Synthesis of π-Extended Fluoranthenes via a KHMDS-Promoted Anionic-Radical Reaction Cascade.
Ogawa, Naoki; Yamaoka, Yousuke; Yamada, Ken-Ichi; Takasu, Kiyosei; Organic letters 19 (2017) 3327–3330; doi:10.1021/acs.orglett.7b01538

data_1546278
_publ_section_title
;
 Synthesis of \p-Extended Fluoranthenes via a KHMDS-Promoted
 Anionic-Radical Reaction Cascade.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3327
_journal_page_last               3330
_journal_paper_doi               10.1021/acs.orglett.7b01538
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C28 H22 O'
_chemical_formula_sum            'C28 H22 O'
_chemical_formula_weight         374.45
_chemical_name_systematic        170401NO
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.099(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5228(2)
_cell_length_b                   7.47940(10)
_cell_length_c                   17.7719(3)
_cell_measurement_reflns_used    7674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6040
_cell_measurement_theta_min      3.2560
_cell_volume                     1937.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.959
_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     -7.00  30.00   0.50    0.98    --    0.00  23.00 104.00   74
  2  \w    -19.00   6.00   0.50    3.93    --    5.00  23.00 104.00   50
  3  \w   -122.00 -97.00   0.50    3.93    --  -97.80  23.00 104.00   50
  4  \w    -89.00 -42.00   0.50    0.98    --    0.00  60.00  30.00   94
  5  \w    -84.00 -56.00   0.50    3.93    --    5.00  60.00  60.00   56
  6  \w    -80.00 -35.00   0.50    3.93    --    5.00  57.00 150.00   90
  7  \w    -70.00 -45.00   0.50    3.93    --    5.00  60.00 120.00   50
  8  \w   -162.00 -30.00   0.50    3.93    --  -97.80  29.00  60.00  264
  9  \w   -187.00-106.00   0.50    3.93    --  -97.80  60.00   0.00  162
 10  \w   -173.00-148.00   0.50    3.93    --  -97.80  60.00  90.00   50
 11  \w    -53.00  -8.00   0.50    3.93    --  -97.80  43.00   0.00   90
 12  \w   -187.00-110.00   0.50    3.93    --  -97.80  43.00   0.00  154
 13  \w   -186.00-107.00   0.50    3.93    --  -97.80  57.00 150.00  158
 14  \w   -146.00-121.00   0.50    3.93    --  -97.80  29.00  90.00   50
 15  \w   -116.00  -8.00   0.50    3.93    --  -97.80  29.00  90.00  216
 16  \w   -105.00 -34.00   0.50    3.93    --  -97.80  57.00   0.00  142
 17  \w   -169.00-144.00   0.50    3.93    --  -97.80  57.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0878336000
_diffrn_orient_matrix_UB_12      0.0791944000
_diffrn_orient_matrix_UB_13      -0.0084403000
_diffrn_orient_matrix_UB_21      0.0420052000
_diffrn_orient_matrix_UB_22      0.0197462000
_diffrn_orient_matrix_UB_23      0.0917208000
_diffrn_orient_matrix_UB_31      0.0412022000
_diffrn_orient_matrix_UB_32      -0.1890848000
_diffrn_orient_matrix_UB_33      0.0059934000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10566
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.011
_diffrn_reflns_theta_min         3.269
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_preparation       2+2
_exptl_crystal_recrystallization_method 'recrystalization from hexanes/EtOAc'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0727P)^2^+0.6732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3512
_reflns_number_total             3722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01538_si_002.cif
_cod_data_source_block           170401no
_cod_depositor_comments
'Adding full bibliography for 1546278--1546279.cif.'
_cod_database_code               1546278
_chemical_oxdiff_formula         'C28 H22 O1'
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C20(H20), C7(H7), C19(H19), C10(H10), C17(H17), C18(H18),
 C26(H26), C8(H8), C25(H25), C23(H23), C9(H9), C24(H24)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              37098
_shelx_hkl_checksum              51116
_shelx_shelxl_version_number     2016/6
_olex2_exptl_crystal_mounting_method ring
_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 1.666
_oxdiff_exptl_absorpt_empirical_full_min 0.751