Conformational flexibility of fused tetracenedione propellers obtained from one-pot reductive dimerization of acetylenic quinones.
Vasilevsky, Sergei F.; Baranov, Denis S.; Mamatyuk, Victor I.; Fadeev, Dmitry S.; Gatilov, Yurii V.; Stepanov, Aleksandr A.; Vasilieva, Nadezhda V.; Alabugin, Igor V.; The Journal of organic chemistry 80 (2015) 1618–1631; doi:10.1021/jo502543b

data_4030562
_publ_section_title
;
 Conformational flexibility of fused tetracenedione propellers obtained
 from one-pot reductive dimerization of acetylenic quinones.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1618
_journal_page_last               1631
_journal_paper_doi               10.1021/jo502543b
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_chemical_melting_point          493
_chemical_name_systematic
; 
 2-hydroxy-1-propyl-7H-benzo[d,e]anthracen-7-one 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.966(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.275(2)
_cell_length_b                   18.499(4)
_cell_length_c                   8.4499(19)
_cell_measurement_reflns_used    1528
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.22
_cell_volume                     1435.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9388
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_correction_T_min  0.7921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'CH2Cl2 ethylacetate'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0043(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0539P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                1412
_reflns_number_total             2541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502543b_si_003.cif
_cod_data_source_block           comp7d_b372_CCDC_823560
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030560--4030562.cif.
;
_cod_original_cell_volume        1435.9(6)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4030562