1-Oxo-1H-phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies.
Lenk, Romaric; Tessier, Arnaud; Lefranc, Pierre; Silvestre, Virginie; Planchat, Aurélien; Blot, Virginie; Dubreuil, Didier; Lebreton, Jacques; The Journal of organic chemistry 79 (2014) 9754–9761; doi:10.1021/jo5016932

data_4030024
_publ_section_title
;
 1-Oxo-1H-phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised
 Structure and Mechanistic Studies.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9754
_journal_page_last               9761
_journal_paper_doi               10.1021/jo5016932
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H13 N3 O1 S1'
_chemical_formula_sum            'C19 H13 N3 O S'
_chemical_formula_weight         331.4
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.1130(5)
_cell_length_b                   7.5217(7)
_cell_length_c                   7.293(2)
_cell_measurement_temperature    293
_cell_volume                     1542.2(4)
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21498
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         6.4
_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9533
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'Jana2006  (Petricek, Dusek & Palatinus, 2000)'
_exptl_crystal_density_diffrn    1.4269
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.12
_refine_diff_density_min         -1.69
_refine_ls_abs_structure_details
'  1579 of Friedel pairs used in the refinement'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    2.05
_refine_ls_goodness_of_fit_ref   1.86
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    53
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.0144
_refine_ls_shift/su_mean         0.0023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(\s^2^(I)+0.0004I^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                2568
_reflns_number_total             3602
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5016932_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/saulius/struct/COD-crude-data--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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030023--4030026.cif.
;
_cod_original_cell_volume        1542.1(4)
_cod_original_sg_symbol_Hall     'P -2xac;-2ya;2zc'
_cod_original_formula_sum        'C19 H13 N3 O1 S1'
_cod_database_code               4030024