The Missing C1-C5 Cycloaromatization Reaction: Triplet State Antiaromaticity Relief and Self-Terminating Photorelease of Formaldehyde for Synthesis of Fulvenes from Enynes.
Mohamed, Rana K.; Mondal, Sayantan; Jorner, Kjell; Delgado, Thais Faria; Lobodin, Vladislav V.; Ottosson, Henrik; Alabugin, Igor V.; Journal of the American Chemical Society 137 (2015) 15441–15450; doi:10.1021/jacs.5b07448

data_4129520
_publ_section_title
;
 The Missing C1-C5 Cycloaromatization Reaction: Triplet State
 Antiaromaticity Relief and Self-Terminating Photorelease of Formaldehyde
 for Synthesis of Fulvenes from Enynes.
;
_journal_issue                   49
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15441
_journal_page_last               15450
_journal_paper_doi               10.1021/jacs.5b07448
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         '2(C17 H12 O2)'
_chemical_formula_sum            'C34 H24 O4'
_chemical_formula_weight         496.53
_chemical_name_systematic        Monoclinic
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.781(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7038(8)
_cell_length_b                   6.1582(5)
_cell_length_c                   22.188(2)
_cell_measurement_reflns_used    5656
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.35
_cell_volume                     1183.22(18)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      173.01
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14931
_diffrn_reflns_theta_full        28.98
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         2.35
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1857 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.9359.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.3439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                2382
_reflns_number_total             3135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b07448_si_002.cif
_cod_data_source_block           p21c1
_cod_original_cell_volume        1183.21(18)
_cod_database_code               4129520
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id Rana291
_olex2_submission_special_instructions 'No special instructions were received'