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_1546279
_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        3a
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.10510(10)
_cell_length_b                   12.3289(2)
_cell_length_c                   21.5929(3)
_cell_measurement_reflns_used    6250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0780
_cell_measurement_theta_min      4.0180
_cell_volume                     1891.50(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 1.000
_diffrn_measured_fraction_theta_max 0.978
_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   -175.00 -51.00   0.50    1.00    -- -100.00  60.00  30.00  248
  2  \w   -110.00 -38.00   0.50    1.00    --  -20.00  48.00  70.00  144
  3  \w   -175.00 -60.50   0.50    1.00    -- -100.00   0.00 190.00  229
  4  \w   -165.00 -92.00   0.50    1.00    -- -100.00  48.00 190.00  146
  5  \w   -108.00 -38.00   0.50    1.00    --  -20.00  48.00 150.00  140
  6  \w   -132.50 -60.50   0.50    1.00    -- -100.00  60.00 270.00  144
  7  \w   -173.00-128.00   0.50    1.00    -- -100.00  60.00 150.00   90
  8  \w   -100.50 -53.00   0.50    1.00    --  -20.00  60.00 310.00   95
  9  \w   -175.00-123.00   0.50    1.00    -- -100.00  12.00 190.00  104
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0194800000
_diffrn_orient_matrix_UB_12      0.0201907000
_diffrn_orient_matrix_UB_13      0.0700930000
_diffrn_orient_matrix_UB_21      -0.0568460000
_diffrn_orient_matrix_UB_22      0.1194082000
_diffrn_orient_matrix_UB_23      -0.0094982000
_diffrn_orient_matrix_UB_31      -0.2084470000
_diffrn_orient_matrix_UB_32      -0.0306661000
_diffrn_orient_matrix_UB_33      0.0091794000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8519
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.447
_diffrn_reflns_theta_min         4.095
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86699
_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    1.315
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_preparation       'KHMDS-promoted reaction'
_exptl_crystal_recrystallization_method 'recrystallisation from DCM/hexanes'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1320 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0752P)^2^+0.2205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3421
_reflns_number_total             3614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01538_si_003.cif
_cod_data_source_block           151203no
_cod_depositor_comments
'Adding full bibliography for 1546278--1546279.cif.'
_cod_database_code               1546279
_reflns_odcompleteness_completeness 97.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.28
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C11(H11), C12(H12), C14(H14), C13(H13), C8(H8), C5(H5), C22(H22),
 C7(H7), C19(H19), C6(H6), C20(H20), C23(H23)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_shelx_res_checksum              71413
_shelx_hkl_checksum              210
_shelx_shelxl_version_number     2016/6
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.821