim Cl12: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl5(0.25) Cl6(0.25) C77(0.25) H77(0.25) C78(0.25) H78(0.25)
 Cl7(0.25) Cl8(0.25) Cl9(0.25) Cl10(0.25) C79(0.25) H79(0.25) C80(0.25)
 H80(0.25) Cl11(0.25) Cl12(0.25)
5.a Ternary CH refined with riding coordinates:
 C75(H75), C76(H76), C1(H1), C26(H26), C77(H77), C78(H78), C79(H79), C80(H80)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21),
 C22(H22), C28(H28), C29(H29), C30(H30), C39(H39), C41(H41), C47(H47), C48(H48),
  C50(H50), C51(H51), C58(H58), C60(H60), C66(H66), C67(H67), C69(H69), C70(H70)
5.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C53(H53A,H53B,
 H53C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C62(H62A,H62B,H62C), C63(H63A,
 H63B,H63C), C64(H64A,H64B,H64C), C72(H72A,H72B,H72C), C73(H73A,H73B,H73C),
 C74(H74A,H74B,H74C)
;
_shelx_res_checksum              70172
_shelx_hkl_checksum              92815
_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 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.635