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_4033606
_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 H30 O'
_chemical_formula_sum            'C49 H30 O'
_chemical_formula_weight         634.73
_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   mixed
_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                 107.622(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6312(3)
_cell_length_b                   15.7637(4)
_cell_length_c                   16.8507(5)
_cell_measurement_reflns_used    18957
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      32.1
_cell_measurement_theta_min      2.6
_cell_volume                     3197.77(16)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -13.00  86.00   0.50   20.00    --   11.45  77.00   0.00  198
  2  \w     -8.00  56.00   0.50   20.00    --  -12.39  77.00-120.00  128
  3  \w    -13.00  86.00   0.50   20.00    --   11.45  77.00-150.00  198
  4  \w    -13.00  86.00   0.50   20.00    --   11.45  77.00  90.00  198
  5  \w    -37.00  45.00   0.50   20.00    --  -12.39  77.00 -30.00  164
;
_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      0.0366566000
_diffrn_orient_matrix_UB_12      -0.0200206000
_diffrn_orient_matrix_UB_13      -0.0188142000
_diffrn_orient_matrix_UB_21      -0.0459079000
_diffrn_orient_matrix_UB_22      -0.0120921000
_diffrn_orient_matrix_UB_23      -0.0342616000
_diffrn_orient_matrix_UB_31      0.0046217000
_diffrn_orient_matrix_UB_32      0.0384264000
_diffrn_orient_matrix_UB_33      -0.0205716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         2.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.980
_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            orange
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         9738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.5077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7808
_reflns_number_total             9738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02163_si_003.cif
_cod_data_source_block           ccdc1880919
_cod_original_cell_volume        3197.76(15)
_cod_database_code               4033606
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a 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), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), 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)
;
_shelx_res_checksum              45731
_shelx_hkl_checksum              83409