Benzo[<i>cd</i>]triangulene: A Spin 1/2 Graphene Fragment.
Ravat, Prince; Blacque, Olivier; Juríček, Michal; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02163

data_4033605
_publ_section_title
;
 Benzo[<i>cd</i>]triangulene: A Spin 1/2 Graphene Fragment.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02163
_journal_year                    2019
_chemical_formula_moiety         'C49 H29, 0.2(C6 H14)'
_chemical_formula_sum            'C50.2 H31.8'
_chemical_formula_weight         634.95
_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
_audit_creation_date             2019-07-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5222(2)
_cell_length_b                   5.65100(10)
_cell_length_c                   40.0027(5)
_cell_measurement_reflns_used    22849
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      78.6
_cell_measurement_theta_min      3.7
_cell_volume                     3282.35(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -11.00  41.00   0.50    4.00    --    0.00  89.00  75.00  104
  2  \w    -18.00   7.00   0.50    4.00    --    0.00 -38.00   0.00   50
  3  \w    -14.00  14.00   0.50    4.00    --    0.00 -89.00 -39.00   56
  4  \w    -62.00 -28.00   0.50    4.00    --    0.00 -38.00   0.00   68
  5  \w     -1.00  45.00   0.50    4.00    --    0.00  38.00-150.00   92
  6  \w    -37.00  -2.00   0.50    4.00    --    0.00 115.00-138.64   70
  7  \w     39.00  64.00   0.50   16.00    --  105.75 -30.00  60.00   50
  8  \w     41.00  82.00   0.50   16.00    --  105.75 -73.00 106.51   82
  9  \w     74.00  99.00   0.50   16.00    --  105.75 -94.00 120.00   50
 10  \w     99.00 124.00   0.50   16.00    --  105.75 -73.00 106.51   50
 11  \w    102.00 128.00   0.50   16.00    --  105.75 -90.00  72.09   52
 12  \w     83.00 120.00   0.50   16.00    --  105.75 -61.00  90.00   74
 13  \w     81.00 107.00   0.50   16.00    --  105.75-111.00  30.00   52
 14  \w     63.00 123.00   0.50   16.00    --  105.75 -77.00  30.00  120
 15  \w     67.00 108.00   0.50   16.00    --  105.75 -94.00 -60.00   82
 16  \w     87.00 113.00   0.50   16.00    --  105.75-111.00 -90.00   52
 17  \w     82.00 108.00   0.50   16.00    --  105.75-111.00-150.00   52
 18  \w     82.00 107.00   0.50   16.00    --  105.75 -94.00-120.00   50
 19  \w     99.00 125.00   0.50   16.00    --  105.75 -82.00-121.65   52
 20  \w     81.00 112.00   0.50   16.00    --  105.75-111.00 -60.00   62
 21  \w     85.00 111.00   0.50   16.00    --  105.75 -99.00 -65.45   52
 22  \w     62.00 112.00   0.50   16.00    --  105.75 -61.00 -90.00  100
 23  \w     51.00  77.00   0.50   16.00    --  105.75-111.00 -30.00   52
 24  \w     47.00  98.00   0.50   16.00    --  105.75 -61.00 -30.00  102
 25  \w     52.00 112.00   0.50   16.00    --  105.75-111.00-120.00  120
 26  \w     45.00  71.00   0.50   16.00    --  105.75-111.00-150.00   52
 27  \w     40.00  66.00   0.50   16.00    --  105.75 -94.00-180.00   52
 28  \w     40.00  66.00   0.50   16.00    --  105.75 -45.00-150.00   52
 29  \w     31.00  56.00   0.50   16.00    --  105.75 -45.00-180.00   50
 30  \w     31.00  64.00   0.50   16.00    --  105.75-111.00 -90.00   66
 31  \w     32.00  69.00   0.50   16.00    --  105.75 -45.00 -30.00   74
 32  \w     29.00  67.00   0.50   16.00    --  105.75 -30.00   0.00   76
 33  \w     33.00 110.00   0.50   16.00    --  105.75  -7.00  71.11  154
 34  \w    112.00 150.00   0.50   16.00    --  105.75  45.00  90.00   76
 35  \w    129.00 177.00   0.50   16.00    --  105.75 111.00 150.00   96
 36  \w    105.00 177.00   0.50   16.00    --  105.75  30.00 -30.00  144
 37  \w    139.00 170.00   0.50   16.00    --  105.75 111.00 -90.00   62
 38  \w    111.00 136.00   0.50   16.00    --  105.75 111.00 -90.00   50
 39  \w    105.00 147.00   0.50   16.00    --  105.75 109.00 -29.00   84
 40  \w    102.00 136.00   0.50   16.00    --  105.75  45.00 -60.00   68
 41  \w     94.00 127.00   0.50   16.00    --  105.75  61.00-120.00   66
 42  \w    100.00 142.00   0.50   16.00    --  105.75 111.00-150.00   84
 43  \w     48.00  74.00   0.50   16.00    --  105.75 -90.00  72.09   52
 44  \w     31.00  64.00   0.50   16.00    --  105.75 -94.00 120.00   66
 45  \w     65.00  91.00   0.50   16.00    --  105.75 -17.00 175.73   52
 46  \w     56.00 111.00   0.50   16.00    --  105.75 -15.00 120.00  110
 47  \w     32.00  58.00   0.50   16.00    --  105.75-111.00  30.00   52
 48  \w     76.00 117.00   0.50   16.00    --  105.75 178.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0509559000
_diffrn_orient_matrix_UB_12      0.0566191000
_diffrn_orient_matrix_UB_13      0.0331398000
_diffrn_orient_matrix_UB_21      -0.0095804000
_diffrn_orient_matrix_UB_22      -0.2602373000
_diffrn_orient_matrix_UB_23      0.0108627000
_diffrn_orient_matrix_UB_31      0.0925671000
_diffrn_orient_matrix_UB_32      -0.0580686000
_diffrn_orient_matrix_UB_33      -0.0163611000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            38709
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         3.731
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.13a (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0728P)^2^+1.0127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5802
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02163_si_002.cif
_cod_data_source_block           ccdc1880918
_cod_original_formula_sum        'C50.20 H31.80'
_cod_database_code               4033605
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C50-C51 = C51-C52 = C52-C53 = C53-C54 = C54-C55
 1.54 with sigma of 0.005
 C2-C26B = C24-C26B
 2.52 with sigma of 0.005
 C1-C26A \\sim C1-C26B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C26A \\sim C26B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
Uiso(C50) = Uiso(C51) = Uiso(C52) = Uiso(C53) = Uiso(C54) = Uiso(C55)
4. Others
 Sof(C26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29B)=
 Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=1-FVAR(1)
 Sof(C26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=FVAR(1)
 Fixed Sof: C50(0.2) H50A(0.2) H50B(0.2) H50C(0.2) C51(0.2) H51A(0.2)
 H51B(0.2) C52(0.2) H52A(0.2) H52B(0.2) C53(0.2) H53A(0.2) H53B(0.2) C54(0.2)
 H54A(0.2) H54B(0.2) C55(0.2) H55A(0.2) H55B(0.2) H55C(0.2)
5.a :
 C26A(C27A,C28A,C29A,C30A,C31A), C26B(C27B,C28B,C29B,C30B,C31B)
5.b Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C17(H17), C21(H21),
 C23(H23), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A),
 C27B(H27B), C28B(H28B), C29B(H29B), C30B(H30B), C31B(H31B), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49)
5.d Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C55(H55A,H55B,H55C)
;
_shelx_res_checksum              83405
_shelx_hkl_checksum              28937