Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ.
Guo, Biao; Zhou, Yiming; Zhang, Lei; Hua, Ruimao; The Journal of organic chemistry 80 (2015) 7635–7641; doi:10.1021/acs.joc.5b01219

data_4031316
_publ_section_title
;
 Br\/onsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via
 Isochromenylium Intermediate Formed in Situ.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7635
_journal_page_last               7641
_journal_paper_doi               10.1021/acs.joc.5b01219
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H15 F'
_chemical_formula_sum            'C24 H15 F'
_chemical_formula_weight         322.36
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-09
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7890(4)
_cell_length_b                   11.4354(9)
_cell_length_c                   23.674(3)
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    100.2
_cell_measurement_theta_max      29.3048
_cell_measurement_theta_min      3.4332
_cell_volume                     1567.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      100.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -7.00   22.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8897   77.0000  120.0000 29

  2 omega   57.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8897   77.0000  120.0000 26

  3 omega  -50.00   12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8897  -37.0000  120.0000 62

  4 omega  -14.00   29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8897    0.0000  120.0000 43

  5 omega   14.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210 -152.0000  -53.0000 29

  6 omega   53.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210 -151.0000 -170.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0225453000
_diffrn_orient_matrix_UB_12      -0.0309060000
_diffrn_orient_matrix_UB_13      -0.0253686000
_diffrn_orient_matrix_UB_21      0.0122843000
_diffrn_orient_matrix_UB_22      0.0525664000
_diffrn_orient_matrix_UB_23      -0.0155996000
_diffrn_orient_matrix_UB_31      0.1197990000
_diffrn_orient_matrix_UB_32      -0.0112099000
_diffrn_orient_matrix_UB_33      -0.0031681000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6915
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.1308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2770
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01219_si_001.cif
_cod_data_source_block           exp_2991
_cod_depositor_comments          'Adding full bibliography for 4031316.cif.'
_cod_database_code               4031316
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32